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Travel AI

Ultimate New England Road Trip Itinerary

Last updated: 2024 Jun 14

Historic Boston and Seafood Delights

Morning

Start your day with a classic New England breakfast at Flour Bakery + Cafe, known for its pastries and sandwiches. After breakfast, take a leisurely walk along the Freedom Trail, passing by iconic sites like the Paul Revere House and Faneuil Hall.

Afternoon

For lunch, savor the fresh seafood at Neptune Oyster, a local favorite. Afterward, explore the historic streets of the North End and visit the Old North Church. You can also take a relaxing stroll in the Boston Public Garden.

Evening

In the evening, enjoy a sophisticated dinner at Ostra Boston, known for its Mediterranean-inspired seafood dishes. After dinner, take a sunset cruise in the Boston Harbor to see the city from a different perspective.

Bedtime

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Culinary Delights and Skyline Views

Morning

Indulge in a luxurious brunch at L'Espalier, a renowned fine dining restaurant. After brunch, visit the Isabella Stewart Gardner Museum to admire its art collection and beautiful courtyard.

Afternoon

For a unique experience, have a late afternoon snack at Union Oyster House, the oldest continuously operating restaurant in the United States. Then, take a Duck Tour to see the city's landmarks from both land and water.

Evening

Enjoy a romantic dinner at Top of the Hub, where you can savor delicious food with a panoramic view of the Boston skyline. After dinner, take a leisurely walk along the Charles River Esplanade.

Bedtime

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Coastal Charms and Lighthouse Views

Morning

Depart for Portland, Maine, and start your day with a hearty breakfast at Becky's Diner, a local institution known for its seafood dishes. After breakfast, visit the Portland Head Light and take a scenic walk along the cliffside.

Afternoon

For lunch, enjoy the lobster roll at Bite into Maine, a food truck with stunning views of the ocean. Afterward, explore the charming streets of the Old Port district and visit the local boutiques.

Evening

Have a memorable dinner at Eventide Oyster Co., known for its innovative oyster dishes. After dinner, take a sunset cruise to see the lighthouses dotting the Maine coast.

Bedtime

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