Boston is so pretty! I think I am here at its prettiest time of year: fall. The trees are fiery reds, oranges and yellows and pumpkin displays are on doorsteps, gardens and shop windows.

I have traveled extensively all over the United States, yet for some unfathomable reason, have only just visited Boston!

This post covers my recommendations for where to stay (plus one where not to stay!), things to do and where to eat.

But sometimes when I visit a new place I don’t want to have every hour planned. There’s a wonderful calm and oftentimes magic about wandering, peering, photographing, tasting, turning in another direction and finding a fabulous view or a curious shop.

I have decided that the older I get, the more I want to leave unplanned time for moments of serendipity.

So if you’re like that too, then this post has a bunch of ideas for you to scroll through and see which ones take your fancy, and ignore the rest.

But if you’re the kind of person who likes to go hard-out, peel back the layers and explore your heart out, then you’ll find more than enough things to do in Boston on this list to keep you busy for at least a week!

Of couse Boston is filled with historic sites, most famous for its “Tea Party” in 1773, when 340 chests of tea from England were famously dumped overboard in Boston Harbor, which was just one of the protests that led up to the American Revolutionary War, and ultimately Independence.

The Declaration was signed in 1776 and 2026 marks the 250th birthday of the independance of America. Consequently Boston is a city where today colonial history meets cutting-edge innovation, where cobblestone streets lead to glass skyscrapers and where every neighborhood has its own distinct personality.

I stayed in two neighborhoods and give my hotel reviews below.

*This post contains affiliate links. That means if you make a purchase, I will make a small commission at no extra cost to you.

Getting around Boston

Firstly, one of Boston’s greatest advantages is its walkability. Downtown Boston, Beacon Hill, Back Bay, North End and even Seaport – the main areas you’ll want to visit – are easy to explore on foot, and you’ll discover hidden gems around nearly every corner.

Another way to getting to all the sights without having to taxi is buying a Hop On Hop Off tour ticket. I like to suggest getting a 2-day pass so you can get your bearings on day 1, then use it again the next day when you know where you want to get off and spend a bit more time.

You can also ride the MBTA (affectionately called “the T”) and there is bus service throughout the city. The subway’s four main lines—Red, Orange, Blue, and Green—connect all major neighborhoods and attractions, including North Station for sports fans heading to TD Garden.

Consider getting a CharlieCard for discounted fares, and don’t hesitate to use the commuter rail if you’re venturing to nearby Cambridge or Brookline.

During warmer months, the Bluebikes bike-share program offers another excellent way to navigate the city, with stations throughout Boston and Cambridge.

Plus Uber is a great go-to as nothing is too far and therefore not too expensive. We Uber’d to Harvard and back to Faneuil Hall. I love the flexibility of the app to be picked up and dropped wherever your moments of serendipity find you.

Must-Do Boston Experiences

Take a Duck Tour

Yes it’s kitschy, but with a bonefide comedian as a guide, this tour was a fabulous orientation of the city in a WWII replica amphibian vehicle.

After driving the streets, past historic sights and laughing at so many of the asides and jokes that went over most people’s heads, we drove into the harbor and turned into a boat. We paid our own way on this 80-minute tour and I totally recommend it.

Book your Duck Tour Tickets here >

Walk the Freedom Trail

This 2.5-mile red-brick path is the perfect way to experience Boston’s role in the American Revolution, connecting 16 historical sites from Boston Common to the USS Constitution in the Charlestown Navy Yard. You can take a guided tour or walk it on your own.

We opted for the tour and joined our guide in Boston Common where we set off on foot following the brick Freedom Trail. We stopped at landmarks like the Granary Burial Ground where Samuel Adams lies, Old North Church where Paul Revere’s famous lanterns were hung, Paul Revere House, and Faneuil Hall Marketplace, which has a bustling food hall and souvenir shops to come back to.

It’s a great tour with a passionate guide who walks you through what occured at ach location leading up to the Boston Masacre. Or you can follow the red brick path on your own and do it yourself.

It takes 2.5 hours to walk the trail at a leisurely pace—and is one of the best things to do in the city for learning so much history in a single walk.

Check out this small group Freedom Trail tour >

Visit Cheers Pub

Yep, it’s so cliche for people of a certain age, but as we were staying in Beacon Hill, it was a short walk to the Bull and Finch Pub aka the Cheers Bar, the actual pub used as the exterior of the 1980s hit TV show Cheers, so off we walked the afternoon we arrived.

I expected it to be just another pub inside, but no. They have all the licensed merch you can think of, and two levels of dining and bars that fully embrace the iconic TV show.

While I dived into a bowl of creamy clam chowder, and husband munched on a cheeseburger with an obligatory beer in a Cheers branded mug, 80s music played and all the diners were probably 50+!

Most of the staff are way too young to remember Norm, Diane, Woody, Sam, et al, but the rest of us did!

Wander through Beacon Hill

This picturesque neighborhood features narrow, gas-lit streets along Charles Street and beyond, with brick sidewalks and cute Federal-style rowhouses.

Acorn Street is one of the most photographed streets in America with its cute cobblestones. I had to wait a few minutes for the pouting influencer to leave so I could take my pic.

Visit in autumn to see the fall foliage when the trees are ablaze with color for an especially magical experience. While you’re there, stop by the Massachusetts State House with its iconic golden dome.

Have a drink at The Liberty Hotel

We stayed two nights at the Liberty Hotel (more info below on a few places I recommend to stay) which was once the Charles Street Jail, located in Beacon Hill. An ominous stone prison that was initially lauded for being designed in a humane way.

Unlike the really spooky Eastern State Penitentiary, which was all solitary confinement. (You can read about my terrifying Halloween event experience there!)

But the jail fell into disrepair and was closed in 1990s, only to emerge as a luxry hotel with the metal bars still intact. Come for a drink in the soaring atrium bar or dinner in the Clink – or even stay. You can read my review of The Liberty here.

Walk through Boston Common and Public Garden

America’s oldest public park, Boston Common is a great place for picnicking, ice skating in winter, and people-watching year-round.

The adjacent Public Garden features the famous Swan Boats (closed during winter) and stunning seasonal displays. It holds the title of America’s first public botanical garden, and transforms dramatically with each season, offering something magical year-round on its 24 acres.

Spring is arguably the most spectacular time to visit when thousands of tulips blanket the beds in vibrant colors, typically peaking in late April and early May. The magnolia trees bloom and the Swan Boats return to the lagoon in mid-April for rides through the flowering landscape.

Summer brings lush greenery and a cooling canopy, with families pedaling the boats while ducks and geese glide alongside and children climb on the beloved Make Way for Ducklings bronze statues near the Charles Street entrance.

Autumn transforms the garden into a tapestry of golds, oranges, and reds, with fall foliage typically peaking in mid to late October. The reflection of colorful trees in the lagoon creates fantastic photos (see more of my photo tips for your phone here), and the paths become romantic corridors carpeted with crunching leaves.

Winter after fresh snowfall is a wonderland with snow-dusted trees and the frozen lagoon creating stark, elegant scenes.

The suspension bridge spanning the lagoon serves as the garden’s architectural centerpiece year-round, its Victorian-era design with ornate lampposts transporting you to another era. The garden is open dawn to dusk with free admission, and early morning or late afternoon visits offer the best light and fewer crowds.

Visit the Museum of Fine Arts and Isabella Stewart Gardner Museum

Art lovers will find these among the best museums in the country. Located near Fenway Park, these two museums are world famous yet very different.

The MFA houses an incredible collection spanning continents and centuries, while the Gardner Museum offers a more intimate experience in a stunning Venetian-style palazzo with a gorgeous interior courtyard. Live music performances are also held at the Gardner Museum.

Stroll along the Charles River Esplanade

This scenic parkway offers stunning views of the Boston skyline and Cambridge across the water. It’s perfect for jogging, cycling, or simply relaxing on the grass. The Hatch Shell hosts free concerts with live music during summer months, and nearby beer gardens make it a great spot for evening relaxation.

Visit Harvard University

You don’t have to be a brainiac to go to Harvard! Harvard’s campus is huge, across the Charles River in Cambridge, and is open to the public and you can freely walk through the grounds.

We got an Uber to the Harvard Coop, a book store and souvenir shop filled Harvard goodies, at the intersection of Massachusetts Ave and Harvard St, and walked down to the tree-dotted Harvard Yard, the historic heart of campus with its beautiful brick buildings and tree-lined pathways. Find John Harvard’s and touch the shoe—it’s said to bring good luck.

The main limitations are you can’t go inside buildings. Most academic buildings, dormitories, and libraries (like Widener Library) are restricted to Harvard students, faculty, and staff, so you’ll need to admire those from the outside. But there are some you can.

Free student-led tours are a great option to get a really good feel for the place. They depart from the Smith Campus Center and provide fascinating insights into Harvard’s history, traditions, and student life. The tours are entertaining, informative, and give you access to areas you might otherwise miss. They’re about 45-minutes long.

We spent an hour walking around, taking photos, and enjoying the historic architecture, and browsed the Harvard Book Store, which has all sorts of souvenirs as well as books that make great gifts.

Boston Tea Party Ships & Museum

History buffs shouldn’t miss this interactive museum where you can throw tea overboard just like the colonists did during the American Revolution. It’s one of the fun things to do that brings history to life, and it’s a personal favorite for families and school field trips alike.

It’s located in the river beside Seaport. A good place for lunch for would Jame Hook’s for lobster rolls down here.

Get your Boston Tea Party Museum tickets here >

Take the kids to New England Aquarium

Located on the waterfront, this is a great place for families and anyone who loves marine life. The giant ocean tank is home to sea turtles, including a green sea turtle, along with sharks and hundreds of other species. It’s one of the best parts of Boston’s waterfront attractions.

Museum of Science

Another of Boston’s best museums, this interactive science center offers hands-on exhibits that make it perfect for visitors of all ages. From lightning shows to planetarium presentations, it’s a better place than most to spend a rainy afternoon!

Head to a game or take a tour at Fenway Park

Even if you’re not among the sports fanatics, catching a baseball game at America’s oldest ballpark is a quintessential Boston experience. The energy of Red Sox Nation is infectious and the park’s intimate atmosphere makes every seat feel close to the action.

You can also take guided stadium tours, if you love your baseball history. Check out guided ballpark tours here >

See a Basketball or Hockey game at TD Garden

Always fans of live sport, hubby and me, he got online and bought us tickets to the Celtics.

At TD Garden (home of the Boston Celtics and Boston Bruins), the atmosphere is the main event: loud, proud, and properly Boston. The merch store lured us in and the T-shirt was bought, and I settled on nachos for my dinner. For seats, getting near center (mid-court/center ice) for the best overall view is ideal but pricey. We were in the top corner but had a great time anyway.

Here’s a tip: if you Uber there, walk away from the stadium to get your ride home. It’s a dog’s breakfast trying to get out with roads blocked off and cars jammed up after the game!

Visit Seaport

We moved from pretty Beacon Hill after a couple of nights to Seaport, as I had a blogging conference down there. It was a good opportunity to see two very differnt Boston neighborhoods. There are not a lot of hotels down here, but it’s a vastly different look. All highrise offices, apartments and glass!

The most exciting things was the Christmas market that opened for the holidays when we stayed. (Early November). It’s an ideal location if you’re going on a cruise. In fact that’s that used to be down here, car parking and the port.

Seaport is super close to the Boston Tea Party Museum, and just across the river from James Hook & Co for your lobster roll fix. We actually walked from North End, after visiting Paul Revere’s house and grabbed a lobster roll, then crossed the bridge into Seaport.

You might like to see if the Boston CityPASS is worth it with a bunch of attractions bundled together into one digital pass. It covers four attractions: Admission to New England Aquarium and Museum of Science, admission to any 2 (Boston Harbor City Cruises, View Boston Observation Deck, Franklin Park Zoo, Harvard Museum of Natural History). Check out the Boston CityPASS here >

Or try the Boston Go City Explorer Pass if you want to see everything! This pass gives you discounts on more attractions and tours than CityPASS. Choose any 2, 3, 4, or 5 from about 24 choices, including walking tours and cruiises. Check out the Boston Go City Pass here >

Where to stay in Boston

Beacon Hill

I absolutely loved leafy Beacon Hill and would choose it next time too. It’s within easy walking distance of the Public Garden and the start of the Freedom Trail. It’s cute brick pavements and sitting along the Charles Esplanade.

We stayed at The Liberty Hotel, which I’ve reviewed in this post.

Seaport

After two nights in Beacon Hill, we moved to Seaport as I had a blogging conference over there. Read my views below though as I hated one of the hotels so much we checked out!

Yotel – we stayed the first night and checked out the next day! It’s very chic and super trendy. But oh my, such tiny rooms. I got a corner queen bed room which was small, but actually big enough for our luggage. The issue was the bed. It has a mattress that is bent up like a couch when you walk in, and you press a button to lower it to sleep. However because of that, the mattress is terrible. Talk about roll together. I was still awake at 3am and on my phone trying to find another hotel.

Renaissance – as my conference was down the road at Renaissance, I moved us there. The room was spacious and had harbour views. It’s further to walk from the river and across to North End. But unless you’re on your own, I can’t recommend Yotel!

Another option is The Envoy. That’s located right on the water’s edge, back near Yotel and easy access to North End – and it has a rooftop bar. If money was no object, I’d pick The Envoy next time.

Seaport Hotel Boston is located between Yotel and Rennaissance and would be another good option. Good value. Similar to Yotel in price. I only poked my head in, but the carpet and furnishings looked a bit dated in the lobby bar area. Rennaissance was just more convenient for the conference.

Where to Eat in Boston

Faneuil Hall Marketplace

Yes it’s touristy, but historic hall is now a souvenir shop and there are three marketplace buildings located around it with an incredible variety of food stalls and shops under one roof.

Come here for your lobster rolls and seafood fix! It’s a great spot for groups and picky family members who can’t agree on what to eat, and the people-watching is excellent.

Boston’s North End for Italian Food

Boston’s “Little Italy” is packed with authentic Italian restaurants and bakeries. Choose between Mike’s Pastry and Modern Pastry for excellent cannoli—the rivalry between the two is legendary, and you’ll need to pick a side.

For dinner, Neptune Oyster serves outstanding seafood including an exceptional lobster roll in a cozy setting, though expect a wait.

James Hook & Co

This diner is well-known for serving lobster rolls. Located near the river enroute to Seaport, we got in about 5.45pm and they were closing at 6. There was still a line and with no mucking around, I ordered a lobster roll and a cup of lobster bisque for us to share. When I asked why it was $7 more for melted butter over the mayonaise, the guy said he didn’t know.

So fleeced of the extra $7 I figured I’d better find out. It was a nice add, but woah I could have bought a whole stick of butter for that! They are located in what looks like a shack, deliberately I guess to feel like you’re an old salty. There is outdoor seating and wine is served in plastic cups.

Legal Sea Foods for Classic Clam Chowder

This Boston institution has been perfecting New England clam chowder for decades. Rich, creamy, and loaded with clams, it’s the standard by which all others are judged. Their lobster roll is exceptional too.

Union Oyster House

Dating back to 1826, this is America’s oldest continuously operating restaurant. The oysters are fresh and beautifully presented, and dining here feels like stepping back in time—perfect for history buffs who want their meals with a side of heritage.

South End for Brunch

This trendy neighborhood has become Boston’s culinary epicenter. Try Flour Bakery for incredible pastries and sandwiches, or settle in at The Beehive for brunch with live music.

Try a Boston Cream Pie!

The famous Boston Cream Pie (which is not actually a pie) was invented at the Parker House Hotel, which you will pass on the Freedom Trail. When our guide mentioned it, we made a note and came back to try it!

It’s a cake with custard cream in layers, created by French-Armenian chef Augustine François Anezin. It’s made of two layers of French butter sponge cake, with thick custard, brushed with rum syrup then covered in sliced almonds and chocolate fondant. Boston Cream pie is the official dessert of Massachussets.

Newbury Street

Boston’s premier shopping destination stretches eight blocks through Back Bay, offering everything from high-end designer boutiques to quirky local shops. The Victorian brownstone setting makes window shopping a pleasure.

You’ll find major brands like Sephora and Apple alongside independent stores. Don’t miss Trident Booksellers & Café, a beloved independent bookstore that’s been a local institution since 1984.

Copley Place and Prudential Center

These indoor malls sit across the road from each other and offer a mix of upscale retailers including Neiman Marcus and Tiffany & Co. Perfect for a rainy day or when you need that department store experience.

View Boston is also located at the Prudential Center, so pop up for sweeping skyhigh views over the city and have a bite to eat or a cocktail while you’re up there. Get your View Boston tickets here >

Harvard Square, Cambridge

Cross the river to explore this eclectic shopping district surrounding Harvard University. The Harvard Coop is essential for university memorabilia, while the square’s side streets hide independent bookstores like The Harvard Book Store and Grolier Poetry Book Shop. You’ll also find vintage clothing shops, record stores, and quirky gift boutiques.

SoWa Open Market

Every Sunday from May through October, this South End arts district comes alive with local vendors, vintage sellers, food trucks, and farmers at the popular SoWa farmer’s market. It’s the perfect place to find one-of-a-kind pieces, from handmade jewelry to reclaimed furniture.

The adjacent SoWa Artists Guild features studios and galleries year-round—it’s one of Boston’s best-kept secrets for art lovers.

Charles Street, Beacon Hill

This charming street at the base of Beacon Hill is lined with antique shops, home décor boutiques, and specialty stores. It’s ideal for finding unique gifts, vintage treasures, and classic New England style.

Beacon Hill Books & Cafe is a tiny store and cafe that you may have to wait to get a seat at – and you need to duck your head to walk through the little door!

Blackstone’s of Beacon Hill is perfect for gourmet food gifts, Covet offers curated secondhand and vintage clothing and accessories.

Boomerangs and other vintage treasures

For vintage and secondhand finds, explore the various Boomerangs locations throughout the city, a local thrift chain supporting AIDS Action Committee. Buffalo Exchange in Cambridge and Allston offer curated vintage and contemporary resale.

For serious vintage hunters, The Garment District in Cambridge has a famous “dollar-a-pound” basement where clothing is literally sold by weight.

Downtown Crossing

This pedestrian shopping district centers around Washington Street and features major retailers like Macy’s and Primark, along with smaller shops and street vendors. It’s grittier and more local than Newbury Street, with better deals to be found.

Assembly Row, Somerville

Just outside Boston proper, this newer outdoor shopping center offers a mix of popular chains, restaurants, and a movie theater, all with great views of the Mystic River. It’s easily accessible via the Orange Line and worth the trip for a modern shopping experience.

Local Boutiques Worth Seeking Out

The South End and Jamaica Plain are treasure troves for unique local boutiques. In the South End, check out Patch NYC for whimsical home goods and clothing, or Uniform for minimalist contemporary fashion.

Jamaica Plain’s Centre Street offers eclectic shops like Boomerangs and 40 South Street, which features handmade goods from local artisans.

Where to find the best views in Boston

Skywalk Observatory at Prudential Center

From the 50th floor, you’ll get 360-degree views of Boston, Cambridge, and beyond. The audio tour provides fascinating context about what you’re seeing, and sunset visits are particularly spectacular.

Top of the Hub

Located on the 52nd floor of the Prudential Tower, this restaurant and lounge offers stunning views alongside cocktails and dinner. It’s pricey, but the experience is worth it for a special occasion.

Castle Island and Fort Independence

This South Boston peninsula offers gorgeous harbor views, particularly at sunset. Walk along the waterfront, explore the historic fort, and grab a bite at Sullivan’s, a beloved local spot for hot dogs and fried seafood.

Bunker Hill Monument

Climb the 294 steps to the top of this 221-foot granite obelisk for panoramic views of Boston, Cambridge, and Charlestown. It’s a workout, but the historical significance and views make it worthwhile for anyone interested in American Revolution sites.

Longfellow Bridge

For an iconic view of Boston’s skyline with the Charles River in the foreground, walk or bike across this beautiful bridge connecting Boston and Cambridge. The view is particularly stunning at twilight when the city lights begin to glow.

Insider Tips

Visit the Boston Public Library in Copley Square—it’s an architectural masterpiece with a beautiful courtyard that’s free to explore.

Take the ferry to the Boston Harbor Islands for a quick escape from the city. And if you’re visiting in spring, don’t miss the Boston Public Garden when the tulips are in bloom.

Stay in a couple of locations to explore more than one neighborhood. On this trip we stayed in Beacon Hill and Seaport.

Boston rewards the curious traveler who’s willing to wander beyond the main attractions. Pop into neighborhood pubs, chat with locals in a coffee shop, and don’t be afraid to explore areas like Jamaica Plain, Somerville, or Cambridge. Each has its own character and hidden treasures waiting to be discovered.

Next stop: we took the train to New York City. I wrote this post about the best affordable hotels in New York!