Beantown in a Nutshell: Making the Most of 3 Days in Boston

Post originally Published November 28, 2023 || Last Updated November 28, 2023

See how everyone can now afford to fly Business Class and book 5 Star Hotels with Mighty Travels Premium! Get started for free.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Walk the Freedom Trail

No visit to Boston is complete without walking the Freedom Trail. This 2.5 mile path winds through the heart of the city, connecting 16 historically significant sites related to the American Revolution. As the name implies, the Freedom Trail celebrates Boston's integral role in America's fight for independence from Great Britain.

Though you can tackle the entire trail in one go, most visitors prefer to break it up over a couple of days. That way, you'll have more time to dive into each site along the route. Top stops include the gold-domed Massachusetts State House, the starting point for the Boston Massacre, Paul Revere's home, the Old North Church (where lanterns were hung to signal the British invasion), the USS Constitution, and Bunker Hill.
One of the best parts of walking the Freedom Trail is people watching. Costumed reenactors frequent many of the sites, helping transport you back to colonial times. You may catch British redcoats marching along the street or hear heated debates between revolutionaries like Samuel Adams and John Hancock. At the Old State House, staff in period dress ring bells and read the Declaration of Independence from the balcony.

For the full experience, download the official Freedom Trail app or snag a map from the Visitor Center. Either will provide more context at each stop with photos, videos, and audio clips. The app even offers guided tours led by 18th century citizens.

Though doable on your own, many travelers opt to join a guided tour. Local historians really help the Freedom Trail come alive by adding colorful anecdotes and lesser-known tidbits. Tours run daily, last 2-3 hours, and cost around $20 per person. Most companies offer discounts for children, students, and seniors.
Tour groups are a great option for families. Kids will appreciate the costumed interpreters and treasure hunt-style exploration. Try to visit on a weekend when reenactments are more common. You'll also want to tour during the day since some sites close at dusk. Summer tends to be busiest with school groups.

What else is in this post?

  1. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Walk the Freedom Trail
  2. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Explore Faneuil Hall and Quincy Market
  3. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Tour Harvard and MIT
  4. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Cheer on the Red Sox at Fenway Park
  5. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Stroll the Public Garden and Boston Common
  6. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Indulge in a Food Tour
  7. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Ride the Duck Boats
  8. Beantown in a Nutshell: Making the Most of 3 Days in Boston - Unwind along the Waterfront

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Explore Faneuil Hall and Quincy Market

No trip to Boston is complete without a stop at Faneuil Hall and Quincy Market. Together, these sites encapsulate Boston’s revolutionary spirit and provide a lively dose of people watching, shopping, dining and history.

Faneuil Hall has served as a meeting place and marketplace since 1742 when it was first gifted to Boston by merchant Peter Faneuil. In the 18th century, it was the site of speeches by revolutionaries seeking independence from Britain. Samuel Adams, James Otis and others debated and rallied support for rebellion here. Today, Faneuil Hall continues to host public meetings and political events in its Great Hall. Visitors can observe this symbolic ‘Cradle of Liberty’ and check out historical exhibits on the first and second floors. Costumed guides share stories from the past and highlight artifacts like John Hancock’s coat and Samuel Adams’ signature.
Right behind Faneuil Hall sits the bustling Quincy Market lined with over 40 food merchants and 40 retailers. The market’s colonial-style buildings house everything from chowder shops and bakeries to craft vendors and street performers. It’s a sensory overload with delicious smells wafting through the halls and lively tunes keeping toes tapping. Don’t miss the cannolis at Mike’s or Boston Cream Pie at Montilio’s. Grab a lobster roll and clam chowder bread bowl while taking in the street entertainment.
Wandering Quincy Market is fantastic for people watching and picking up Boston-themed souvenirs. Keep an eye out for ‘Make Way for Ducklings’ statues that pay homage to Robert McCloskey’s children’s book. Let the kids play at the plaza’s fountains to cool off on hot summer days. Pop into stores like Harbor Sweets and Boston Pewter Company to find the perfect mementos.

On weekends, the area transforms into an open air market as vendors set up along the cobblestone walkways. Local artists sell paintings, jewelry, soap and more while fresh produce stands tempt with everything from apples to zucchini bread. Street performers amp up providing free shows for all ages. See talented musicians, magicians, break dancers and gymnasts impress the crowds.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Tour Harvard and MIT

Beantown in a Nutshell: Making the Most of 3 Days in Boston

No trip to Boston is complete without a pilgrimage to two of the world’s most prestigious universities. Harvard and MIT anchor opposite banks of the Charles River, their stately buildings and impeccable lawns beckoning visitors to explore these bastions of academic excellence.

A stroll through Harvard Yard transports you back to colonial times with its brick buildings and shady elm trees. Founded in 1636, Harvard is the oldest university in the United States. Free student-led tours depart daily from the Smith Campus Center, offering glimpses of landmarks like Massachusetts Hall, Holden Chapel and the John Harvard statue. Don’t miss ‘the red line’ embedded in the concrete - folklore says students who cross it before graduating won’t get their diplomas.

For highlights beyond the Yard, consider a self-guided tour via Harvard’s app. It covers all 12 undergraduate houses, the science complex, athletic facilities, museums and more. Architecture buffs will appreciate the varied styles, from Georgian to modernist. Families can explore the Natural History Museum or stop by the Harvard COOP bookstore for crimson merch.

Across the river, MIT also impresses with striking contemporary buildings showcasing tech innovations. The campus seamlessly blends nature with pillars of glass, steel and stone. MIT’s student-led tours provide an insider’s perspective with fun tidbits on student life and famous alumni. Guides are unscripted so you never know what you’ll uncover! Highlights include the Great Dome, Building 7 and the infinite corridor.
For a behind-the-scenes look, book a reservation only tour. Options range from arts facilities like the MIT Museum and List Center to the Edgerton Center maker space brimming with hands-on projects. Visitors can glimpse ongoing research initiatives, student creativity and cool campus architecture.

Both universities boast top-notch art collections sprinkled throughout their campuses. Harvard Art Museums house over 250,000 works spanning centuries and continents. The Sackler features ancient antiquities while the Busch-Reisinger spotlights expressionist and Bauhaus-related art.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Cheer on the Red Sox at Fenway Park

No trip to Boston is complete without catching a game at the beloved Fenway Park, home of the Boston Red Sox. Opened in 1912, Fenway is the oldest ballpark in Major League Baseball. This historic stadium drips with nostalgia and has hosted some of baseball's most memorable moments over the past century.

Even non-sports fans will appreciate Fenway's old-school charm, from the hand-operated scoreboard to the 37-foot tall Green Monster wall in left field. The ballpark is remarkably intimate with just 37,000 seats tucked tightly around the action. You'll always feel close to the game no matter where you sit.

The energy and excitement is palpable on game days as fans flock to Yawkey Way outside the stadium. Street vendors hawk sausages, pretzels and peanuts while live bands amp up the crowds. Generations of Red Sox devotees flood the surrounding streets clad in hats and jerseys.

Once inside, be sure to arrive early to soak up Fenway's ambiance during batting practice. Listen for the signature "crack" of bat meeting ball. And don't forget to visit Pesky's Pole in right field, named after former player Johnny Pesky. It's just 302 feet from home plate, one of baseball's shortest distances. Even better, catch a home run sailing over the Green Monster during a game!

The Red Sox have an illustrious history dating back to 1901. Legends like Ted Williams, Carl Yastrzemski and David Ortiz have dazzled Fenway crowds over the decades. Boston fans are among the most passionate in sports, loyally cheering on their team through heartbreaking losses and glorious championships.

Attending a game allows you to partake in this storied baseball heritage. Join in singing "Sweet Caroline" during the 8th inning stretch. Hear the roar of the crowd after a big play. And witness the Fenway Faithful rallying with every pitch.

Between innings, indulge in classic ballpark fare like Cracker Jacks, hot dogs and ice cold beer. Just be prepared for sticker shock - concessions don't come cheap. Alternatively, grab dinner before the game at one of the restaurants on Landsdowne Street just beyond the outfield wall.

While the Red Sox schedule varies each season, they typically play April through September. Tickets aren't cheap, but snagging a seat in the bleachers or on the Green Monster is worth splurging for. Or try for obstructed view tickets behind a pole for a discount.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Stroll the Public Garden and Boston Common

Beantown in a Nutshell: Making the Most of 3 Days in Boston

Boston's Public Garden and Common provide the perfect green respites after touring historic sites or traipsing bustling downtown streets. Just footsteps from Boston Common stands America's first public botanical garden, the 24-acre Public Garden. Its pathways meander past lagoons, willow trees, footbridges and flowerbeds. See why Bostonians affectionately refer to this oasis as "the Garden."

Spring showcases vibrant tulips and daffodils while summer blooms flaunt roses and water lilies. Don't miss the iconic Swan Boats launched in 1877 - pedaling around the lagoon offers scenic views of weeping willows dipping into the water. For literary fans, keep your eyes peeled for the bronze "Make Way for Ducklings" statues of Mrs. Mallard and her brood. This children's book classic was set in the Public Garden.

Beyond flora and fauna, the park landmarks monuments commemorating the Civil War, George Washington and a tribute to the Smurfit-Stone Building. Concerts draw crowds to the park on summer evenings. Or pack a picnic to unwind on the lawn.

Adjacent Boston Common dates back to 1634 as America's oldest city park. The 50-acre green space fills with sunbathers, frisbee tossers, lunchtime strollers and more. Seasonal programs range from free yoga classes to theater performances on the Parkman Bandstand.
Follow the footprints embedded along the pathways commemorating Martin Luther King Jr.'s 1965 march from the Common. Then check out the granite Relief Memorial honoring the Boston Massacre just across Tremont Street.

Kids flock to the bronze Frog Pond spray pool in summer and ice skating rink in winter. Nearby artists and craft vendors set up shop at the Park Street Station plaza. Don't miss the iconic "Cheers" Bull & Finch Pub on Beacon Street.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Indulge in a Food Tour

No visit to Boston is complete without indulging in the city’s phenomenal food scene. Boston boasts a dynamic culinary landscape spanning everything from classic chowders to cutting-edge cuisines. Food tours offer the perfect opportunity to taste your way through Beantown’s best bites and meet fellow travelers who share your passion for flavor.

Boston Food Tours run 3-hour adventures hitting up to 8 tasting locations in Back Bay, North End, Chinatown and beyond. Options range from Sweets and Treats to Pizza and Pasta focused tours. Guides share historic tidbits between stops and take you to spots only the locals know. Tours run daily with plenty of weekend and evening options.
Kat from California did the North End tour and raved, “Our guide was extremely knowledgeable about the area and all the food spots. We tried everything from arancini and cannolis to fresh pasta and pizza. I would have never found some of the places on my own!”

Sarah from DC loved the variety on the Sweets and Treats tour: “We started off with doughnuts, tried several types of cookies, and even had unlimited chocolate and gelato! It was fun talking food with the other guests and not feeling guilty for indulging.”

North End Food Tours also specializes in Boston’s Italian quarter, hitting everything from salumerie to bakeries. Tours run daily at 11am and include 6 tasting stops. Guests appreciate the small group sizes and mix of iconic spots like Mike’s Pastry plus mom and pop shops off the beaten path.

Sailor from Seattle said, “This was the highlight of my trip! I tried focaccia, pizza, cheese, olive oil and of course, cannoli. Our guide gave us great tips for exploring more of the North End neighborhood.”

Food Tours of America lets you double down on Italian cuisine with a 2-hour North End Market Tour plus a 2-hour North End Restaurants Tour. It’s the perfect pairing to appreciate this ethnic enclave’s markets, delis, cafes and dining establishments. Tours run weekends only.

Melanie from LA loved the combo: “I got to meet North End shopkeepers and sample their creations, then our guide took us to a fabulous sit-down Italian meal. She knew the restaurant owners so we were treated like VIPs the whole night!”

Urban Adventures serves up food tours with a side of local interaction. Their 3-hour Back Bay experience includes chatting with shopkeepers at the historic Quincy Market. Chinatown tours mean talking with restaurant chefs about regional Chinese fare before eating.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Ride the Duck Boats

No trip to Boston is complete without a ride on the Duck Boats, the city's famous amphibious vehicles that take you on a tour by land and water. These WWII-era vehicles have been transformed into open-air sightseeing boats that splash down into the Charles River halfway through the tour. It's a quirky yet quintessential Boston experience.

Mark from Nashville calls it a must-do: "The Duck Boats are such a unique way to see Boston. We drove by all the famous landmarks like the State House, Faneuil Hall and Beacon Hill. Then suddenly we were plunging right into the Charles River for amazing views of the skyline and bridges."

Tours last about 80 minutes with lively narration from the captains pointing out landmarks and sharing Boston history, trivia and jokes along the way. Guests say the drivers are a real highlight with their enthusiastic personalities and passion for the city.
Duck tours run year-round but are especially enjoyable in summer when the window panels are peeled back for warm breezes off the river. Be sure to dress appropriately as it gets breezy on the water. Rain ponchos are provided when needed. Tours depart frequently from Prudential Center, Museum of Science, New England Aquarium and Faneuil Hall Marketplace.

Tickets cost around $40 for adults and $27 for kids under 12. Book in advance online for the best rates since tours often sell out, especially during peak times. Arrive at least 30 minutes early to snap photos with the Ducks before departure.

While the route varies, all tours cover top landmarks like Cheers Beacon Hill, Old North Church, the gold-domed State House and Bunker Hill. Splashing into the river means cooling breezes and panoramic city views.

Mary from LA loved this unique perspective: "Seeing the Boston skyline from the middle of the Charles River was amazing! It was so fun floating by the harbor, science museum and airport."

The Duck Boats originally served during WWII before becoming popular for sightseeing tours in the '90s. Riding them connects you to Boston's rich maritime history while taking in all the top sites.

Beantown in a Nutshell: Making the Most of 3 Days in Boston - Unwind along the Waterfront

After packing in historic sites, raucous ball games, and indulgent food tours, you'll want to unwind along Boston's scenic waterfront. Here you'll find inviting green spaces, captivating views, and plenty of opportunities for relaxation.

Make your way to Christopher Columbus Park along the harbor for prime people watching and waterfront strolling. Artists, street performers, and food vendors fill this lively 9-acre park from spring through fall. Stake out a bench facing the harbor or spread a picnic blanket on the grassy slope. Watch boats glide across the harbor while snacking on Italian goodies from nearby delis. Let the kids run wild at the park’s nautical-themed playground.
Just next door, Long Wharf stretches nearly a mile along the harbor dotted with restaurants, shops, and ferries. Grab takeout lobster rolls from Yankee Lobster Company and find a perch on the pier to enjoy harbor views. Or hop aboard a boat tour for a cruise around the bay. Architecture buffs should check out the Custom House Tower overlooking the wharf – this iconic 1902 skyscraper was Boston’s tallest for decades.

Farther south, amble along Fort Point Channel appreciating steel and brick warehouses now converted to trendy condos and offices. Pop into DRINK for craft cocktails on their breezy patio right over the water. Kids will marvel at the Old Northern Avenue Bridge, a steel cantilever bridge that looks plucked from the Industrial Revolution.

For more maritime action, cross the channel to Fan Pier. Watch fishing boats unload fresh catches while sea lions circle hoping for snacks. Then make your way to the Institute of Contemporary Art jutting dramatically over Boston Harbor. The cantilevered glass building seems to float right over the water. After admiring cutting-edge art installations, unwind on the museum’s harbor-view deck with a coffee or cocktail.

Just beyond Fan Pier sits the leafy Rose Kennedy Greenway, a mile-long stretch of gardens and fountains perfect for stretching your legs. Pack a frisbee or bike to really enjoy the green space. As you stroll inland, browse the local art and craft booths of the Greenway Open Market. And don’t miss the whimsicalBoston Harbor Fog Sculpturebillowing rings of mist skyward.

Heading back downtown, poke your head into Rowes Wharf Plaza to ogle luxury yachts and gaze across the harbor. The surrounding mega hotels host lively patio bars and restaurants for unwinding. Or simply find a quiet bench along the harbor walk and take in a glowing sunset over the water.

See how everyone can now afford to fly Business Class and book 5 Star Hotels with Mighty Travels Premium! Get started for free.