This post was originally published on A Globe Well Travelled in 2016. The content has been revised and updated with fresh information.
My two trips to Boston couldn’t have been more different.
I’ve visited Boston twice — first in August 2011 as part of an organised group tour, and again in January 2016 when I returned with my husband for a weekend getaway. Visiting in the middle of summer and the depths of winter meant I got to see two sides of the city, from its bustling waterfront to its snow-covered parks.
Our winter visit was particularly memorable thanks to an unexpected snowfall. We’d been living in New York City at the time, where winter had been unusually slow to arrive, so seeing Boston covered in snow was a real treat. It ended up being one of my favourite memories from the trip!
What I particularly like about Boston is how much you can fit into a relatively short visit. There’s plenty of history, of course, but also great food, beautiful parks, interesting neighbourhoods, and a few quirky local traditions.
If you’re planning your first visit, here are 12 of the best things to do in Boston, based on what I discovered across my two trips.
Quick summary:
Planning your first trip to Boston? Discover 12 essential activities, from exploring Beacon Hill and following the Freedom Trail to visiting Harvard University and sampling local food. This guide shares my favourite Boston attractions, unique experiences, and practical sightseeing tips.
Recommended tours:
🚶 Official Freedom Trail Walking Tour – Explore 11 historic sites with a period-costumed guide on this 90-minute walking tour.
⛴️ Boston Harbor Historical Sightseeing Cruise – Discover Boston’s maritime history while cruising past the USS Constitution and other famous waterfront landmarks.
🎓 Harvard Campus Tour — Explore the world-famous Harvard grounds on a student-led walking tour.
🍝 North End Secret Food Tour — Taste Boston’s Italian heritage through cannoli, clam chowder, lobster rolls, and more.
12 best things to do in Boston
1. Follow the Freedom Trail
Yes, the Freedom Trail absolutely deserves its spot on every list of things to do in Boston. It’s touristy, sure — but also one of the best ways to understand the city’s past while seeing a huge slice of downtown on foot. The trail is 2.5 miles (4 km) long and marked by a red brick line that winds past 16 historic landmarks, including the Massachusetts State House, Granary Burying Ground, Old South Meeting House, and Paul Revere’s House.
If you want to do the trail independently you can follow this map. I loved how easy it was to follow — you can simply start at the Boston Common Visitor Center and walk at your own pace. It’s a choose-your-own-adventure kind of trail: linger at the spots that interest you, skip the ones that don’t, and stop for food whenever you’re tempted (which… is often).
🚶 If you’d prefer to learn more about Boston’s Revolutionary history, you can join the official Freedom Trail walking tour, led by a guide dressed in 18th-century costume. The 90-minute tour covers 11 of the trail’s 16 historic sites, making it a great option if you’re short on time or don’t want to walk the entire route.
If you’re short on time or energy, you can stop at Copp’s Hill Burying Ground in the North End, which cuts the walk down while still giving you a great feel for the trail.
If you’re following the entire Freedom Trail, you’ll also make your way to Charlestown, where you can explore the historic USS Constitution at Charlestown Navy Yard. I’ve included more about visiting the ship and exploring Boston Harbor in the next section.
2. Explore Boston Harbor and the USS Constitution
Boston has a fascinating maritime history, and one of the best places to discover it is at Charlestown Navy Yard, just across the harbor from downtown Boston. This historic waterfront site is home to the famous USS Constitution, nicknamed ‘Old Ironsides’.
Nicknamed ‘Old Ironsides’, this historic warship was launched in 1797 and is the oldest commissioned warship still afloat. I visited on my first trip to Boston and loved exploring its wooden decks, complete with cannons and an incredible network of ropes and rigging. Best of all, boarding the ship is free!
I also spent some time out on Boston Harbor, where I got some lovely views of the city skyline from the water.
⛴️ If you’d like to do something similar, the Boston Historical Sightseeing Cruise departs from Long Wharf and passes landmarks including the USS Constitution, Bunker Hill Monument, and the North End, with commentary about Boston’s Revolutionary history.
3. Wander around Beacon Hill
Beacon Hill has got to be one of the most adorable neighbourhoods on the planet. Its narrow, gas-lit streets and perfectly preserved 19th-century brick row houses make it one of the most photogenic places in Boston. We spent about an hour just wandering, but honestly, you could easily spend half a day here if you love architecture and charming city nooks as much as I do.
Make sure you walk down Acorn Street, often called the most photographed street in America, though Chestnut Street is just as dreamy and far less crowded. Beacon Hill is also home to cute boutique shops, independent cafés, and plenty of doorways that made me stop every two seconds for a photo. I followed this guide for the route along Chestnut Street and Acorn Street.
4. Explore Boston Common and the Public Garden
Boston Common is America’s oldest public park, dating back to 1634. It’s a lovely place to escape the busy city streets, with wide open lawns, walking paths, and the famous Frog Pond, which transforms into an ice-skating rink during winter.
One of my favourite memories from Boston actually happened here. We’d already explored the Common on our first day, but when it started snowing the following evening, we couldn’t resist going back! We were living in New York City at the time, and it had been an unusually long wait for the first snowfall of the season. We were so excited that we ended up dancing around in the snow like a couple of kids.
Right next door is the Boston Public Garden, America’s first public botanical garden. With its landscaped flower beds, winding paths, and picturesque lagoon, it’s one of the prettiest places in Boston for a leisurely stroll (and for taking a million photos!). I particularly loved the charming footbridge across the lagoon.
If you’re visiting between April and September, you can also take a ride on the famous Swan Boats, which have been operating since 1877. These traditional pedal-powered boats take passengers on a relaxing 10–15 minute ride around the lagoon.
Unfortunately, the Swan Boats weren’t operating during my winter visit, so I missed out on this experience. Tickets can be purchased directly at the dock without advance booking, and adult tickets cost $4.75 USD (as of 2026). Check the official Swan Boats website for current prices and seasonal operating dates.
5. Eat at Quincy Market
Locals will tell you Quincy Market is touristy — and they’re not wrong. But you know what? It’s also full of delicious food, and the architecture alone is worth seeing. The main hall is a long, historic marketplace lined with food stalls offering everything from clam chowder and lobster rolls to flaky pastries, Greek platters, mac and cheese, and baked goods galore.
It’s a great lunch stop if you’re exploring downtown or finishing the Freedom Trail. Grab food from a few different stalls and head outside to the surrounding plazas to eat and soak up the lively atmosphere.
6. Sample some Boston Cream Pie
You can’t visit Boston and skip its namesake dessert — even if it’s technically a cake! Boston Cream Pie is a soft yellow sponge filled with creamy custard and topped with glossy chocolate ganache.
The dessert was invented at the historic Parker House Hotel in 1856, and you can still try the original recipe at the Omni Parker House Hotel on School Street. It’s a great place to stop for a sweet treat while exploring downtown Boston.
I picked up a slice at Café Bella Vita in Beacon Hill (which has unfortunately closed since I visited Boston in 2016), but there are plenty of other spots that now serve excellent versions, such as Flour Bakery.
7. Explore the Boston Public Library
If you’re into architecture, photography, or simply beautiful indoor spaces, the Boston Public Library is a must-see. It’s one of the most stunning libraries I’ve ever visited, with a grand marble staircase, arched windows, and a European-style courtyard that feels like it belongs in Italy rather than New England.
The highlight for me was the Bates Reading Room — a long hall lined with lamps and green-shaded lights that make the whole space glow. It’s quiet, atmospheric, and incredibly photogenic. A quick tram ride on the E Line takes you straight there from downtown, making it an easy stop to add to your Boston itinerary.
8. Explore Harvard University
Harvard is one of the most prestigious universities in the world, and its historic campus is well worth exploring while you’re in Boston. Located in Cambridge, it’s an easy subway ride on the Red Line from downtown Boston, with Harvard Yard just a short walk from Harvard Station.
I’d actually visited Harvard once before, but I still enjoyed wandering around the beautiful old brick buildings and leafy courtyards on my second visit.
We downloaded a self-guided walking tour from the Harvard website, but to be honest, we found it rather difficult to follow. Harvard now has a Visit Harvard mobile app, which may be an improvement from the tour that I followed.
🎓 Alternatively, you can book a guided Harvard Campus Tour which are run by university students. I did this the first time I visited Harvard, and it was great — the guides mix history with funny anecdotes and give you insider knowledge you’d never get on your own.
9. Visit the Museum of Fine Arts
The Museum of Fine Arts is one of Boston’s best attractions, with an enormous collection spanning everything from ancient Egyptian artefacts and European masterpieces to Asian art and contemporary works. You could easily spend a few hours wandering through its galleries.
Some family members had recommended the museum to us, but we were a little put off by the admission price. Luckily, I checked the website before our visit and discovered that we happened to be there on a holiday when admission was free. What a win!
General admission now costs $30 USD for adults (as of 2026), but it’s worth checking the museum’s website for discounts. The museum offers pay-what-you-wish admission on the third Thursday of each month after 5pm (minimum $5), along with occasional free admission days for Massachusetts residents.
10. Eat Italian food in North End
Boston’s North End is the city’s Little Italy — a maze of narrow streets packed with Italian restaurants, bakeries, gelato shops, and centuries-old buildings. It’s one of the oldest neighbourhoods in Boston and one of the tastiest.
🍝 If you can’t decide where to eat, a North End secret food tour is a great way to sample chowder, lobster rolls, cured meats, pastries, and more while learning about the area’s history.
11. Experience Boston’s Irish pub culture
Boston has a famously strong Irish heritage, so it’s no surprise that the city has plenty of Irish pubs (more than in almost any other US city). Visiting at least one is practically a rite of passage!
We chose the historic JJ Foley’s, a historic local favourite that felt like a blend of traditional pub and sports bar. Their pub grub was also on point.
👻 If you’re interested in Boston’s darker history, you could also join a Boos and Brews Haunted Pub Crawl, which visits nine historic and supposedly haunted locations, including four pubs. Along the way, you’ll hear spooky stories about some of Boston’s most famous figures.
12. Try Candlepin Bowling
If you’re looking for something a little different to do in Boston, give candlepin bowling a try. This quirky New England tradition is similar to regular ten-pin bowling, but with tall, narrow pins and smaller bowling balls that don’t have finger holes.
The rules are a little different, too. You get three balls per frame instead of two, and the fallen pins aren’t cleared away between throws, making it surprisingly challenging!
I tried candlepin bowling at Boston Bowl in Dorchester, and it was such a fun way to spend an evening. The venue still offers candlepin bowling alongside regular ten-pin lanes, so it’s a great option if you’re looking for an unusual indoor activity during your Boston trip.
Where to stay in Boston
For a first visit to Boston, I’d recommend staying somewhere central so you can explore many of the city’s attractions on foot. Downtown Boston and Back Bay are both excellent options, with plenty of hotels, restaurants and public transport connections.
Downtown is particularly convenient for the Freedom Trail, Quincy Market and Boston Harbor, while Back Bay is a lovely area close to Boston Public Garden, Boston Public Library and the shops along Newbury Street.
On my last visit, my husband and I stayed at HI Boston Hostel, near Chinatown. It was a great budget-friendly base for sightseeing, with a convenient location and a focus on sustainable travel. If you’re travelling on a tighter budget, it’s still worth considering!
FAQs about visiting Boston
How many days do you need in Boston?
I’d recommend spending 2–3 days in Boston to see the main attractions. My husband and I explored the city over a weekend, but an extra day would be ideal for visiting museums, taking guided tours, or exploring Cambridge.
Is Boston a walkable city?
Yes! Boston is a wonderfully walkable city, with attractions like Beacon Hill, Boston Common, Quincy Market, and the North End all relatively close together. For places further away, the city’s public transport system (known as the T) makes getting around easy.
What is the best time of year to visit Boston?
Autumn (September–October) is especially beautiful for its colourful foliage, while spring (April–May) brings milder weather. I visited in winter and loved seeing Boston dusted with snow, though you’ll need to pack plenty of warm clothing!
Do you need a car to explore Boston?
No, you won’t need a car if you’re staying in central Boston. Most major attractions are accessible on foot or by public transport. We stayed near Chinatown and found it easy to explore the city without a car.
Leave a Reply