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Historic Trails and Gourmet Delights in Boston

Historic Trails and Gourmet Delights in Boston Itinerary

Last updated: 2024 Jun 14

Freedom and Flavors in the City

Morning
Begin your Boston adventure with a hearty breakfast at Mike's Pastry, famous for its delectable pastries and Italian treats. After fueling up, take a stroll through the historic Boston Common, the oldest public park in the United States. Immerse yourself in history with a guided Freedom Trail Walking Tour, passing by 16 significant historical sites.
Afternoon
For lunch, head to Union Oyster House, America's oldest restaurant, and savor their renowned seafood dishes. Post-lunch, visit the revolutionary Boston Tea Party Ships & Museum for an interactive tour, reliving the iconic event that changed the course of history. Later, enjoy the convenience of the Boston Hop-on Hop-off Old Town Trolley Tour to explore the city at your own pace.
Evening
As the sun sets, indulge in a sumptuous dinner at Top of the Hub, which offers breathtaking panoramic views of the city. Afterward, experience the Boston Harbor on a Historical Sightseeing Cruise, witnessing the city's skyline and passing by notable landmarks under the starry sky.
Bedtime
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Harborside History and Culinary Charms

Morning
Enjoy a delightful breakfast at Row 34, known for its fresh seafood and oyster bar. Post-breakfast, take a serene walk along the Charles River, soaking in the scenic views and the tranquility it offers. Visit the iconic USS Constitution, the world's oldest commissioned warship afloat, and the adjacent Bunker Hill Monument for a dose of maritime and revolutionary history.
Afternoon
For lunch, head to Legal Sea Foods, a local favorite, and enjoy their signature New England clam chowder. Afterward, visit the vibrant Faneuil Hall Marketplace and Quincy Market for some shopping and entertainment, with street performers and a variety of shops and eateries.
Evening
Dine at The Capital Grille, where you can indulge in a luxurious steak dinner. Afterward, take a leisurely stroll through the North End, also known as Boston's "Little Italy," and explore the neighborhood's charming streets and rich culinary offerings.
Bedtime
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A Day of Academic Exploration and Exquisite Eats

Morning
Start your day with a visit to the prestigious Harvard University in nearby Cambridge. Enjoy a guided Harvard University Student- Guided Walking Tour to learn about the history and culture of this esteemed institution. For breakfast, try the famous donuts at Kane's Donuts, a local favorite near Harvard Square.
Afternoon
After the tour, explore the neighboring Massachusetts Institute of Technology (MIT) and visit the MIT Museum to witness cutting-edge innovation and technology. For lunch, head to Giacomo's Ristorante for some of the best Italian cuisine in the city.
Evening
Return to Boston and enjoy a sophisticated dinner at No. 9 Park, known for its refined French and Italian-inspired dishes. Cap off the evening with a visit to After Dark at View Boston Observatory (Adults Only), where you can enjoy a drink with a stunning 360-degree view of the city lights.
Bedtime
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Specters and Spectacles of the Night

Morning
Kick off your morning with a visit to the Salem Witch Museum Admission Ticket in the nearby historic town of Salem. Immerse yourself in the history of the Salem witch trials and the witchcraft hysteria of 1692. For breakfast, try the delightful pastries at Au Bon Pain in Salem.
Afternoon
Return to Boston and have lunch at Santarpio's Pizza, a local institution known for its classic, no-frills pizza. Spend your afternoon exploring the exhibits and collections at the View Boston Observatory Entry Ticket, gaining a new perspective on the city and its history.
Evening
For dinner, enjoy the innovative Japanese cuisine at O Ya, where the sushi and sashimi are a work of art. Conclude your day with a Boston Harbor Sunset Yacht Cruise, basking in the glow of the setting sun and the stunning waterfront views.
Bedtime
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Revolutionary Revelations and Culinary Capstones

Morning
Begin your final day with a visit to the Paul Revere House, the oldest remaining structure in downtown Boston, and the nearby Granary Burying Ground, the final resting place of many notable figures from the American Revolution. Enjoy a historic breakfast at Neptune Oyster, known for its fresh seafood and oyster bar.
Afternoon
For lunch, savor the flavors of the North End with a food experience at Mamma Maria, offering classic Italian dishes in an elegant setting. Spend your afternoon at the Longfellow House (Washington's Headquarters), exploring the home of poet Henry Wadsworth Longfellow and its beautiful gardens.
Evening
Conclude your trip with a memorable dinner at Menton, a fine dining experience that represents the best of French cuisine. Reflect on your journey over a glass of wine and the restaurant's exquisite desserts, celebrating the end of a historic and gastronomic adventure in Boston.
Bedtime
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