3-DAY Boston, Massachusetts ITINERARY

Boston is Massachusetts' capital and largest city. Founded in 1630, it's one of the oldest cities in the U.S. The key role it played in the American Revolution is highlighted on the Freedom Trail, a 2.5-mile walking route of historic sites that tells the story of the nation's founding. One stop, former meeting house Faneuil Hall, is a popular marketplace, per Google.

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Must do, must see, must try:


Walk through history on the 2.5 mile tour and take a journey through how USA started. 


Need I say more? Try this life changing food. With a local beer. Enjoy!


Watch the Boston Red Soxs or take a tour, either way stop and see the historical stadium.

The Perfect 3-Day BOSTON Itinerary


AirBnB close to the Seaport district 

Hotel: Revere Hotel ($$$), Aloft Boston Seaport ($$), YOTEL Boston ($$)


Fall is the perfect time so you can enjoy the change of season, but get there before the snow falls. Preferably early November. 


The itinerary pieces activities together that are walk-able, but Lyft to the outskirts. Don't rent a car, it's too expensive paying for parking.


Language is English

Currency: US Dollar


Great city for an interactive history lesson, that doesn't end with a quiz. Many places to visit, to drink at and eat at throughout the days. Also, this is an American city Bucket List must.

Boston is a historical, quaint city full of colonial buildings, history, sunshine, beer/tea and will provide a bond between you and the founding of the country. This place is proud. Proud of themselves as a town, proud to be associated with the history and any Bostonian will tell you; and the accent is pretty amazing.

Boston is one of the biggest cities in the country, but it has a town feeling. 

Day one

Early Flight

Check-in at the hotel and drop off bags

11 AM – Hop On Hop Off Boston Tours; time spent 2 hours (full ride), $38 USD (deals online)

  • Sights include: Downtown, Theater District, Waterfront District, historical and Redcoat spots, Boston Massacre, Ballpark, Boston Convention & Exposition Center, Old State House and more

  • Grants you free admission to the Old State House Museum, Boston Harbor Cruise, $10 off admission to Boston Tea Party Ships & Museum – and more that you’ll do!

  • Or if you are a movie buff, make time to take the Boston Movie Mile Walking Tour ($25 USD), or if you want an in-depth tour, try the Boston TV and Movie Sites Tour

1 PM Lunch – Lansdowne Pub ($$, Bar)

2 PM – Tour the home of the Boston Red Sox with a Fenway Park Tour; time spent is 1.5 hours, $20 USD

3:30 PM Drink – Boston Beer Works on Fenway ($$, Brewery) or Cheers on Beacon Hill ($$, American)

  • ​If you grab a pint at Cheers, walk around the corner and venture down Acorn Street; the most frequently photographed street in the United States.

4:30 PM – Enjoy a stroll through Boston Public Garden and ride the Swan Boats; time spent is 1 hour, $4 USD. Then wonder over to Boston Common, America’s oldest park!

  • If you’re book lover, travel toward Brattle Book Shop to see America’s oldest book shop​

6 PM – See the city from 50 floors high on the Skywalk Observatory; time spent is 1 hour, $20 USD

7:30 PM Dinner – dine in North End at L’Osteria ($$, Italian), try the lobster ravioli

Dessert at Modern Pastry ($, Bakery) for a cannoli

Return to the hotel of explore the North End and Little Italy

Day Two

8:30 AM – a Big Breakfast at the Friendly Toast ($$, Breakfast & Brunch)

  • Day Option - visit Salem

10:15 AM – Take a Freedom Trail Walking Tour; time spent is 2 hours, $12 USD, or use this map for a solo walk

Return to Old State House (time spent is 30 minutes, free tour) for an in-depth look or shop at the Faneuil Hall Marketplace (Outdoor-Indoor Mall)

1:30 PM – Lunch on the Waterfront at Union Oyster House ($$, Oyster Bar & Restaurant) oldest restaurant in America

2:30 PM – Visit the Boston Tea Party Ships & Museum; time spent is 1.5 hours, $28 USD

4:30 PM – USS Constitution Cruise & Boat Tour through Boston Harbor Cruise; time spent is 1.5 hours, $23 USD

6:30 PM – Enjoy dinner and a view at Legal Sea Foods ($$$, Seafood)

  • Must try the clam chowder​

Day Three

Breakfast at Union Square Donuts ($, Donut Shop) because you need a Sea Salted Bourbon Caramel donut in your life.

10 AM – New England Aquarium Whale Watch through Boston Harbor Cruise; time spent is 3-4 hours, $53 USD

  • Bring a lunch & snack, water, jacket, sneakers, sunscreen, sunglasses and a hat

  • Buy the combo ticket for the Aquarium, $74 USD

2 PM – Marvel at the New England Aquarium; time spent is 2 hours. $28 USD

4 PM Late Lunch – Jacob Wirth Co. ($$, German), second oldest restaurant in Boston

  • Get a German beer, wurst over sauerkraut on pretzel bun, red cabbage and German potato salad

5 PM – Check-out of the hotel

Evening flight home. Goodbye Boston.

helpful links
Travel a GO-Go

Use the Google map on the left to get a lay of the land and see all the fun spots that you'll visit. Download the free PDF by clicking the icon below to have this itinerary at your finger-tips. 

How to Use the Map: Click the tab in the top left hand corner to view the layers (days, points of interest, route).

If you click the star, this map will be added to your Google Map account. To view, open your Google Maps, click the menu button "Your Places", select the map and it will open. 


Boston attracts hundreds of visitors each year due to its historical sights and more. Besides the Red Sox, Boston offers a lively throwback to history, beautiful parks and walking tours where you can catch up on everything you missed in History class.


This itinerary was created from the Personalized Itinerary on Your Trip tab. Get your personalized itinerary for anywhere in the world but answering a few questions. 

Happy Travels, 

- Itinerary Traveler

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