Boston, a city steeped in American history, is renowned not only for the Red Sox baseball team and New England Clam Chowder but also as the birthplace of the American Revolution. Visiting Boston, you’ll be captivated by its rich history, vibrant culture, and iconic landmarks. While three days might seem insufficient to fully explore this capital city’s beauty, a meticulously designed Boston Massachusetts walking tour allows you to maximize your trip.
Day 1: Exploring Boston from the Water and Local Cuisine
Boston is surrounded by water, with nearly a quarter of its area being water, including Boston Harbor, the Charles River, and a portion of the Atlantic Ocean. This unique location bestows Boston with remarkable privileges, breathtaking scenery, fresh seafood, and countless exciting riverside activities.
To begin your Boston exploration, energize yourself with lunch at Boston Sail Loft Restaurant, a popular spot near the New England Aquarium. Here, you can savor renowned local dishes like clam chowder, lobster rolls, and excellent local beers. Boston Sail Loft’s clam chowder is particularly praised for its delicious flavor and fresh ingredients. Don’t forget to buy an extra portion to take away for later!
In the afternoon, experience a Whale Watching Cruise combined with a visit to the New England Aquarium. You can choose to take the cruise in the morning and explore the aquarium in the afternoon, or vice versa. Either way, this will be an unforgettable experience during your Boston trip.
Boston Harbor skyline at nightBoston Harbor skyline at night
The whale watching cruise is equipped with a modern catamaran, among the largest and most comfortable available, featuring outdoor observation decks and air-conditioned indoor cabins with comfortable seating, snacks, and drinks. Experienced naturalists will accompany you, sharing fascinating insights about whales as the cruise heads to Stellwagen Bank National Marine Sanctuary, a rich feeding ground for whales, dolphins, seabirds, and other marine life. You’ll have the chance to admire various large whale species such as humpback whales, finback whales, and minke whales, as well as other rare whale species. City Cruises is a proud member of Whale SENSE, committed to responsible whale watching practices. The whale watching tour lasts approximately four hours, but your exploration journey is far from over!
The New England Aquarium is a global leader in ocean conservation and discovery, as well as a popular visitor attraction and a major public education resource in the region. The centerpiece of the aquarium is the Giant Ocean Tank, located in the center of the main building. This 200,000-gallon tank simulates a Caribbean coral reef with over 1,000 marine animals. Visitors can gently touch cownose rays, Atlantic rays, and epaulette sharks at the Ray Touch Tank, then explore Science of Sharks with shark species from around the world. The lively penguin colony surrounding the Giant Ocean Tank is also a special attraction. Here, you’ll see over 60 penguins, each named and with educational information about their species. The two penguin species living at the aquarium are African penguins and Rockhopper penguins. Next, head to the Edge of the Sea tide pool, where you can feed starfish, hold hermit crabs, and encounter lobsters. Aquarium educators are always available to answer your questions about these marine creatures. The New England Aquarium offers exciting experiences for visitors of all ages.
Jellyfish in an aquarium tankJellyfish in an aquarium tank
Conclude your day of exploration by strolling along Newbury Street, one of the most expensive streets in the world. This area is famous for dining and entertainment, with beautiful 19th-century brownstone buildings housing hundreds of retail stores and restaurants. Visit Amorino Gelato Al Naturale to indulge in sweet treats like hot drinks, macarons, waffles, crepes, and especially their renowned gelato.
Day 2: Discovering Boston’s History on a Walking Tour
Day two is dedicated to exploring Boston’s colonial and American Revolution history with the Old Town Trolley Tour Silver Pass. The convenient double-decker trolley will take you to 18 famous stops throughout the city, allowing you to hop on and off at your leisure. Throughout the journey, you’ll hear live narration about Boston’s history.
Your first stop is Faneuil Hall Marketplace, the “home of free speech” and the “Cradle of Liberty.” Faneuil Hall was once the site of America’s first Town Meeting. Although not initially intended for revolutionary political activities, it became a gathering place for events that shaped national history. Local artisans and craftspeople display handmade products on wooden carts, creating a distinctive historical atmosphere. Over 40 local businesses sell unique handcrafted items, attracting many visitors each year. Tourists and locals gather here to enjoy world-class street performances, from juggling and acrobatics to various other acts.
Cobblestone street in BostonCobblestone street in Boston
Hop off the trolley at the Seaport District, where you’ll find the Boston Children’s Museum, Boston Fire Museum, and Boston Tea Party Ships & Museum. Here, you can stroll along the waterfront, shop for souvenirs, enjoy dining, and explore. The Institute of Contemporary Art is a unique architectural structure made of metal and glass, prominently situated on the water.
The Boston Children’s Museum is an ideal destination for families, with award-winning exhibitions and programs designed for children and families, covering science, culture, and the arts. Founded by a group of teachers in 1913, the Boston Children’s Museum pioneered the “hands-on” approach. To this day, it remains one of the few children’s museums in the United States to maintain a collection of artifacts. Check the museum’s activity schedule in advance as they often change throughout the year.
Next, join the Two if by Sea: Paul Revere’s VIP Freedom Trail Tour, the most comprehensive Freedom Trail walking tour in Boston. The tour lasts approximately 3 hours, and weekend operating hours may vary, so it’s advisable to check the schedule beforehand. Enjoy a private guided tour and follow in the footsteps of Paul Revere at his former home in the North End. A highlight of the tour is a private visit to Old North Church, the oldest church in the city. This church is famous for the event where Robert Newman and Captain John Pulling, Jr. climbed the steeple and hung two lanterns, signaling to Paul Revere that the British troops were advancing to Lexington by sea, not by land. This event ignited the American Revolution.
Paul Revere’s House is the next stop on the journey. On the night of April 18, 1775, Paul Revere left this house to begin his legendary ride. Today, the house still stands, becoming a national historic landmark and the oldest building in Boston in the greater metropolitan area. Paul Revere’s life was long and filled with contributions in industry, politics, and public service. On the night of April 18, 1775, he received news and set out for Lexington to warn John Hancock and Samuel Adams about the approaching British troops. An obituary in the Boston Intelligencer remarked, “seldom has the tomb closed upon a life so honorable and useful.” He is buried in Boston’s Granary Burying Ground.
Take a moment to reflect at the site of the Boston Massacre, where after months of tension due to taxes and occupation, Boston residents and British soldiers clashed on the streets of Boston, resulting in the deaths of five civilians. This event led to protests against the Crown, forcing troops to evacuate Boston and paving the way for the American Revolution.
Fenway Park in BostonFenway Park in Boston
Boston’s most beloved landmark is Fenway Park, home of the Boston Red Sox baseball team. It’s a must-visit destination for sports enthusiasts and history buffs alike. The park is famous for its uniquely shaped field and the towering left-field wall known as the Green Monster. Dedicate about an hour to tour this iconic baseball stadium.
After a long day of exploration, head to the North End for dinner at La Summa Cucina Italiana. This cozy family-run restaurant is a hidden gem you shouldn’t miss. Although slightly tucked away, La Summa Cucina Italiana is worth the search for its excellent service and delicious food.
A trip to Boston wouldn’t be complete without a sweet cannoli from Mike’s Pastries. End your day of exploration with this famous cannoli, a treat that has captured the hearts of both Bostonians and visitors for years.
Day 3: Exploring Salem – The Mystical Witch City
On the final day of your Boston exploration, take time to visit Salem via the Salem Ferry. The 50-minute ferry ride offers stunning views of the Boston skyline, Salem, and the New England coastline. Enjoy snacks and drinks onboard before embarking on your Salem adventure.
Your first destination in Salem is the Real Pirates Salem Museum, which preserves over three hundred years of pirate history. Here, you’ll discover real treasures, real pirates, and the story of pirate captain “Black Sam” Bellamy. This family-friendly tour provides an authentic experience of the slave ship Whydah, along with over fifty other ships that “Black Sam” Bellamy captured. You’ll witness the only authenticated pirate treasure in the world ever recovered. Allocate about two hours to explore this museum. The museum opens at 10:00 AM daily.
Salem is renowned for its fresh seafood, and this small coastal town has plenty of restaurants to choose from. Try Turner’s Seafood, an excellent family-owned restaurant located inside the historic Lyceum Hall, famous for serving the freshest seafood, shipped from Turner Fisheries of Boston.
Next, visit the Salem Witch Museum to explore the story of the most infamous witch hunt in Western history. The Salem witch trials remain a haunting event. The museum recreates the dramatic scene of the dark period of 1692 through life-size stage settings, figures, lighting, and narration. Note that some parts of the museum have sensitive themes, which may not be suitable for young children. Spend about an hour at this exhibition.
If you’re traveling with children, consider visiting the Peabody Essex Museum during your Salem exploration day. This museum appeals to all ages with hands-on activities, discovery drawers, games, and interactive computer stations. Take advantage of the free Gallery Explorer Kits, which help children engage in a museum-wide scavenger hunt.
Before leaving Salem to return to Boston, don’t forget to visit Ye Olde Pepper Candy Companie, the oldest continuously operating candy store in America, to buy a special gift or indulge in tempting sweets.