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Travel AI

10-Day New England Road Trip Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Historic Boston

Morning

Start your day with a visit to Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 locations significant to the history of the United States. This activity will give you a comprehensive overview of Boston's rich history and is perfect for history enthusiasts.

Afternoon

For lunch, head over to Neptune Oyster, a highly-rated seafood restaurant known for its fresh oysters and lobster rolls. Afterward, explore Faneuil Hall Marketplace, a vibrant marketplace with shops, eateries, and street performers. Spend some time shopping and soaking in the lively atmosphere.

Evening

In the evening, enjoy dinner at Ostra, an upscale Mediterranean seafood restaurant. After dinner, take a leisurely stroll through Boston Public Garden, America's first public botanical garden. The beautifully landscaped gardens are perfect for an evening walk.

Bedtime

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4.54
Freedom Trail
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4.59
Faneuil Hall Marketplace
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Witch Trials and Maritime History in Salem

Morning

Begin your day with breakfast at Red’s Sandwich Shop, a local favorite known for its hearty breakfast options. Then visit the iconic Salem Witch Museum to learn about the infamous witch trials of 1692 through exhibits and presentations.

Afternoon

For lunch, dine at Turner’s Seafood, which offers fresh seafood dishes in a historic setting. Afterward, explore the historic waterfront area at Pickering Wharf. This area is filled with unique shops and offers beautiful views of Salem Harbor.

Evening

End your day with dinner at Ledger Restaurant & Bar, housed in an old bank building offering modern American cuisine. After dinner, join the spooky Salem Night Tour Haunt and History Guided Night Tour to delve into Salem's haunted past.

Bedtime

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4.67
Salem Witch Museum
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5.00
Pickering Wharf
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Seaside Charm in Portsmouth

Morning

Start your morning with breakfast at The Friendly Toast, known for its eclectic menu and vibrant atmosphere. Then embark on the Portsmouth Historic Neighborhoods Guided Bike Tour to explore Portsmouth's charming neighborhoods and historical sites.

Afternoon

Have lunch at Jumpin' Jay's Fish Cafe, famous for its fresh seafood dishes. In the afternoon, take part in the self-guided tour of Portsmouth's haunted sites with the Portsmouth Self-Guided Haunted Walking Audio Tour. It's an engaging way to learn about local legends and ghost stories.

Evening

For dinner, visit Black Trumpet Bistro, offering farm-to-table cuisine in a cozy setting. Conclude your evening by strolling along Prescott Park on the waterfront or enjoying live music if there's an event happening.

Bedtime

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Portsmouth Historic Neighborhoods Guided Bike Tour
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4.57
Portsmouth Self-Guided Haunted Walking Audio Tour
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Discovering Portland's Coastal Beauty

Morning

Begin your day with coffee and pastries from Tandem Coffee and Bakery. Then head out on the popular activity: Portland Trolley City Tour with Portland Head Light Stop. This tour provides insights into Portland’s history while stopping at one of Maine’s most iconic lighthouses.

Afternoon

Enjoy lunch at Eventide Oyster Co. where you can savor their famous brown butter lobster roll among other delicious offerings. Post-lunch activities include exploring Old Port using Smartphone Old Port Portland ME Audio Walking Tour APP/GPS, which guides you through this historic district filled with cobblestone streets and brick buildings.

Evening

Dine at Fore Street for dinner where wood-grilled dishes are served up in an industrial-chic setting using locally sourced ingredients from nearby farms or fisheries before taking a sunset cruise: Portland Sunset Lighthouse Cruise in Casco Bay with Drinks to end your day on a relaxing note.

Bedtime

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4.82
Portland Trolley City Tour with Portland Head Light Stop
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5.00
Smartphone Old Port Portland ME Audio Walking Tour APP/GPS
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Nature and Adventure in Bar Harbor

Morning

Start your day with breakfast at Jeannie's Great Maine Breakfast, known for its hearty and delicious morning meals. Afterward, head to Acadia National Park for a morning hike. The park offers stunning views of the coastline, mountains, and forests.

Afternoon

For lunch, visit Side Street Cafe, a popular spot offering a variety of dishes including seafood and vegetarian options. Post-lunch, continue exploring Acadia with the Ocean Path Acadia Self-Guided Walking Audio Tour, which will guide you along the scenic Ocean Path.

Evening

End your day with dinner at Havana, an upscale restaurant known for its Latin-inspired cuisine. After dinner, take part in the Bar Harbor Haunted Ghost Walking Tour to learn about the spooky history of Bar Harbor.

Bedtime

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4.57
Acadia National Park
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5.00
Ocean Path Acadia Self-Guided Walking Audio Tour
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Exploring White Mountains

Morning

The Sunrise Shack is a great place to start your day with breakfast before heading out to explore the White Mountains. Begin your adventure at the Mount Washington Observatory Weather Discovery Center, where you can learn about the unique weather patterns of Mount Washington.

Afternoon

Flatbread Company offers delicious wood-fired pizzas for lunch. Spend your afternoon hiking or driving through some of the scenic routes in the White Mountains area. The Kancamagus Highway is particularly famous for its breathtaking views.

Evening

Moat Mountain Smokehouse & Brewing Co. is perfect for dinner, offering a variety of smoked meats and craft beers brewed on-site. End your evening by relaxing at one of the many scenic overlooks or perhaps enjoying some stargazing.

Bedtime

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Mount Washington Observatory Weather Discovery Center
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Charming Stowe

Morning

Butler's Pantry is an excellent choice for breakfast with its cozy atmosphere and hearty meals. Afterward, embark on a half-day local brewery tour: Stowe Vermont Half-Day Local Brewery Tour. This tour will give you a taste of some of Vermont's finest craft beers.

Afternoon

Idletyme Brewing Company offers both great food and beer for lunch. Spend your afternoon exploring Stowe's charming downtown area or take part in an outdoor activity like hiking or biking.

Evening

Harrison's Restaurant & Bar provides a delightful dining experience with locally sourced ingredients and creative dishes. End your evening by relaxing at one of Stowe's scenic spots or perhaps enjoying some live music if available.

Bedtime

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5.00
Stowe Vermont Half-Day Local Brewery Tour
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Burlington’s Scenic Beauty

Morning

Start off with breakfast at Penny Cluse Cafe, known for its creative menu and cozy ambiance.Afterward,enjoy Smartphone-Guided Walking Tour of Burlington[612380] to explore Burlington’s vibrant downtown area filled with shops,cafes,and historic sites.

Afternoon

For lunch,dine at The Farmhouse Tap & Grill,which offers farm-to-table cuisine using locally sourced ingredients.Post-lunch activities include taking part in Burlington VT Scavenger Hunt[587024],a fun way to discover hidden gems around town.

Evening

End your day with dinner at Hen of the Wood,an upscale restaurant known for its seasonal dishes crafted from local ingredients.After dinner,take a leisurely stroll along Lake Champlain’s waterfront or enjoy some live music if there are any events happening.

Bedtime

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Smartphone-Guided Walking Tour of Burlington[612380]
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Burlington VT Scavenger Hunt[587024]
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Cultural Delights in The Berkshires

Morning

Start your day with breakfast at a local café before heading to National Gallery of Art. This museum offers an extensive collection of art from various periods and styles, making it a perfect spot for art enthusiasts.

Afternoon

For lunch, visit a nearby restaurant to enjoy some local cuisine. Afterward, explore The Smithsonian, which is known for its vast array of exhibits covering history, science, and culture. Spend the afternoon immersing yourself in the rich cultural offerings.

Evening

End your day with dinner at a highly-rated restaurant in the area. After dinner, take a leisurely stroll through Georgetown, known for its charming streets and historic architecture.

Bedtime

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4.81
National Gallery of Art
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4.38
The Smithsonian
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Historic Providence

Morning

Begin your day with breakfast at Nick's on Broadway, known for its creative and delicious breakfast options. Then join the Welcome to Providence Walking Tour to get an overview of the city's rich history and significant landmarks.

Afternoon

For lunch, dine at Hemenway's Seafood Grill & Oyster Bar, which offers fresh seafood dishes in a lovely setting. Post-lunch activities include exploring the vibrant arts scene with the Creative Capital Art and Architecture Tour of Providence,

Evening