Boston Itinerary – 3 Days in Boston for First Timers

In Boston for vacation but unsure how to maximize your time? If you’ve only got 3 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 Sightseeing Trolley
  • Fenway Park Tour
  • Skywalk Observatory
  • Freedom Trail Walking Tour
  • Old State House
  • USS Constitution Cruise
  • Whale Watch
  • New England Aquarium
  • Swan Boat Ride

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 days in Boston itinerary is just one of many ways to experience the area.

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 – Boston Trolley Ride

Image Credit: City View Trolley

Image Credit: City View Trolley

This hop-on, hop-off Boston 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. Your ticket is good for two full days so you can use it whenever!

Stop #2 – Fenway Park Tour


Sports lovers and history fans alike will not want to leave Boston without taking the opportunity to tour Fenway Park, truly a magnificent and 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!)

Grab a bite 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 #3 – Skywalk Observatory


After you explore the Fenway area a bit, we suggest heading over towards the Prudential Center area on Boylston Street.

There you can ascend to the top of the Prudential Center for a stop 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 #1 – 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.

Stop #2 – Old State House


This is one of the stops along the Freedom Trail Walking Tour, but Boston’s Old State House is worth a special shout out in this itinerary.

Explore at your own pace and enjoy tours and performances (every thirty minutes) led by our fun, interactive guides or fully costumed Revolutionary characters!

Highlights include John Hancock’s lavish red velvet coat, arms and ammunition from Revolutionary War battles, and tea salvaged from the Boston Tea Party.

Lunch on the Waterfront

When you are ready, head towards the waterfront area as 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 – 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.


Stop #1 – New England Aquarium Whale Watch


Using your bonus option with the 3-Day Go Boston® Card, hop aboard a New England Aquarium 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.

Stop #2 – 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.

Stop#3 – Swan Boat Ride


By Captain-tucker (Own work) [CC BY-SA 3.0], via Wikimedia Commons

 The Boston Swan Boats are one of among the most iconic sites in the city.

The pond and the boats are found in Boston’s gorgeous public gardens, which many Bostonians consider their favorite part of the city.

Made famous in stories like Make Way for Ducklings and The Trumpet of the Swan, the Swan Boats are the only vessels of their kind in the world.

Shopping on Newbury Street

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.

Let’s Recap

So there’s a local’s suggestion for how to spend your three days in Boston. It’s an itinerary that’s jam-packed with everything that a first time visitor to Boston really shouldn’t miss.

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 be able to enjoy select extra discounts on shopping and dining options with your pass.

Go Boston Card

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