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5-Day Boston Holiday Extravaganza Itinerary
Last updated: 2024 Jun 14Historic Beginnings and Festive Cruises
Morning
Start your Boston adventure with a guided walking tour of the Freedom Trail, immersing yourself in the city's rich history. Afterward, enjoy a hearty breakfast at Bostonia Public House, known for its historic ambiance and delicious American cuisine.
Afternoon
Spend your afternoon exploring the sea with a Historical Sightseeing Cruise and then indulge in a gourmet brunch on a Boston Harbor Gourmet Brunch Cruise. Afterward, take a leisurely stroll through the vibrant North End, also known as Little Italy, and enjoy the charming streets and local shops.
Evening
For dinner, experience the unique atmosphere of The Black Rose, an iconic Irish pub in the heart of the city. Afterward, continue the evening with the Cocoa and Carols Holiday Cruise, where you can enjoy the festive lights and live holiday music on the water.
Bedtime
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University and Aquarium Exploration
Morning
Start your day with a visit to the prestigious Harvard University and take a self-guided walking tour of the campus. Afterward, enjoy a delightful breakfast at 4th Wall Restaurant & Bar, known for its cozy atmosphere and diverse menu.
Afternoon
Explore the wonders of the underwater world at the New England Aquarium with a skip-the-line entry. For lunch, head to The Tip Tap Room and savor their unique selection of craft beers and delicious dishes.
Evening
Dine at Yvonne's, a sophisticated supper club with a touch of mystery. After dinner, take a relaxing Charles River cruise to enjoy the city's skyline from a different perspective.
Bedtime
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Park Tours and Cultural Delights
Morning
Embark on a guided tour of the iconic Fenway Park, home of the Boston Red Sox. After the tour, enjoy a classic American breakfast at Bleacher Bar, where you can also catch a glimpse of the stadium from a unique vantage point.
Afternoon
Immerse yourself in the cultural and culinary scene of Faneuil Hall Marketplace. Explore the historic market and enjoy lunch at Quincy Market, where you'll find a variety of food options to suit any palate.
Evening
Experience the vibrant atmosphere of the Back Bay and enjoy a delightful dinner at Five Horses Tavern - South End, known for its warm hospitality and extensive beer selection. Afterward, take a leisurely walk through the charming streets of the neighborhood.
Bedtime
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Cambridge and Science Wonders
Morning
Cross the river to Cambridge and start your day with a self-guided walking tour of the Harvard Campus. For breakfast, enjoy the cozy ambiance and delicious food at Birch Bar.
Afternoon
Explore the innovative exhibits at the MIT Museum with a public tour of the Massachusetts Institute of Technology (MIT). For lunch, head to Porters Bar and Grill and savor their pub-style menu.
Evening
Return to Boston and enjoy a delightful dinner at The Bell In Hand Tavern, the oldest tavern in America. Afterward, take a guided tour of the Boston Tea Party Ships and Museum to learn about this pivotal event in American history.
Bedtime
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Witch Trials and Haunted History
Morning
Take a day trip to the nearby city of Salem and start with a guided walking tour of the 1692 Witchcraft Trials sites. For breakfast, enjoy the casual atmosphere and delicious food at Mr. Dooley's Boston.
Afternoon
Dive deeper into Salem's spooky history with the Ghosts, Witches, & Warlocks Guided Walking Tour. For lunch, visit Solas Irish Pub and experience their authentic Irish fare.
Evening
Conclude your Salem visit with the Night Tour Haunt and History Guided Night Tour, exploring the city's haunted past under the cover of darkness. Return to Boston for a final dinner at Silvertone Bar & Grill, known for its classic American dishes and extensive drink menu.
Bedtime
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