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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. Taste your way around Boston
- 2. Explore the Freedom Trail with an expert guide
- 3. Enjoy Boston’s most iconic green spaces
- 4. Eat, shop, and wander at Faneuil Hall and Quincy Market
- 5. Go behind the scenes of the historic Fenway Park
- 6. Relive the Boston Tea Party at the historic ships and museum
- 7. Discover marine life along the waterfront
- 8. Go whale watching
- 9. See more historic sights on a bicycle
- 10. Step inside Boston’s oldest taverns
- 11. Visit Boston’s renowned museums
- 12. Discover Boston’s famous artisanal donuts (and historic sights!)
- 13. See Boston’s top sights on a convenient hop-on hop-off trolley
- 14. Explore Harvard Square & Harvard University
- 15. Treat yourself to a chocolate-filled art walk through Back Bay
- Where to Stay in Boston, Massachusetts
- Thanks for reading!
- Why We Book Tours with Viator
- Renting a Car in the USA
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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, and learn local stories and tips
- Inclusions: Guide, all food tastings, private tour (if option selected)
- Rating: 4.8 stars (check 1,400+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
You might have a long list of food spots in Boston, but no idea where to start or what’s actually worth trying. That’s where this North End food tour comes in, offering one of the tastiest ways to explore one of the city’s most iconic neighborhoods.
As you eat your way through the North End, a knowledgeable local guide shares context and history along the way, while leading you to tucked-away spots you likely wouldn’t find on your own. Think handwritten menus, tiny storefronts, and recipes that have been passed down for generations. It’s an easy-to-follow route, but you’ll be on your feet, so comfortable shoes are a good idea.
The tour typically kicks off with a buttery lobster roll and a rich cup of warm, creamy clam chowder before winding through the neighborhood’s brick alleys. Along the way, you’ll sample fresh brick-oven pizza, handmade pasta, and classic Italian pastries like tiramisu and cannoli. It’s easily some of the best desserts you’ll find in Boston!
You’ll also stop by Boston Public Market to try local sausage, plus there’s a “secret dish” waiting at the end. And don’t let the word “tasting” fool you—everything adds up to a full, satisfying meal, so it’s best to arrive hungry.
By the end, you’ll be full, happy, and probably already planning a return visit to a few favorite spots. Doing this food tour early in your trip is a great way to get your bearings and your appetite completely 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 4,400+ 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. Enjoy Boston’s most iconic green spaces

One of the best things to do in Boston is surprisingly simple—head outside and let the city’s historic parks do the rest. Boston Common is the oldest public park in the U.S., and while you may stop here if you do the #2 Freedom Trail tour, it’s worth coming back on your own to slow things down and actually enjoy it. We loved wandering the wide paths, watching locals picnic or walk their dogs, and taking a breather in the middle of the city’s constant buzz.
Right next door, the Public Garden feels like a completely different world. It’s more polished and peaceful, with winding paths, colorful flower beds, and a scenic lagoon that’s especially beautiful in spring and summer.
This is where you’ll find the famous Swan Boats, which operate seasonally—typically from spring through fall. Yes, they’re touristy, but drifting across the water is a classic Boston experience. Don’t miss the Make Way for Ducklings statues by Nancy Schön either. They’re a quick stop, but they’re one of the city’s most beloved landmarks.
Before you leave the area, take a quick two-block detour to Copley Square to see Trinity Church. This historic church is one of Boston’s most iconic landmarks, and its striking architecture makes it well worth a short stop, especially if you’re into photography. The reflections from the nearby Hancock Tower are amazing!
4. Eat, shop, and wander at Faneuil Hall and Quincy Market


If you’re hungry in Boston, there’s a very good chance you’ll end up at Faneuil Hall and Quincy Market—and for good reason. This historic marketplace is one of the city’s most popular spots for food, shopping, and people-watching, all packed into one lively area. It’s the social heart of Boston, where local culture, street performers, and nonstop energy come together.
Quincy Market is filled with food vendors serving just about everything you can imagine. Lobster rolls, clam chowder, oversized slices of pizza, cannoli—if you’re craving it, you’ll find it here. We grabbed lunch here and loved being able to sample a few different things instead of committing to a sit-down restaurant. If you haven’t tried a lobster roll in Boston yet (or you’re ready for another one), this is the perfect place. Boston Chowda Co and Wicked Lobsta are both solid go-to options.
Beyond the food, the surrounding Faneuil Hall Marketplace is fun to explore on foot. The open-air spaces are usually buzzing with street performers and musicians, and there’s plenty of shopping if you want to browse between bites. Some tours pass through this area, but it’s much better experienced on your own, so you can wander freely and take it all in.
Plan to spend about an hour here, though if you want to browse the shops or stop to watch a street performance, giving yourself closer to 90 minutes is well worth it.
5. 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, and relive the Red Sox’s World Series wins
- Inclusions: Professional Fenway Park guide, one-hour tour, access to the Fenway Park Living Museum, and sit atop the Green Monster
- Rating: 4.7 stars (check 3,000+ 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.
If you aren’t visiting Boston during baseball season, this is a great way to dive into Red Sox fandom. It’s not just a stadium tour; it was a closer look 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!
6. 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 2,500+ 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 this guided tour of the Boston Tea Party Ships and Museum lets you do, turning a major moment in American history into a fully interactive experience.
The tour begins at the Meeting House, where costumed guides, heated dialogue, and protest chants pull you straight into the tension of December 16, 1773. It feels like being dropped into the middle of the crowd just before history unfolds.
From there, you’ll board two replica ships, the Eleanor and the Beaver, and take part in the most famous moment of the night by tossing “tea” into Boston Harbor. The experience is hands-on and theatrical, with character actors, immersive storytelling, and just enough audience participation to make it memorable without feeling awkward.
Inside the museum, you’ll see original artifacts like the Robinson Tea Chest, one of only two known to survive from that night. A short film ties everything together, connecting the Boston Tea Party to events like Paul Revere’s ride and the first shots of the American Revolution.
The experience wraps up in Abigail’s Tea Room, where you can sample historic tea blends, including some similar to those dumped into the harbor, while continuing the conversation with actors still in character. It’s a fun, unexpected way to end the visit!
Relive the moment that sparked a revolution, and secure your spot on this tour here!
7. Discover marine life along the waterfront


If you’re looking to mix iconic sights with something a little different, discovering marine life along Boston’s waterfront—penguins included—is a great place to start. The New England Aquarium sits right on the harbor and is especially popular with first-time visitors thanks to its central location and easy-to-navigate layout.
Inside, the massive central ocean tank steals the show. You can spiral your way up around it while watching sharks, rays, and tropical fish glide through the water. The aquarium is also home to playful penguins, colorful reef fish, and a wide variety of marine life that makes the experience fun even if you’re not usually an “aquarium person.” Admission runs around $34 USD, and it’s well worth it if you want a break from walking while still seeing something memorable.
Even if you don’t go inside, the area around the aquarium is worth exploring. The outdoor penguin viewing areas are free, and they’re a fun, quick stop along the waterfront. From here, take a walk along the Boston Harborwalk or head toward nearby Long Wharf for some of the best harbor views in the city. You’ll see boats, ferries, and the skyline all in one place, making this an easy spot to slow down and enjoy Boston from a different perspective.
8. Go whale watching


- Duration: 3.5 hours
- Time: Multiple departure times from 10 am–3:30 pm (available from mid-May through October)
- 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: 4.4 stars (check 3,100+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
You may have heard that whale watching in Boston is a must, but also wonder if it’s worth spending a day on the water with no guarantee of seeing anything. That’s what makes this guided whale-watching cruise such a solid choice—it comes with a sighting guarantee, meaning you can come back for free if whales don’t make an appearance. It takes the pressure off and lets you fully enjoy the experience.
The tour departs from Central Wharf aboard a high-speed catamaran and heads out to Stellwagen Bank Marine Sanctuary, a nutrient-rich feeding ground just off the coast. The ride is smooth and surprisingly fast, which means less travel time and more time spent where the whales actually are.
Along the way, a naturalist from the New England Aquarium narrates the trip, pointing out wildlife and explaining what you’re seeing. Humpback whales are frequent visitors here, and it’s not uncommon to watch them breach, slap the water with their fins, or roll onto their sides at the surface.
The naturalists add depth to the experience by sharing names, behaviors, and conservation insights that help you appreciate just how special this ecosystem is. Between the views, the wildlife, and the educational aspect, this cruise offers a powerful look at Boston’s wild side—and it’s an experience that tends to stick with you long after you’re back on land.
Secure your spot on this cruise here and experience Boston’s incredible marine world!
9. See more historic sights on a bicycle


- Duration: 2.5–3 hours
- Time: 10 am (available from March through October)
- 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 600+ 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.
10. 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!
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.
11. Visit Boston’s renowned museums


Boston is one of the best cities in the U.S. for museum lovers, with world-class institutions covering art, science, and history. Whether you’re traveling with kids, visiting for the first time, or just want a break from walking, these museums are some of the city’s most popular and rewarding places to spend a few hours.
Museum of Science
If you want something hands-on and high-energy, the Museum of Science is an easy win. This massive space is filled with interactive exhibits covering everything from space and engineering to biology and climate science. It’s especially fun if you’re traveling with kids, but adults will find plenty to stay engaged too. Plan to spend a few hours here—tickets run about $33 USD, and time tends to fly by.
Museum of Fine Arts, Boston
Art lovers will want to make time for the Museum of Fine Arts, Boston (MFA), one of the largest and most impressive art museums in the country. With more than 100 galleries, the collection spans ancient Egyptian artifacts, Impressionist paintings, American classics, and modern works. Even if museums aren’t usually your thing, the variety here makes it easy to find something that grabs your attention. Entry costs around $30 USD.
Isabella Stewart Gardner Museum
For a museum experience that feels completely different, the Isabella Stewart Gardner Museum stands out. Designed like a Venetian palace, it’s centered around a stunning indoor courtyard and filled with intimate, eclectic galleries. The museum is also famously tied to one of the largest unsolved art heists in history, which adds an extra layer of intrigue as you explore. Tickets are about $22 USD and well worth it for something truly unique.
12. 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 1,000+ 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!
13. 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 (available from April through November)
- 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 2,800+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Boston is a great city for walking, but after a few days of cobblestone streets and back-to-back neighborhoods, a break from all that foot traffic can be very welcome. That’s where this hop-on, hop-off trolley tour comes in, offering a comfortable way to see more of the city without wearing yourself out.
The loop covers Boston’s major neighborhoods and attractions, and you can choose between a one- or two-day pass depending on how much time you have. It’s especially helpful early in a trip, giving you a better sense of how the city is laid out while making it easy to move between sights.
Along the route, you can hop off at places like Faneuil Hall, Boston Common, and the USS Constitution, picking up quirky facts and historical stories along the way. Even familiar landmarks tend to feel more interesting when you hear the background behind them as you go.
The North End is another standout stop, with stories shared en route that help bring the neighborhood’s history and character to life. The trolley is also handy later in the day when you don’t feel like trekking back from areas like the Seaport or navigating public transit with tired legs.
Overall, this trolley tour is an easy, step-saving way to explore Boston while learning a bit more about the city along the way. Whether you ride the full loop or use it to hop between highlights, it’s a flexible and practical addition to any Boston itinerary.
Book your pass here and see Boston one trolley stop at a time!
14. Explore Harvard Square & Harvard University

If you’ve ever wondered what it feels like to stroll through one of the most famous universities in the world, Harvard Square is the place to do it. Just across the river in Cambridge, Harvard University is the oldest university in the U.S., and walking through its campus feels like stepping into a piece of American history—without needing a tour or a plan. It’s easy to get here on the Red Line, making it a simple trip from downtown Boston.
Start in Harvard Square, the lively heart of the area, where cafés, bookstores, street performers, and students rushing between classes give the neighborhood its nonstop energy. From there, wander into nearby Harvard Yard to explore the campus itself. The historic brick buildings, leafy courtyards, and quiet paths make it easy to slow down and soak in the atmosphere, even on a busy day.
What we love most about this area is the mix of old and new. One minute you’re walking past centuries-old buildings, and the next you’re grabbing coffee, browsing a bookstore, or stopping to watch a street performance. It’s casual, lively, and completely different from downtown Boston, making it a fun change of pace and one of the most enjoyable places to explore on foot.
15. 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!
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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!
How to Spend THREE DAYS in Boston, Massachusetts: 3-Day Itinerary
How to Spend THREE DAYS in New York City: 3-Day Itinerary
25 BEST Things to do in Washington, DC
10 BEST Tours in Philadelphia for Food, History, and Hidden Gems

