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Historical Boston and Culinary Delights: 5-Day Trip Itinerary Itinerary
Last updated: 2024 Jun 14Freedom Trail and Harbor Cruise
Morning
Begin your Boston adventure with a hearty breakfast at The Common Man Concord, known for its classic American fare. After breakfast, embark on a self-guided audio tour of the Freedom Trail, visiting iconic landmarks such as the Massachusetts State House and the Paul Revere House.
Afternoon
For lunch, savor the flavors of Boston's North End on a Secret Food Tour, where you'll enjoy pizza, meats, and cheese. Afterward, take a leisurely Historical Sightseeing Cruise to learn about the city's maritime history and enjoy stunning views of the skyline.
Evening
Dine at Red Blazer Restaurant & Pub, offering a cozy atmosphere and a diverse menu. Cap off the evening with the Boston After Dark at View Boston Observatory (Adults Only), where you can enjoy city views with a drink in hand.
Bedtime
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Revolutionary Boston and Donut Delights
Morning
Start with a guided walking tour of the Freedom Trail, immersing yourself in the history of the American Revolution. Grab a donut or two on the Delicious Donut Tour with Tastings as you explore the city's landmarks.
Afternoon
Enjoy a lunch break at DJ's Bistro, a local favorite with a diverse menu. Spend the afternoon at the Boston Tea Party Ships and Museum Interactive Tour, where you'll participate in the "destruction of the tea" reenactment.
Evening
Dine at Eureka!, known for its innovative cuisine and craft beers. Conclude the day with the 1.5-Hour Ghosts and Gravestones Tour, delving into Boston's darker history with entertaining guides.
Bedtime
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University and Ballpark Excursion
Morning
Enjoy breakfast at Tandy's Pub & Grille, a laid-back spot with a great selection. Take a student-guided walking tour of Harvard University in nearby Cambridge, exploring the historic campus and its famous landmarks.
Afternoon
Head back to Boston for a guided tour of the legendary Fenway Park, home of the Red Sox. For lunch, visit Vinnie's Bar & Grill for a casual dining experience.
Evening
Dine at Lazy Dog Restaurant & Bar, offering a relaxed atmosphere and dog-friendly patio. Afterward, you can enjoy the vibrant nightlife at local bars and lounges.
Bedtime
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Trolley Tour and Culinary Cruise
Morning
Start with a convenient Hop-on Hop-off Old Town Trolley Tour, allowing you to explore the city's top attractions at your own pace. Grab a coffee and light bite at Lima before hopping on the trolley.
Afternoon
Have a leisurely lunch at Fiore, known for its elegant ambiance and Italian cuisine. Afterward, indulge in the North End Pizza Tour with 3 Slices and Cannoli, a guided culinary journey through Boston's famous pizza scene.
Evening
For dinner, experience the flavors of Barcos Sports & Seafood, offering a wide range of dishes in a lively setting. Cap off the night with live music and cocktails at Kodiak Cocktail Bar & Music Lounge.
Bedtime
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Literary and Leisurely Day in Concord
Morning
Take a day trip to the nearby town of Concord, Massachusetts. Begin with a visit to the Massachusetts Institute of Technology (MIT) for a public tour, immersing yourself in the innovative spirit of the institute.
Afternoon
Enjoy a leisurely lunch at Iron Thunder Saloon & Grill Concord, a biker-friendly spot with a diverse menu. Afterward, explore the literary history of Concord with visits to Walden Pond and the Louisa May Alcott's Orchard House.
Evening
Return to Boston and dine at Vineyards Restaurant and Bar, offering a sophisticated dining experience. Reflect on your trip with a serene Sunset Cruise on the harbor, enjoying the city's skyline as the sun sets.
Bedtime
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