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Thinking about spending a few days in Boston? Let’s help you plan your trip.
Boston blends rich history, cutting-edge culture, and some of the best food in the country—all packed into a city that’s easy (and fun) to explore on foot. With a little planning, you can cover the highlights, find a few hidden gems, and still leave time for lobster rolls and waterfront strolls.
After a few trips (and plenty of trial and error), we’ve crafted what we think is the ultimate way to spend three days in Boston. From historic landmarks to local eats you shouldn’t miss, this guide will help you make the absolute most of your time in one of America’s most iconic cities.
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 was this Freedom Trail tour! History came to life as our guide took us by Revolutionary War sights, monuments, and some of the oldest buildings in the country.
Check out the 4,100+ 5-star reviews and book this tour here!
Day 1
Breakfast – The Paramount
Start your first day in Boston the right way with breakfast at The Paramount, a beloved local spot that’s been serving up crowd-pleasers since 1937. Everything is made fresh to order, from massive omelets to thick-cut French toast dusted with powdered sugar.
The vibe inside is casual and bustling as soon as the doors open at 8 am, but the line moves quickly (and trust me, it’s worth the wait). Plus, with dishes averaging around $10–$15 USD, it’s easy on the wallet compared to other spots around Beacon Hill.
Even better, it’s only a 4-minute walk to the meeting point for the first tour of the day—no Ubers or parking headaches needed. Honestly, driving in Boston is a nightmare, so sticking to walking or public transport will save you a lot of time and stress.
Morning – Explore the Freedom Trail with an expert guide
After breakfast, it’s time to dive straight into Boston’s history—and trust me, you’ll want a guide for this. We tried following the Freedom Trail on our own once, but without context, it honestly just felt like a sidewalk with plaques. Booking this small-group walking tour changed everything and ended up being one of our favorite experiences in the city.
Our guide, Tracy, was an absolute legend! Sharp, funny, and unbelievably passionate about Boston’s past, she made every stop feel like we were standing right in the middle of a turning point in history.
We started at Boston Common and worked our way to Copp’s Hill Terrace, visiting all 16 official landmarks—from the site of the Boston Massacre to Paul Revere’s House. Standing in the Granary Burying Ground next to the graves of John Hancock and Samuel Adams was surreal, and hearing about the fiery speeches at Faneuil Hall gave me chills.
Even better, the group was capped at just 12 people, so it felt personal, relaxed, and we could actually ask questions and have real conversations along the way. Tracy’s storytelling made the chaos of 1760s Boston come to life, and historical figures felt like real people, not just textbook names.
Tours start as early as 9:15 am and last about 2.5 hours, so there’s plenty of flexibility to fit this in between breakfast and lunch. With over 4,000 five-star reviews, this popular tour fills up fast—grab your spot early so you don’t miss out!
Reserve our FAVORITE tour in Boston here before it sells out!
Lunch – Quincy Market/Faneuil Hall for lunch
After soaking up all that Revolutionary War history, you’ll probably be ready for a lunch break, and Quincy Market at Faneuil Hall is the perfect spot. This historic market is packed with food vendors serving up just about everything you can imagine. Lobster rolls, clam chowder, giant slices of pizza, cannoli—if you’re craving it, you’ll find it here.
It’s just a 15-minute walk from the end of the Freedom Trail tour, and wandering through the lively hallways is half the fun. We grabbed lunch here and loved being able to sample a few different things instead of sitting down at a traditional restaurant. Plus, the atmosphere is buzzing with street performers, musicians, and plenty of people-watching opportunities while you eat.
Plan to spend about an hour here, though if you want to browse the shops or catch a street performance, you might want to give yourself closer to 90 minutes.
Once you’re done fueling up, it’s time to head toward your next adventure at Fenway Park. Since Fenway is a bit further away, we recommend either grabbing an Uber (about a 12-minute drive) or hopping on public transportation (about 30 minutes).
Afternoon – Tour the historic Fenway Park
No trip to Boston feels complete without stepping inside Fenway Park—and we wanted to do more than just watch a game from a cramped seat. Booking this guided tour turned out to be the best way to experience it.
Our guide, Mike, was a walking encyclopedia with the energy of a true fan. He led us through the press box, past vintage displays in the concourses, and right up to Pesky’s Pole. His stories and trivia made it feel like we had backstage access to Red Sox history.
The best moment? Sitting on top of the Green Monster, Fenway’s iconic 37-foot (11-meter) wall. From up there, the view was unreal—and for a second, we could imagine snagging a fly ball or crushing a homer over that famous green.
We also explored the Fenway Park Living Museum, packed with game-used bats, World Series memorabilia, and historic photos you won’t see anywhere else.
The tour lasts about an hour, with multiple start times throughout the day, so it’s easy to fit in. It does book up fast, though, so you can swap this with the Freedom Trail tour in the morning or explore the museum first if needed.
If you’re in town during baseball season (March/April through September), catching a Red Sox game is a bucket-list experience. There’s nothing like Fenway on game day!
Experience Fenway the right way and book this popular tour here!
Mid-afternoon – Visit the Museum of Fine Arts
After exploring Fenway, it’s time to shift gears a bit and dive into Boston’s incredible art scene. Just an 11-minute walk from the ballpark, the Museum of Fine Arts (MFA) is one of the most celebrated art museums in the world—and trust me, even if you’re not a huge “museum person,” it’s worth the visit.
The collection here is massive, covering everything from ancient Egyptian artifacts to French Impressionist paintings and American classics. We spent a few hours wandering through the galleries and still felt like we barely scratched the surface. Whether you’re into Japanese art, Renaissance masterpieces, or giant contemporary installations, there’s something here that’ll stop you in your tracks.
The museum closes at 5 pm most days, so make sure to time your visit right. (It’s closed on Tuesdays, and stays open later until 10 pm on Thursdays and Fridays—perfect if you want a more relaxed evening visit!) Either way, you’ll have plenty of time to explore some highlights before heading into the evening portion of your day.
Evening – Explore Back Bay
After soaking in the art scene, spend your evening in one of Boston’s most beautiful and stylish neighborhoods: Back Bay. This upscale area is known for its elegant brownstones, trendy boutiques, and a huge variety of bars and restaurants.
It’s about a 26-minute walk from the Museum of Fine Arts if you’re up for a stroll, or a 15-minute ride on public transit if your feet need a break. Either way, we loved just wandering around and popping into shops along Newbury Street, grabbing a drink, and taking in the energy of the area. Back Bay has this lively yet polished vibe that feels very “Boston” without being overly touristy.
When you’re ready for dinner, we highly recommend Joe’s on Newbury. It’s casual but still stylish, with a menu full of comfort food favorites. We grabbed a table outside and enjoyed people-watching while digging into classic New England dishes. Definitely try the lobster roll or the clam chowder if you’re in the mood for something local!
Related Read: If you’re continuing your East Coast travels, check out our 3-day New York City itinerary for the best trip suggestions!
Day 2
Morning – Walk the Rose Kennedy Greenway
Kick off your second day in Boston with a relaxing stroll along the Rose Kennedy Greenway. This beautiful stretch of parks, gardens, and art installations was once a tangled mess of highways—until Boston pulled off one of the most ambitious urban projects in U.S. history, known as “The Big Dig.”
The city buried the highway underground and turned the surface into this incredible greenspace, and you can really feel how proud Bostonians are of it.
We grabbed some coffee and wandered through the Greenway, soaking up the fresh air, public art, and fountains along the way. It’s the perfect low-key start to the morning, and a great chance to take in a different side of the city before jumping into the day’s bigger activities.
Don’t eat breakfast just yet—we’re heading straight into a food tour next, and you’ll want to save room! Bonus: the Greenway is right next to where the tour begins, so you’ll be perfectly positioned to roll into the next stop without needing extra transportation.
Mid-morning – Take a food tour in the North End
After your Greenway stroll, head into one of Boston’s tastiest neighborhoods—the North End. With so many must-try spots and no idea where to start, we booked this food tour, and it turned out to be the most delicious way to explore the city.
Our guide, Jack, was full of energy and clearly loved sharing his hometown with us. He wove just the right amount of history into the experience as we ate our way through the North End’s tucked-away gems. They’re the kind of places with handwritten menus, tiny storefronts, and recipes passed down through generations.
We kicked things off with a buttery lobster roll and creamy clam chowder, then wandered through the North End’s brick alleys sampling brick oven pizza, handmade pasta, and the best tiramisu and cannoli we had on our trip. We also stopped at the Boston Public Market for local sausage. And yes, the secret dish at the end is absolutely worth the wait.
Don’t be fooled by the word “tasting”—it all adds up to a full, satisfying meal.
The tour runs from about 11:00 am to 2:30 pm, with a few other time options if you book a private tour or plan well in advance. It wraps up just around the block from Paul Revere’s House, so if the tour doesn’t include a stop there, definitely swing by afterward to check it out.
By the end, we were full, happy, and already plotting a return trip to our favorite spots!
Book this popular food tour here and eat your way through Boston!
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.
Afternoon – Boston Commons
After filling up on North End treats, spend a relaxed afternoon exploring Boston Common, the oldest public park in America. Steeped in history and right in the heart of the city, it’s the perfect place to slow down, stretch your legs, and soak in some green space.
Wander through the Common and make your way over to the beautiful Boston Public Garden next door. It’s a little more manicured and peaceful, with winding paths, colorful flower beds, and the famous Swan Boats. Yes, it’s touristy, but riding the swan boats across the lagoon is classic Boston!
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!).
Evening – Check out Beacon Hill
Spend your evening in one of Boston’s most charming neighborhoods—Beacon Hill. In the evening, the gas-lit lanterns and cobblestone streets give the whole area this cozy, lively vibe that’s perfect for a sunset stroll.
Start at Acorn Street, one of the most photographed streets in the entire city. With its narrow cobblestones, historic brick row houses, and ivy-draped windows, it feels like you’ve stepped back in time. It’s a quick visit, but it’s iconic and definitely worth seeing while you’re in the area.
From there, take your time wandering through the surrounding streets. Beacon Hill is packed with adorable shops, pubs, and hidden alleyways that are fun to explore, especially when everything’s lit up at night.
When you’re ready for dinner, head over to Antonio’s Cucina Italiano, a cozy local spot known for hearty Italian dishes and a relaxed, welcoming vibe. We loved the homemade pasta and classic red sauce dishes. It’s the kind of no-frills, delicious meal that hits the spot after a full day of exploring.
Drinks – Roxanne’s
After dinner, keep the night going with drinks at Roxanne’s, a cozy spot known for affordable craft cocktails and a laid-back vibe. It’s the perfect place to wind down without the stuffy cocktail bar attitude—just great drinks, good music, and a relaxed atmosphere.
The menu features a creative mix of classics and house specialties, and everything is priced really reasonably for Boston’s bar scene. We loved that it felt stylish without being over the top.
Whether you’re in the mood for a bold mezcal cocktail, a refreshing spritz, or something totally off the menu, the bartenders here are super friendly and always ready to recommend something fun. It’s the ideal low-key finish to a full day of sightseeing, eating, and exploring.
Related Read: Looking for more fun activities? Check out the 10 best things to do in Boston to add to this itinerary!
Day 3
Breakfast – Mike & Patty’s Bay Village
Kick off your third day in Boston with breakfast at Mike & Patty’s in Bay Village—a tiny, beloved sandwich shop that locals can’t get enough of. This cozy spot might be small (there are only a few seats inside), but what it lacks in size it more than makes up for in flavor.
We grabbed breakfast sandwiches here before a busy day of sightseeing, and it was the perfect fuel. Everything is made fresh to order, with golden, buttery bread and creative twists on the classics. The Fancy (with bacon, avocado, cheese, and egg) is my favorite, but you really can’t go wrong with anything on the menu.
Since space is limited, plan to grab your sandwich to go and enjoy it outside if the weather’s nice.
Morning – Check out Chinatown
After breakfast, enjoy a slow stroll through Chinatown as you make your way toward the next tour. It’s about a 30-minute walk from Mike & Patty’s to the tour meeting point, and passing through Chinatown in the morning is an experience all on its own.
The neighborhood is busy and full of life early in the day, with markets setting up, vendors unloading goods, and the streets buzzing with energy. We loved just wandering and taking it all in. Make sure to stop by the iconic Chinatown Gate, a beautiful, historic landmark that marks the entrance to the neighborhood.
Since your next tour doesn’t start until 11:00 am, you’ll have plenty of time to soak up the sights, snap some photos, and maybe even pop into a bakery for a quick sweet treat if you’re still feeling a little hungry. It’s a perfect, easy-paced way to start the morning before diving into the next adventure.
Mid-morning – Visit Boston Tea Party Ships & Museum
It’s one thing to read about the Boston Tea Party, but standing on a replica ship and tossing “tea” into the harbor during this guided museum tour brought the story to life in a way that books and movies never could.
The tour began at the Meeting House, where costumed guides and protest chants pulled us into the tension of December 16, 1773. After the rally, we boarded replica ships and tossed “tea” into the harbor, just like the Patriots. The whole experience was theatrical, hands-on, and filled with immersive scenes and audience participation.
Inside the museum, we explored original artifacts like the Robinson Tea Chest (one of only two left) and watched a short film that tied it all together, from Paul Revere’s ride to the first shots of the Revolution. We finished in Abigail’s Tea Room, sipping historic tea blends and chatting with the in-character guides—even the tea tasting felt like stepping back in time.
There are lots of tour times available, but we recommend aiming for a slot between 11:00 am and 12:00 pm. That way, you’ll have plenty of time afterward to explore the Seaport District, grab some lunch, and make your way over to the harbor for your afternoon whale watching tour.
This isn’t your average museum. It’s part show, part history, and totally unforgettable. Don’t miss your chance to step into the revolution!
Relive the moment that sparked a revolution—secure your spot here!
Lunch – Get a lobster roll from The Barking Crab
After diving into Boston’s revolutionary history, it’s time to refuel with one of the city’s most iconic dishes—a lobster roll from The Barking Crab. This waterfront seafood shack is a Boston classic, and while it’s casual and a little touristy, the lobster rolls here are seriously good. Fresh, buttery, and piled high!
Once you’ve had your fill, spend some time exploring the Seaport District. This area has exploded in recent years with trendy restaurants, bars, shops, and public spaces right along the harbor. If you have extra time, swing by Harpoon Brewery for a quick drink or just enjoy a walk along the waterfront to take in the views.
When you’re ready, it’s about a 17-minute walk from Seaport to the meeting point for your whale watching tour. Give yourself a little extra time to stroll over—the harbor views along the way are part of the fun!
Afternoon – Go whale watching
Whale watching in Boston is a must, but we weren’t sure it was worth spending half a day on a boat with no guarantee of seeing anything. That’s why we booked this guided cruise from Central Wharf, which promises a whale sighting or a free pass to return. It took the pressure off and turned into an experience we’ll be talking about for a long time.
We boarded a high-speed catamaran and cruised smoothly out to the Stellwagen Bank Marine Sanctuary, a rich feeding ground just off the coast. Booking the 2:30 pm tour worked perfectly—we wrapped up around 6:00 pm, just in time for dinner.
A naturalist from the New England Aquarium narrated the trip, and it didn’t take long before we spotted humpbacks breaching, slapping the water, and even rolling onto their sides like they were waving. One of the best moments was seeing two mothers with calves swimming together. A baby whale breaching over 20 times right in front of us!
The naturalists brought the whales to life with names, backstories, and conservation insights that made every encounter feel personal and meaningful. By the end, we weren’t just watching whales, we were cheering for them.
We returned to shore with amazing photos, huge smiles, and a brand-new appreciation for Boston’s wild side. This is absolutely one of those experiences that sticks with you long after the trip is over.
We returned to shore with amazing photos, huge smiles, and a brand-new appreciation for Boston’s wild side. It’s no surprise this tour has over 2,000 five-star reviews—it’s easily one of those experiences that sticks with you long after the trip is over.
Secure your spot on this whale watching cruise here!
Dinner – Carmelina’s
After an unforgettable afternoon on the water, treat yourself to dinner at Carmelina’s, a cozy and highly praised spot in the North End. It’s just an 11-minute walk from where the whale watching tour ends, making it an easy and delicious way to wrap up your day.
Carmelina’s serves up Italian comfort food with a Sicilian twist—hearty pasta dishes, rich sauces, and bold flavors that feel like a warm hug after a full day of exploring. The kitchen is open to the dining room, which gives the whole place a lively, welcoming energy. We loved how every dish felt both traditional and creative at the same time.
Make a reservation online, especially for dinner, as this place fills up fast (and for good reason). It’s the perfect spot to kick back, enjoy a great meal, and toast to your last night in Boston!
Where to Stay in Boston
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!
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!
Three days is the perfect amount of time to experience Boston! In a city as historic and modern as Boston, there is so much to see. But after following this itinerary ourselves, I know that you’ll experience the best of the city in just a few short days!
Before you go, be sure to check out our other USA blogs! We’ve covered a lot of ground in this country and have tons of resources to help you plan your next trip. Here are a few more blogs to inspire your travels – cheers!
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