Boston Itinerary - 3 Days in Boston for First Timers

Our jam-packed guide will help you make long-lasting memories during your short stay in Boston!

Published: July 18, 2024
boston

In Boston for a brief vacation but unsure how to maximize your time? If you only have 3 days in Boston, we have some great suggestions for what to do on your trip. This Boston itinerary encompasses tons of activities and attractions to help you see the best of Boston.

Boston city

We've also included both indoor and outdoor options, so you can make the most of your trip regardless of which time of year you're visiting. 

This 3-day itinerary includes:

  • Hop-on Hop-off Sightseeing Trolley
  • Fenway Park Tour
  • Freedom Trail Walking Tour
  • Old State House
  • Institute of Contemporary Art or USS Constitution Cruise
  • Boston Children's Museum or Boston Whale Watch Cruise
  • New England Aquarium
  • Mary Baker Eddy Library

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

Day 1 Stop #1: Boston trolley ride

This Hop On Hop Off Boston Trolley Tour is the perfect introduction to Boston. It will take you all around the city and past all the big landmarks and highlights. It's a convenient way to get to some of the major attractions, or a fun and easy way to see the city.

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

Your onboard guide will narrate your tour, so you will learn all about Boston's unique history as you ride. 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. It can take one to two hours to ride the entire route, depending on traffic, so keep that in mind when planning your day.

Stop #2: Fenway Park Tour

Fenway Park tour

Sports fans will not want to leave Boston without taking the opportunity to tour Fenway Park, the home of the world-famous Boston Red Sox. Truly a magnificent and historical stadium, Fenway Park is the oldest ballpark in Major League Baseball.

You will learn all about the park's history on the one-hour tour. 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 - there's an excellent gift shop.

Of course, watching a baseball game is always a fun addition to any seasonal vacation. Why not pick up a few tickets while you're in town?

Day 2 Stop #1: Freedom Trail walking tour

Boston freedom trail

Another must-do Boston attraction, the Freedom Trail Walking Tour is a great on-foot perspective of the city’s historical hotspots, hosted by actors in eighteenth-century costumes. Your guides will teach you about the stories and secrets of the main figures and significant events of the American Revolution.

Plus, you'll hear 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.

Be sure to check out our post on all the Freedom Trail sites and locations that you will see during your tour. Tours run throughout the day, but hours vary seasonally and by day of the week.

Stop #2: Old State House

Boston 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 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.

Stop #3: Institute of Contemporary Art (indoor option)

Institute of contemporary art

Art lovers will find much to admire in Boston’s iconic Institute of Contemporary Art. From the gorgeous and distinctive building itself to the astonishing works within, you won't be short of inspiration. Home to some of the most cutting-edge works in contemporary art across the globe, the ICA offers only the most thought-provoking and inspiring works of art to visitors.

Even if you've been before, the ICA features frequently changing exhibitions alongside a well-curated permanent collection, so there's always something new to see. Located in a completely revitalized waterfront neighborhood in Boston, the ICA is also an excellent stop on a larger itinerary that includes dining, shopping, and other top attractions.

The ICA also offers some special programming, so be sure to consult the event calendar before your visit to see if anything interests you.

The gift shop also features both upscale and affordable goods that reflect a modern art aesthetic, so it's a great place to find presents and souvenirs. We recommend reserving 2-3 hours of your day to explore the ICA.

💰 >> See how you can save up to 50% on Boston attractions

Stop #3: USS Constitution Cruise (outdoor option)

USS constitution

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." Visit her home in the Charlestown Navy Yard and disembark for a tour of the famous ship and adjacent Naval Museum. If you choose not to get off and explore, you can just 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! This cruise is sold on a first-come, first-served basis. Tours run seasonally (typically late March through early November) and run multiple times per day, so they are easy to schedule.

Getting in: đŸŽŸïž Admission is available on all Go City® Boston passes. Just show your pass at the admission desk and you're in.

Day 3 Stop #1: Boston Children's Museum (indoor option)

Children play in the playground

The dynamic, interactive Boston Children’s Museum is the perfect place for kids to play and learn. All exhibits are designed to make your kids think as they explore and grow as they engage with unique objects and interfaces. For example, children love the Art Studio, where they can create to their heart’s content.

They will learn about shapes, colors, tools, and forms while they express themselves artistically. Another popular area is the New Balance Foundation Climb. It's a 3-story climbing sculpture that’s part activity, part puzzle, and all fun! They also offer a wide variety of special programming and unique activities. Be sure to consult their operating calendar before you visit to see what’s going on during your trip.

Stop #1: New England Aquarium Whale Watch (outdoor option)

Whale watching

This New England Aquarium Whale Watch cruise will take you out into the Atlantic Ocean. Cruise out to the Stellwagen Bank Marine Sanctuary, home to various species of whales and dolphins. You’ll spot many seabirds, but the highlight will be the wide variety of whales, from humpback whales to finback and minke whales.

If you have a video camera or a smartphone, we recommend bringing it along on this cruise. We also recommend making reservations in advance and be sure to mention that you have a Go City Boston pass while making reservations. Arrive at least 30 minutes before your cruise time; the cruise will take approximately four hours.

Stop #2: New England Aquarium

New England Aquarium

The New England Aquarium is bound to be a favorite with the kids, and adults will find so much to 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 lovable, goofy penguins! There's also a delightful IMAX movie available onsite (rotating regularly), which comes at a small additional cost. Since there’s so much to see and do here, we recommend reserving at least two hours for this attraction.

Before you go, read our guide for New England Aquarium top tips.

Stop #3: Mary Baker Eddy Library (indoor option)

Another excellent place for the family to expand their minds is the Mary Baker Eddy Library and Mapparium. This attraction offers the resources and exhibits of a research library alongside the fun and excitement of an interactive museum. Visit the Hall of Ideas, where you can follow an interactive exhibit that traces inspirational quotes from historical figures. Then, head to the Quest Gallery, which focuses on the life and times of Mary Baker Eddy herself.

Don’t forget about the stunning Mapparium! This massive painted glass globe illustrates the circulation of knowledge throughout the globe with colored lights and shapes. Honor a woman who fought for education and women’s rights in the nineteenth century with a visit to this fascinating attraction.

Stop #3: Swan Boat Ride (outdoor option)

Swan boats Boston

The Swan Boats of Boston are among the most iconic characters in the city. The pond and the boats are found in Boston's gorgeous public gardens. Many Bostonians consider this 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. Ride on this historic vessel with your sweetheart or your friends, and enjoy the opportunity to soak up the beauty of the surrounding gardens.

Save on admission to top Boston attractions with Go City®

Jam-packed with everything that a first-time visitor to Boston really shouldn't miss, this itinerary should give you a great starting point on how to spend three days in this exciting city.

Discover our full line-up of Boston attractions including the Fenway Park Tour, the View Boston Observation Deck, the Boston Children's Museum, and more.

đŸ€© >> If you want to see and do as much as you can, our All-Inclusive Pass is for you.

😎 >> If you want to pick just a few attractions and visit at your own pace, our Explorer Pass is the perfect option.

So grab whichever Boston attraction pass suits you, and go see the city's best bits!

Katie Sagal
Go City Travel Expert

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Things to do in Boston for Pride Day

Boston’s Pride For The People parade and festival is one of the biggest, brightest and most beautiful in the States, pulling in several thousand participants and around a million spectators for its week-long celebration of love, diversity and inclusion. Baked beans, the Boston Red Sox and that bar ‘where everybody knows your name’ ain't the only thinks to get excited about around these parts: there are also some fine, buzzy ‘gayborhoods’ to explore, like South End, Jones Hill and Jamaica Plain, all of which transform into oceans of rainbow flags and lights for Pride. The week promises all manner of events across the city, from burlesque nights to brewery cookouts, fashion shows and queer cinema. Raise your rainbow flag and dive in for our guide to all the best things to do in Boston on and around Pride Day… Pride Parade, Block Party & Festival There will be oodles of fun LGBTQ+ events taking place in Boston through Pride Month, with the majority happening in the days leading up to the parade and festival. We’re talking movie screenings, drag brunches, community events, queer walking tours, picnics, bar crawls and much more. The top of the iconic Prudential Tower will light up in rainbow colors to kick off Pride Month and again on the day of the parade, in support of the LGBTQ+ community. Check local listings for further info and tickets on all June events in Boston. The big day usually lands on the first or second Saturday of June, when revelers line the streets of the South End to catch a glimpse of outrageous floats, flamboyant drag queens, marching bands, stilt walkers and all manner of other extravagantly garbed participants and performers. The Boston Pride For The People Parade kicks off late morning at Copley Square, painting its celebratory rainbow across the South End before landing up at Boston Common for a top-notch family festival complete with DJs, drag queens and international headline acts. The festival is free and runs from around midday until early evening. Meanwhile, over at City Plaza, there’s a slightly more grown-up vibe at the free Pride Block Party, which runs for a couple more hours after the Boston Common festival wraps up. This one’s for 21+ attendees only, and promises rather more risqué entertainment in the form of foul-mouthed drag kings and queens, pole dancers and more. New England craft breweries provide the lubrication and DJs spin the party tunes until around 8PM. Top Tip: Boston Pride for the People recommends Arlington St and Boylston St subway stations on the green line or Back Bay Station on the orange line for the best Parade-viewing opportunities. But get there in plenty of time as it does get extremely busy! Find about more about the next Boston Pride For The People event here. Boston Pride After Parties Fear not: the end of ‘official’ festivities does not mean the party’s over. Far from it, in fact. Indeed, Boston’s Pride after parties are the stuff of legend. Hit up South End stalwart Club Café on Columbus Avenue for some of its legendary cabaret and late-night dancing. The fabulous Liberty Hotel – an utterly transformed former prison in Beacon Hill – usually has a number of events running through Pride Month, including brunches, fashion parades and more. That there will be DJs and live acts playing into the small hours on Pride Saturday is a given. Try the lively Midway Café, a well-established dive bar in Jamaica Plain with regular live music, or mosey over to Dorchester dBar for craft cocktails and all-night dancing at one of Boston’s best-loved LGBTQ+ clubs. It’s the morning after the night before, so what better than a rejuvenating drag brunch to help brush those cobwebs away? There will be dozens of these running across Boston during Pride Month, with local favorites including South End Mexican restaurant Cósmica, the Boston Summer Shack over in Back Bay, and the aforementioned Liberty Hotel. Bloody Marys and mimosas naturally come as standard. Again, local listings are your friend for the latest info on all Boston club nights and brunches. LGBTQ+ Culture in Boston Something of a trailblazer, Boston is one of those places that’s very much *steeped* in history. Not only the birthplace of the American Revolution, it’s also the capital of Massachusetts, famously the first US state to legalize gay marriage. Go Boston! As a result, there’s plenty of queer culture to explore, and this is brought to the fore during Pride Month, where museums, walking tours and even castles get in on the action. The Freedom Trail comprises 16 historic Boston monuments and locations that, between them, contain the entire history of Beantown. There are walking tours of the route – which includes Boston Common, the 17th-century King’s Chapel cemetery and Paul Revere’s House, year-round, many with guides in period dress. Pride Month sees the addition of an excellent ‘Rainbow Revolutionaries’ option, highlighting key players in Boston’s LGBTQ+ community (and their fight for liberty) through the ages. For something a little (ok: a lot) more light-hearted, pop on your heels and hop aboard a drag-tacular trolley tour of Boston’s most significant female and queer landmarks. However, we’d recommend flat shoes for top Boston LGBTQ+ walking tours like this one. It’s also worth a day trip out to Hammond Castle and museum up the coast in Gloucester. Founder John Hammond is something of an LGBTQ+ Massachusetts icon so it’s no surprise that there are several special events running here throughout Pride Month, including exhibitions, readings and film screenings. Visit Boston’s Top Attractions If you’re in town for a few days and fancy fitting some serious Beantown sightseeing around all that drinking, dancing and drag-brunching, the Go Boston pass is your friend. Choose an Explorer or All-Inclusive option, depending on whether you have specific attractions in your sights or simply want the freedom to visit as many as you’d like over several days. The pass can save you up to 50% on standard entry prices for Boston tours, activities and attractions and includes: The View Boston Observation Deck, up top of the iconic Prudential Tower. A tour of Fenway Park Stadium, home of the legendary Boston Red Sox. A ride on the famous Boston swan boats. The absolute treasure trove of art and artifacts that is the Boston Museum of Fine Arts. A sunset cruise of the Charles River Basin. A guided tour of the charming clapboard farmhouse in nearby Concord, where Louisa May Alcott wrote (and set) American literary masterpiece ‘Little Women’. ...and much more! Find out more and choose your Boston attractions pass here.
Stuart Bak
Stuart Bak

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