Boston is such a unique place to visit with its great mix of history, city life, walkable neighborhoods, and delicious food. I have lived and visited Boston so often over the years; it still draws me back. This itinerary will share my suggestions of things to do and experience to give you the optimal visit for your time in this wonderful city.
Boston is more than just a big city, it is more “cozy” than most big cities since it is historical, with many landmarks and neighborhoods closely knit together. There are also many green parks and green spaces, like Boston Common, Boston Public Garden, neighborhood gardens, etc. You also see the diversity and all the flavors it brings to its neighborhoods and food. This itinerary is to help guide you to the best way to spend your perfect 2 or 3 days in Boston whether you are here on a weekday or a long weekend. There is so much to see and you can’t do it all in 2 to 3 days, but you can choose from this itinerary what may meet your interests. But make sure you take in some of the historic sites on The Freedom Trail since Boston is so important to the history of the United States.
Besides its historical past, the Boston area is a vibrant hub of education, technology, and arts. I hope to share ideas on what you can see, do, and experience while you are in the Boston area. The city is very walkable; the oldest parts of the old town are very compact, but the green spaces and parks provide a place to stop and relax. I hope to give you this “go-to” guide for your extraordinary visit to one of America’s iconic cities, Boston.
Read more: The Ultimate 2 Day Boston Itinerary (A Local’s Guide)Disclosure: This post contains affiliate links. This means that if you make a purchase or booking, I may receive a small commission at no additional cost to you.Travels of Sarah Fay is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to amazon.com and affiliated sites at no cost to you.
A Brief History of Boston
Boston is a city of 621 thousand, but with the metro area encompassing close to 4.4 million people in 2024. It is one of the top 10 metro areas in the USA. While it’s large and well known, it is one of the oldest cities in the USA, established by the Puritan settlers in 1630. It quickly became a center of political, social, and economic significance. It played a crucial role in the American Revolution, with events like the Boston Massacre and the Boston Tea Party. These were some of the stepping stones to America’s independence. (See Boston’s Freedom Trail below)
Over the years, the Boston area has grown with phenomenal educational institutions like Harvard, MIT, Boston University, Tufts, Boston College and so many more. There have been many innovations from great institutions and companies that have a strong historical background and are still so highly regarded.
Boston also has so many unique neighborhoods that contribute to the diversity you’ll experience in the city. Some neighborhoods include Beacon Hill, Back Bay, China Town, the Historic North End with its Italian community, “Southie” and its Irish roots, to even newer developed areas like the Seaport. Boston with its historic roots has continued to evolve with changes over the years and is a “must-see” premier city to visit. Having lived here and grown up going to Boston’s many attractions, I know you can’t go to them all, but this 2-Day Boston itinerary will certainly give you some great ideas to make this your best Boston trip.
Boston Weather
Boston is a great “4 season city”, with hot summers and cold winters and it can be wonderful no matter when you visit. Summers are so popular in Boston since it is a very walkable city, it is on the waterfront and kids are on summer vacation. But the fall’s Leaf Peeping Season is also popular. No matter what time of year I would make sure you have layers of clothes since the temperature can be fickle and change during the day. No matter what season, there is always something to do in Boston. Also remember that certain activities like sports teams, whale watching, the Boston Pops, etc. are seasonal, so check schedules. Here are the typical seasonal temperatures:
- Spring (March to May): Spring has mild weather 45F to 65F with occasional rain showers are common (you know, April showers bring May flowers…).
- Summer (June to August): Summer is warm to hot with temps ranging from 70F to 85F, but if there is humidity, it can make it feel hotter.
- Fall (September to November): Fall is crisp and cool with temps from 55F to 70F. Fall foliage is in October and a beautiful time to visit.
- Winter (December to February): Winters in Boston can be very cold with temps of 25F to 40F. Snow is common in January and February. Just take that into account for your wardrobe and flights, if any. But winter also has sports like basketball, hockey, skiing not far away, or skating on the Frog Pond in Common Park.
Best Time to Visit Boston
The most popular time to visit Boston is the summer! There is just so much to do indoors like museums, etc. to the outdoors, like the waterfront, walks in the parks, beaches, etc. But you may consider the shoulder season in late spring (May and June) to early Fall (September and October). During the shoulder season, the weather is more pleasant and you can walk around various neighborhoods more without intense cold or heat. It is likely less crowded vs the summer season (I like shoulder season).
How to get to Boston
You can get to Boston by driving, flying, and taking a train or bus as noted below. The major highways are I-95, I-93, and I-90. Logan Airport is the primary airport, but I have often used Amtrak to travel to Boston. The main train station is Boston’s South Station which has both trains, MBTA, and buses. Boston is 3-4 hours from New York City, 1 hour to Providence, RI, and 2 hours to Portland, Maine.
- Boston Logan International Airport (Code- BOS) – The primary airport is Boston’s Logan Airport, but T.F. Green International Airport (Code PVD) near Providence, RI is an alternative and then drive. Another option is to fly into Manchester-Boston Regional Airport (Code MHT) in New Hampshire and drive into Boston.
- Roads – The main highways are above, but there are many local routes, should you be in traffic like Mass. Highway 28, which even heads out to Cape Cod, Route 6 on Cape Cod, and southern Mass/RI. Rt.24 connects to Brocton and New Bedford, MA, and stretches to Newport, RI. Highway I-90 the Massachusetts Turnpike is a toll road connecting Boston to the western MA and into New York (basically a main route from East to Western Mass.).
- Train – Amtrak does have trains that leave out of South Station for points south, like NYC, DC, Florida, etc., and some north, like Portland, Maine.
- Bus – There are bus services to Boston such as Greyhound, Peter Pan, etc. with connections to many cities including, NYC, Maine, New Hampshire, Vermont, Rhode Island, etc.
How to get around Boston?
Boston is one of the most walkable cities in the US per the recent USA Today. It is very historic and the blocks are more compact, streets (especially Beacon Hill) can be narrow or not all neatly in a row. Some of the top spots and museums to visit
- Bikes / Scooters / Rental Cars: The city also has many e-bikes and great bike paths to make it easier to get around. There are quite a few bikes in the summer (or scouters). Another great service if you want to walk but need a car for the day is www.Kyte.com. Kyte brings the rental car to you. They will even pick it up from your hotel, as long as you are near public transport (that is how they get back). I used it recently and it worked well and the cars are newer models.
Bikes are another option. Many use the Blue Bikes (www.bluebikes.com) located throughout town. They have day passes or shorter rides with 2-hour limits. The prices vary on the type but are affordable. Boston also has good bike paths too.
- Walking: Depending on where you are staying, you may be able to walk around part of the city, depending on your interests. It is a very walkable city. Some will take a mixture of public transport, and rideshare part of the way, depending on traffic and cost.
- Public Transportation: Public transport is provided by the MBTA (Massachusetts Department of Transportation www.MBTA.com), with the local subway being called the “T”. Sometimes if a line is closed temporarily, say for a sports game, etc. they will provide a bus for that route. You may want to check the MBTA site. The MBTA also provides buses, subway, and ferry services to Eastern Mass and parts of Rhode Island. In the summer there are low-cost water taxis that will take you to various parts of Boston Harbor, like the Seaport area, casino, etc.
- Uber / Lyft: Both ride services are available in Boston and are quite popular. During rush hours, etc. you may experience surge pricing.
Day 1 of 2-Day Itinerary in Boston
Breakfast, Cafes, and Coffee Shops in Boston – On the first day you need to start strong by having a good breakfast since you may be walking, especially the Freedom Trail. Now some of you may have breakfast already at your hotel or home, but here are some suggestions for a great breakfast or cafe that can keep you caffeinated. One quick way to get more packed in is to get a coffee and walk through Boston Common and see the State House, both on the Freedom Trail.
Breakfast
North Street Grille (in the North End) www.bestbrunchboston.com voted one of the best brunches.
South Street Diner (near South Station) www.southstreetdiner.com The diner was built in 1947 and is open 24 hours a day.
Milkweed 1508 Tremont Street www.eatatmilkweed.com They have a great breakfast selection. It’s located not too far from the hospitals and the Museum of Fine Arts.
The Friendly Toast (Back Bay area) www.thefriendlytoast.com another great place with tasty dishes.
South End Buttery www.southendbuttery.com on Shawmut Avenue. This is another option. Check out their website since they also offer brunches on certain days.
Best Boston Cafes
Depending on where you are staying or if you need a midday pick-me-up, you can grab a coffee or latte along the way.
- Thinking Cup www.thinkingcup.com They serve Stumptown Coffee from Portland Oregon I recently visited, a great tasting roast. It’s a popular place with Locations in the North End (Hanover Street), Boston Commons (Tremont Street), and Back Bay (Newbury Street).
- Tatte Bakery & Cafe www.tattebakery.com A very awesome aesthetic; it is located throughout Boston. This is a great place to have coffee, lattes, tasty pastries, etc. In historic Beacon Hill, they have a location on Charles Street. Their Seaport location also has a dinner menu.
- George Howell Coffee (Downtown) www.georgehowellcoffee.com located in the Boston Public Market and within The Godfrey Hotel at Downtown Crossing would likely be their closest locations.
- Note: Mini Cider Donuts – If you go to the Boston Public Market say you are on the Freedom Trail, maybe stop at the Red Apple Farm booth to get their Mini Cider Donuts. I love them and they are made to order so they are warm and “soooo” tasty (especially with your coffee).red-apple-farm
- Beacon Hill Books and Cafe is located on one of my favorite streets in Boston in the Back Bay- Charles Street. This is a perfect place for a girls day out for brunch or afternoon tea. It is also a cute multilevel book store. Definitely worth a trip!
- Dunkin’ Donut (www.dunkindonuts.com) Trying local cafes but well I am sure you saw ads about Dunkin’ Donuts or at least one location on your trip. They have coffee, donuts, and breakfast sandwiches at reasonable prices. And, technically, it is local in a way. It was founded in the nearby suburb of Quincy, MA (home of the 2nd and 6th US Presidents John Adams and John Quincy Adams). Plus I figure you have seen the Super Bowl “DunKing” commercial with Ben Affleck and Matt Damon taking on Tom Brady. I always loved my Dunkin’ and their donuts.
Boston Freedom Trail.
One of the best ways to see Boston on the first day is to take either a tour of the city on a Hop-On Hop-Off Bus or a walking tour. But if you have less time or want to save a few dollars, is to walk the Freedom Trail. The self-guided tour will bring you to many historic places during the American Revolution. Several of these options are noted below. But with great weather outside many like to walk the trail, which is about 2.5 miles through the center of Boston.
Freedom Trail Tours
The Freedom Trail: The Freedom Trail goes to 16 historic sites around Downtown, the North End, Charlestown, etc. like The Old North Church, Faneuil Hall, etc. They take you through many of the sites involved with the American Revolution. Notably, the walk sounds long, but it is only 2.5 miles long and ends at the USS Constitution.
The walk itself is free if you do it on your own, but some of the places like the museums associated may have a cost. For instance, you walk by Paul Revere’s house in the North End, you can see it without paying to go in. The walk takes about 90 minutes and you can always go back to some of the spots that interest you. Some like the statue of Paul Revere don’t cost a thing. You can go on a professional tour or there are also online guides you can get. If you want to take the official Walk into History tour of the trail. You can buy tickets online here: www.thefreedomtrail.org
The official trail starts at the Boston Common Visitor Information Center at 139 Tremont Street. The actual Trail is outlined on the sidewalk as you pass by the 16 Trail stops. The official tour prices start at $17 for adults and lower for students, etc.
Self-Guided Option
Another option is to download the self-guided audio tour from the National Park Service www.nps.gov It is free.
Boston’s Self-Guided Freedom Trail
Boston Freedom Trail was designated in 1951 and is a red brick path on the City of Boston’s sidewalks that will lead you to the Trail’s 16 historic sites. It’s a great collection of historic museums, churches, meeting houses, burial grounds, history markers, parks, etc. from the American Revolution era. The Trail goes through Downtown Boston, the North End, and Charlestown. It winds through these areas, which are some of the oldest neighborhoods of Boston. Some are just plaques so you can do this trail in a reasonable time or come back and see a site you especially like. The trail is 2.5 miles and very walkable.
Boston Common: (Free)
I would start in the “Common” as they call it, it’s the heart of many Bostontian’s activities. You can stop and get a coffee and have a quick walk through the park and enjoy your coffee or pastry (maybe at Tatte Bakery on Charles Street). This is the USA’s first park, which was established in 1634. You will see the Frog Pond in the park (which has ice skating in the winter). This is the hub of the city! Next, you head toward the corner to see the Boston State House.
While you are there you may want to stroll through Boston Public Garden across the street. This was the nation’s first public botanical garden in the US and dates back to 1837. It is more decorative and flowery, with a Victorian flair. There are 80+ plant species and the famous Swan Boats you can rent in the warmer months. This garden is also a National Landmark www.nps.gov
Acorn Street
When you are in the area of Beacon Hill do not miss taking a photo on the famous Acorn Street!
Boston State House: (Free)
The beautiful gold-domed state house dates back to 1798 and serves as Massachusetts seat of government. It is free to go inside and they offer free building tours. Info on scheduling a tour: State House Tours
Park Street Church: (Free)
The church was constructed on the corner of Park and Tremont Streets in 1809. It was a great beacon in the city and became one of Boston’s first landmarks. As you look back up the street seeing the view of the Common and Statehouse it looks awesome. (Before the church, this was the site of the city’s first granary buildings.) This is an operating church with services so keep that in mind. www.parkstreet.org
Granary Burying Ground: (Free)
This historic burial ground was established in 1660 Tremont Street on the Freedom Trail has 2,345 markers/headstones (although there are likely over 5,000 buried here). It’s the nation’s 2nd burying ground.
This is where Revolutionary figures like Paul Revere, John Hancock, and the Boston Massacre victims are buried. You can learn more about them as you walk the trail. Some places like this stop can be a short visit or maybe you try to find the exact historic graves. Granary Burying Ground (U.S. National Park Service
King’s Chapel
Close by the Granary is King’s Chapel from 1749 and the King’s Chapel Burying Ground, also on the Trail. It dates back to 1686 and this is the first Anglican Church in Boston. This is the first English burial ground. Notably, the Chapel’s interior is a great example of the Georgian church. However, many church followers came from England or Nova Scotia in 1776 and were the Loyalist opposition. You can learn more at www.kings-chapel.org There is a $5 admission; there is also a guided tour for $8-10 for the church.
The burial ground is free to enter and is managed by the city. John Winthrop, the first Governor of Massachusetts, and Mary Chilton, the first woman on the Mayflower, are buried here, as are many other original settlers to the area. There is a unique skull and crossbones headstone you may want to check out, it is a great example.
Boston Latin School Plaque
This school was founded in 1635 on this spot on the Trail. Benjamin Franklin was one of its famous students. The school provided education for males of any income level. While the school is no longer in this location, there is a mosaic and statue of Mr. Franklin here commemorating it. (Notably, Matt Damon and Ben Affleck also are more recent grads from the school.)
Old Corner Bookstore
As you walk on the Freedom Trail, it will take you by the Old Corner Bookstore which was constructed in 1718 and is the first commercial building in Boston. While now it houses other retail spaces (to save it from demolition in 1960), it once housed the 19th-century publisher Ticknor and Fields. They published various works by famous authors such as Thoreau, Longfellow, Hawthorne, etc., as well as the Atlantic Monthly.It’s located at 238 Washington Street and School Street. https://www.nps.gov/places/old-corner-bookstore.htm
Note: Across the street from the bookstore, there is a sculpture of the Boston Irish Famine Memorial. Many Irish settled in Boston during and after the famine that occurred in Ireland from 1845 to 1852.
Old South Meeting House
Located on Washington Street, this is the famous meeting house where many Bostonians met to challenge the British policies that led to the Boston Tea Party on December 16, 1773. Over 5,000 colonists met here to dispute the taxes on tea. The building itself was constructed in 1729. Admission is $15 for adults, students/seniors $14, and $8 for under 12. Also if you buy this ticket it will cover the Old State House as well. Old South Meeting House | The Freedom Trail
Old State House – Boston National Historical Park
It was built in 1713. In the 1700’s the old state house was the seat of colonial power and later after independence, the state government. (The new State House is now across from Boston Common). This was also the site of the Boston Massacre in 1770 and this is where the 1st bloodshed of the American Revolution occurred.
Then on July 18, 1776, this location was the first place the Declaration of Independence was read to the public from the balcony. It costs $15, etc. to go in to see it, but that also covers you if you go into the Old South Meeting House.
Old State House – Boston National Historical Park (U.S. National Park Service)
Other Tours To Do In Boston
Hop-On Hop-Off Tours: All can be purchased at www.getyourguide.com
Old Town Trolley Tour: Another great way to see a new city is the all-day Hop-On Hop-Off tour. This may make it a little easier. Sometimes, I have taken the trip all the way around and then go back around and get off at the stops that interest me the most. The prices start at $52 for a day. But you can buy a 2-day pass too.
Hop-On Hop-Off Double Decker Bus Tour: This is another option. I know some like the open-air top deck. The prices are similar and start at $52.
Boston Duck Tour: Another popular tour in Boston is the Duck Tour in amphibious vehicles. You get the bonus of the Charles River on this tour. It’s an 80-minute tour of the city with the “ConDUCtors” narrating along the way. They will “quack” you up. The cost is $52.99 and lower for military, seniors, and kids. Kids under 3 are $10.99. This may be a good option if you have kids.
Food Tour: There are numerous Boston food tours that include seafood given the ocean is at Boston’s door while walking by some of the great stops on the Trail vehicle getting fantastic food along the way. There is even one tour just for pizza, given the strong Italian influence of the Italian North End. Boston Pizza Tours offers great pizza and other food tours. I even went on their “Boston Seafood Lovers Tours” with www.getyourguide.com even though I know the city well. This is a great way to try different restaurants on the Freedom Trail. The tour is 2.5 hours so you can build into your schedule. They also offer a Historic Boston Tavern Tour (I don’t drink, but love seafood).
Walking Tours: There are various types of walking tours as well. Some even have folks dressed in Colonial costumes, you will see them in Boston Common quite often. Some tours also go over to areas like Harvard, etc., including Pub Crawls, etc. there is something for everyone. Again, they can be found on www.GetYourGuide.com and if you have kids, they may enjoy those dressed in costume.
Lunch / Snack Intermission Day 1 in Boston
At this point, if you stop for food you may want to eat in Quincy Market or wait for the tasty Italian North End section of the trail (unless you want that for dinner).
North End Boston – The north end, with the heart being Hanover Street, is the hub for the Italian-Americans in the city. It’s just a hop, skip, and a jump from downtown. While it was once the neighborhood for those moving to the USA from abroad, it’s primarily now Italians and has many restaurants, especially along Hanover Street. There are many great places to try whatever your budget.
The most recent restaurant I ate at was Bencotto‘s, it was great and in the summer the glass windows are open to the street. Others include Strega, Carmelina’s, Giacomo’s, and Bacco (Bacco’s off the side street and I like their weekday happy hour). Some restaurants are smaller like The Daily Catch North End and some only take cash (so be prepared). You can’t go wrong in this neighborhood.
Affordable Budget Restaurants in the North End: There are some other places where you can have great sandwiches, subs, pizza by the slice, etc., at great prices. Some choices are:
- Monica’s Mercato at 130 Salem Street a block off Hanover Street: Monica’s sandwiches (called subs) are the best! I often go there to get one to bring to the airport if I’m heading out of town. I love the Italian sub with their fresh meats and breads, etc. You can also get one if you plan a picnic and they offer many other tasty treats to bring home or to your hotel for a great meal. www.monicasnorthend.com
- Bricco Panetteria: Located at 11 Board Alley, it is right behind 241 Hanover. It too is a great place for a chicken parmesan sandwich, pasta, etc. Bricco Panetteria in Boston MA
- Galleria Umberto: (Most Affordable) This place has counter service with great Italian favorites like legendary Sicilian pizza (square slices), Sicilian arancini, calzones, etc. all at super reasonable prices. But beware, they open until they sell out say 2-3 pm, and only accept cash (there are ATMs on Hanover Street).
They do have tables you can sit at, but this is an “old time” place that looks like it dates back to the 1950s and you will see many locals getting food here. I have been here too many times to say, especially while I was in college. It’s great for a quick snack or lunch. It’s located at 289 Hanover Street and they have a Facebook page.
Boston Sail Loft: If you only want a great snack or if you are in search of a great cup of Boston “Chowda”, try the Sail Loft. I recently had a bowl of their famous chowder (they have cups too) with the famous oyster crackers. It was so creamy and tasty; you can have a cup for under $10. They are a little more off the beaten path of Hanover Street, but it’s so good. www.thebostonsailloft.com
Cafes and Bakeries in the North End of Boston
There are many cafes in Boston’s North End, some are Italian with the latest football (soccer) game on with folks sipping on the espresso, or having a great cannoli. Some of my favorites are on Hanover Street.
- Caffe Vittoria is Boston’s first cafe, folks like Pacino, etc. have been here and it opened in 1929.
- Mike’s Pastry is a long-time favorite bakery, they do not have tables since they are very busy! People come largely for their cannoli. They also have other locations in Boston, but the original is the one in the North End. You can compare it with Modern Bakery across the street.
- Modern Bakery does have seats inside and you can even go downstairs to the bar. They have cannoli and some delicious other bakery items. They have reasonably priced cup cakes
- Bova’s Bakery, next to Monica’s Mercato off Salem Street, is another North End favorite. It has been there since 1932 and has pastries, breads, cookies, sandwiches, etc. It is a favorite “to-go” spot for a great snack and is open 24 hours. There are just so many great places selling all kinds of espresso drinks. You will see locals sipping on them while talking and enjoying the day.
Other popular ones in this area are Caffe Paradiso and Thinking Cup, although Thinking Cup is a more modern type cafe and is located throughout Boston. These two are also on Hanover Street.
Back to the Freedom Trail
After lunch, you may want to finish up the Freedom Trail unless you have another type of tour or event (or game/museum) and leave this portion to the 2nd day.
Faneuil Hall – (Free)
A little further down the road, a popular stop on the Trail is Faneuil Hall, the first meeting place in Boston and often called the Cradle of Liberty. It’s great to see the 2nd-floor meeting room. On the first floor, the National Park Service www.nps.gov has many brochures of the historic past. At one time this building was sadly part of slavery history and you can learn more about that past here. This building’s 1st floor also has gift shops, souvenirs, etc. Faneuil Hall – Boston National Historical Park (U.S. National Park Service)
Quincy Market – (Free)
Across from Faneuil Hall is www.Quincy-Market.com, it was built in 1826. Local merchants had outgrown the market space at Faneuil Hall and they needed more space. It is now a food hall with many food stalls serving great fare. You will notice between the two buildings and along the sides, there are many street performers entertaining the people passing by. This is a great place to grab a bite or snack.
Boston Public Market: (Free, not on the Trail)
This is like an indoor farmers market, this newer food hall has some great food options too. It is just down the street from Quincy Market www.bostonpublicmarket.org
Boston Haymarket – (No charge to enter)
As you come out of the markets Haymarket is the local farmer’s market dating back to 1820. It is only open Friday and Saturday. It’s an open-air market on Blackstone Street, between Hanover Street and North Street. They sell fresh produce, fruits, vegetables, etc. www.haymarketboston.org
Paul Revere House
Continuing along the Trail, you get to Paul Revere’s House in the North End of Boston. It is the oldest remaining residence in Boston. Depending on your time you can either see the outside of the home without an admission fee, or take the self-guided tour of the inside for a fee. Paul Revere was a silversmith, but more importantly, he was one of the Midnight Riders of April 18th, 1775 which indicated the British were coming. It is generally open 10 am-5 pm and closed January through March. I would check the schedule online in case it changes. The cost to go in is $6/person and you can tour the 4 rooms. It takes 15-25 minutes. www.paulreverehouse.org
Note: You have now crossed from Downtown to the North End. The North End is the oldest residential neighborhood with very narrow streets dating to the 1630s. Originally the Puritans were here followed by various group, including the Irish, Jewish, etc., and most recently the Italians starting in the early 1930’s. You will now see this area with its many streets with the primary street being Hanover Street, with its many restaurants, bakeries, shops, etc. It is a great place for dinner or a snack after your trail tour (see Restaurants above).
Old North Church
The Old North Church was established in 1723 and it’s where Paul Revere and one other man started their famous “midnight ride”. Paul Revere asked 3 other Boston Patriots to watch the British troop movement and hang lanterns in the steeple to send the patriot militia a warning if the British were coming. The “One if By Land and Two if by Sea”, means if the British were coming on the Charles River by boat hang 2 lanterns, or one lantern if they were using land.
Two lanterns were hung, thus Paul Revere and 2 others began their journey to Lexington and Concord (you know, that is where the first shot heard “around the world” occurred, but that’s a story for another day). Old North Church is a national landmark and can be seen by Salem Street, but you can see it also near the famous Paul Revere Statue on the Trail. General admission $5 self-guided and see the site for other tours available (including the crypt). www.oldnorth.com and Paul Revere Monument
Copp’s Hill Burying Ground – (Free)
This is the last burial ground on the Trail and contains over 10,000 burials and is the 2nd oldest burying ground in Boston, founded in 1659. It is set up on a hill where a windmill once stood. Robert Newman, one of the men who held the lanterns in the Old North Church is buried here, as are other artisans, craftsmen, etc. from the North End. Reportedly many free African Americans are reported to be buried in the Potter’s Field section of the grounds just off the Charter Street side of the grounds. Copp’s Hill Burying Ground | The Freedom Trail
USS Constitution and USS Constitution Museum
The next section is across the North Washington Street Bridge and is an easy walk into Charlestown, to see the USS Constitution launched in 1797. It is the oldest commissioned warship in the US. It was in many battles including the War of 1812 and is nicknamed “Old Ironside”. The ship is owned by the US Navy and there is no fee to go on when opened; it is only open Wed-Sunday from 10 am to 4 pm. This is great especially if you have kids. USS CONSTITUTION
The USS Constitution Museum provides information on the ship’s history and is open daily from 9 am-6 pm. The fee is donation-based, with a recommended amount of $5-$15. www.ussconstitutionmuseum.org
Bunker Hill Monument and Bunker Hill Museum: (Free)
This is the final stop on the Trail. On June 17th, 1775, this is the hill where the first pitched battle between British troops and the Patriot soldiers took place. It was called the Battle of Bunker Hill. This spot is commemorated with a 221-foot obelisk made of granite and has 294 steps to the top. It is free but closed on Monday and Tuesday. Only 20 people can go in at any time to climb it. Bunker Hill – Boston National Historical Park (U.S. National Park Service)
Day 1 Dinner:
Dinner is great in the Italian North End otherwise two great options for dinner or things to do after all that walking include:
The View at Prudential Center (“Pru”)- The View encompasses the top 3 floors of the Prudential Center’s 52-floor building in the historic Boston Back Bay, not far from Boston Commons. It offers stunning 360-degree views of the city. I loved going to the large inside and outside observation decks to see the sunset. There are interactive displays that provide information on Boston. https://viewboston.com/ General admission is $10.
After taking in the sights on the observation floors and seeing the sunset, we had dinner in The Beacon Bistro restaurant with its awesome views. They also have a great bar called Stratus; offering the highest rooftop bar with great city views. If you plan to eat there, I suggest making reservations, but I loved the food! The Beacon is a premier restaurant, but for a lower budget option, there is the Eataly Boston on the first floor of the Prudential. It has various Italian food options, including to-go items and foods to prepare at home. I love exploring the choices there. Eataly Boston: restaurants and private dining
Joe’s on Newbury– If you are looking for an American favorite, Joe’s on Newbury www.joesonnewbury.com is another great dinner option for traditional American fare, like a massive hamburger. It’s on Newbury Street, close to the Prudential. You will also see some great shopping on Newbury Street or in the Prudential Center.
Union Oyster House– One last spot I’ll mention if you want one of the oldest restaurants in Boston is Union Oyster House near Quincy Market. It has traditional American foods including oysters, chowder, etc. in the original 1826 building (41 Union Street). I’ve been here many times and love it. www.unionoysterhouse.com
What to do at night in Boston?
Tour or see a game at Boston Fenway Park This is the oldest baseball park in the country and I find it reasonable. I recently went to a game and preferred a covered seat. Some loving baseball may like the Tour of Fenway Park. I have known some that have done that, it’s a great option especially if there is no game. I love the “Green Monster”. www.getyourguide.com for tour and www.mlb.com for tickets. Notably the tour is one hour and you arrive 15 minutes prior to your time.
Tour or see a game at TD Garden– This is the home of the Boston Celtics and the Boston Bruins (hockey). www.TDGarden.com The tour is 1-1.5 hours. I haven’t taken the tour, but I have seen basketball games at the Garden.
Theater District– One must not forget that Boston has a great theater district as well www.boston-theater.com You can check the various shows in the area. There are also food options near it and it’s close to Boston’s Chinatown.
Boston Pops or Boston Symphony Orchestra– Another great show option is the Boston Pops or the BSO. You may have seen the Pops on PBS or Boston’s 4th of July show. I loved going here, of course, you would have to be there when in season. www.bso.org
Day 2 Itinerary of Boston
Day 1 may have resulted in many steps taking you on a walking tour through historic Boston. Today you may want to tour a museum or two, depending on your preferences. You may also like to do something more thrilling, like going on a whale-watching tour. Below I broke down the options of Museums to see in Boston, a whale watching tour and this takes into account exploring more areas like the waterfront and the Seaport district.
Museum of Fine Arts (MFA) – www.mfa.org
The MFA is a great art museum located on Huntington Avenue. Tickets are $27 for adults, with various discounts on certain days or kids, etc. per the website. There are also some $5 after 5 days on certain Thursdays. I have been to the MFA many times through the years and love it. There is also a gift store and restaurant in the museum. Founded in 1870, this is the 20th largest museum in the world. There are over 8,000 paintings including works from Gaugin, Rembrandt, Degas, Sargent, and others. It’s a “must-see” for art lovers.
Isabella Stewart Gardner Museum – www.gardnermuseum.org
Admission is $20 for adults, $13 for students, and free to kids under 17. Lite bites, coffee, etc. are available in Cafe G while you visit the museum. The art museum houses significant European, Asian, and American art and was founded in 1903. Isabella Gardner wanted her museum to encourage education of the arts and give the public access to see such lovely arts, tapestries, sculptures, etc. Besides the art, it has a beautiful courtyard that houses seasonal flowers and plants that is a favorite of photographers. Note that it is closed on Tuesdays. It is located on Evans Way, near the MFA.
The Great Art Robbery– largest heist in history: In 1990, 13 art pieces worth over $500 million were stolen from the museum and the robbery was never solved. Just remember, this museum and others often have limits on the size of your bag or backpack, or have cloakrooms to house your jackets, etc.
Institute of Contemporary Art (ICA) – www.icaboston.org
The ICA was founded in 1936 but relocated to its new building in 2006 to the Seaport district on the waterfront. It houses contemporary art and exhibition spaces. The museum is closed on Mondays. Tickets cost are generally $20 and youth under 18 are free. Besides having exhibitions and galleries, they have unique seating areas inside and outside that overlook the waterfront. They also have a cafe with indoor/outdoor seating, so it’s a great way to see the ships sailing in the harbor. (Some Thursday nights are free after 5 pm; check the dates on their site.)
New England Aquarium
Another great waterfront attraction on Boston’s Central Wharf is the NE Aquarium which has been here for over 50 years. Ticket prices vary, $34 for adults and kids under 3 are free. In addition to having the exhibitions, there is a movie theater offering various movies including 3D, with the highest ticket price of $10. You also can buy combo tickets. Like many museums/attractions, they have timed tickets, so you may want to plan accordingly. They also have a Harbor View Cafe if you get hungry. It generally takes 2-2.5 hours depending on your style, but this is a great place especially if you have kids.
Whale Watching Catamaran Tour
Recently I enjoyed a great whale-watching tour via www.getyourguide.com. I truly loved it and boarded the tour on the wharf. You will also see some other harbor tours or sunset tours that are available. It was a great adventure and I highly recommend it. Not only can you see whales and dolphins, it is a great view of the Boston skyline from the water! The tour was 3.5 hours and tickets were from $79.87.
Boston Ghost and Graveyard Tour
To be honest this is the one thing I haven’t done, but may be an intriguing tour to take. I have taken this type of tour in other cities and countries, but having lived in Boston, I just wanted to be clear I haven’t been but heard it is a great option. It too can be booked via www.getyourguide.com Boston has an interesting long past, so I am sure there are some interesting colorful stories. The price last I checked was $47.20. There are also some age limits, no minors are allowed unaccompanied, etc. so kids may not be allowed. Just check when booking.
The FRIENDS Experience at The Central Perk
The Central Perk is the perfect cafe to experience if you are a Friends fan. It is located on Newbury Street where you can get a latte, food, etc. in a setting like the Friends TV show. I loved it and it’s quite cool for fans of the show. My latte was great, as was the food, and there is no cost for entry! Stop and have a latte with your friends. In full disclosure, I am a huge fan of the show!
John F. Kennedy Presidential Library and Museum
If you are a fan of Presidential libraries, you may want to go see JFK’s Library. It’s near UMass Boston. The cost is $18 or less (kids under 12 are free) and the website will show various discounts available. www.jfklibrary.org
Central Public Library at Copley Square
The Boston Public Library was established in 1848 and is the first free public library in the United States. You may say, why would I mention the library, well it has some magnificent artwork, architecture, and activities, from a public radio station to a Newsfeed snack bar and Map Room Tea Lounge. It’s an extraordinary building to see or have high tea in the lounge. Be sure to enter through the main historic entrance. Central Library in Copley Square | Boston Public Library
Also if you go out the entrance on Boylston Street, you may be able to see the line for the Boston Marathon. Also across from the Library is the Boston Marathon Survivor Memorial (at 755 Boylston). Three were killed and over 260 were injured in 2013. It was a tough period in Boston history, but as they say, you must be Boston Strong.
Boston For the Kids (Or for the Kid in You)
Growing up I had been to these museums many times (the Aquarium is one too):
- Boston Children’s Museum – in Seaport (www.bostonchildrensmuseum.org) This is the 2nd oldest children’s museum in the country.
- Boston Science Museum – can be for adults and kids. They also have great movies they offer, including IMAX, as well as their Planetarium. The museum is an icon, sitting on the Charles River. This is probably best for kids over 7 years old.
- Boston Tea Party Ship and Museum – off Congress Street and is a fun way to learn more about patriotic history.It’s the #1 Patriotic Attraction with the reenactment of the Boston Tea Party that started the American Revolution, with the “Sons of Liberty” in their patriotic costumes. There is also a museum you can visit. Plus you get to board an 18th-century ship to see more about life at sea. You may get to “dump the tea in the sea” too! The ticket prices are from $35 .
- Boston Duck Boat Tour – A fun way to see Boston for kids (or big kids) is on Boston Duck Tours Besides the land tour, you get to go on the Charles River via the WWII amphibious vehicle. I loved going on a Duck Boat! It’s an 80-minute tour and costs are about $58.
Restaurants in Boston on Day 2
Depending on what you want to schedule on day 2 in Boston, you may want to try some of the restaurants mentioned previously. But there are so many great places to try. Unless you are on an evening dinner cruise (www.getyourguide.com), you may want to explore the Boston’s Seaport District. This is one of the newest places with great restaurants.
Restaurants in Seaport District
One of the newest areas in Boston is the Seaport, where there is an amazing amount of restaurants to try, from some on the waterfront to rooftops. It’s also a great place to stroll along and see the various restaurants, stores, bars, etc.
- Legal Sea Food– One favorite is Legal Sea Foods – Harborside www.legalseafoods.com. I love the top roof deck where you can eat and have drinks while enjoying the harbor view. They also have inside and outdoor seating in their lower-level restaurant. I’ve been here many times and love the view when you can see the waterfront. Eating here is reasonably priced and you can enjoy the waterfront!
- Moxie’s– A newer place nearby is Moxies Boston Seaport Restaurant (www.moxies.com). Mark Wahlberg was there for an event when I went to eat there recently and the food was fantastic. It has outdoor and indoor seating and a second floor with a balcony. Besides the typical bar drinks, they also have some great mocktails!
- Strega Italiano Seaport– Another one of my favorites is Strega Italiano Seaport www.stregaitaliano.com. Strega’s first restaurant started in Boston’s North End, but expanded with this location in Seaport! This was a wonderful experience with great food in this stunning restaurant (and the staff was awesome too).
Seaport has many popular restaurants including Ocean Prime, Morton’s Steakhouse, Del Frisco’s, etc. In the center of Seaport’s rows of restaurants and towers, you will see the seasonal Cisco Brewers Seaport Craft Beer Market (www.ciscobrewers.com), with food carts, craft beer, entertainment, etc. Cisco originated on Nantucket Island if you aren’t familiar with it. Further down near the industrial area you also may see Harpoon Brewery (www.harpoonbrewery.com); I love their pretzels.
A lower key place to eat in Seaport is Tatte Bakery with its’ “elegant comfort food” (www.tattebakery.com). They have several cafe locations throughout Boston, including one on Charles Street, but the Seaport location also has more of an elevated menu for dinner/meals. I was there recently and really enjoyed the vibe of Tatte.
3 Days in Boston Itinerary
If you are in Boston for 3 days or a long holiday weekend, you can certainly find tours and things to do in Boston on the lists above. Perhaps you can try some longer tours, more food, etc.
Day Trips from Boston
You may want to consider a day trip from Boston if you have the time. Below I have listed some great ideas for day trips from Boston.
- Best Day Trips From Boston, Massachusetts
- Cape Cod Travel Guide: A New England Summer Escape
- The Berkshires An Ultimate Guide to the Shire
- Things To Do In Plymouth Massachusetts – A Perfect Day or Weekend Trip From Boston
- For those that have more time: The Perfect 4 Day Boston to Maine Roadtrip
Hop-On Hop-Off Tours: All can be purchased at www.getyourguide.com
Old Town Trolley Tour: Another great way to see a new city is the all-day Hop-On Hop-Off tour. This may make it a little easier. Sometimes, I have taken the trip all the way around and then go back around and get off at the stops that interest me the most. The prices start at $52 for a day. But you can buy a 2-day pass too.
Boston Duck Tour: Another popular tour in Boston is the Duck Tour in amphibious vehicles. You get the bonus of the Charles River on this tour. It’s an 80-minute tour of the city with the “ConDUCtors” narrating along the way. They will “quack” you up. The cost is $52.99 and lower for military, seniors, and kids. Kids under 3 are $10.99. This may be a good option if you have kids.
Food Tour: There are numerous Boston food tours that include seafood given the ocean is at Boston’s door while walking by some of the great stops on the Trail vehicle getting fantastic food along the way. There is even one tour just for pizza, given the strong Italian influence of the Italian North End. Boston Pizza Tours offers great pizza and other food tours www.bostonpizzatours.com I even went on their “Boston Seafood Lovers Tours” with www.getyourguide.com even though I know the city well. This is a great way to try different restaurants on the Freedom Trail. The tour is 2.5 hours so you can build into your schedule. They also offer a Historic Boston Tavern Tour (I don’t drink, but love seafood).
Walking Tours: There are various types of walking tours as well. Some even have folks dressed in Colonial costumes, you will see them in Boston Common quite often. Some tours also go over to areas like Harvard, etc., including Pub Crawls, etc. there is something for everyone. Again, they can be found on www.GetYourGuide.com and if you have kids, they may enjoy those dressed in costume.
Boston – “A Must See”
Boston is truly a “must-see” city. While I have lived and worked in Boston, it was hard to limit choices to the above, since there are so many things to do in Boston. Boston is a city steeped in history (and tea), culture, and culinary delights, offering visitors a unique blend of old-world charm and modern innovation. Whether you are exploring its revolutionary past as you walk the Freedom Trail, savor the fresh seafood at iconic eateries, or soak in the vibrant art scene and parks, Boston promises an unforgettable experience. Plan your trip during your optimal season and don’t miss out on the city’s diverse attractions, museums, historical spots, and dining options. With this ultimate itinerary from a local traveler, you are ready to embark on a memorable journey through Boston, the heart of New England. Remember, Enjoy the Journey!
Hotels in Boston – In case you need a place to stay!!
Boston has many great hotels being a popular destination with hotels, inns, and AirBnBs for all budgets. You will find a limited number of hostels if you are on a budget. Many can be found at www.booking.com Depending on how many days you stay in Boston, you may want to stay central to the action, like Downtown Boston, Beacon Hill, Back Bay, North End, or the Seaport area of Boston. I have gone many times over the years and stayed in various hotels, including the W (www.marriott.com), the historic Omni Parker House (www.omnihotels.com), Hampton Inn in Cambridge, 2 Doubletrees including the one near the JFK Library, Homewood Suites in Brookline.
There are several on the waterfront and wharf area, and now there are many new hotels in the Seaport district. I have stayed in various ones depending on what I planned on doing while in town. Boston can be quite pricey, but I suggest making reservations as soon as you know your dates since the city is in high demand.
Budget Accommodations in Boston: If on a budget, the HI Boston Hostel is well located near Chinatown, the Theater District, Boston Common, and South Station. It too can sell out since there are only a few hostels, but this one is part of a large organization and is modern, and eco-friendly, with dorms and private rooms. www.hiusa.org or make the reservation on www.booking.com to compare rates.
Is Boston Safe?
Yes, I felt safe traveling around the area. Boston is ranked 13th in America for being the safest place to live. I feel safe as a solo traveler and solo woman traveler, throughout the years of traveling and living in Boston. As in any large city, be careful at night or if you have bags in the car while parked, etc.
Fun Facts about Boston Massachusetts
-The Fig Newton, one of my favorite cookies, was named after Newton, a suburb of Boston
-Boston built some of the “firsts” in the nation, the one that lives on today is the first subway line. Boston had the first one in the nation; built in 1897 known as the Tremont Street Subway. It was the 3rd in the world to use electric traction. The “T” still is in use.
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Sarah Errafay
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