Best of Beantown: Where to Eat, Drink, and Explore in Boston

Revisit the Largest Art Heist in History at the Isabella Stewart Gardener Museum

Art enthusiasts will be captivated by the Isabella Stewart Gardner Museum. Housed in a stunning 15th-century Venetian-style palace, the museum features an eclectic collection of art, from European, Asian, and American pieces to rare books and manuscripts. The lush, indoor courtyard garden is a highlight, offering a tranquil spot to admire the beautiful surroundings. It's also famous for being the place where the largest art heist in history took place. The vandals were never caught - and due to the museum's founder stipulating the museum never be changed, the empty frames of the stolen paintings still hang in the museum to this day.

Eat and Shop your way through Back Bay

Go to a Game or See a Concert at Fenway Park

No trip to Boston is complete without visiting Fenway Park, one of the most famous and beloved baseball stadiums in the world. Home to the Boston Red Sox, Fenway offers an authentic slice of Americana. Whether you’re catching a Red Sox game or attending a concert, the energy and history of this iconic venue are palpable. Be sure to take a tour of the park to learn about its storied past and see the legendary Green Monster up close.

Wander Along the Rose Kennedy Greenway

The Rose Kennedy Greenway is a mile-and-a-half-long series of parks and public spaces that wind through several Boston neighborhoods. This urban oasis is perfect for a relaxing walk, featuring art installations, fountains, gardens, and even a carousel. During the warmer months, the Greenway hosts food trucks, markets, and various events, making it a vibrant hub of activity. It's a great way to see the old-school charm of Chinatown and the South End, as well as the sprawling and swanky Financial District.

Recreate the Most Famous Protest in History at the Boston Tea Party Ships & Museum

History buffs will relish a visit to the Boston Tea Party Ships & Museum. This interactive museum brings to life the events of December 16, 1773, with live reenactments, multimedia exhibits, and the opportunity to toss tea into the harbor. It’s an engaging way to learn about a pivotal moment in American history.

Have A Pastry Contest in the North End

The North End of Boston is also known as "Little Italy" and it is home to so many fantastic restaurants. You can't go to Boston without having a slice at Regina Pizzeria, some clam chowder at Neptune Oyster, and most importantly sampling cannoli from Mike’s Pastry, Modern Pastry, and Bova to see who has the best (Spoiler Alert: It's Mike's).

See the Good Will Hunting Bench in Boston Commons

Boston Common, America’s oldest public park, offers a serene escape in the heart of the city. Spread across 50 acres, it’s perfect for a leisurely stroll, a picnic, or even a swan boat ride on the adjacent Public Garden’s lagoon. In winter, the park transforms with an ice-skating rink at Frog Pond, making it a year-round attraction.

Grab a Drink Where Everybody Knows your Name

Fans of the iconic TV show "Cheers" can visit the bar that inspired it. Located on Beacon Street, the Cheers Bar is a beloved spot for both tourists and locals. The exterior is instantly recognizable, and inside, you’ll find memorabilia and a replica of the TV show’s set. Enjoy a meal or a drink and soak in the nostalgia of this famous watering hole.

Prematurely Blue Yourself at the Blue Man Group

For a unique and unforgettable entertainment experience, catch a performance by the Blue Man Group at the Charles Playhouse. This quirky and innovative show combines music, comedy, and multimedia theatrics to create an evening of fun and surprises that will leave you in awe. Although the Blue Man Group seems like a Vegas act, and it did start in New York, it’s actually been running in Boston just as long - and some of the performers in Boston have been Blue men for over 15 years. 

Learn about our History on the Freedom Trail

The Freedom Trail is a 2.5-mile-long path that takes you through 16 of Boston’s most significant historical sites. Starting at Boston Common and ending at the Bunker Hill Monument, the trail includes landmarks like the Massachusetts State House, Paul Revere’s House, and the Old North Church. Follow the red brick path and delve into the rich history that shaped the nation.

Hop Aboard A Duck Boat

One of the most unique ways to see Boston is by taking a ride on a Duck Boat. These amphibious vehicles offer an engaging and informative tour of the city's historical landmarks on both land and water. Departing from several locations, the Duck Boat tour provides a comprehensive overview of Boston's history, architecture, and culture, culminating with a splash into the Charles River for a memorable aquatic adventure.

Get Artistic at the WNDR Museum

The WNDR Museum is a relatively new addition to Boston’s cultural landscape, offering an immersive experience that blends art, technology, and science. This interactive museum features a variety of exhibits designed to engage all your senses and provoke thought. Each installation is an adventure, providing a unique opportunity to explore the boundaries of creativity and innovation.

Get Lost in the Charm of Beacon Hill

Stepping into Beacon Hill feels like traveling back in time. This historic neighborhood is renowned for its picturesque streets lined with gas lamps, brick sidewalks, and beautifully preserved Federal-style row houses. Acorn Street, one of the most photographed streets in America, is a must-see. Don't miss Louisburg Square, home to some of Boston's most exclusive residences. While you’re in the area, visit the Boston Athenaeum, one of the oldest independent libraries in the United States.

The can't miss stop has to be Beacon Hills Books & Cafe, which is the most adorable bookshop on earth, it's 3 stories with a 3rd floor that has mini doors for kids, and a train that runs across the top of the walls through tunnels into other rooms. It also has an incredible (but small) cafe perfect for brunch, just be prepared for a long wait.

Joanne Chang All Day, Every Day

Joanne Chang is a celebrity chef and baker who started in Cambridge and was known in college as the "Chocolate Chip Cookie Girl", but has gone on to win many James Beard awards and open up 10 bakeries in Boston known as Flour Bakery. The entire menu is delicious but we highly recommend the stick buns or cinnamon rolls, you can't come to Boston and not stop at Flour. She and her husband also opened up a new age Chinese restaurant in the South End called Myers + Chang which is a buzzy and delicious destination for dinner (don't miss the pork belly bao buns).