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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!
Don’t Miss Out On Our Top Choice!
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did in Boston is this walking tour of the Freedom Trail! We were in a small group with an amazing guide who brought history to life as we explored all 16 official historic landmarks. It’s perfect for first-time visitors!
- Don’t Miss Out On Our Top Choice!
- Things to do in Boston, Massachusetts
- 1. Go behind the scenes of the historic Fenway Park
- 2. Explore the Freedom Trail with an expert guide
- 3. Taste your way around Boston
- 4. Relive the Boston Tea Party at the historic ships and museum
- 5. See more historic sights on a bicycle
- 6. Take a day trip to Martha’s Vineyard
- 7. Go whale watching
- 8. Discover Boston’s famous artisanal donuts (and historic sights!)
- 9. See Boston’s top sights on a convenient hop-on hop-off trolley
- 10. Take a sightseeing cruise of Boston Harbor on a historic Tall Ship
- Where to Stay in Boston, Massachusetts
- Thanks for reading!
- Why We Book Tours with Viator
- Renting a Car in the USA
- Don't Forget Travel Insurance!
Things to do in Boston, Massachusetts
1. 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!
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. 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!
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. Take a day trip to Martha’s Vineyard
- Duration: 13 hours
- Time: 7 am
- Highlights: Explore Martha’s Vineyard and Oaks Bluffs on a day trip from Boston, visit Cape Cod with a mini tour of Falmouth, see the Nobska lighthouse, upgrade to include a guided tour of the entire island and lunch
- Inclusions: Driver/guide, ground and boat transport, hotel pickup and drop-off, snacks, bottled water, maps, discount food card, live commentary on board, ferry tickets
- Rating: 4.5 stars (check 340+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Planning a day trip to Martha’s Vineyard from Boston sounded like a headache—messing with ferry schedules, long drives, and figuring out what to do once we got there. That’s why we’re so glad we did this full-day tour. From hotel pickup to ferry tickets, snacks, and water, everything was handled for us, which meant we could just relax and enjoy the island.
Our guide, Matt, was awesome. He shared great stories about Boston, Cape Cod, and the surrounding areas during the drive and kept things fun and informative without overloading us with facts. We even made a scenic stop at Nobska Lighthouse and had time to explore Falmouth’s coastal roads before boarding the ferry to Oak Bluffs.
Once on the island, we opted for the small-group tour upgrade and lunch, and we’re so glad we did. Instead of aimlessly wandering the touristy area near the harbor, we explored all six towns with another guide, who gave us great island insight and fun stories and even pointed out places we wouldn’t have known to visit otherwise.
The return was just as smooth. Matt met us right off the ferry and brought us back to our hotel without a hitch.
This tour made visiting Martha’s Vineyard stress-free and totally worth it. Book the island tour upgrade—you’ll see way more than you could on your own. It felt like a road trip, ferry ride, and sightseeing adventure all in one, and it was one of our favorite days in Boston.
Experience Martha’s Vineyard without the stress, and book this tour here!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator 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. Take a sightseeing cruise of Boston Harbor on a historic Tall Ship
- Duration: 1.5–2 hours
- Time: Multiple departure times from 12-4 pm
- Highlights: Explore Boston by boat with a cruise on the Liberty Star, try your hand at sailing by helping the crew, your captain creates a route depending on wind direction
- Inclusions: Classic tall ship sightseeing cruise of Boston Harbor, drinks and snacks available for purchase
- Rating: 4.7 stars (check 450+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
After a few days of city walking tours, museums, and traffic noise, we were craving something more relaxing. That’s why we booked this sailing cruise on Boston Harbor—and it ended up being the peaceful reset we didn’t know we needed.
We boarded the Liberty Star, a classic schooner with plenty of deck space to stretch out, feel the breeze, and take in the skyline from a totally new angle. There’s something timeless about the creak of the rigging and the snap of the sails—it instantly puts you in a different headspace.
The crew was welcoming and friendly from the start, making sure everyone was comfortable and answering all kinds of questions as we sailed. Watching them hoist the sails and explain how the wind moved us along was surprisingly fun. Gliding across the harbor made the city feel quieter, calmer, and somehow even cooler.
Depending on the wind, your route might pass Fort Independence or head toward the Charlestown Navy Yard and the USS Constitution. Either way, it’s all about relaxing, chatting with the crew, or just zoning out to the sound of the waves.
It was the perfect change of pace in the middle of a busy Boston itinerary. Grab a drink, find a spot on deck, and enjoy one of the city’s most scenic experiences!
Book this tall ship cruise here and get flexible payment options!
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!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
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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