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5-Day Scenic and Historical Road Trip Itinerary

Last updated: 2024 Jun 14

Historical Highlights of Virginia

Morning

Start your journey with a visit to the Franciscan Monastery of the Holy Land in America. This serene and beautiful site offers a peaceful start to your trip, allowing you to appreciate the historical architecture and lush gardens. Afterward, head over to Founding Farmers for a hearty breakfast featuring farm-to-table dishes that showcase local ingredients.

Afternoon

Continue your exploration with a visit to the Steven F. Udvar-Hazy Center, an annex of the National Air and Space Museum. Here, you can marvel at an impressive collection of aircraft and space artifacts. For lunch, stop by The Capital Grille for a sophisticated dining experience with classic American fare.

Evening

In the evening, take part in the Richmond Private City Tour by Tuk Tuk. This guided tour will give you an intimate look at Richmond's rich history and vibrant culture. End your day with dinner at Lemaire, known for its elegant Southern cuisine.

Bedtime

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Franciscan Monastery of the Holy Land in America
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Steven F. Udvar-Hazy Center
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Colonial Virginia Adventures

Morning

Begin your day with a visit to Colonial Williamsburg, where you can step back in time and experience life in colonial America. The living history museum offers interactive exhibits and reenactments that are both educational and entertaining. Enjoy breakfast at Blue Talon Bistro, which serves up delicious French-inspired dishes.

Afternoon

After exploring Colonial Williamsburg, head over to the nearby Jamestown Settlement. This historic site provides insight into America's first permanent English colony through galleries, films, and outdoor living-history areas. For lunch, dine at Fat Canary, known for its creative American cuisine.

Evening

Conclude your day with a visit to the American Revolution Museum at Yorktown. The museum offers comprehensive exhibits on the Revolutionary War era. For dinner, savor local seafood at Riverwalk Restaurant, offering beautiful views of the York River.

Bedtime

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Colonial Williamsburg
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Jamestown Settlement
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Scenic Drives Through Virginia's Beauty

Morning

Embark on a scenic drive along the famous Blue Ridge Parkway, known for its breathtaking views of mountains and valleys. Stop by overlooks and trails along the way to fully appreciate nature's beauty. Enjoy breakfast at one of the charming roadside diners like Mabry Mill Restaurant & Gift Shop, famous for its pancakes.

Afternoon

Continue your scenic journey with a visit to Shenandoah National Park where you can take part in activities like hiking or simply enjoy a picnic amidst stunning landscapes. For lunch, stop by Skyland Dining Room within the park for hearty meals with panoramic views.

Evening

End your day with some adventure by participating in Whitewater Rafting on the Fall Lower Gauley - Friday. This thrilling activity will provide an adrenaline rush as you navigate through rapids surrounded by picturesque scenery. Afterward, relax over dinner at The Palisades Restaurant, offering farm-to-table Appalachian cuisine.

Bedtime

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Blue Ridge Parkway
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Shenandoah National Park
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Exploring Coastal Maine

Morning

Start your day with a visit to the iconic Portland Head Light. This historic lighthouse offers stunning views of the rugged coastline and is a perfect spot for morning photography. Enjoy breakfast at The Holy Donut, known for its unique potato donuts and delicious coffee.

Afternoon

After exploring the lighthouse, head over to Casco Bay for a scenic boat tour. The bay is dotted with picturesque islands and offers opportunities for wildlife spotting. For lunch, dine at Eventide Oyster Co., famous for its fresh seafood and innovative dishes.

Evening

Conclude your day with a visit to the charming Eastern Promenade. This historic park offers beautiful walking trails and panoramic views of Casco Bay. Participate in the Portland Food Walking Tour with Tastings to sample local delicacies from various eateries. End your evening with dinner at Fore Street, known for its farm-to-table cuisine and cozy ambiance.

Bedtime

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Portland Head Light
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Casco Bay
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Historical Sites and Scenic Views

Morning

Acadia National Park Small Group Guided Tour is a must-visit destination in Maine. Start your day early to explore this stunning national park, known for its diverse landscapes, including mountains, forests, and coastal areas. Enjoy breakfast at Jordan Pond House Restaurant within the park, famous for its popovers and tea.

Afternoon

Boothbay Harbor's Walk Through Time, a Guided History Tour will take you through the rich history of this charming coastal town. For lunch, stop by The Thistle Inn Restaurant, offering fresh seafood and classic New England dishes.

Evening

Schooner Apple Jack 2 Hr Sunset Sail from Boothbay Harbor provides a perfect ending to your day. This sunset sail offers breathtaking views of the harbor and surrounding islands. For dinner, enjoy a meal at Boathouse Bistro Tapas Bar & Restaurant, known for its creative tapas menu and waterfront views.

Bedtime

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