Bostonia

Day Trips

Make the most of your day with our curated plans, packed with Bostonia's hidden gems and unique experiences!

day 1
Exploring the Freedom Trail
morning
:

Start your day with a walk along the historic Freedom Trail, which spans 2.5 miles and guides you through 16 significant sites in Boston. Be sure to visit the Massachusetts State House and the Park Street Church, immersing yourself in the rich history of the American Revolution. Don't forget to stop by the Granary Burying Ground, where prominent figures like Paul Revere are laid to rest.

afternoon
:

Continue your journey on the Freedom Trail, making your way towards the Old North Church and the famous ‘Paul Revere’s Ride’ system of lanterns. Enjoy lunch at a nearby café, perhaps savoring a classic New England clam chowder. This afternoon, allow your curiosity to guide you as you hop between various historical sites, soaking up the immersive atmosphere of Boston's past.

evening
:

As the sun sets, treat yourself to dinner at a charming restaurant in the North End, famous for its Italian cuisine. Afterward, take a leisurely stroll through the neighborhood, indulging in a dessert from one of the many renowned pastry shops. The evening ambiance, with streets illuminated and lively chatter filling the air, will make you feel the pulse of Boston at night.

day 2
Harvard and Cambridge Adventures
morning
:

Begin your day in Cambridge by visiting the iconic Harvard University campus. Stroll through Harvard Yard, soaking in the academic atmosphere, and check out the Harvard Art Museums for a dose of culture. A leisurely breakfast at a nearby café will energize you for the day ahead.

afternoon
:

Spend the afternoon exploring the various museums and attractions in Cambridge, including the MIT Museum and the picturesque Charles River. Perhaps indulge in a picnic lunch at the banks of the river, soaking in the beautiful views and vibrant college atmosphere. Don’t miss the chance to pop into local shops that showcase unique creations by local artisans.

evening
:

For dinner, explore a trendy restaurant in Cambridge, where farm-to-table concepts reign supreme. Afterward, catch a performance at the American Repertory Theater, known for its innovative and groundbreaking productions. As the evening winds down, take a moment to reflect on your day amidst the lively streets of this intellectual hub.

day 3
A Day in Beacon Hill
morning
:

Start your day in the historic Beacon Hill neighborhood, where cobblestone streets and gas-lit lamps set a picturesque backdrop. Enjoy a scrumptious breakfast at a local bistro while admiring the charming architecture that has captivated visitors for centuries. Wander through the narrow streets, discovering boutique shops and hidden gardens.

afternoon
:

After lunch, visit the nearby Boston Common and Public Garden, where you can enjoy a relaxing walk amidst lush greenery and vibrant flower displays. Take a swan boat ride on the lagoon for a quintessential Boston experience. This afternoon can also be spent visiting the Isabella Stewart Gardner Museum, known for its stunning art collection and beautiful courtyard.

evening
:

As evening falls, make your way to a cozy restaurant in Beacon Hill for a superb dining experience featuring seasonal dishes. After dinner, enjoy a scenic evening stroll through the neighborhood, admiring the illuminated historic homes. Wind down with a nightcap at a local pub, soaking in the welcoming, community-rich vibe.

day 4
Navigating the North End
morning
:

Kick off your day in the North End, Boston’s Italian quarter, with a traditional espresso and pastries from a local bakery. Explore the area's narrow, bustling streets, visiting historic sites such as the Old North Church. Engage with friendly locals and vendors to learn about the neighborhood's rich Italian heritage.

afternoon
:

For lunch, enjoy a delicious plate of pasta at one of the North End's renowned restaurants. Post-meal, explore the Paul Revere House, where you can delve into colonial history. The afternoon is perfect for leisure shopping and tasting some delicious Italian gelato.

evening
:

As night approaches, enjoy an authentic Italian dinner, followed by a walk to the waterfront for breathtaking views of the city skyline. The North End often offers various street performances, so take a moment to enjoy the vibrant street life. End your evening with a delightful dessert at a famous pastry shop, indulging in a cannoli or tiramisu.

day 5
Museum Day in the City
morning
:

Spend the day immersing yourself in Boston's rich array of museums, beginning with the Museum of Fine Arts. Marvel at collections spanning thousands of years, from ancient artifacts to contemporary works of art. Grab a light breakfast at the museum café to fuel your exploration.

afternoon
:

After the Museum of Fine Arts, visit the Boston Science Museum, which is perfect for all ages with its interactive exhibits and IMAX theater. Enjoy a casual lunch at the museum's café as you soak in the vibrant, intellectual atmosphere. This afternoon, don’t forget to explore the nearby Charles River Esplanade, offering stunning views of the city skyline and opportunities for cycling or walking.

evening
:

Wrap up your museum day with dinner at a nearby restaurant specializing in local seafood. After dining, enjoy a unique evening experience at a live science show or an engaging lecture at one of Boston’s many educational spaces. Reflect on your day of learning as you relax with a nightcap at a cozy bar, perhaps seeking out some local craft beer.

day 6
A Cultural Immersion at Fenway
morning
:

Kick off your day with a visit to Fenway Park, a must for any sports fan, where you can take a guided tour of the iconic baseball stadium. Learn about the park’s history and its significance to Boston culture. Afterwards, grab breakfast at a nearby café, perhaps sampling a local favorite dish.

afternoon
:

Experience the vibrant atmosphere of the Fenway area, where you can visit the nearby Museum of Fine Arts or explore the tranquility of the Emerald Necklace parks. Enjoy lunch at a cozy spot, indulging in American comfort food or picnic treats as you enjoy the fresh air. Consider catching a matinee show or live performance at the nearby Boston Symphony Hall if your schedule allows.

evening
:

As evening descends, head back to Fenway Park for an exciting game if the Red Sox are playing. The atmosphere is electrifying and filled with passionate fans cheering for their team. Afterward, unwind with dinner at a sports bar, where you can relish in the celebratory mood of Boston culture.

day 7
Shopping and Sights on Newbury Street
morning
:

Begin your day with a leisurely breakfast at a cafe on Newbury Street, where the charming ambiance pairs perfectly with rich coffee and pastries. Spend some time browsing the eclectic mix of high-end shops, boutiques, and local stores lining the street. Explore the nearby Boston Public Library, known for its stunning architecture and great reading rooms.

afternoon
:

Continue your shopping spree before enjoying lunch at a trendy bistro. Post-lunch, you may want to take in a gallery or two featuring local artists’ work, further enriching your day in the Back Bay area. Wander through the tranquil landscaped areas of the Commonwealth Avenue Mall for a moment of relaxation.

evening
:

As dusk approaches, enjoy dinner at one of Newbury Street's many acclaimed restaurants, offering an array of international cuisines. After dinner, catch a cocktail at a chic lounge or rooftop bar as you watch the bustling streets below. This vibrant area offers wonderful ambiance for a memorable evening stroll as shops begin to close and lights illuminate the sidewalks.

day 8
A Day in the South End
morning
:

Start your day in the South End with coffee and a freshly baked pastry from a local café. Then, spend some time wandering through the historic streets, admiring the Victorian brownstones and local art galleries that dot the neighborhood. Engage with artists displaying work in the South End’s many studios and galleries as you soak in the creative atmosphere.

afternoon
:

Enjoy lunch at a trendy eatery that presents a diverse menu focusing on seasonal ingredients and local sourcing. Post-lunch, visit the Boston Center for the Arts to discover more about the local arts scene and perhaps catch an exhibition. This afternoon is also perfect for exploring the local parks and green spaces nearby, providing a nice relaxing atmosphere.

evening
:

As night falls, treat yourself to dinner at a restaurant known for its innovative cuisine, featuring an inviting ambiance and exceptional service. After dinner, enjoy the South End's lively nightlife, with many bars and lounges offering unique craft cocktails and live music. Take a leisurely stroll through this vibrant neighborhood, enjoying the artful displays and dynamic energy of the community.

day 9
Cruising Boston Harbor
morning
:

Kickstart your day with a breakfast that offers a view of the Boston Harbor. Then, embark on a scenic cruise around the harbor, giving you unique vistas of the city skyline and historical sites like the Bunker Hill Monument. The fresh sea air and gentle waves set a refreshing tone for your day.

afternoon
:

After your harbor adventure, enjoy lunch at one of the waterfront restaurants that serve fresh seafood dishes. Consider visiting the Aquarium or simply relaxing at the water's edge with a cold drink. This afternoon, take a leisurely walk along the harborwalk to appreciate the stunning waterfront views.

evening
:

As the sun sets, take a dinner cruise for a perfect blend of dining and spectacular city lights. Enjoy a delightful meal while sailing past historic landmarks illuminated against the night sky. Wrap up your day with a relaxing stroll along the waterfront, soaking in the peaceful harbor ambiance.

Discover Bostonia

Read more in our Bostonia 2025 Travel Guide.

Bostonia Travel Guide