Boston, MA: A Weekend Travel Itinerary
Boston, the vibrant capital of Massachusetts, effortlessly blends history, culture, and modernity, making it an ideal weekend getaway. Rich in historical landmarks, world-class museums, and picturesque neighborhoods, Boston teems with activities and attractions for exploration. What's more, getting to this captivating city is a breeze, thanks to its conveniently located airport. Having lived in Boston for seven years after university, I have had the opportunity to uncover some hidden gems and create a curated list of my favorite things to do and recommend to visitors. This ultimate itinerary is perfect if you're visiting Boston for either 2 days or 3 days.
Friday
4:00 PM: Check-in at the Kimpton Nine Zero Hotel
Kick off your weekend with a stay at the Kimpton Nine Zero Hotel, located in the heart of downtown Boston. The hotel's stylish decor and amenities, including a complimentary wine hour, make for a comfortable and convenient stay.
6:00 PM: Dinner in the Seaport:
The Seaport District, once an industrial area, has transformed into one of Boston's most vibrant neighborhoods. It's a hub for innovation and modern living, boasting a stunning waterfront setting. This area is known for its sleek architecture, upscale restaurants, and trendy bars. The Institute of Contemporary Art (ICA) is a highlight here, offering cutting-edge art in a striking building with waterfront views. The Seaport also has a variety of outdoor spaces, including the scenic Harborwalk, perfect for leisurely strolls along the water. Shopping enthusiasts will find a range of boutiques and high-end stores, making it a fashionable destination for retail therapy.
Nautilus Pier 4: This waterfront restaurant offers a fusion of global seafood in an upscale, nautical-themed setting. Perfect for those who enjoy inventive seafood dishes and a lively atmosphere.
Lola 42: A trendy spot known for its sushi and diverse menu that includes everything from burgers to bao buns. Ideal for diners looking for variety and a chic environment.
Committee: A Mediterranean-inspired eatery that serves meze-style dishes, perfect for sharing. The vibrant decor and creative cocktails make it a great spot for a fun, social meal.
Row 34: Specializing in fresh seafood and craft beer, this industrial-chic restaurant is a must-visit for oyster lovers and those who appreciate a refined, yet laid-back ambiance.
SUNSET: View from Harbor Walk
A scenic waterfront path offering stunning views of the Boston skyline and historic sites.
8:00 PM: Game Night at Puttshack or Flight Club
After dinner, head to a game bar like Puttshack or Flight Club for some fun and friendly competition. These bars offer interactive games like mini-golf and darts, as well as delicious drinks and snacks.
Saturday
9:00 AM: Breakfast at Tatte Bakery
Start your day with breakfast at Tatte Bakery, a Boston institution known for its delicious pastries and coffee. The chain has several locations throughout the city, but the Beacon Hill location is particularly charming.
10:00 AM: Walk the Freedom Trail
No trip to Boston is complete without a walk along the Freedom Trail, a 2.5-mile route that takes you through the city's most historic sites. Start at Boston Common and end at the Bunker Hill Monument, taking in landmarks like the Massachusetts State House and Paul Revere's House along the way.
12:00 PM: Lunch Options along the Freedom Trail
Neptune Oyster: Famous for its intimate setting and exceptional seafood, especially the lobster roll. Ideal for a classic New England seafood experience.
James Hook & Co: A no-frills, counter-service spot known for its fresh lobster and seafood sandwiches. Perfect for a quick, authentic taste of Boston’s seafood.
Kured: Specializing in artisan charcuterie boards, this place is perfect for those who enjoy a casual yet sophisticated lunch with a variety of meats and cheeses.
2:00 PM: Tour Fenway Park
Take a tour of Fenway Park, home of the Boston Red Sox. The hour-long tour takes you behind the scenes of the historic ballpark, from the Green Monster to the dugout. Even if you're not a baseball fan, it's an incredible experience and worth the time!
4:00 PM: Visit the Isabella Stewart Gardner Museum
End your afternoon with a visit to the Isabella Stewart Gardner Museum, a stunning museum housed in a Venetian-style palazzo. The museum features an impressive collection of art and artifacts, including works by Titian, Rembrandt, and John Singer Sargent - there's even a scandal that remains one of the most notorious art heists in history.
6:00 PM: Dinner in the South End
The South End is a picturesque neighborhood known for its Victorian brownstone buildings and a rich history. It's a favorite among foodies, artists, and young professionals. The area is renowned for its diverse dining scene, featuring everything from high-end restaurants to cozy cafes and bistros. The South End is also a cultural hotspot, with numerous art galleries, studios, and the Boston Center for the Arts. The neighborhood has a strong community feel, reflected in its charming local markets and community gardens. Its tree-lined streets and parks, like the Southwest Corridor Park, add to its serene and inviting ambiance.
Toro: A renowned Spanish tapas restaurant offering a wide array of dishes in a lively, rustic setting. Great for those who enjoy sharing and trying different flavors.
Barcelona: A wine bar and restaurant that serves a variety of Spanish-influenced small plates in a warm, inviting atmosphere. Ideal for wine enthusiasts and foodies alike.
B&G Oysters: A modern yet cozy oyster bar known for its extensive selection of oysters and classic seafood dishes. A must-visit for oyster lovers.
Kava: A Mediterranean neo-bistro, offering a unique blend of flavors in a sleek and modern setting. Perfect for an elegant, flavor-packed meal.
8:00 PM: Bar Recommendations
Lolita Back Bay: An edgy and stylish Mexican-inspired cocktail bar, known for its gothic ambiance and extensive tequila and mezcal selection right off Copley Square. Perfect for those who enjoy a vibrant atmosphere with a hint of mystery.
Hecate: A chic, witchcraft-themed bar offering an intriguing cocktail menu in a mystical setting. Ideal for those looking for a unique and enchanting night out.
Mariel: A Cuban-inspired bar with a lively atmosphere, serving up classic and innovative cocktails. The vibrant decor and Latin music make it a great choice for a fun, energetic evening.
Bar Pallino: A modern, minimalist wine bar focusing on natural wines. This spot is perfect for wine connoisseurs and those seeking a relaxed, sophisticated environment.
Yvonne's: A trendy and eclectic speakeasy-style bar, offering creative cocktails and a swanky, hidden-away feel. Ideal for those who appreciate a blend of the modern and the vintage.
Offsuit: An intimate, hidden gem known for its bespoke cocktails and stylish, cozy ambiance. Perfect for a more low-key, personalized drinking experience.
Krasi: A Greek wine bar with a lively vibe, offering a wide selection of Greek wines and small plates. A great choice for those looking to explore unique wines in a bustling setting.
Zuma: An upscale, contemporary Japanese restaurant with a sophisticated bar area, known for its sake and innovative cocktails. Ideal for those seeking a luxurious and modern Asian-inspired experience.
JJ Foley's: One of Boston's oldest and most traditional Irish pubs, offering a wide range of beers and classic pub fare in a warm, inviting atmosphere. Perfect for those who enjoy a classic pub experience with a rich history.
Bukowski Tavern: A laid-back bar with locations in Cambridge and Boston, known for its extensive beer selection and quirky, literary-themed decor. It's ideal for beer lovers and those seeking a casual, hip atmosphere.
No. 9 Park: An elegant bar located near the Boston Common, known for its sophisticated cocktails and upscale ambiance. This is a great choice for those looking to indulge in a more luxurious night out.
The Beehive: A bohemian-style bar and eatery in the South End, known for its live jazz music, eclectic decor, and an excellent selection of cocktails and wines. It's perfect for those seeking a lively, artistic atmosphere.
Bell In Hand Tavern: As one of America's oldest taverns, located near Faneuil Hall, it offers a historic feel with a selection of beers and pub fare. Live music and a lively crowd make it a fun, casual spot.
Sunday
9:00 AM: Breakfast at Flour Bakery
Start your day with breakfast at Flour Bakery, a local favorite known for its delicious baked goods and coffee. The sticky buns and breakfast sandwiches are particularly popular.
10:00 AM: Explore the Boston Public Library
After breakfast, head to the Boston Public Library, one of the oldest and most beautiful libraries in the country. The library's architecture and impressive collection of books and manuscripts make it a must-visit for book lovers.
12:00 PM: Lunch at Quincy Market
For lunch, head to Quincy Market, a historic marketplace that's home to dozens of food stalls and restaurants. Sample a variety of local favorites, from lobster rolls to clam chowder.
2:00 PM: Unique Experience
Cap off your weekend with one of Boston's unique experiences.
Tour of Harpoon Brewery: Dive into Boston's craft beer scene with a tour of the Harpoon Brewery. Learn about the brewing process, explore the facility, and enjoy a beer-tasting session. Ideal for beer enthusiasts and those curious about local brews.
The View – Boston’s Indoor/Outdoor Observatory: Experience breathtaking views of the city from this observatory. Whether you choose the indoor or outdoor option, you'll get a panoramic perspective of Boston's skyline, making it a great activity for photographers and sightseers alike.
Public Tour of Harvard University: Walk through the historic grounds of one of the world’s most prestigious universities. The tour provides insights into the university's history, architecture, and famous alumni. Perfect for history buffs and those interested in academia.
Kayaking on the Charles River: For a more active experience, rent a kayak and paddle along the Charles River.
Boston Duck Tour: Explore Boston by land and water on a unique amphibious vehicle. These tours offer a fun and informative overview of the city's major landmarks. It's a family-friendly option that combines education and entertainment.
Visit the New England Aquarium: Immerse yourself in marine life at the New England Aquarium. With a variety of sea creatures, including a giant ocean tank, it’s a fascinating visit for all ages, especially for those interested in marine biology and conservation.
Boston Ghost Tours: Dive into the spooky side of Boston with a ghost tour. These tours highlight the city’s haunted history and mysterious past, making it an intriguing option for those who love a bit of eerie storytelling.
Stroll through the Boston Public Garden: Unwind with a leisurely walk through this beautiful park. The garden features stunning floral displays, sculptures, and the famous Swan Boats. It's a peaceful escape that showcases the city's natural beauty and is perfect for relaxation and photography.
4:00 PM: Coffee and Shopping on Newbury Street
End your weekend with a relaxing stroll down Newbury Street, a popular shopping and dining destination in Boston's Back Bay neighborhood. Grab a coffee at one of the many cafes and browse the eclectic mix of shops, from high-end fashion boutiques to vintage record stores.
6:00 PM: Dinner at North End
Often referred to as Boston's Little Italy, the North End is one of the city's oldest and most historic neighborhoods. It is famous for its authentic Italian restaurants, pastry shops, and espresso bars. The narrow, winding streets are full of character, leading to significant historical sites like the Paul Revere House and the Old North Church. The North End is not just about Italian cuisine; it's also rich in colonial history and offers a quaint, old-world charm unique to this area of Boston. The neighborhood's lively atmosphere, especially during Italian festivals and summer feasts, makes it a lively and culturally rich area to explore.
Daily Catch: A cozy, family-run Sicilian-style seafood restaurant known for its black pasta and fresh, simple dishes. Ideal for an intimate, authentic Italian seafood meal.
Trattoria il Panino: This trattoria offers a traditional Italian experience with its hearty pasta dishes and warm, rustic ambiance. Perfect for those seeking a classic Italian meal.
Antico Forno: Known for its wood-fired pizzas and traditional Italian entrees, this restaurant offers a cozy, casual dining experience with a touch of authenticity.
Dessert at Mike's Pastry
End your meal with a sweet treat from this iconic pastry shop, famous for its cannolis and wide array of Italian pastries, located in Boston's historic North End.
8:00 PM: Departure
In conclusion, Boston truly stands out as a remarkable weekend destination, offering a perfect blend of historical charm and modern attractions. With its convenient airport and a myriad of captivating experiences, this city has something to offer for every visitor. Whether you're exploring the iconic Freedom Trail, immersing yourself in the vibrant arts scene, or indulging in the delectable local cuisine, Boston promises an unforgettable experience. So, pack your bags and get ready to embark on a memorable journey through the captivating streets of this remarkable city.