Ultimate 16-Day Boston and Beyond Adventure Itinerary

Enjoy a morning walk along the Charles River and then head to the MIT Museum for a fascinating exploration of science and technology. Grab a coffee and light bite at 4th Wall Restaurant & Bar to start your day.

Spend your afternoon strolling through the vibrant Kendall Square and indulge in a diverse lunch at Lincoln Tavern & Restaurant. Afterward, take a self-guided audio tour of the Massachusetts Institute of Technology (MIT) to admire its innovative campus.

Dine at Bostonia Public House, where the historic and the modern effortlessly blend in both the decor and the menu. After dinner, catch a performance at the Boston After Dark at View Boston Observatory (Adults Only), enjoying the city lights from above.

Begin with a visit to the hallowed grounds of Fenway Park for a guided tour, learning about the history of the Red Sox and the stadium. Have breakfast at Bleacher Bar, where you can enjoy a unique view of Fenway Park from inside.

Explore the lush greenery of the Franklin Park Zoo, home to a wide variety of animals from around the world. For lunch, head to Yard House at the nearby Fenway area, known for its extensive menu and great beer selection.

Relax and enjoy the evening at the Longfellow House (Washington's Headquarters), taking a guided tour to learn about its rich history. For dinner, experience the vibrant atmosphere and live music at The Beehive Restaurant, located in the Boston Center for the Arts complex.

Embark on a Boston's North End Secret Food Tour to discover the hidden culinary gems of this historic neighborhood. Sample a variety of Italian specialties while learning about the area's history and culture. The tour will also provide a satisfying breakfast.

After the food tour, take a leisurely walk to the nearby Paul Revere House and Quincy Market for some post-lunch exploration. Enjoy the diverse food options at Quincy Market and the unique atmosphere of this historic marketplace.

For dinner, savor the flavors of New England at OAK Long Bar + Kitchen, located in the Fairmont Copley Plaza. End the evening with a delightful dessert and cocktail pairing at Back Bay Social, known for its innovative drinks and lively ambiance.

Start your day with a visit to the New England Aquarium, where you can explore the marine life of the region. Have a quick breakfast at Solas Irish Pub before immersing yourself in the underwater world.

After the aquarium, take a relaxing harbor cruise with the Boston Harbor Historic Sightseeing Cruise. Enjoy the fresh sea breeze and learn about the city's maritime history. For lunch, the onboard options will provide a delightful meal with a view.

Dine at Five Horses Tavern - South End, known for its cozy atmosphere and extensive beer selection. Afterward, take a stroll along the South End, known for its beautiful Victorian brownstones and vibrant arts scene.

Begin with a hearty breakfast at Emmets, an Irish pub with a warm and welcoming atmosphere. Then, take a self-guided tour of the John Harvard Statue in Harvard Yard, followed by a visit to the Harvard Museum of Natural History to explore its impressive collections.

Enjoy a leisurely lunch at French Quarter, where you can indulge in the flavors of New Orleans in the heart of Boston. Afterward, take a guided student-led walking tour of the historic Harvard University campus, immersing yourself in the prestigious institution's rich history and academic culture.

Dine at The White Bull Tavern, offering a cozy and intimate setting with a menu featuring a modern twist on classic tavern fare. Conclude your literary day with a visit to the Harvard Square, where you can explore the eclectic mix of shops, bookstores, and street performances.

Start your day with a visit to the Salem 1692 Witchcraft Trials Walk, immersing yourself in the chilling history of the Salem witch trials. Enjoy breakfast at The White Bull Tavern before departing for Salem.

Upon arrival in Salem, take a guided walking tour of the Salem Secrets of Salem Hidden History Walking Tour, uncovering the lesser-known stories and locations of the city's past. For lunch, dine at The Black Rose, which offers a diverse menu in a historic setting.

As the sun sets, experience the supernatural side of Salem with the Salem Night Tour Haunt and History Guided Night Tour. After the tour, enjoy a hauntingly delicious dinner at The Bell In Hand Tavern, known for its lively atmosphere and pub-style cuisine.

Begin your day with a visit to the Institute of Contemporary Art (ICA), where you can explore the cutting-edge works of contemporary artists. Enjoy a breakfast with a view at the museum's Water Cafe, offering a selection of light and fresh fare.

After the museum, take a leisurely walk through the Fort Point and Seaport District, two vibrant and rapidly developing neighborhoods. For lunch, stop by Row 34, known for its fresh seafood and extensive oyster selection.

Dine at Mr. Dooley's Boston, an authentic Irish pub with live music and a menu featuring classic pub dishes. After dinner, enjoy a performance at the Boston Symphony Orchestra or the Boston Pops for a memorable evening of music.

Start your day with a visit to the Isabella Stewart Gardner Museum, a unique and intimate art museum housed in a stunning Venetian-style palace. Enjoy a breakfast at the museum's Cafe G [1243], known for its elegant ambiance and European-inspired menu.

Explore the lesser-known side of Boston with a visit to the Arnold Arboretum, where you can enjoy a peaceful walk among a diverse collection of trees and plants. For lunch, head to The Salty Pig, a neighborhood spot offering a range of charcuterie, pizzas, and pastas.

Dine at Drink, a renowned cocktail bar where the expert bartenders will craft a personalized drink based on your preferences. Afterward, take a stroll through the South End, known for its beautiful brownstones and a wide variety of art galleries.

Start your day with a visit to the Berklee College of Music, where you can explore the campus and learn about the prestigious music institution. Enjoy a breakfast at The Beehive Restaurant, known for its live music and eclectic menu.

Afterward, take a walk down Newbury Street, known for its upscale boutiques and galleries. For lunch, stop by Stephi's on Tremont, a neighborhood favorite offering a range of American comfort food.

Dine at Clio, a Michelin-starred restaurant known for its innovative and creative dishes. After dinner, catch a show at the House of Blues or enjoy a night of dancing at The Grand, one of Boston's premier nightlife spots.

Begin your day with a visit to the Museum of Science, where you can explore interactive exhibits and catch an IMAX film. Enjoy a breakfast at Flour Bakery + Cafe, known for its delicious pastries and sandwiches.

After the museum, take a walk along the Charles River Esplanade and enjoy the scenic views. For lunch, head to Myers + Chang, a lively eatery serving inventive Chinese and Southeast Asian dishes.

Dine at Bar Mezzana, a coastal Italian restaurant with a focus on crudo and pasta. After dinner, take a leisurely stroll through the South End, known for its beautiful brownstones and vibrant restaurant scene.

Start your day with a relaxing breakfast at Tatte Bakery & Cafe, known for its fresh pastries and artisanal coffee. Afterward, take a peaceful walk through the Arnold Arboretum, enjoying the tranquility of nature.

For lunch, head to Row 34, a warm and inviting seafood restaurant with a focus on oysters. Afterward, spend the afternoon browsing the boutiques and galleries of Newbury Street.

Dine at The Salty Pig, a neighborhood spot offering a range of charcuterie, pizzas, and pastas. After dinner, catch a performance at the Boston Symphony Orchestra or the Boston Pops for a memorable evening of music.

Start your day with a visit to the Isabella Stewart Gardner Museum, a unique and intimate art museum housed in a stunning Venetian-style palace. Enjoy a breakfast at the museum's Cafe G [1243], known for its elegant ambiance and European-inspired menu.

Explore the vibrant neighborhood of Jamaica Plain, known for its diverse community and beautiful green spaces. For lunch, head to The Haven, a Scottish restaurant offering a range of traditional dishes and a wide selection of whiskies.

Dine at Toro, a Barcelona-style tapas restaurant with a lively and energetic atmosphere. After dinner, take a walk along the South End, known for its beautiful brownstones and a wide variety of art galleries.

Begin with a visit to the John F. Kennedy Presidential Library and Museum, where you can learn about the life and legacy of the 35th President of the United States. Enjoy a breakfast at Flour Bakery + Cafe, known for its delicious pastries and sandwiches.

After the museum, take a walk along the Columbia Road and enjoy the views of the water. For lunch, head to Myers + Chang, a lively eatery serving inventive Chinese and Southeast Asian dishes.

Dine at Bar Mezzana, a coastal Italian restaurant with a focus on crudo and pasta. After dinner, take a leisurely stroll through the South End, known for its beautiful brownstones and vibrant restaurant scene.

Start your day with a visit to the New England Aquarium, where you can explore the marine life of the region. Have a quick breakfast at Solas Irish Pub before immersing yourself in the underwater world.

After the aquarium, take a relaxing harbor cruise with the Boston Harbor Historic Sightseeing Cruise. Enjoy the fresh sea breeze and learn about the city's maritime history. For lunch, the onboard options will provide a delightful meal with a view.

Dine at Five Horses Tavern - South End, known for its cozy atmosphere and extensive beer selection. Afterward, take a stroll along the South End, known for its beautiful Victorian brownstones and vibrant arts scene.

Enjoy a final breakfast at Lincoln Tavern & Restaurant, reminiscing about the culinary journey you've experienced in Boston.

Spend your last afternoon in the city at leisure, perhaps doing some last-minute shopping on Newbury Street or taking a walk through the Public Garden and Commonwealth Avenue Mall.

For your farewell dinner, indulge in the elegant ambiance and exquisite cuisine of L'Espalier, a highly acclaimed fine dining restaurant in Boston. Raise a glass to the memories made in this historic city.