Boston Travel Guide: History, Sailing, Food & More!

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Boston is hands-down one of the most scenic and interesting cities in the United States. The Massachusetts capital is like a beautiful waterfront playground with entertainment and activities for people of all backgrounds. The city’s waterfront neighborhoods, colonial architecture, sun-kissed parks and, of course, its cosmopolitan food scene make Boston one of the most beautiful places to visit in the country.

A rather small and very walkable city (compared to, say, New York, Chicago or Los Angeles), Boston is the perfect place to explore on a weekend getaway. So, if you are completely sold and want to venture out and discover the Hub, below we’ve listed some awesome things to do and places to visit that will help you make your stay in Boston a memorable one.

What to Do in Boston

Test your history knowledge with the Freedom Trail.

Boston is arguably the most historical city in the United States. Since its founding in the 17th century, the city has been a significant political, commercial, financial and educational center. The first British settlers founded the 13 colonies starting in New England. Boston is also where the American Revolution first started, where the Boston Tea Party took place and where colonists took a stand against the British at Bunker Hill.

Nowadays, Boston’s most visited neighborhoods are packed with historical sites. A great way to learn more about Boston’s history is to follow the Freedom Trail, a 2.5-mile guided walking tour around Boston’s most historically significant sites like Faneuil Hall, Quincy Market and the Old State House on State Street. You can buy tickets for the tour and get more information about schedules by visiting the Freedom Trail Foundation’s website.

Take a tour of Fenway Park.

Fenway Park is one the smallest, yet most famous, ballparks in the United States.

If you want to experience the city like a true local, you can’t leave without visiting Fenway Park. Bostonians’ pride for their sports teams is an animal of its own kind, and one of the city’s most beloved teams is the iconic Boston Red Sox. Their stadium, Fenway Park, located on Kenmore Square, is part of the National Register of Historic Places and is considered one of the best known sports venues in the world—after all, it is the most Instagrammed place in the state of Massachusetts!

If you are not in town long enough to catch a game, you can certainly take a tour of the ballpark where you will see the Red Sox Hall of Fame, and even have the chance to sit atop of the famous Green Monster! The tours are available every day and last about one hour. You can buy tickets and find more information here.

Sail around the Boston Harbor.

Boston’s Tea Party and Ship Museum seen from the water.

One of the coolest ways to explore Boston is from the water, especially if you are in town in summer or late spring! Yes, there are many cruises and boat tours that could take you around the Charles River or the Boston Harbor, but if you love adventure and are a fan of DIY, there is a much more fun way to do it. You can rent a mini-speed boat at India Wharf Marina in the Boston Harbor and have a 90-minute adventure sailing around the harbor and Quincy Bay. You can go at a gentle pace or pick up a little bit of speed and see the city from its best angle!

The speed boats seat two people and, during the tour, you will see famous sites such as South Station, the Boston Tea Party & Ship Museum, the Charlestown Navy Yard, the Boston Harbor Hotel, JFK Library and other famous places of interest. If you want to rent a boat on a weekend, it is a good idea to reserve it in advance as the tours often sell out in the summer. You can book a time here and see more information about rates and schedules.

Check out the shops on Newbury Street.

Newbury Street in Boston’s Back Bay neighborhood, not far from the iconic Boston Common and the Public Garden, is the most famous shopping area in the city. The street is a popular stop for both locals and visitors, not only for the commercial nature of the district but because of its scenery and history. Newbury Street has broad tree-lined sidewalks and its buildings, almost all erected in the 19th century, feature European design elements. Back in the 1800s, the entire neighborhood was a part of the Boston Harbor.

Nowadays, the street is also very well-known for housing Boston’s high-end fashion shops, from famous designers to independent and local artists. It has even been called the ‘Rodeo Drive of the East!’ Also, in the summer, Newbury is usually filled with outdoor performers, musicians and various street vendors.

Stroll around Harvard University.

Harvard University’s Memorial Hall was built to honor the veterans of the American Civil War.

As you may have seen in many movies, Harvard University is the oldest and perhaps the most famous university in the United States. An icon of the state of Massachusetts’ education tradition, Harvard is one of the eight Ivy League schools and has often been recognized as one of the best higher education institutions in the world.

The main campus stretches across the center of Cambridge in the ever vibrant neighborhood of Harvard Square and is always open to the public. The most iconic part is the Harvard Yard, where you will see many of the campus libraries, the Memorial Church, academic buildings such as Saver Hall and University Hall, and several freshman dormitories. If you visit in the summer, most college students will be gone and you will be able to peacefully stroll around and enjoy the beautifully eclectic architecture the campus features – from colonial buildings and Ivy-classic brick structures like Massachusetts Hall to Romanesque and Bauhaus exponents like Harkness Commons. Also, another attraction on campus is Memorial Hall, a Victorian Gothic building just north of the Harvard Yard that commemorates the victims of the American Civil War.

Harvard has made history for being the oldest higher education institution in the country and also for the achievements and world recognition earned by its graduates. The university is the alma matter of some of America’s (and the world’s) most remarkable leaders such as John F. Kennedy, Theodore and Franklin D. Roosevelt, U.N. Secretary General Ban Ki-moon and President Barack Obama.

Businessman and entrepreneur Mark Zuckerberg actually created the social network Facebook during his time at Harvard. Also, Hollywood stars Matt Damon, Natalie Portman and Ashley Judd, as well as late-night host Conan O’Brien, hold degrees from Harvard University.

Find a place to eat.

Brazilian picanha and feijoada with Guaraná Antartica, Brazil’s most iconic soft drink.

Boston’s food scene is as diverse and rich as the city itself. The coastal location allows for fresh seafood delicacies to hit the tables daily, but Boston has much more to offer than clam chowder and scallops. Options are countless, as food from across the globe can be found in the many ethnic neighborhoods of Beantown.

Go to Chinatown for noodles and dumplings, check out the North End for pasta and cannoli, hit Jamaica Plain for jerk chicken and empanadas! There are so many options for grub that it can be overwhelming, so here are some recommendations on where to find the some of best food in the area.

Oasis Brazilain Steakhouse in Medford

A typical Brazilian meal at Oasis: picanha, sweet fried plantain, fried cassava and mixed greens with  raisins and farofa.

The Boston area is home to a large Brazilian community. Along with their love for futebol, they have brought to Massachusetts their amazing cuisine traditions. Meat, beans, sweet plantains, cassava and pork are some of the main ingredients that make Brazilian food so fantastic (apologies to any vegan readers).

A great place to explore Brazilian culture and eat like a local is Oasis Brazilian Steakhouse, a famous eatery in west Medford, around 20 minutes north of Boston. It would be a sin to watch a Brazil game and not try a bowl of feijoda (pork and black beans stew), picanha (sirloin) and mandioca freita con linguica (deep fried cassava with pork sausage).

Rincón Limeño in East Boston

Peruvian cuisine is known worldwide for the freshness and spiciness of its dishes, and even though the Peruvian community in Boston is smaller than the Brazilian, there are many places where you can try Peru’s most iconic dishes.

The best Peruvian eatery, hands down, is Rincón Limeño in East Boston, which serves specialties like ceviche, tiradito, causa and suspiro limeño.

Food Trucks at the Rose Kennedy Greenway

More than 30 food trucks offer lunch options during the summer at the Rose Kennedy Greenway.

The Rose Kennedy Greenway, a long public parks area that stretches on Atlantic Avenue from Boston’s South Station to the North End, is the perfect place to take a walk (or a nap), observe the flower gardens, and connect with nature in the middle of Boston’s Financial District. But also, it’s the perfect place to eat—especially if you are an adventurous foodie on a budget.

In the summer, the Greenway usually features more than 30 food trucks offering treats and exotic meals. You can try Vietnamese noodles from Bon Me, buttery sandwiches from Roxy’s Grilled Cheese, ice-cream cookie sandwiches from The Cookie Monstah, jerk chicken from Jamaica Mi Hungry, Mexican tortas from Tenoch, and many other yummy treats!

The Boston Burger Company

As you can see, Boston has a lot to offer in the ethnic cuisine department, but the eating tour doesn’t end there. Another trend that has shaped the city’s food scene is the reinvention of some American classics, and in the case of this place, the reinvention of decadent grass-fed Angus burgers.

Boston Burger Company is one the most famous spots among Boston’s meat lovers. The company has three locations (Boylston Street in Boston’s Back Bay neighborhood, Davis Square in Somerville and Mass Avenue in Cambridge) and their menu includes some of the most innovative, and one could say exotic, burgers out there: the King has peanut butter, bacon, and fried bananas; the 420 Burger has mozzarella sticks, fried mac ‘n’ cheese, onion rings, fries, bacon, bbq sauce and cheese; the Pilgrim (a turkey burger) has homemade cranberry mayo, stuffing and American cheese.

Where to Stay

Boston offers visitors accommodation options to fit every budget, from high-end boutique hotels to hip hostels and modern Airbnbs. Here, you will find some ideas to help you figure out where to stay based on your preferences.

Hostels Downtown

If you stay downtown, you will be a short walk away from the famous Boston Common.

Boston is a popular destination for Millennials and, as you might know, they are often on the lookout for cheap deals. Therefore, to satisfy this demand, the city of Boston has plenty of hostels where you can share a room for just a few bucks and be sure you’re staying right in the heart of town.

One of the best hostels is Hostelling International Boston, a trendy, super-clean and friendly staffed space in Boston’s Theater District, close to the Boston Common, Faneuil Hall and most train lines. You can read more about HI Boston and book here.

Book a ticket to Boston on Wanderu.com or by downloading the Wanderu app, and enjoy your visit to Beantown! 

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About the author
Karina Barriga Albring

Karina Barriga Albring

I'm a writer, journalist, soccer lover and hot sauce enthusiast born and bred in the mighty Andes. Wanderlust hit me hard at a young age and since then, it keeps me up at night. NYC and Modena, Italy changed my life, but my favorite destination is still Rio de Janeiro – and not only for the 'futebol'!
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