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One of the most famous historical cities of the United States, Boston offers fantastic sites to explore and places to eat! After living on the outskirts of this city, and sometimes commuting in for work for the past decade, I’ve discovered many of charms to share and have plenty of ideas of what to do in Boston! Depending on the time of year you visit there are numerous seasonal outdoor and year-round indoor activities to enjoy. I hope you don’t overlook Boston, Massachusetts when planning your next trip!

Note: This post contains affiliate links. Although you won’t pay any more, FTB will make a small commission from any tours you book through the links.

What to do in Boston

Boston was one of the hotbeds for the American Revolution, for those of you that don’t know. Famous events such as for events such as the Boston Massacre, Paul Revere’s Midnight Ride and the Boston Tea Party to name a few are still preserved for you to visit to this day. Even if you’re not a history buff, there’s something for everyone as the city is rich with sports, culture, and modern attractions you can explore as well! Several of my friends have visited me in Boston and I’ve served as their local guide. Here are some of my top recommendations. In the brackets, I indicate the closest subway stop for your reference to each location, which you can find more information under “Getting Around in Boston”.

Skywalk Observatory

As a Bostonian, I actually hadn’t discovered this obvious attraction until one of my friends visited. For the best 360° view of the city (if you don’t know someone who works in 200 Claredon formerly John Hancock Tower), you can ascend to the 52nd floor of the Prudential Tower. Not only does Skywalk Observatory [Prudential E, Hynes, Copley, ] spectacular view, they also offer a self-guided audio tour with numerous interactive exhibits helping you discover the city’s rich history! I loved learning about all of the different immigrants that moved here to develop Boston’s well-known neighborhoods. They have short movies and an interactive quiz show game to determine if you could answer any of the questions for U.S. Citizenship.

Skywalk Prudential Tower View

Skywalk Prudential Tower View

I’d recommend checking beforehand with them on the day which you wish to visit to make sure that they do not have the time slot blocked off for an event. Sadly when I visited there was one corner reserved for a party so we missed a section of the view!  It’s also the perfect location to watch the sunset at night.

Boston Common (Free)

One of the best places to start is by visiting America’s oldest park, Boston Common [Boylston or Park St.], which is also conveniently located in Downtown. This park has a deep history as evidenced by all of the statues and monuments throughout. It was unfortunately also one of the sites for numerous witch trials. There groups that offer guided ghost tours you can schedule, which conveniently originated by the burial site in the Common. During the winter when the Frog Pond freezes over many people love ice skating in the park. During the summer this is also a popular site for pop-up concerts and events. The Common is directly next to the Massachusetts State House on the and charming Beacon Hill neighborhood. In addition, you’ll be happy to know that the Common is just adjacent to the Public Garden!

Public Garden (Free)

For more floral features we stroll across to the Public Garden [Arlington], which is also America’s first public botanical garden. During the warmer seasons, visitors are welcomed with colorful flowers and trees. The Make Way for Duckling statues inspired by the popular children’s book set in Boston is quite popular. The statues are often decorated for notable sports milestones. My favorite activity is taking a short and relaxing ride on one of the swan boats! Mid-April through Labor Day they offer rides to the public for a nominal fee. The boat takes you under the bridge for a ~ 15-minute ride on the pond where you can view the Swans and Ducks.

Boston Public Garden Swan Boat

Boston Public Garden Swan Boat

Freedom Trail Guided or Self-Guided

The 2.5-mile trail is marked by a red line and 16 stops from Boston Common to the Bunker Hill Monument in Charlestown. Each stop represents a significant site of U.S. history. Many of the guided tours only visit 11 of the 16 stops starting from the Boston Common ending at Faneuil Hall [Government Center]. Faneuil Hall itself is a huge shopping area so you can easily stop here to eat and check out the street performers before continuing to your next stop. There’s a separate tour for the remainder through the North End neighborhood. The guided tours all have characters dressed in colonial clothes sharing the history at each of the sites. I personally have only visited about half of the list, so if you opt for self-guided you can just visit the ones that interest you.

Boston Public Library (Free)

Visiting a library might sound boring, but I promise the Boston Public Library [Copley] is beautiful and completely worth strolling through. On the main floor, you can enter the open-air courtyard where you will see a gorgeous fountain with many marble statues. There are seating areas for you to relax or read. While you ascend the flights of stairs there are other impressive marble sculptures and mural artworks by prominent artists. The reading room may be the most photographed area with its green lamps on long desks underneath the stunning architecture of the high arched ceilings. You must go and see for yourself!

Boston Public Library

Boston Public Library

Museum of Fine Arts

I could spend hours in my favorite museum, the Museum of Fine Arts (MFA). In addition to their 450,000+ art pieces on 3 floors, the MFA [Museum of Fine Arts E or Ruggles] also has a rotating exhibit. You can check their website to see what is currently there and upcoming for your trip. Each time I’ve visited, there are always new works to view such as paintings, sculptures, photographs and ancient artifacts. You can prepare for your visit by viewing their floor plan if you have specific exhibits you want to explore. One of my favorite collections was the various musical instruments and seeing the intricate designs on each of the beautiful harps. They also have a sizable collection of mesmerizing contemporary art on display.

Are you planning an ‘All American’ trip? Head over to our blog section to find more inspiration and get planning!

Harbor Cruise or Duck Boat

Boston has beautiful views on their harbor of the Atlantic Ocean as well as on the Charles River across to Cambridge. I’d recommend choosing either the Harbor Cruise or the Duck Boat tour as the experiences for me were comparable depending on what you are looking for. The Duck Boat tour is more family-friendly and offers a both on land and water ride. When I was younger I had a fun memory of the duckbill quacker toy and pretending to “steer the boat”, but not much of the history and fun facts. If you opt for the harbor cruise you can choose the topic of the ride and interval of time ranging from 45 minutes to 2.5 hours. The harbor cruises depart from either Long Wharf or Rowe’s Wharf. The cruise I tried was a ~ 2.5-hour cruise around all of Boston’s small islands (i.e. Spectacle, Georges, Peddocks, Lovell, etc…) which also included an all you can eat brunch! Our narrator provided us several historical facts and local tidbits I wasn’t aware of!

Cruise round Harbor Islands

Cruise round Harbor Islands

The Go Boston All Inclusive pass gives you access to many of the city’s top attractions and lets you skip the line!

Where to eat & drink in Boston

Boston has so many food and drink options so it may be difficult to decide! Here are some suggestions to help you choose when you’re tired from exploring all the things there are to do in Boston!


L’Espalier [Copley]

My absolute favorite French and modern New England style restaurant in Back Bay neighborhood! Take the elevator up to the second floor to enjoy culinary masterpieces with top-notch service. I still remember those delightful Gouda eclair starters and creamy Foie Gras.

Neptune Oysters [Haymarket]

Boston is famous for their seafood! You can’t visit and not try “the best”, right? Expect lines at almost every hour in this small restaurant for possibly a 4-hour wait. However, it’ll all be worth it once you try one of their Neptune Burgers, Lobster Roll, or Crudo Specials. (You can always kill time and visit the other Freedom trail stops in the North End!)

Boston Chops* [Back Bay]

Do love a great steak?! Then I’d highly recommend Boston Chops for you. Sure Boston has tons of other upscale steakhouse chains, but this place has a great modern ambiance and fantastic service. Not to mention they also have one of the best buttery popovers I’ve ever tasted to whet your appetite! Plus during the warmer months, they have outdoor seating option.

*If you happen to plan your trip during Restaurant Week or Dine Out Boston, many of the fine dining restaurants offer a prix fixe menu which includes 3 courses for you to try at a fraction of the regular cost.

Boston Chops Popover

Boston Chops Popover


Parish Cafe [Arlington]

Two locations in the heart of Boston this restaurant offers some of the tastiest sandwiches I’ve ever tried! Now these aren’t your simple cafeteria sandwiches, they were created by chefs with national recognition. One of my favorites is The Zuni Roll!

Cheers Restaurant [Park St.]

Have you seen the American sitcom Cheers? The location in Beacon Hill is the one that inspired that TV show. If you’re a fan or just want to experience visiting a famous location then it’s definitely worth grabbing a drink or food here. There are of course iconic pieces and you can take photos with the cardboard cutouts of Norm and Diane. There’s also a “replica” located in Faneuil Hall.

Pomodoro [Haymarket]

There are endless fantastic Italian restaurant options in the North End! Pomodoro is one of those small, cash only restaurants that serves a fantastic Italian meal! I highly recommend the Fradiavolo. The meal ended with a complimentary tiramisu!

Gaslight [Back Bay or Broadway]

Located in South End, this one’s a bit farther from the public transit. Gaslight, a French brasserie style restaurant offers wonderful brunch options. I love the ambiance of the restaurant with the Parisian zinc bar and charming antique decor.

Gogi on the Block – Food Truck (weekdays only)

For lunch on weekdays, food trucks are an amazing and affordable option! Check Boston Food trucks online for the schedule of the area you’re in. Many food trucks also have a twitter account which broadcasts their location.

Gogi on the Block, a modern Korean BBQ is my favorite! You can choose a rice bowl, burrito or salad filled with your protein choice. My usual is the Bulgogi Beef with either white rice or their kimchee fried rice. Plus the owner of the food truck is super friendly!

Gogi Food Truck

Gogi Food Truck

Samuel Adams Brewery [Stony Brook or Green St.]

What’s more Boston than Sam Adams? He was a prominent figure of the American Revolution now used for beer sales. This location in the Jamaica Plain (JP) neighborhood is a fun way to sample some tasty drinks while learning about their history. Their Tap Room also offers exclusive flavors.

Harpoon Brewery [Northern Ave]

Harpoon offers brewery tours and some of the best pretzels I’ve ever tasted! You can choose either a regular salted or cinnamon sugar pretzel. Each one comes with a choice of 2 dipping sauces. Their list of dipping sauces alone is reason to keep going back (i.e. IPA cheese, Ale Mustard) to their roomy beer hall. They also have a huge variety of their year round, seasonal and limited release available to try.


Modern Pastry or Mike’s Pastry [Haymarket]

The age old debate of which Pastry shop has the best cannoli? Visit one or both to decide for yourself. They’re also conveniently located directly across the street from each other in the North End.  Of course if the other colorful marzipan, lobster tails, butter cookies, cakes, biscotti catch your eye by all means try them all!

Tatte Bakery & Cafe

With 3 locations in Boston, 1 in Brookline, and 4 in Cambridge it’s no doubt about this bakery’s popularity. Aside from their delectable fresh cheesecakes and other sweet treats, they also serve food! I especially loved their chocolate brioche. You can stop in for breakfast, lunch or dinner too.

Tatte Bakery

Tatte Bakery


Boston is not a huge city, so if the weather is nice, walking is the best option. If you love bicycling, you can try our bike share program called Hubway. Short 30 minute rides between stations are free. Each additional 30 minutes is an additional fee. You can purchase a 24 hour or 72 hour pass. Keep in mind there’s a huge fee if you lose the bike or it gets stolen. If you rent or drive your own car, good luck with using GPS Maps! I still constantly get lost driving around with all of the rotaries and narrow one way streets. Plus keep in mind parking will cost you an arm and a leg in the garage.

For locations that are further apart, the MBTA Subway or as we typically call it “the T” is an affordable option. The T is actually the oldest subway The first step is purchasing a CharlieTicket (paper) or obtaining a Charlie Card (plastic) at one of the stations. The plastic card saves you $0.50 for each ride. You can also buy daily or weekly passes if you calculate how often you anticipate using the T. The MBTA website is a good resource to find out specific schedules or changes for each line and their Twitter account gives real time updates of any service delays.

There are 4 main lines denoted by color on the MBTA map: Green, Orange, Red, Blue. You might also see gray and purple on there and that represents the Silver Line (buses connected to T) and the Commuter Rail. The main ones I indicated are the four colors and I color coded the destinations I recommended throughout. When you get to the station you will see signs for “Inbound” and “Outbound” along with the end destination. Inbound and Outbound is kind of confusing but Inbound generally means headed towards downtown Boston and Outbound means headed away.  This is important since there are a few train stations where the 2 directions have 2 separate entrances and you can’t cross over once you’ve passed the ticket gate!



The Green line for some reason is split into 4 sub-lines to make matters more confusing: B, C, D and E. So you’ll want to check on the map whether the line you’re on goes there or you’ll have to transfer. Be careful on “Game Days” for the Red Sox since the 1 hour before and after the game mean that most of the trains will be filled to the brim by Kenmore or Fenway stops! I can’t tell you how many times I’ve had to wait for 5 trains to pass by before I could get on.



There are a few hostels around Boston that range from $25-50 night such as HI Boston and American Youth Hostel. Check their websites for the room options of which type of dorm style you would like.


A couple budget options are some chains that my family and I have stayed with in the past Holiday Inn Express and Ramada near the Dorchester neighborhood of Boston off of the Red Line.

As for mid-range hotels, I’d recommend the Hyatt Regency located right in Downtown Boston. There’s also the Boston Park Plaza or Omni Parker House in Back Bay. The Omni is longest continually operated hotel in New England and also known as the most haunted hotel in New England!

If you’re looking for the full luxurious experience then the Ritz Carlton and the Mandarin Oriental both in Back Bay are worth considering. These hotels offer all the amenities and more. The Mandarin is located adjacent to the splurge restaurant, L’Espalier I mentioned earlier too.

There are also a couple boutique hotels under the Kimpton brand the Kimpton Onyx across the street from the North End and Kimpton Nine Zero in Downtown.


Red Sox, Celtics or Bruins Game

If you are a fan of the baseball, basketball or hockey sports Boston has plenty to offer! Fenway Park [Kenmore / Fenway D], the oldest Major League Baseball location offers tours to the public if you want to get the history and behind the scenes experience before the game. If you’re interested in a basketball or hockey game, the TD Garden [North Station] arena is the place to go as its easily convertible for sports and even large concerts. If you’re interested in American Football then you’ll have to leave the city and visit Gillette Stadium in Foxboro accessible by Commuter Rail.

Fenway Park

Fenway Park

New England Aquarium

While this might not be the largest aquarium, this one has its own charm! Even if you’re stopping by the Long Wharf area for a boat cruise it’s worth stopping by the entrance to see the free seals. Inside they have a spiral walkway around their gigantic tank with information about all of the aquatic creatures featured. You can also combine it with a trip to the nearby Imax!

Museum of Science

I remember visiting the Museum of Science [Science Park/West End] several times when I was younger and one time recently with friends. It’s a great family-friendly activity with tons of fun and educational exhibits to check out! They also have a live show at certain hours.

Charles River to Cambridge

I didn’t mention any locations in Cambridge above, but it’s worth checking out the city next door along the beautiful river.  There are several paths great for walking or biking. During the summer you can also rent a kayak on the river at Kendall/MIT area to tour the city by water.

Charles River

View over Charles River

Become a Quest Master at Boda Borg

If you are visiting with friends or family, you can try all of the quests at Boda Borg [Malden Center] if you have a team of 3 to 5 people. Now this one isn’t in Boston, but it’s accessible by T! This is currently the ONLY location in North America, and its original location is in Sweden. The quests combine elements of “Escape Room”, teamwork and leveling up by completing each room. Depending on the quest it could require mental or physical strength some of them are a blend of both. One of my favorites was “Escape from Alcatraz” where your team works together in an amazingly decorated prison.

Make sure you get the most out of your trip to Boston with these activities!


When visiting, I’d highly recommend checking the weather forecast daily, as it’s often unpredictable, changing hour to hour. A light waterproof rain jacket has become of my staples to avoid the dreaded inverted umbrella due to wind tunnels.

For purchasing items such as souvenirs in Boston, we have a 6.25% sales tax on all items except non-restaurant food and clothing articles under $175. If you’re dining out at restaurants or purchasing prepared food there’s also an additional 0.75% tax.

If you’re taking the T and notice “moderate” or “severe” delays on the website/Twitter, it’s sometimes best to walk or order a rideshare vehicle. Unfortunately, minor delays and trains on “standby” are a common occurrence so I  factor this into my travel sometimes still running late.

I hope you have a fantastic time visiting Boston with some of my recommendations! It’s truly a city that offers something for everyone.

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Hanna Gao

Hanna Gao

FTB Member

Hanna is a financial consultant living on the outskirts of Boston traveling to clients with helping them with their accounting and finance needs. She loves sharing her unique experiences whether it be terrific or terrible and offering tips to future visitors. When Hanna is not planning her next adventure, she writes extremely detailed unapologetically honest reviews of her experiences such as guided tours, local attractions, unforgettable restaurants and discovering hidden gems.

Find out more and read some of her unapologetically honest reviews at Rated by Hanna or connect with her on FacebookInstagramTwitter and Pinterest.