38 wicked awesome reasons to go to Boston

Boston is a growing metropolitan city that manages to hold onto its historical charm and walkability. Read our guide for the top sights, restaurants, and bars to experience while in Beantown. Hot tip: if you’re going on St Patty’s Day, check out our guide for the holiday.

Streets of Boston
Along the Freedom Trail – photo via @the.nomadic.hijabi


What to see & do in Boston

  • Institute of Contemporary Art. The main showstopper at this art museum is the building’s own architecture (it’s uber modern exterior is in sharp contrast to the city’s many historical buildings).
  • Isabella Stewart Gardner Museum. Isabella Stewart Gardner’s palace-like home has been turned into a museum housing her extensive and varied collection of art from all over the world. Snap a pic in the gorgeous sky-lit courtyard.
  • Catch some sports:
    • Head to Fenway Park to watch a summer Red Sox game. Hot tip: fans are passionate about their team so best not insult the Red Sox (or the Patriots while you’re at it).
    • Checkout TD Garden for either a Bruins or Celtics game.
Fenway Park
Fenway Park – photo via @ghudson5


  • Boston Public Garden. The first public botanical garden in America (built in 1837). Wander these beautifully manicured Victorian gardens and take a 15-minute ride on the lagoon in one of the Swan Boats.
    • Plus, just across the street is the Boston Common (America’s first park)
Boston Common
Boston Common – photo via @dj.odell


  • Freedom Trail. If it’s your first time in Boston, you can’t miss the Freedom Trail. While it sounds a bit touristy, following the 2.5 mile path brings you to 16 different Revolutionary-War era sites (including the home of Paul Revere) and teaches you a lot of history in a very interactive way. We suggest downloading a map and following it on your own.
  • Take a tour of Harvard University. You don’t have to be a prospective student to tour our nation’s oldest university. Download the audio tour and wander the campus on your own time.
  • Read a book at the Reading Room of the Boston Public Library. This library opened in 1895 and the Reading Room’s vaulted ceilings and arched windows seem straight out of a Harry Potter film.
Boston Public Library
Boston Public Library – photo via @frolova


  • Go shopping:
    • Shop on Newbury Street (aka the 90210 of Boston) for high-end finds.
    • Or try Assembly Row in Somerville for outlet shopping, movies and outdoor dining all alongside the Charles River.
  • HarpoonFest – every year in late spring, local brewery Harpoon hosts this beer festival as a way to kick off the summer season. Watch live bands perform, grab some grub at one of the many local food trucks, take a tour for the brewery, and drink lots and lots of beer.
  • Head to South Boston with friends for fun on the swings at Lawn on D. Lawn on D is a popular summertime park with glowing circular swings, ping pong tables, outdoor games, a bar, and more.
  • Boston Tea Party Tour in the Financial District. Relive the period of the US’s independence by visiting fully-restored ships, grabbing a cup in Abigail’s Tea Room, and even throwing a bit overboard yourself in the tea-throwing ceremony.
  • Duck Boats. Touristy? Yes. But fun? Also yes. See the Boston sights (including the pub where Cheers was filmed and the Bunker Hill monument) from both land and sea (well, the Charles River).
Duck Boat Tours
Duck Boat Tours – photo via @yukari.bostonian


  • Berklee School of Music’s Summer in the City series of concerts. More than 400 free performances throughout the Boston area from May to September. Check the schedule to see what’s happening during your visit.
  • Best views:
    • The view spanning Boston to Cambridge along the Massachusetts Avenue Bridge
    • From the rooftop at the Liberty Hotel.
    • Or, for a completely different view head to the Arnold Arboretum (265 acres of beautifully-kept grounds).
  • Hit the town:
    • Whisky Saigon (modern night club with a packed dancefloor)
    • The Burren in Somerville (an Irish pub with live bands and dancing)
    • Ned Devine’s (chill Irish pub by day and dance club by night)
    • Howl at the Moon (live band with talented musicians who take requests from the crowd)



Where to eat & drink in Boston

Indulge in some of the best Italian food this side of the Atlantic in the North End. But don’t quite fill up on pizza and pasta, you’ll want to save room for some classic New England Clam Chowda and/or Lobster Rolls.

Regina Pizza
Regina Pizza – photo via @thebrooklynbite


  • Regina Pizzeria. You can’t come to the North End without a stop at Regina. The vibe is classic, no-frills pizza diner leaving the pie to be the star of the show. There’ll probably be a line out the door but don’t be deterred.
  • Giacomo’s Ristorante. Be prepared to pay in cash, to wait in line, and for some of the best and authentic Italian food you can find in Boston, and that is saying something. You can’t miss the Lobster Ravioli (served with diced tomatoes and covered in a garlic cream sauce)—it’s fresh & flavorful with a perfectly tender filling.
  • Mike’s Pastry. Founded in 1946, Mike’s is a North End establishment for cannolis. Smooth & creamy ricotta cheese fills these huge Italian delicacies in an array of flavors.
Mike's Pastry Boston
Mike’s Pastry – photo via @travelthink


  • Tiger Mama. Come to this Thai restaurant for flavorful food and a hip atmosphere (dim lighting, lush plants, and tropical drinks served in coconuts). Don’t miss the Crispy Chili Potatoes.
  • Pho Pasteur. Craving something a bit different? Try Vietnamese pho in Chinatown. Cheap, tasty, and perfect for when the temperature outside drops.
  • Faneuil Hall Marketplace. Inside the marketplace, you’ll find quick local eats: everything from lobster rolls to clam chowder to seafood. And once you’re there, you can check out the history of Faneuil Hall (it was the site of many meetings & protests in Revolutionary-era America).
Lobster Rolls in Faneuil Hall – photo via @slyquinn


  • Sip Wine Bar & Kitchen. This wine bar has an intimate vibe, an extensive drink selection, and flavorful foods. Plus, sushi rolls that are to die for.
  • Boston Public Market. Want to cook some of your own food? Check out this year-round indoor market for locally-sourced & fresh produce, meats, treats and more.
Matcha tea from Boston Public Market
Matcha tea from Boston Public Market – photo via @mo.jody


  • South End Buttery. While many Bostonians prefer the $1 coffee at Dunkin’ Doughnuts, we suggest heading to a café like South End Buttery where you can get a creamy latte and an excellent brunch to boot. Plus, avocado toast.
  • Thinking Cup. Thinking Cup is Newbury Street’s answer to a café: an instagrammable interior with artfully decorated desserts and latte art tulips. Plus, the food is delicious.
  • Café Luna. A cozy breakfast place in Cambridge that serves simple but hearty food. Our faves are the fluffy lemon ricotta pancakes and the lobster eggs benedict.
  • Boston Burger Co. The burgers here are obviously killer but if you’re coming to Boston Burger Co, you’re going to need to get a Freakfrappe. What is that? Try a frappe with more toppings than you could even begin to imagine (see below).
  • Also, check out Blackbird Doughnuts
Boston Burger Co Freakfrappe
A Boston Burger Co Freakfrappe



  • Brewery tour of Sam Adams. The tour is free (!) as are samples, making this a can’t miss stop on your Boston getaway.
  • Night Shift Brewing. A little off-the-beaten-path but the selection of beers is impressive. Grab a mug and sit on the outdoor patio or play your friends at cornhole. Keep an eye out for the food trucks!
  • Rooftop at Revere. $30 entry gets you access to both the pool and the bar at this hip lounge. Make the most of your money and spend an afternoon lounging in a cabana poolside.
  • Beantown Pub. Located along the Freedom Trail so stop by once you’re weary of walking. Get an ale and a Paul Revere (pastrami sandwich with corned beef, swiss cheese, onions and honey djion mustard).



Where to stay in Boston

These are some of our favorite neighborhoods for visiting the city:

  • Back Bay – Back Bay has tons of bars & restaurants so there is always something to do.
  • Fenway – Home of Fenway Park (aka Red Sox Nation)
  • North End – The heart of Boston’s Little Italy and the center of many of the city’s touristy sights
  • Somerville – Somerville is known for its young vibe and newly-minted post-grads. A relaxing, yet fun city in Davis and Porter Square on the weekend with live bands and a fun crowd.


Boston, MA
Boston – photo via @photomarkk


Leave a Reply

Your email address will not be published. Required fields are marked *