10 Best Things to do in Boston, Massachusetts

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Planning a trip to Boston, Massachusetts? You’ve come to the right place!

We’ve spent a lot of time exploring Boston, and each visit has only deepened our appreciation for the city’s unique blend of Revolutionary history, passionate sports culture, and vibrant neighborhoods. From our first stroll down the cobblestones of the Freedom Trail to tasting cannoli in the North End and sitting on top of the Green Monster at Fenway Park, Boston quickly became one of our favorite U.S. destinations.

Whether you’re a first-timer or coming back for more, this list of the best things to do in Boston covers the tours, local experiences, and hidden gems that truly make this city shine. Let’s dive right in!

Things to do in Boston, Massachusetts

1. Taste your way around Boston

• Duration: 3.5 hours 
• Time: Multiple departure times from 11 am–4 pm
• Highlights: Sample classic Boston bites and get a personal introduction to the North End’s Italian heritage on this small-group food tour, enjoy enough samples to add up to a full meal, learn local stories and tips
• Inclusions: Guide, all food tastings, private tour (if option selected)
• Rating: 4.8 stars (check 1,000+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

We had a list of food spots in Boston—but no idea where to start or what was actually worth trying. That’s why we booked this North End food tour, and it ended up being the tastiest way to explore one of the city’s most iconic neighborhoods.

Our guide, Jack, was full of energy and clearly loved sharing his city. He mixed in just the right amount of history as we ate our way through this Italian-American enclave, stopping at tucked-away spots we never would’ve found on our own. The kind with handwritten menus, tiny storefronts, and generations-old recipes.

We started with a buttery lobster roll and a rich cup of warm, creamy clam chowder, then wandered through the North End’s brick alleys, sampling fresh brick oven pizza, handmade pasta, and classic Italian pastries like tiramisu and cannoli. They were easily the best desserts we had in Boston!

We also visited Boston Public Market to try local sausage, plus there’s a “secret dish” at the end, and trust us—it’s worth the wait! And don’t let the word “tasting” fool you—it all absolutely adds up to a full meal.

By the end, we were full, happy, and already making plans to revisit a few favorite spots. Do this food tour early in your trip—it’s a great way to get your bearings (and your belly) satisfied.

Book this popular food tour here and eat your way through Boston!

2. Explore the Freedom Trail with an expert guide

• Duration: 2.5 hours
• Time: Multiple departure times from 9 am–4:30 pm
• Highlights: Dive into the history of the American Revolution on this small-group walking tour of Boston, see all 16 official historic landmarks on the Freedom Trail, and learn about the tumultuous time between 1760 and 1775
• Inclusions: Historian guide, all 16 landmarks along the Freedom Trail, Downtown Boston, North End
• Rating: 4.9 stars (check 4,200+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

We tried following the Freedom Trail on our own—but without context, it just felt like a sidewalk with plaques. That’s why we booked this small-group walking tour down the Freedom Trail, and it turned out to be our favorite experience in Boston.

Our guide, Tracy, was an absolute legend! Sharp, funny, and seriously passionate about the city’s past, she made every stop feel like we’d stepped into a turning point in history. 

We started in Boston Common and followed the trail all the way to Copp’s Hill Terrace, stopping at all 16 official landmarks along the way—from the site of the Boston Massacre to Paul Revere’s House. We stood in the Granary Burying Ground next to the graves of John Hancock and Samuel Adams, and at Faneuil Hall, Tracy explained how fiery speeches there helped spark a revolution.

Her storytelling pulled us into the chaos of 1760s Boston, and she had a way of making historical figures feel less like textbook names and more like real people navigating a revolution.

What made it even better was the small group—just 12 of us—which meant we could actually ask questions and have real conversations along the way. It felt personal, relaxed, and packed with substance.

This tour fills up fast (for good reason), so check out thousands of 5-star reviews here and book this one early. You won’t regret it!

Reserve our FAVORITE tour in Boston here before it sells out!

3. Go behind the scenes of the historic Fenway Park

• Duration: 1 hour
• Time: Multiple departure times from 9 am–5 pm
• Highlights: Guided history tour of Fenway Park, revisit the careers of famous Red Sox players, discover stadium artifacts and photographs, relive the Red Sox’s World Series wins
• Inclusions: Professional Fenway Park guide, one-hour tour, access to the Fenway Park Living Museum, sit atop the Green Monster
• Rating: 4.7 stars (check 2,400+ reviews here)
• Free cancellation: No
• Price: Check price here!

We wanted to experience Fenway Park, but not from a cramped seat with no clue about its deeper history. So, instead, we booked this guided tour, and it was the best way to take it all in.

With our guide, Mike, leading the way, we got the full behind-the-scenes experience. We climbed up to the press box, walked through the concourses filled with vintage displays, and even stood beside Pesky’s Pole. Mike had this infectious energy and knew every stat, nickname, and wild story, it felt like we were being shown around by a lifelong fan who somehow knew everyone.

But the best part was sitting on top of the Green Monster, Fenway’s legendary 37-foot/11-meter-high left field wall that’s both a fan favorite and a player’s nightmare. From up there, the view of the field was unreal, and for a second, we imagined what it would be like to catch a fly ball or crush a homer over that iconic green wall.

Mike’s storytelling brought the place to life. He wove together over a century of Red Sox history, from Babe Ruth’s early days to Big Papi’s unforgettable moments. We even wandered through the Fenway Park Living Museum, packed with game-used bats, World Series memorabilia, and photos you won’t find anywhere else.

What made it truly special was how connected we felt. This wasn’t just a stadium tour, it was a deep dive into Boston pride. We left with a whole new appreciation for the Red Sox, the fans, and the city itself!

Experience Fenway the right way and book this popular tour here!

4. Relive the Boston Tea Party at the historic ships and museum

• Duration: 1 hour
• Time: Multiple departure times from 10 am–4 pm
• Highlights: Guided tour of the Boston Tea Party Ships and Museum, explore restored tea ships and throw tea into Boston Harbor, learn how the act began the American Revolution, see historic tea chests
• Inclusions: Live narrated guided tour, skip-the-line admission to the Boston Tea Party Ships and Museum
• Rating: 4.7 stars (check 2,000+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

It’s one thing to read about the Boston Tea Party—but it’s another to stand on the deck of a replica ship and toss “tea” into the harbor yourself. That’s exactly what we did on this guided tour of the Boston Tea Party Ships and Museum. It was an interactive experience that pulled us straight into one of the most pivotal moments in American history.

The tour began at the Meeting House, where costumed guides and echoing protest chants pulled us into the tension of December 16, 1773. It felt like standing in the crowd moments before history was made.

Next, we boarded two replica ships—the Eleanor and the Beaver—and actually tossed “tea” into the harbor, just like the Patriots did. The experience was hands-on and theatrical, with character actors, immersive scenes, and just the right amount of audience participation to pull us into the story.

Inside the museum, we saw original artifacts like the Robinson Tea Chest, one of only two remaining from that night, and watched a short film that tied everything together, from Paul Revere’s ride to the first shots of the Revolution.

We ended in Abigail’s Tea Room, sipping historic tea blends (including some of the same types dumped into the harbor) while chatting with the actors still in character. Even the tea tasting felt like a step back in time!

This isn’t your average museum—it’s part show, part history, and totally memorable. Don’t miss your chance to step into the revolution!

Relive the moment that sparked a revolution, and secure your spot on this tour here!

5. See more historic sights on a bicycle

• Duration: 2.5–3 hours
• Time: 10 am
• Highlights: Guided bike tour exploring Boston’s top attractions, pedal along the Freedom Trail and through areas like Charlestown, Boston Common, Copley Square, the historic North End, Back Bay, and Fenway Park
• Inclusions: City bike or e-bike tour of Boston (depending on option selected), helmets
• Rating: 4.8 stars (check 570+ reviews here)
• Free cancellation: No
• Price: Check price here!

Boston is super walkable—but the neighborhoods are spread out, and we had no idea how to see it all without wasting the day. So, we joined this guided bike tour of the city, and it turned out to be the most efficient (and fun) way to cover a lot of ground without missing the good stuff.

Our guide, Bob, was prepared, easygoing, and full of great recommendations—from historical insights to local food spots we revisited later. After getting fitted for our city bikes (there’s also an option to book an e-bike), we hit the road.

We rode through Back Bay, Charlestown, Beacon Hill, and the North End, weaving through narrow streets and open parks as Bob shared stories from each neighborhood. We pedaled past Copley Square to see Trinity Church and Boston Common, stopping outside Fenway Park to snap photos and hear fun facts about the Red Sox.

There were scenic stretches, too—cruising along the Charles River Esplanade with skyline views reflecting off the water and gliding through the South End’s quiet, tree-lined streets lined with historic brownstones.

Bob pointed out hidden details at spots like the Christian Science Plaza and the Museum of Fine Arts and gave us a local’s take on the Rose Kennedy Greenway, from its rotating art to the best places to grab a snack nearby.

This tour was the perfect way to get a feel for the city early in our trip. Whether you go classic or e-bike, don’t miss the chance to see Boston on two wheels!

Reserve your ride here and see the best of Boston without breaking a sweat!

Related Read: Want to make the most of your time in Boston? Check out our itinerary for how to spend three days here—it covers the must-sees and leaves room for good food and strolls.

6. Step inside Boston’s oldest taverns

• Duration: 3 hours 30 minutes
• Time: 2 pm
• Highlights: Explore historic neighborhoods and iconic taverns, enjoy classic Boston snacks at two stops, take a scenic Boston Harbor ferry ride, see Freedom Trail landmarks like the USS Constitution and Bunker Hill Monument, and end with a famous North End cannoli
• Inclusions: Professional local guide, two beverages, snacks and an appetizer at each tavern stop, scenic ferry ride across Boston Harbor, visit to America’s oldest tavern, cannoli from a famous North End bakery
• Rating: 4.8 stars (check 150+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

There’s something undeniably cool about walking into a cozy old tavern and realizing that people like Paul Revere and George Washington once grabbed a seat in the very same room. That’s the kind of vibe that makes this historic taverns tour so much fun! We love experiences that mix great storytelling with good snacks, and this one has that perfect balance of history, flavor, and a little bit of Boston attitude.

The tour kicks off in the North End, which is already one of our favorite spots in the city. Wandering those narrow brick streets, hearing wild stories you’d never find in a guidebook, and settling in for your first round of tavern bites feels like the ideal way to warm into the afternoon.

The groups are small, which keeps things casual and gives the guide space to share all the quirky, entertaining details that make Boston’s past so interesting.

Then comes one of the best parts: hopping on the ferry across Boston Harbor. It’s such a fun surprise in the middle of a city tour. Between the breeze, the skyline views, and the quick ride into Charlestown, it gives the whole experience this laid-back, adventure-like feel.

What we really love is how easy this tour is to enjoy. You’re learning without feeling like you’re in a classroom, snacking your way through two very different neighborhoods, and getting just enough history to make everything click together. If you want a tour that’s social, tasty, and packed with personality, this is such a fun way to experience Boston.

Taste your way through some of the most iconic taverns and book this tour here!

7. Go whale watching

• Duration: 3.5 hours
• Time: Multiple departure times from 9 am–3:30 pm
• Highlights: Guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary, see humpbacks, finbacks, and the critically endangered right whales
• Inclusions: New England Aquarium naturalist guide, high-speed catamaran, food and beverages available for purchase
• Rating: 4.5 stars (check 2,800+ reviews here)
• Free cancellation: No
• Price: Check price here!

We’d heard whale watching in Boston was a must—but we weren’t sure it was worth spending the day on a boat with no promise of actually seeing anything. That’s why we booked this guided cruise—it guarantees a whale sighting, or you get a free pass to come back and try again. Not only did it take the pressure off, it ended up being one of the most incredible experiences of our trip.

We boarded a high-speed catamaran in Central Wharf and cruised out to Stellwagen Bank Marine Sanctuary, a rich feeding ground just off the coast. The ride was smooth and surprisingly fast, which meant more time with the whales and less time just getting there.

With a naturalist from the New England Aquarium narrating the trip, we knew what to look for and what we were seeing—and it didn’t take long. We watched humpbacks breach, slap the water with their fins, and even roll onto their sides like they were waving at us. At one point, we saw two mothers with calves swimming together and another baby breaching over 20 times. It was unreal!

The naturalists brought the whole experience to life with names, backstories, and conservation info that made us care even more about these incredible creatures.

We came back with amazing photos and a huge appreciation for Boston’s wild side. This is one of those experiences that sticks with you and is easily one of the best things we did in Boston!

Secure your spot on this cruise here and step into Boston’s incredible marine world!

8. Discover Boston’s famous artisanal donuts (and historic sights!)

• Duration: 2 hours
• Time: Multiple departure times from 9 am– 2 pm
• Highlights: Discover and dig into Boston’s artisanal donuts on a walking tour, browse a market, eat a delicious bakery treat, and explore historic neighborhoods such as North End between tastings
• Inclusions: Guide, donuts
• Rating: 4.9 stars (check 820+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

Boston’s donut scene is legit, but most of the best spots are tucked away in neighborhoods you might not wander into on your own. That’s why we booked this donut tour, and it turned out to be one of the most fun (and tastiest) things we did in the city.

Our guide, Catherine, was fantastic. She had deep knowledge of both Boston’s food scene and its history, and she made the whole experience feel personal and relaxed. 

We kicked things off with coffee and donuts from Kane’s, one of the city’s most iconic shops, before heading to Boston Public Market to browse the local food vendors and try warm apple cider donuts. They were perfectly spiced, pillowy on the inside, and finished with just the right sugary crunch!

From there, we explored the Rose Kennedy Greenway and strolled through the North End, stopping at Bova’s Bakery for their take on the Boston cream donut, which was ridiculously good. We wrapped things up at Union Square Donuts, where the rotating flavors stole the show. I still think about the brown butter hazelnut one!

Between the food, fun, and local flavor, the donut tour really hit the spot. But don’t just take our word for it, read hundreds of 5-star reviews here to see why travelers rave about this experience!

Reserve your spot on this one-of-a-kind donut tour here!

9. See Boston’s top sights on a convenient hop-on hop-off trolley

• Duration: 1 or 2 days
• Time: Open hours vary from 9 am–5 pm
• Highlights: Explore the best of Boston on this hop-on hop-off trolley tour, board at one of the stops, then hop off wherever you like, explore independently, and get back onto the bus when you’re ready, or just ride the 2-hour loop in one go
• Inclusions: Narrated trolley tour of Boston, 1 or 2-day trolley pass (depending on option selected), bonus GPS self-guided walking tour via an app, discounts to some top attractions
• Rating: 4.4 stars (check 2,400+ reviews here)
• Free cancellation: Yes
• Price: Check price here!

We really enjoy walking around Boston—but after a few days of cobblestone streets and back-to-back neighborhoods, our feet were begging for a break. That’s why we grabbed a pass for this hop-on hop-off trolley tour, and it turned out to be the perfect way to explore more without wearing ourselves out.

The loop covers all the major neighborhoods and attractions, and you can choose from a one- or two-day pass depending on how much time you have. It was a great way to get our bearings early in the trip and understand how the city was laid out. 

Along the way, we hopped off at Faneuil Hall, the Boston Common, and the USS Constitution, catching quirky facts and historical stories we hadn’t heard before. It added a fun new layer to places we thought we already knew.

One of our favorite stops was the North End—hearing the stories behind it while en route made the neighborhood’s history and charm come alive in a whole new way. The trolley also came in handy later in the day when we didn’t want to trek back from the Seaport or navigate the T, especially with tired legs and a couple of bakery boxes in tow.

This trolley tour is an easy, step-saving way to see the city and sneak in some local knowledge along the way. Whether you ride the whole loop or use it to hop around, it’s well worth adding to your Boston itinerary.

Book your pass here and see Boston one trolley stop at a time!

10. Treat yourself to a chocolate-filled art walk through Back Bay

• Duration: 2 hours 30 minutes
• Time: 11:30 am, 3 pm
• Highlights: Explore Back Bay’s iconic architecture, sample treats from top chocolate vendors, visit two local art galleries featuring works from the 16th to 21st centuries, stroll Newbury Street and Commonwealth Avenue Mall
• Inclusions: Hot chocolate, cookies and cupcakes, chocolate hazelnut cake, visits to two art galleries, professional guide, curated list of the guide’s favorite things to do in Boston
• Rating: 5 stars (check glowing reviews here)
• Free cancellation: Yes
• Price: Check price here!

If you’re all about culture, sweets, and a leisurely city stroll, this Back Bay chocolate and art walk is the pick for you! We’re big fans of experiences that feel a little indulgent but still give you a sense of place, and this one delivers on both fronts. Back Bay has some of the prettiest streets in Boston, so getting to explore it while sampling treats is a very welcome bonus.

The tour starts near the Prudential Center, where you ease into things with your first taste of the day. From there, you wander along Newbury Street, which is packed with boutique shops, galleries, and some of the city’s best bakeries. Between the hot chocolate, cookies, cupcakes, and a slice of chocolate hazelnut cake, you get a full lineup of Back Bay’s sweetest offerings without having to hunt down the right spots yourself.

What really makes this tour stand out is how naturally the art element fits in. You step inside two different galleries with works spanning centuries, and each stop adds a nice break between tastings. It is a great way to see another side of the neighborhood and soak up a bit of Boston’s creative scene. Even the walk along Commonwealth Avenue Mall feels special, with its row houses, sculptures, and tree-lined path that gives Back Bay so much of its charm.

The group size stays small, which keeps things relaxed and gives you time to chat with your guide. It is also a great chance to meet fellow chocolate lovers and browse a few shops before or after the tour. If you want something lighthearted, tasty, and just a little bit fancy, this sweet stroll through Back Bay is a very easy yes.

Book this tasty, eye-opening tour with FREE cancellation here!

Where to Stay in Boston, Massachusetts

Boston is a lively, historic city with no shortage of great hotel options to match every kind of traveler. From high-end luxury stays to cozy mid-range spots and budget-friendly picks, you’ll have no trouble finding a place that suits your needs.

To help you narrow things down, we’ve rounded up the best places to stay in Boston—no matter your budget or travel style. So you can spend less time planning and more time discovering everything in this iconic city!

Luxury – $$$

Located in the heart of Boston’s Back Bay, the Four Seasons Hotel One Dalton Street, Boston blends modern design with unmatched service in a sleek 5-star setting. Floor-to-ceiling windows showcase sweeping skyline views, while amenities like an indoor heated pool, top-tier spa, and gourmet dining elevate your stay. You’re within walking distance of Fenway Park, the Museum of Fine Arts, and the city’s best shopping.

Room rates typically range from $760–$2,000+ USD per night, depending on room type and season. Book your luxury stay now on Booking.com.

Mid-range – $$

Club Quarters Hotel Faneuil Hall, Boston, is a great mid-range stay in the city’s historic Financial District, just steps from Quincy Market and the Freedom Trail. The modern rooms come with free Wi-Fi, flat-screen TVs, and workspaces—ideal for both sightseeing and business trips. Guests love the on-site restaurant, cozy lounge with a fireplace, and complimentary coffee and water stations. The location is hard to beat, with subway access just a few blocks away.

Rooms typically range from $250–$500 USD per night. Check availability for your travel dates on Booking.com.

Budget – $

For budget-friendly accommodation in Boston, HI Boston Hostel is a standout choice! Set in the Theater District just steps from Boston Common, this clean and social hostel offers dorm-style beds and private rooms with en-suite bathrooms. Guests can enjoy a free breakfast, lounge in the game room, or join organized events to explore the city. The location is unbeatable—just minutes from public transit, shops, and restaurants.

Private rooms start at around $200 USD per night, while dorm beds go for about $55 USD. Head to Booking.com to lock in your stay!

For more options, see all of Boston’s hotels listed here!

Related Read: For more hotel options, have a look at our Where to Stay guide that breaks down Boston’s best areas and hotels!

Renting a Car in the USA

The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.

We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.

Tips for Renting a Car in the USA

• Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
• Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
• Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
• Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.

What You Need to Rent a Car in the USA

• A valid driver’s license from your home country.
• An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
• A credit card in the driver’s name is typically required for the security deposit.
• Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.

Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!

Thanks for reading!

We love exploring Boston and hope that this guide has given you plenty of ideas for your trip! From the amazing food to the history around every corner, Boston is one of those cities we plan to keep coming back to. We never get bored here!

If your travels are taking you to other destinations in the U.S., have a look at all our USA blogs here. We have step-by-step itineraries, tour recommendations, and tips to make your trip amazing!

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