The Best of Boston in 3 Days Itinerary

In Boston for a long weekend, but unsure how to maximize your time? If you’ve only got three days in Boston, we have some great suggestions for what to see and do on your trip.

This Boston itinerary encompasses a wide variety of activities and attractions, so it really helps you to see the best of Boston in a limited amount of time.

This itinerary includes:

  • Hop On Hop Off Trolley Tour
  • USS Constitution Cruise
  • New England Aquarium
  • Fenway Park Tour
  • Skywalk Observatory
  • Whale Watch
  • Freedom Trail Walking Tour

Only have a few days in Boston? We’ve also put together a 1 day and 2 day itinerary.

Save on Attraction Admission

Pick up a 3-Day Go Boston® Card and save off combined admission vs paying at the gate.

Remember, this 3 day itinerary is just one of many ways to experience Boston.

The Go Boston® Card gives you the flexibility to create your own itinerary, so you can choose from dozens of top attractions and create a vacation tailored to your interests.


Stop #1 – Beantown Trolley


This hop-on, hop-off trolley is the perfect introduction to Boston. It will take you all around the city past all the big landmarks and highlights, and is a convenient way to get to some of the major attractions.

Some highlights of your trolley tour include the historic North End, Quincy Market, the USS Constitution and the Bunker Hill Monument, the Theater District and Chinatown, the Boston Public Gardens, and more!

Getting In: Be sure to pick up your ticket in advance at any of the designated pickup locations. Time on the trolley will vary according to your plans (the full length is 110 minutes if you don’t hop off), but your ticket is good for two full days so you can use it whenever!

Stop #2 – USS Constitution Cruise


Who doesn’t love historic vessels, especially in a waterfront city like Boston? The USS Constitution Cruise brings you up close and personal with ‘Old Ironsides’ at her home in the Charlestown Navy Yard and allows you the option to disembark for a tour of the famous ship and adjacent Naval Museum.

You can sit back and relax on this delightful and informative cruise through the Boston Harbor.

Either way, it’s a great opportunity for some photos of the iconic Boston skyline.

Getting In: This cruise is sold on first-come, first-served basis. March 28–November 22: Daily, every hour on the half hour 10:30am-4:30pm. Hours change seasonally. Please check attraction website for exact schedule.

Lunch on the Waterfront

Since you’ll be in the waterfront area after disembarking from your cruise, this is a good place to stop for lunch. There’s a nearby Legal Sea Foods that’s always a great bet, or the popular Union Oyster House is just a few blocks away. If you’re not feeling seafood, there are plenty of options around the nearby City Hall Plaza.

Stop #3 – New England Aquarium


The New England Aquarium is bound to be a favorite with the kids, and adults will find so much explore as well! The four-story Caribbean coral reef is one of the most popular exhibits, filled with tons of tropical fish and other exotic creatures.

Be sure to visit the Shark and Ray Touch Tank and take the opportunity to interact with those fascinating creatures. And don’t forget about the Aquarium’s stars – the loveable, goofy penguins!

Getting In: Since there’s so much to see and do here, we recommend reserving at least two hours for this attraction.

Dinner in the North End

After you’ve enjoyed immersing yourself in the world of marine life, it’s time to head to the North End for dinner.

A mecca for authentic Italian restaurants and bakeries, it’s a must-visit neighborhood on your Boston itinerary.

There are tons of options to choose from, including the famous Regina Pizzeria and Mike’s Pastry (be warned – there will be long lines at both!).


Stop #1 – Fenway Park Tour


Sports lovers and history fans alike will not want to leave Boston without taking the opportunity to tour this magnificent historical stadium. Fenway Park is actually the oldest ballpark in Major League Baseball, so it’s chock full of significant places and people.

Some highlights include the famed Green Monster wall, the Fisk Pole, Duffy’s Cliff, The Triangle, the Lone Red Seat and more! Don’t forget to stop for souvenirs!

Getting In: Tours run daily between 9:00 am – 5:30 pm, or 3 hours before game time. We recommend leaving at least an hour for this attraction (including time to shop at the Yawkey Way Store!)

Lunch near Fenway

Since this area is also home to a number of colleges, there are tons of eating options around here. You’ll find everything from Panera and Chipotle to great local restaurants like the Lansdowne Pub and Boston Beer Works.

Stop #2 – Skywalk Observatory


After lunch, hop on the Green Line for a ride over to the Prudential Center area on Boylston Street.

Then, ascend to the top of the Prudential Center for a trip to the popular Skywalk Observatory, with its 360-degree views of metro Boston. Definitely bring your camera to this attraction!

Located 50 floors up in the air, this is actually Boston’s only sky-high vantage point. You’ll also find a number of interactive exhibits and historical displays located throughout the Observatory, so you’ll learn about the buildings you’re seeing below.

Getting In: We recommend reserving between 30 minutes to an hour for this attraction.

Stop #3 – Shopping on Newbury Street

This is your opportunity to really explore Boston like a local. Newbury Street and Boylston Street are filled with tons of local shops and big-name chains, spanning the gamut from Cartier to H&M.

The Prudential Center Mall itself is also a great shopping destination, featuring everything from restaurants and clothing boutiques to bookstores.

Dinner on Newbury Street

Along with all of the shops, there are plenty of tasty dining options here. From cupcakes and pizza to classic American and chic café fare, you can find practically anything you feel like eating in this neighborhood

Joe’s American Grill is a popular favorite with families, or Sonsie is a fun, trendy local spot.


Stop #1 – Whale Watch


Using your bonus option with the 3-Day Go Boston® Card, hop aboard Boston Harbor Cruises’ popular Whale Watch! This cruise will take you out into the Atlantic Ocean to the Stellwagen Bank Marine Sanctuary, home to giant marine mammals including various species of whale and dolphin.

You’ll also see a number of sea birds and other marine life, but the highlight is going to be the potentially wide variety of whales that you may encounter.

Species of whales in the neighborhood include humpback whales, finback whales, and minke whales. If you have a video camera or a phone capable of taking video, we recommend bringing it along on this cruise.

Getting In: We do recommend making reservations in advance. Arrive at least 30 minutes before your cruise time; the cruise will take at approximately four hours.

Lunch aboard the Whale Watch

Either bring a sack lunch or purchase food aboard the cruise – since the cruise will last from 10:00 – 2:00 or 12:00 – 4:00, you’ll definitely want to eat something en route. Snacks, sandwiches, and beverages are all available for purchase.

Stop #2 – Freedom Trail Walking Tour


Another must-do Boston attraction, the Freedom Trail Walking Tour is a great on-foot perspective of the city’s historical hotspots.

This guided tour (hosted by actors in 18th century costume!) will also teach you about the stories and secrets of the main figures and significant events of the American Revolution, plus some insider info about Boston’s history as a whole.

You could also opt to walk the red brick line throughout the city without a guide – it will give you more flexibility in time and distance, but without the background info.

Getting In: Tours run throughout the day, but hours vary seasonally and by day of the week. If you’re coming from the Whale Watch, you’re probably catching the last tour of the day.

Dinner in Downtown

While where you end the day depends upon where you deviate from the Freedom Trail, if you’ve taken the guided tour you’ll be deposited back on the Boston Common – right in the heart of downtown Boston.

This area is filled with great dining options, from high-end steak places to casual sandwich eateries. If you’re feeling adventurous (and aren’t too tired from walking), venture a bit south into the Theater District / Chinatown area for some really delicious cuisine.

Let’s Recap

So there’s a suggestion for how to spend your three days in Boston. It’s an itinerary that’s jam-packed with everything must-do and can’t-miss about Boston, plus some fun extras!

If you visit these included attractions with your 3-Day Go Boston® Card, you’ll save big off combined admission cost vs. paying at the gate. You’ll also get extra discounts on shopping and dining options with your card.

Go Boston Card

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