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Roam Around

Historical Boston and Diverse Dining in 4 Days Itinerary

Last updated: 2024 Jun 14

Walking Through History on the Freedom Trail

Morning

Start your historical journey with a hearty American breakfast at The Capital Grille, known for its elegant atmosphere and delicious dishes. Afterward, immerse yourself in the rich past of Boston by embarking on a Boston Small Group Freedom Trail History Walking Tour. Explore iconic sites like the Boston Common, Massachusetts State House, and the Granary Burying Ground.

Afternoon

For lunch, savor Italian cuisine at Mamma Maria, a local favorite in the North End. Afterward, continue your journey along the Freedom Trail, visiting the Boston Old State House and the Faneuil Hall Marketplace. Conclude your afternoon with a visit to the USS Constitution, also known as "Old Ironsides."

Evening

Enjoy a sophisticated dinner at L'Espalier, known for its French-inspired cuisine and elegant setting. After dinner, take a leisurely stroll along the waterfront to soak in the evening ambiance of the city.

Bedtime

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4.91
Boston Small Group Freedom Trail History Walking Tour
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4.49
Boston Common
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Exploring Academic Excellence at Harvard and MIT

Morning

Indulge in a delightful brunch at Craigie on Main, a renowned spot for its innovative dishes. Afterward, take a walk through the historic Harvard University campus, including Harvard Yard and the John Harvard Statue. Explore the Harvard Museum of Natural History for a deeper understanding of the natural world.

Afternoon

For a late lunch, experience the vibrant flavors of Spanish cuisine at Toro. Afterward, cross the river to visit the Massachusetts Institute of Technology (MIT) and explore the MIT Museum. Take a leisurely walk around Kendall Square before heading back to Boston.

Evening

Dine at Oleana, a Mediterranean-inspired restaurant known for its intimate atmosphere and delectable dishes. After dinner, take a relaxing evening stroll through the charming streets of Cambridge.

Bedtime

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4.25
Harvard University
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3.69
John Harvard Statue
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A Day of Sports and Revolution

Morning

Start your day with a classic American breakfast at Myers + Chang, a beloved spot for its Asian-inspired dishes. After breakfast, take a guided tour of Fenway Park, home of the Boston Red Sox, and immerse yourself in the history of this iconic ballpark.

Afternoon

For lunch, enjoy a variety of seafood options at Row 34, known for its fresh oysters and relaxed atmosphere. Afterward, visit the Boston Tea Party Ships & Museum for an interactive experience that brings the historic event to life.

Evening

Dine at Eastern Standard Kitchen & Drinks, a brasserie-style restaurant offering a wide range of dishes. After dinner, take a leisurely evening stroll along the Charles River Esplanade and enjoy the beautiful views of the city.

Bedtime

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4.19
Fenway Park
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4.22
Boston Tea Party Ships & Museum
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Aquatic Wonders and Serene Gardens

Morning

Enjoy a leisurely breakfast at Neptune Oyster, a popular spot for its fresh seafood and oyster bar. After breakfast, spend the morning exploring the fascinating marine life at the New England Aquarium. Be sure to catch the captivating penguin feeding session.

Afternoon

For a late lunch, head to Giacomo's Ristorante in the North End and savor their famous Italian dishes. Afterward, take a relaxing stroll through the picturesque Boston Public Garden and enjoy a swan boat ride on the pond.

Evening

Conclude your Boston adventure with a memorable dinner at Top of the Hub, where you can enjoy panoramic views of the city skyline. Indulge in a fine dining experience before heading to the Skywalk Observatory to take in the city lights.

Bedtime

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