Boston Tours, Trips & Vacations 2024 / 2025

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Storm the fort at Castle Island

Being a city built on the harbor that opens right up to the Atlantic Ocean, Boston’s rich history surrounds the sea. Castle Island is no exception to this: this little island is home to a huge fort, which was once a line of defence against any naval invaders. Today, it’s just a fun place to go visit. Located right on Pleasure Bay, next to the strip of South Boston’s beaches, explore the fort and climb to the top for a view of the city. If it’s a nice day, be sure to pack a picnic: this sunny spot is the perfect place to enjoy a summer beer.
Tour Harvard

Harvard University is an icon of Boston. While most of us won’t ever get to attend this legendary institution, that doesn’t mean we can’t get a feel for what life is like in its little village. Take a few hours to wander around the Harvard Grounds, or better yet, jump on a student-led walking tour. You’ll be able to see some of its most iconic sites, including Harvard Square, which is lined with food stores and retailers, the Harvard Memorial Church (which you’ll definitely recognise from a few Hollywood movies) and the Sackler Art Museum.
Visit the Boston Public Library

We get it, you’re probably not that keen to study while you’re on holiday. But trust us, a trip to the Boston Public Library won’t feel like homework. This magnificent building was founded in 1848 and has one of the biggest collections in the US – second only to the Library of Congress – including early copies of Shakespeare. But it’s not the books that are the highlight of this activity; it’s the opulence of the architecture. Walk through the halls to discover marble staircases, incredible chandeliers and Italian Renaissance-inspired murals. Once you’re done drooling over the interiors, take a breather in the courtyard. You’ll instantly feel like you’ve been transported to baroque Europe.
See the Symphony Hall

Another regular cameo star in Hollywood movies, Boston’s Symphony Hall is one of the city’s most treasured sites. Built in 1900 to house the Boston Symphony Orchestra, this building is still home to that same orchestra today. While you’re more likely to catch a classical show, the occasional contemporary performance pops up every now and then. If you’re a music lover and keen to go behind the scenes, you’ll be able to join a tour of the Symphony Hall. Usually led by members of the Orchestra or other insiders, discover the stories of the great musicians, composers and conductors who have filled these halls.
Watch a match at the legendary Fenway Park

Boston and baseball go together like peanut butter and jelly. Fenway Park is considered something like a sacred site for baseball fans, especially lovers of the Boston Red Sox. This Major League baseball team has a rich history of its own, boasting some of the game’s best players, like Babe Ruth, Tim Williams and Carl Yastrzemski. Enjoy America’s favorite pastime like the locals do, sitting for hours in the summer sun with a beer in hand. When you get hungry, grab a hotdog or a lobster roll. And the best part? Asking locals to explain the rules of the game is a great way to make friends who can show you around the city.

Things to do in Boston

Boston Early Music Festival
Music

Bostonians are proud of their history and culture, and they really let it show at this festival. The Boston Early Music Festival is a not-for-profit festival that celebrates classic music. Staging Shakespearian plays and Baroque Operas, even if you’re not into classical music, you’ll enjoy this – if nothing else but for the medieval costumes.
Together Boston
Music

Together Boston is an annual music festival that emphasises the unity of music, art and technology. Filled with awesome light and tech installations and hosting some impressive line ups, this festival is a little intellectual and a little avant garde. It’s usually held around September each year.
Outside the Box
Music

Outside the Box is a free, week-long festival that begins on the Fourth of July. Founded and supported by late philanthropist Ted Cutler, this proud Bostonian’s vision for the festival was to promote Boston’s thriving arts culture and get people dancing on streets. Largely filled with musical acts, Outside the Box also hosts a variety of other artists and performers.
Chocolate Festival
Food

Every year, the Harvard Square Business Association throws a huge party in celebration of chocolate. And we’re very okay with that. Find rows of vendors selling delicious chocolate-themed treats. Down all that good stuff and then dance off your sugar rush to the sounds of local musicians playing in the square. Sounds pretty sweet to us.
Boston Pops Fourth of July
Culture

The Fourth of July – or American Independence Day – is one of the biggest holidays in the US. If you find yourself in Boston over this festive time, get yourself down to Boston Pops. Held at the Edward A. Hatch Memorial Shell, an outdoor amphitheatre on the Charles River Esplanade in Boston, you’ll find a night of free music, fireworks and good vibes.

Top 5 Festivals in Boston

Bostonians love a good party and a bit of culture. If music is your thing, rest assured it really sings in Boston. Art lovers and foodies, fear not: there are a few festivities here for you, too. Here are our picks for the top 5 festivals to hit up in Boston.

USS Constitution

Located in the Charlestown Navy Yard, the USS Constitution Museum is a part of the Boston National Historical Park. What was once a former boatyard, this museum is an ode to the Boston Navy Fleet, specially the USS Constitution. The museum is full of naval history and stories of those who once sailed this grand ship.
Isabella Stewart Gardner Gardens

A patron of the arts, the Isabella Stewart Gardner Museum was opened in 1903 by Isabella herself. This Venetian-inspired building houses a huge collection of European, Asian and American Art. But the real draw card is its stunning, manicured gardens. This place will give you a taste of that silver spoon life.
Institute of Contemporary Art

The Institute of Contemporary Art was founded as the Boston Museum of Modern Art in 1936, with its very first show an exhibition of Paul Gauguin’s masterpieces. Located on the river in South Boston, this minimalistic building exhibits a variety of contemporary art, including video installations and performance art.
John F. Kennedy Presidential Library and Museum

Located next to the Harvard University Campus, the John F. Kennedy Presidential Library and Museum acts as both a place of study, as well as the place that houses the complete records of the Presidential era. Even if you’re not interested in politics, the building itself is a stunning example of 20th century modern architecture. Snap it for the ‘gram.
Harvard Museum of Natural History

You’d expect one of the finest institutions in the world to have a killer museum, and the Harvard Museum of Natural History really steps up to the plate. Drawing from three of the university’s research schools, discover insects, marine life and dinosaur skeletons in amazing displays.

Top 5 Museums & Galleries in Boston

As one of the oldest and most political cities in the US, Boston is rich in history. Culturally quite progressive – and home to some of the best universities in the world – there’s so much to learn about history, art and science in Boston. Here are our picks for the best Boston museums.

Secret burger
It’s hard to go wrong with a burger in Boston, but if you’re going out of your way to find something special, get yourself down to Craigie on Main. Their secret burger is regarded as one of the best in the city. If you want to get your hands on it, you better get down there early: they only make 18 of these bad boys a day.

_{Best eaten at}
_{Craigie on Main, 853 Main St, Cambridge, MA 02139}
Boston Cream Pie
Did you even go to Boston if you didn’t have a Cream Pie? This buttery sponge cake is filled with custard or cream and topped with chocolate glaze. While you can find this delicious dessert anywhere, go back to the place that created the icon: Omni Parker House.

_{Best eaten at}
_{Omni Parker House, 60 School St, MA 02108}
Brown Butter Lobster Roll
If you’re going to catch a ball game at Fenway Park, make sure you experience it like a true Bostonian. Swing by Eventide Fenway and pick up a lobster roll. Crispy, fried lobster chunks are nestled in a hotdog bun and drowned in brown butter sauce. Will it be one of the best things you’ll ever put in your mouth? Probably.

_{Best eaten at}
_{Eventide Fenway, 1321 Boylston St, MA 02215}
Torta
Somewhere between a taco and a burger, the tortas at Tenoch Mexican restaurant will really hit the spot. Soft, chewy telera bread are stuffed with beans, chipotle mayo, avocado, cheese and salad. And the meat? Choose between pork, chicken, fish or beef fillings. Go with friends so you can try everything.

_{Best eaten at}
_{Tenoch Mexican, 3 Lewis St, MA 02109}
Baked Alaska
Contrary to its name, Baked Alaska isn’t really from Alaska; it’s from Louisiana. But Oleana Mediterranean Restaurant does an amazing bite-sized rendition: coconut icecream and passionfruit caramel on top of a cakey base, which is all smothered in meringue. And then set on fire. It will take all of 2.5 seconds for this to become your new-favorite dessert.

_{Best eaten at}
_{Oleana, 134 Hampshire St, Cambridge, MA 02139}

Food in Boston

Burgers, cream pies and brown butter on everything: Boston really knows how to eat. For some good local grub, chow down on a lobster roll and clam chowder. Once you’ve ticked off all the American staples, branch out and try some of the variety of flavors, including some amazing Mexican and Mediterranean fusion.