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14 Days Exploring New England Itinerary

Last updated: 2024 Jun 14

Discovering Boston's Historic Charm

Morning

Start your day with a hearty breakfast at The Friendly Toast, known for its creative and delicious dishes. After breakfast, explore the historic Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 significant historical sites.

Afternoon

For lunch, head to Union Oyster House, one of the oldest restaurants in America. In the afternoon, visit the Boston Tea Party Ships and Museum, where you can relive the historic event that sparked the American Revolution.

Evening

Enjoy dinner at Neptune Oyster, famous for its seafood dishes. After dinner, take a relaxing evening stroll along the Boston Harborwalk, offering beautiful views of the waterfront.

Bedtime

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4.43
Boston Tea Party Ships and Museum
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4.27
Boston Harborwalk
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Cultural Day in Boston

Morning

Begin your day with breakfast at Tatte Bakery & Cafe. Then visit the renowned Museum of Fine Arts, home to an extensive collection of art from around the world.

Afternoon

Have lunch at Myers + Chang, known for its Asian-inspired dishes. Spend your afternoon exploring the beautiful grounds of Boston Public Garden, America's first public botanical garden.

Evening

Dine at Oleana Restaurant, which offers Mediterranean cuisine. End your day with a performance at the historic Boston Symphony Hall.

Bedtime

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Boston Public Garden
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Portland's Coastal Beauty

Morning

Start with breakfast at Hot Suppa, known for its Southern comfort food. Visit the iconic Portland Head Light, one of Maine's most photographed lighthouses.

Afternoon

Enjoy lunch at Eventide Oyster Co. and then explore the vibrant Old Port district with its cobblestone streets and unique shops.

Evening

Dine at Fore Street Restaurant, which focuses on locally sourced ingredients. After dinner, take a sunset cruise on Casco Bay to enjoy stunning coastal views.

Bedtime

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4.55
Portland Head Light
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Exploring Acadia National Park

Morning

Have breakfast at a local favorite spot in Bar Harbor before heading into Acadia National Park. Start your exploration with a hike on one of Acadia's many trails such as Cadillac Mountain or Jordan Pond Path.

Afternoon

For lunch, have a picnic in Acadia National Park while enjoying breathtaking views. Continue exploring other parts of the park like Sand Beach or Thunder Hole.

Evening

Return to Bar Harbor for dinner at Side Street Cafe. Afterward, enjoy some stargazing within Acadia National Park – it's known for its dark skies and clear nights.

Bedtime

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Charming Burlington by Lake Champlain

Morning

Begin your day with breakfast at Penny Cluse Cafe. Spend your morning strolling along Church Street Marketplace – an outdoor pedestrian mall lined with shops and cafes.

Afternoon

Have lunch at The Farmhouse Tap & Grill before visiting ECHO Leahy Center for Lake Champlain – an interactive science museum focused on ecology and culture of Lake Champlain region.

Evening

Dine at Henry's Diner followed by an evening walk along Burlington Waterfront Park where you can catch beautiful sunset views over Lake Champlain.

Bedtime

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