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5-Day New England Fly Drive Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Historic Boston

Morning

Start your day with a visit to the iconic Freedom Trail. This 2.5-mile-long path through downtown Boston passes by 16 locations significant to the history of the United States. It's a great way to immerse yourself in the rich history of New England.

Afternoon

Head over to Quincy Market for lunch and enjoy a variety of local foods. Afterward, explore the nearby Faneuil Hall Marketplace for some shopping and street performances.

Evening

Dine at The Peacock Mercantile for an exquisite dinner experience featuring local New England cuisine.

Bedtime

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Charming Coastal Maine

Morning

Drive up to Portland, Maine and start your day with a visit to the Portland Head Light. This historic lighthouse offers stunning views of the rugged coastline and is perfect for photography enthusiasts.

Afternoon

Enjoy a seafood lunch at Reel 'Em Inn Bar & Grill, known for its fresh catches and relaxed atmosphere. After lunch, take a stroll through the Old Port district with its cobblestone streets and unique shops.

Evening

Have dinner at Rusty's Saloon and Grill, where you can savor hearty meals in a cozy setting.

Bedtime

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Nature and Art in New Hampshire

Morning

Drive over to the White Mountains region in New Hampshire. Start your day with a scenic hike on one of the many trails available in Franconia Notch State Park. The Flume Gorge is particularly popular for its stunning natural beauty.

Afternoon

For lunch, head to C&N Cafe which offers delicious comfort food perfect after a morning hike. Spend your afternoon visiting The Frost Place in Franconia - Robert Frost's former home turned museum dedicated to his life and poetry.

Evening

Enjoy dinner at The Broken Brick Roadhouse, known for its rustic charm and delectable dishes.

Bedtime

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Cultural Day in Providence

Morning

Drive down to Providence, Rhode Island. Begin your day with a visit to the RISD Museum which houses an impressive collection of fine art from various periods and cultures.

Afternoon

Lunch at Pastime Club & Steakhouse where you can enjoy classic American fare in an elegant setting. Afterward, take a leisurely walk around Waterplace Park or explore Federal Hill - Providence's Little Italy.

Evening

End your day with dinner at one of Providence's renowned restaurants before heading back to your accommodation.

Bedtime

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Relaxing in the Berkshires

Morning

Start your day with a visit to the Norman Rockwell Museum in Stockbridge. This museum houses the largest collection of original Rockwell art and offers a glimpse into the life and work of one of America's most beloved artists.

Afternoon

For lunch, head to The Peacock Mercantile which offers a delightful menu with locally sourced ingredients. After lunch, take a scenic drive through the Berkshires and enjoy the beautiful fall foliage if you're visiting in autumn.

Evening

End your day with dinner at Rusty's Saloon and Grill, where you can enjoy hearty meals in a cozy setting. If you have time, catch a performance at Tanglewood, the summer home of the Boston Symphony Orchestra.

Bedtime

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