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Roam Around

Historic Charleston, Savannah, and Hilton Head Island Exploration Itinerary

Last updated: 2024 Jun 14

Historic Charleston's Charm

Morning

Start your day with a delightful breakfast at Hominy Grill, known for its Southern comfort food. Afterward, immerse yourself in the history of Charleston with a visit to the Charleston City Market. Explore the market's stalls and pick up some unique souvenirs.

Afternoon

For lunch, savor the fresh seafood at Fleet Landing Restaurant & Bar with views of the water. In the afternoon, take a relaxing walk through the iconic Rainbow Row and the nearby The Battery and White Point Garden. Enjoy the antebellum architecture and the sea breeze.

Evening

In the evening, have a memorable dining experience at Husk, known for its innovative Southern cuisine. After dinner, take a leisurely stroll along the historic streets of Charleston, soaking in the charm of the gas lantern-lit alleys.

Bedtime

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4.67
Charleston City Market
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4.81
Rainbow Row
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Plantation Legacy and Church History

Morning

Enjoy a classic Southern breakfast at The Darling Oyster Bar. Then, visit the Boone Hall Plantation & Gardens, known for its Avenue of Oaks and rich history. Take a guided tour to learn about the Gullah culture and the plantation's past.

Afternoon

For lunch, head to Magnolias and indulge in contemporary Southern cuisine. Afterward, explore the historic St. Michael's Church and St Philips Church, two architectural gems with significant roles in Charleston's history.

Evening

Dine at Slightly North of Broad (SNOB), a local favorite for Lowcountry dishes. After dinner, take a ghost tour to discover the haunted past of Charleston, adding a spooky twist to your evening.

Bedtime

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4.26
Boone Hall Plantation & Gardens
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4.85
St. Michael's Church
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Museums and Culinary Delights

Morning

Start your day with a visit to the Charleston Museum, the oldest museum in the United States. Explore the exhibits showcasing the history of Charleston and the Lowcountry. Afterward, take a leisurely walk in the Charleston Waterfront Park.

Afternoon

For lunch, try the innovative Asian cuisine at Xiao Bao Biscuit. In the afternoon, visit the Gibbes Museum of Art to admire its collection of American art. After the museum, take a rest at a local cafe like The Macintosh.

Evening

Indulge in a fine dining experience at FIG, known for its seasonal and locally sourced ingredients. After dinner, take a historic walking tour to learn more about the hidden stories of Charleston's streets and alleys.

Bedtime

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4.53
Charleston Museum
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4.78
Charleston Waterfront Park
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Savannah's Southern Elegance

Morning

Arrive in Savannah and start your day with a delicious breakfast at The Grey. Then, take a guided tour of the Historic District of Savannah, known for its oak-lined streets and historic homes. Visit the Cathedral of St. John the Baptist.

Afternoon

For lunch, enjoy the farm-to-table cuisine at The Collins Quarter. Afterward, explore the Bonaventure Cemetery, a hauntingly beautiful site with intricate sculptures and a rich history. Take a guided tour to learn about the famous residents.

Evening

Dine at The Olde Pink House, a Savannah institution with a romantic ambiance. After dinner, join a ghost tour to experience the supernatural side of Savannah's historic district.

Bedtime

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Savannah's Riverfront and Art Scene

Morning

Start your day with a riverside breakfast at Treylor Park. Then, explore the River Street, lined with shops, galleries, and restaurants. Visit the Telfair Museums to see a diverse collection of art.

Afternoon

For lunch, try the Southern fusion cuisine at Cotton & Rye. In the afternoon, take a Savannah Art Walk to discover the city's vibrant art scene. Visit the local galleries and meet the artists.

Evening

Enjoy a seafood dinner at Desposito's Seafood Restaurant and then take a Haunted Pub Crawl to hear ghost stories and enjoy the local brews.

Bedtime

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Savannah Art Walk
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Haunted Pub Crawl
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Beachside Bliss and Island Adventures

Morning

Travel to Hilton Head Island and start your day with a beachfront breakfast at The Sea Shack. Then, relax on the sandy shores of Coligny Beach Park or take a dip in the ocean. Enjoy the laid-back island vibes.

Afternoon

For lunch, try the fresh seafood at Hudson's Seafood House on the Docks. In the afternoon, explore the Pinckney Island National Wildlife Refuge and spot the local wildlife. You can also enjoy water activities like kayaking or paddleboarding.

Evening

Dine at Skull Creek Boathouse with views of the water and live music. After dinner, take a sunset cruise to see the island from a different perspective and enjoy the coastal breeze.

Bedtime

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Pinckney Island National Wildlife Refuge
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Island Relaxation and Farewell

Morning

On your last day, have a leisurely breakfast at Palmetto Bay Sunrise Cafe and spend the morning relaxing on the beach or exploring the Harbour Town Lighthouse and Museum. Take in the panoramic views from the top of the lighthouse.

Afternoon

For lunch, enjoy the waterfront dining at The Salty Dog Cafe. Afterward, take a Dolphin Watching Cruise to see the playful dolphins in the waters around Hilton Head Island.

Evening

End your trip with a memorable dinner at Alexander's Restaurant & Wine Bar and a leisurely walk along the marina. Reflect on your historic and relaxing journey through Charleston, Savannah, and Hilton Head Island.

Bedtime

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