The Best of Boston in 3 Days Itinerary

Boston is just one of those cities that we simply can't get enough of. Beantown's chock full of diverse cultural experiences, world-class museums, New England food (gotta love it), renowned architecture, and some of the nation's favorite attractions.

Most Boston visitors don't have enough time to do everything in one trip and it can be difficult to decide what to do and when to do it. However, that just got a whole lot easier with the Go Boston Card "Best of Boston in 3 Days" itinerary.

Our expoerts have done all the research and planning to get you to as many top attractions as possible and we didn't just stop with attractions. We've scoped out some of the best restaurants and activities, too.

By following this itinerary, you'll optimize your savings with Smart Destinations.

Day 1: Historic Boston

Attractions: Freedom Trail Walk Into History Tour, USS Constitution Cruise, USS Constitution Museum, Faneuil Hall/Quincy Market, Boston Common

Dining: Boston Common Coffee, Durgin-Park, Strega Ristorante, Mike's Pastry or Modern Pastry

9:30 A.M: Start the Day Off Right

Start off the day like a true Bostonian at Boston Common Coffee Co. in Downtown Crossing. It's a hot spot coffee shop, but it's spacious and rarely crowded or loud. There's seating for all types, including couches, bar tables, and regular tables.

Then, make your way over to the Boston Common, just a short 5-minute walk away.

11 A.M: Take a Walk on the Freedom Trail

Boston's Freedom Trail
Historical impersonators guide visitors along the Freedom Trail

At the Boston Common, head to the Visitor Center, located along the Tremont Street side of the Common. It's here that you'll start your guided Freedom Trail Walk into History Tour. You'll follow the legendary red-brick path around the downtown area to the most historic sites, like the State House, King's Chapel Burying Ground, and the site of the Boston Massacre. Finally, the guided portion of your tour will end at Faneuil Hall marketplace.

12:30 PM: Faneuil Hall Marketplace

At Faneuil Hall, there's plenty to do and see...and eat. If you're not hungry after the 90-minute tour, shop around or simply explore the area. You'll be sure to find several street performers, and it's a great place for photo ops. It's also the perfect place to grab a souvenir with some local flair.

When you're ready, get lunch at the Boston staple, Durgin-Park. People have been pouring into Durgin-Park since 1827, but the waits aren't usually very long if you don't mind being seated at a long table with other people (this is the traditional style and we recommend giving it a try!). Enjoy huge portions of ribs, seafood, salad, Boston-baked beans, and all the New England classics.

3:30 PM: Visiting the Charlestown Navy Yard

USS Constitution U.S. Navy photo by Journalist 1st Class Dave Kaylor
The USS Constitution navy frigate

Give your feet a break for the afternoon while continuing to the last portion of the Freedom Trail. From Faneuil Hall, walk 5-10 minutes to Long Wharf (just walk down State Street), which will take you to "Old Ironsides" with some great site-seeing along the way, like views of Bunker Hill Monument and The Boston Tea Party Boat. Disembark at the ship and explore its interior, or check out the USS Constitution Museum, both of which are located in Charlestown Navy Yard.

In the Evening

Chocolate chip cannoli from Mike's Pastry via Mike's Pastry

Make your way back to the mainland and hit the North End; it's about 15 minutes in total. Walk from the Navy Yard to the bus stop at Chelsea St. & Warren St. Then hop on the 93 bus (part of the T system) and get off at the Washington St. at Medford St. Stop. Now you'll be in the corner of "Little Italy." Take a right on Causeway Street, then a right on Prince Street. Walk about a third of a mile down Prince Street, and take a left on Hanover to arrive at Strega Ristorante, your Italian dinner destination.

Save room for dessert at Modern Pastry or Mike's Pastry, both on Hanover Street and both legendary.

Optional Evening Activities

Hennesey's of Boston To experience downtown Boston's nightlife, check out the bar voted "Best Irish Bar in Boston" by Improper Bostonian magazine 5 times. Hennesey's has 2 floors, 3 bars, and a live cover band on the weekends. Its Irish pub atmosphere attracts locals and tourists alike.
Address: 25 Union St.

Boston Gondolas Enjoy a private tour of the Esplanade on authentic Venetian gondolas. Bring your own wine or champagne and Boston Gondolas will provide glasses, ice, crackers, cheese, chocolates, and blankets. The gondola tours are one of the best-kept secrets in Boston. The gondola tours are one of the best-kept secrets in Boston, and with your Boston Go Card you'll receive a $15-$25 savings on your tour.
Address: Charles River Esplanade, Storrow Drive.

Shear Madness This interactive, hilarious "whodunit" has been voted "Best Comedy of the Year" seven times by The Boston Globe. It's a great chance to see the best of Boston's improv scene, and you'll save $10 with your Boston Go Card.

Day 2: Coast & Culture

Attractions: Beantown Trolley Tour, New England Aquarium, Institute of Contemporary Art, Beacon Hill

Dining: Elephant & Castle, Cheers-Beacon Hill, The Daily Catch

8:00 AM: Breakfast is Served

Start out your day with breakfast at Elephant & Castle on Devonshire Street in the heart of the downtown Financial District. They serve up the best British Classics, and you can get 20% off breakfast with your Go Boston Card.

9:30 AM: Pick Up Your Tickets to the Beantown Trolley Tour

Beantown Trolley Tour

Head to Faneuil Hall to pick up your 2-day ticket for the Hop On/Hop Off Beantown Trolley Tour. It's only about a 7-minute walk. Head down Devonshire Street toward State Street, take a right on State and then a quick left on Congress St. Walk until you see Faneuil Hall on your right. Here, you'll find a red kiosk shaped like a trolley car where you can get your ticket.

10:00 AM: Visit the New England Aquarium

From here, walk once again towards the Long Wharf (down State Street), but this time your stop will be the New England Aquarium. Plan to spend a couple of hours exploring the Aquarium.

12:00 PM: Hop On!

From the Aquarium, hop on the Beantown Trolley and enjoy your narrated city tour until you reach the Cheers stop (about halfway through the tour).

12:45 PM: Hop Off to Get Some Lunch

Enjoy 10% off your lunch at the ORIGINAL "Cheers" restaurant. After lunch, take a walk around the historic and unique Beacon Hill neighborhood.

2:30 PM: Hop On Again!

Hop back on the trolley in front of the Shaw Memorial, right on Beacon St (this is not the same stop you got off at). From Beacon Hill, the trolley will take you through the West End in a loop down to the Seaport District.

3:30 PM: Enjoy the Institute of Contemporary Art

Make your departure from the trolley when you are at the Seaport Hotel stop and walk to the Institute of Contemporary Art. Plan to spend 1-2 hours here.

In the Evening

Spend your evening exploring Boston's lovely waterfront. Eat dinner the New England way at a seafood restaurant like The Daily Catch where you can save 15% on dinner with your Go Boston Card.

Optional Evening Activities

Atlantic Beer Garden For the best of Boston's waterfront nightlife, head to Atlantic Beer Garden. ABG is best known for its fantastic views of the water and the Boston skyline from their rooftop patio. There's lots of space and a small dance floor, but expect it to get quite crowded; get there early if you don't want to wait in long lines.
Address: 146 Northern Ave

Bikes@Night Tour by Urban AdvenTours Although it starts in the North End, this relaxing and fun ride focuses on Boston's beautiful waterfront as the sun goes down and the lights come on. It's about a 2 hour tour and all levels of bikers are welcomed.
Address: The North End along Columbus Park

Day 3: Back Bay, Fenway, Cambridge

Attractions: Beantown Trolley, Fenway Park Tour, MIT Museum, Newbury Street, Prudential Center, Copley Square

Dining: Croissant du Jour, Cask n' Flagon, Emma's Pizzeria

8:00 AM: Good Morning!

Start your morning bright and early in the Back Bay with breakfast at Croissant du Jour on St. James Street. It offers fast service, good seating, and fair prices; plus, it's close to your next stop: Newbury Street!

9:00 AM: Walk Along Newbury Street

After breakfast, cross over to Newbury, and start making your way down the street that is one of the best-known shopping destinations in the nation. You'll find everything from local souvenir shops to world-renowned high-end boutiques.

11:00 AM: All Aboard the Beantown Trolley!

When you reach Copley Square, hop back on the Beantown Trolley. The trolley will first take you past the Prudential Center, where you can either get off and shop some more or stay on until you get to Fenway Park.

12:00 PM: Are You a Baseball Fan?

Take a tour of Fenway Park, the oldest ballpark in Major League Baseball. The tour will last about an hour and brings you atop the Green Monster, into the dugout, and up to the press box.

1:30 PM: Let's Do Lunch

Eat lunch like a true Sox fan at the Cask n' Flagon at the corner of Lansdowne Street and Brookline Ave. It's right outside the park and a classic Boston restaurant and bar.

3:00 PM: Cambridge Bound

Hop back on the Beantown Trolley and ride over the lovely Charles River to Boston's sister city, Cambridge. Get off at the Kendall/MIT Stop. From Kendall, it's about a 15 minute walk to the MIT Museum. Start out walking down Portland St. toward Main St.

3:30 PM: MIT Museum, Anyone?

Arrive at the MIT Museum and discover Boston's technical side with the latest in innovation and science at the museum of one of the nation's most distinguished colleges.

In the Evening

Sit down for dinner at Emma's Pizzeria on Hampshire Street, back towards the Kendall MIT Stop. Emma's serves delicious thin crust pizza at a reasonable price and boasts quick service. Plus, its convenient location near Kendall Station means you can hop back on the T and either head back downtown or check out Harvard Square.

Optional Evening Activities:

Kendall Square Cinema Catch a flick at this unique, independent theater. Kendall's beloved cinema features intriguing independent films, foreign language films, restored classics, and documentaries. It's also noted for its architectural design and considered one of Boston's cultural epicenters.
Address: One Kendall Square, Cambridge

The Middle East This Cambridge restaurant and nightclub features 3 live-music performance rooms, 2 family-style restaurants with full-service bars, and an elegant restaurant named ZuZu. It's a great place to grab a drink while enjoying some great local music. You'll definitely get the full Cambridge experience with staff and customers that are an international mix of musicians, students, townspeople, and professionals.
Address: 472/480 Mass Ave., Cambridge

The Comedy Studio The Comedy Studio (located about the Hong Kong Restaurant) offers innovative comedy shows every Wednesday thru Sunday night, starting at 8 p.m. The Comedy Studio offers a casual, open atmosphere for sharing food and drinks. They are particularly known for their Scorpion Bowls, and a full Chinese food menu is available downstairs.
Address: 1236 Mass Ave. Cambridge

Burdick Café If you have a sweet tooth, Burdick chocolate is what you want. Burdick serves a variety of tasty pastries, candies, and drinks. The hot chocolate drinks are made with melted shaved chocolate and are simply "to die for" (and they can be served cold, too!). Burdick is Harvard Square's best spot to grab a sweet treat or drink.
Address: 52 Brattle Street, Cambridge

Buy Now & Save!

With this 3-day itinerary, you'll pay less than the gate prices for the top Boston attractions. Plus, you'll get great discounts on meals and activities with your Go Boston Card. Your Go Boston Card will include admission into all of our Boston attractions, so feel free to alter our itinerary to meet your needs.

Save 20% to 55% on Boston's Top Attractions

Build Your Own Custom Pass

  • Bundle 2+ attractions
  • Save a guaranteed 20%

All-Inclusive Pass

up to
  • 45+ attractions
  • One low price
  • Save up to 55%

Boston Travel Tips