Weekend in Boston: The Perfect 3-Day Itinerary

Last Updated on March 6, 2024

Looking to spend a weekend in Boston? We have visited Boston a few times now, and have designed this 3-day Boston itinerary to help you make the most of your escape.

Aptly named the “Cradle of Modern America,” Boston is known as the nation’s pioneer, where the first subway system, first public school and first public park were created. For a city with so many impressive accolades to its name, Boston is welcoming and charming, and gives off a big town feel.

For that reason, it makes for an excellent weekend trip for good reason. Boston is a city where history and modernity perform a tango, and every cobblestone has a story to tell. Its blend of historical charm with modernity, coupled with unpredictable weather, Boston warrants advanced preparation before hopping on a plane. Here is my detailed Boston itinerary for those who intend to spend a weekend in Boston. I promise it’ll make you want to come back for more!

3 days in Boston Itinerary

Boston Itinerary Day 1: Learn Boston’s History

Visit Historic Freedom Trail

Begin your Boston weekend trip by strapping on your comfiest walking shoes and hitting the Freedom Trail. Embark on a 4km journey through downtown Boston that leads you through 16 distinct historical sites, several of which were pivotal in the American Revolution. Trace the path of the founding fathers as you stroll through the pages of American history along this trail.

Step into history at the iconic Boston Common, the oldest public park in the US. As you venture north from the park, a historical journey unfolds through the charming North End. Discover landmarks like the Massachusetts State House, the solemn King’s Chapel Burial Ground, the Old South Meeting House, and the Old State House, among others.

The Old State House stands witness to the Boston Massacre, an event that sparked the flames of the Revolutionary War. While most sites here are free to access, the Old State House requires an entrance fee. If you want to learn all about Boston’s history, I recommend booking a guided tour of the Freedom Trail.

Check out Instagram-Worthy Beacon Hill

Beacon Hill, a storied enclave in Boston, unfolds like a picturesque postcard. Renowned for its timeless charm, Acorn Street is one of the most photographed streets in the US. The cobblestone pathways adorned with vintage lanterns and brick residences make this neighborhood an aesthetic masterpiece.

Next up; head to Charles Street, the heartbeat of Beacon Hill, where boutique stores beckon, chocolate confections tempt, and sweet shops entice. While here, explore, and discover everything from fine wines to refreshing juices along this delightful avenue.

Head to Chinatown for Lunch

From Beacon Hill, take a short stroll to the enchanting and lively Chinatown. There is a chic eatery in Chinatown that will cater to all your gourmet needs. Empire Garden not only offers delectable dim sum every day, but it’s the ambiance that truly steals the show.

Found within the walls of a former theater, this restaurant is a spectacle in itself. It’s a visual feast, a true embodiment of grandeur that adds extra magic to your dining experience. If you are a foodie then you will love this place.

Visit Boston Common and Boston Public Garden

After that scrumptious meal, make your way to the nearby Boston Common and Boston Public Garden. Established in 1839, the Boston Public Garden was the first public botanical garden in the US. Unlike the neighboring Boston Common, the Boston Public Garden has a distinctly ornamental style.

Enclosed by an elegant Victorian cast-iron fence, the public garden showcases winding pathways adorned with statues, fountains, and a diverse array of trees and plants. There is also a six-acre pond offering visitors the delightful option to embark on swan boat rides.

Boston Common has been a pivotal player in shaping the history of conservation, landscape architecture, military and political affairs, and recreation within Massachusetts. Its historical significance for the city also reflects comparable models implemented by American conservationists across the nation.

Join Boston Ghosts and Gravestones Trolley Tour

As night falls, embark upon the spine-chilling journey aboard the “Trolley of the Doomed” and delve into the eerie side of Boston. Known as the best ghost tour in Boston, this tour is realistic and dramatic, and will definitely send a chill down your spin. Discover the supernatural antics unfolding at the Omni Parker House, unravel the mysterious tale of the Boston Strangler, and pay a visit to King’s Chapel cemetery, where the bones of the departed once served as a gruesome currency for Ephraim Littlefield.

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Boston Itinerary Day 2: Explore Fenway Park

On day two of your weekend trip to Boston, get ready to explore some of the city’s finest museums and the iconic Fenway Park neighborhood. Kickstart your morning with a delightful breakfast at Cafe Bonjour, where their menu is a true culinary delight. Indulge in classics like hazelnut spread and strawberries or savor the sweet simplicity of banana fosters. The chic eatery also offers a Strawberry Patch featuring house-made rhubarb jam crowned with a luscious lemon custard sauce.

Visit the Museum of Fine Arts (MFA)

Boston is home to several museums making it incredibly hard to pick out a few. However, the Museum of Fine Arts is a must-visit gallery for your Boston itinerary. Housing more Monets than any museum outside Paris, an assembly of Japanese art, priceless treasures from Egypt, and an array of American art, this museum is a global artistic haven. With each step, transport yourself to different ages, as you engage with exhibits designed to inspire your artistic responsiveness.

Check out Isabella Stewart Gardner Museum

In the heart of Boston, where art and audacity join hands in a dance of whimsy, lies the Isabella Stewart Gardner Museum. A visit to this cultural haven is like stepping into a time-traveling tea party hosted by a spirited art aficionado.

Isabella Stewart Gardner, the audacious soul behind this artistic haven, orchestrated the creation of her wide-ranging playground, and the result is nothing short of magical. Step into the enchanting courtyard, a lush oasis surrounded by balconies adorned with flowers and sculptures. It’s like stumbling upon a secret garden amid the bustling city.

Visit Fenway Park

Fenway Park‘s legacy is intimately intertwined with the soul of Boston, and for city residents, this iconic ballpark is nothing short of sacred ground. Located in the Fenway neighborhood from which it takes its name, its verdant structure stands tall. The glow of night games illuminates the Boston skyline, visible from miles away.

A guided tour of Fenway Park is the best way to explore the entirety of the stadium while delving into the rich history of the Sox. This excursion offers unobstructed views of the ballpark, allowing you to see iconic features like the Green Monster, the press box, and even the rooftop vegetable garden.

Led by passionate Red Sox guides, this tour promises an insider’s perspective. If you visit Boston during baseball season, make sure to attend a game – it’s the best way to spend your Friday night in the city.

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Boston Itinerary Day 3: Venture Further out

For the last day of your Boston itinerary, get an early start at the Boston Public Market. The year-round indoor marketplace showcases a delectable array of artisanal delights sourced from local New England vendors. Start your morning by picking out the city’s breakfast favorites. Choose a bagel from the Bagel Guild, a delicious crepe at the Bon Appetit Creperie, or indulge in a Boston cream donut at Union Square Donuts.

Visit Faneuil Hall

After breakfast, your next destination will be Faneuil Hall, a storied locale that has served as a meeting hall and marketplace for over 270 years. Wander along the charming cobblestone street, immersing yourself in the rich history of this cultural focal point. Explore the vibrant Faneuil Hall Marketplace (Quincy Market) lined with shops, restaurants, and stalls.

When it’s time for lunch, you’ll find numerous options in this area. However, for an authentic taste of Boston, order a bread bowl of clam chowder from the renowned Boston Chowda Co. – a truly iconic treat!

Join Duck Tours

Guiding you on this adventure are ConDUCKtors, a lively bunch ready to welcome you aboard a World War II amphibious vehicle known as a DUCK. As you traverse the city, catching glimpses of landmarks like the Old State House, the ConDUCKtors regale you with intriguing tidbits about the sites.

The real highlight, however, is the amphibious nature of your vessel. Brace yourself for an exhilarating splashdown in the Charles River, treating you to an unparalleled view of the Boston skyline. Note: The Duck Tours remain closed from November to early spring.

Visit the New England Aquarium

Immerse yourself in a world of conservation and inventive solutions at this aquarium true to its mission of addressing challenges facing ocean life. Spend an enriching afternoon exploring the captivating Indo-Pacific Coral Reef exhibit, or watch the playful penguins at the Penguin Colony exhibit. The aquarium is a destination that combines entertainment and education, making it ideal for an afternoon of exploration.

Check out Boston’s Theater District

End your weekend trip to Boston with a captivating performance in the Theater District. There are countless live productions here. However, we advise you to secure tickets in advance based on your preferences.

The Boston Opera House, an opulent venue, hosts dazzling live productions of touring Broadway shows. Alternatively, explore Emerson College’s Colonial Theatre, where you can often catch shows before they make their Broadway debut at more affordable rates.

The Wang Theatre, fashioned after the Paris Opera House, exudes opulence and hosts a diverse array of performances. Regardless of your choice, your night promises to be a world-class entertainment experience in the heart of Boston’s cultural scene.

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Boston Travel Guide

Day Trips from Boston

If you have a bit more time, we’ve concocted a whimsical guide to Boston day trips that will have you escaping the city limits faster than you can say “lobstah roll.”

Nantucket Island

Nantucket Island is famed for its pristine sandy beaches, picturesque gray-shingled cottages adorned with vibrant blooms, and an iconic lighthouse that stands as a beacon of coastal charm. To catch a ferry to Nantucket, you need to venture to Hyannis on Cape Cod. Once there, seize the freedom to tailor your day to your desires. Pedal through the island’s scenic paths on a rented bike, unwind on the sun-kissed beaches, indulge in delectable fresh seafood, or go on a scavenger hunt – the choice is yours.

Provincetown

Provincetown is the eclectic gem at the tip of Cape Cod where the lobster traps are as colorful as the characters you’ll meet. Forget what you know about quaint New England towns; Provincetown is a vibrant kaleidoscope of art, culture, and just the right amount of quirk.

To get there, take the Provincetown Fast Ferry departing from Long Wharf, just next to the New England Aquarium in the heart of Boston. In just 90 minutes, you’ll disembark at in Provincetown, ready to explore the vibrant charm of this coastal haven.

Newport

The opulent Newport from the Gilded Age still command admiration with their grandeur—after all, that was their primary purpose. If you find yourself with time for just one estate tour, make it The Breakers. Located close to the International Tennis Hall of Fame, the Audrain Auto Museum offers a dynamic exhibition of remarkable cars within a stunning Art Deco structure.

To reach Newport, take a commuter rail from South Station into North Kingstown (a journey of 1.5 to 2 hours) and then take a taxi or Uber to reach Newport. Keep in mind that the train schedule has limited daily trips, so planning ahead is essential.

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How to Get around Boston

For your weekend trip to Boston, we recommend packing comfortable and season-appropriate footwear because you’ll be doing lots of walking. Downtown Boston is compact, spanning about two square miles, making it an easily navigable area on foot. Despite subway stations in the city center being close to each other, walking makes more sense than waiting for one.

Should you decide to navigate the city using the subway system, aka the ‘T,’ consider a seven-day unlimited pass or a reloadable plastic CharlieCard. The seven-day pass makes sense for stays longer than a couple of days, covering rides on the Charlestown ferry. If you prefer a pay-as-you-go approach, the CharlieCard offers a 50-cent discount on regular subway fares ($2.25 instead of $2.75).

Unless you opt to stay outside the city center, a car is not essential for your weekend in Boston. Most hotels in Boston tack on a daily parking fee of over $40, and securing street parking frequently demands a neighborhood permit which is designated for residents only.

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Best Time to Visit Boston

While summer is the peak tourist season in Boston, fall emerges as a strong contender for the best time to explore the bustling city. By September, the weather takes a turn towards drier and more pleasant conditions, with October showcasing a vibrant display of foliage. Spring is a great alternative despite bringing a bit of uncertainty in terms of weather, but the blooming blossoms add a captivating touch.

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Where to Stay in Boston

Boston’s hotels and Airbnb rentals often spring surprises on its visitors, with third-floor walk-ups, steep staircases, creaky floors, or more snug quarters than they might expect. If you’re seeking modern comforts, please verify whether a location offers elevator service, air conditioning, and other amenities, as these conveniences aren’t guaranteed.

Budget: HI Boston

Scoring super cheap accommodation in Boston can be quite the challenge, so look no further than HI Boston in Downtown. Priced at a wallet-friendly $40 per night, this hostel is a top-notch choice. Boasting a communal kitchen, common area, and meeting rooms, HI Boston goes the extra mile for budget-conscious travelers. Book your stay here.

Mid-range: Copley House

Nestled in the pulsating core of Back Bay, Copley House features apartment-style rooms and suites set within the timeless charm of traditional brick-row houses. Copley presents diverse apartments catering to every kind of traveler. Plus, you will find so many shops and restaurants along the trendy Newbury and Boylston Streets. Book here.

Luxury: AC Hotel by Marriott Boston Cleveland Circle

Nestled just 3 miles away from Fenway Park, the AC Hotel offers comfortable lodgings with a fitness center, private parking, a shared lounge, and a bar. Priced at $261 for a weekend night, this hotel easily connects to the entire city through the MBTA Green Line. Book here.

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Enjoy Your Weekend in Boston!

Feel free to print out this Boston itinerary and bring it with you on your weekend getaway! I have packed this itinerary with all the best things you can do in Boston in 3 days, so get ready to have a blast.

Be sure to leave a comment below if you have any questions. Read more of my US articles to get idea for your next weekend trip:

• Weekend in New York
• Weekend in Seattle
• Weekend in Los Angeles
• Weekend in San Francisco
• Weekend in Miami
• California Road Trip Itinerary
• Arizona Road Trip Itinerary
• Florida Road Trip Itinerary
• Best National Parks in USA

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