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Charleston and Hilton Head 8-Day Adventure Itinerary
Last updated: 2024 Jun 14Historic Charleston Exploration
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 stalls and pick up some local crafts and souvenirs.
Afternoon
For lunch, savor the fresh seafood at Fleet Landing Restaurant & Bar with views of the water. Afterward, take a guided tour of the Old Exchange & Provost Dungeon to learn about the city's colonial past.
Evening
Enjoy a sophisticated dinner at Husk, known for its innovative Southern cuisine. Take a leisurely walk along The Battery and White Point Garden to admire the historic mansions and ocean views.
Bedtime
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4.67Charleston City Market
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4.67Charleston City Market
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4.76Old Exchange & Provost Dungeon
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4.76Old Exchange & Provost Dungeon
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Mansion and Plantation Day
Morning
Indulge in a delicious brunch at 82 Queen, a charming Southern restaurant. Afterward, visit the Nathaniel Russell House to experience the grandeur of a historic Charleston mansion.
Afternoon
For a late afternoon snack, stop by The Darling Oyster Bar for some fresh oysters. Then, take a scenic drive to Magnolia Plantation and Gardens to explore the beautiful gardens and learn about Lowcountry history.
Evening
Dine at Magnolias, a renowned restaurant for its upscale Southern cuisine. After dinner, relax at a local bar like Prohibition for a taste of Charleston's nightlife.
Bedtime
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4.25Nathaniel Russell House
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4.25Nathaniel Russell House
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4.49Magnolia Plantation and Gardens
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4.49Magnolia Plantation and Gardens
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Art and Museum Day
Morning
Start your day with a leisurely breakfast at The Macintosh, known for its farm-to-table fare. Then, visit the Gibbes Museum of Art to admire a diverse collection of American art.
Afternoon
For lunch, enjoy the vibrant flavors of Asian cuisine at Xiao Bao Biscuit. Afterward, take a stroll to the Charleston Museum to delve into the city's rich history.
Evening
Dine at FIG, a favorite for its Mediterranean-inspired dishes. After dinner, take a relaxing walk along the Charleston Waterfront Park.
Bedtime
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4.41Gibbes Museum of Art
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4.41Gibbes Museum of Art
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4.53Charleston Museum
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4.53Charleston Museum
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Churches and Culinary Delights
Morning
Enjoy a traditional Southern breakfast at Poogan's Porch, a charming restaurant in a historic Victorian house. Then, take a self-guided tour of the many beautiful churches in Charleston, including St. Michael's Church, St Philips Church, and Circular Congregational Church.
Afternoon
For lunch, try the innovative cuisine at The Obstinate Daughter on Sullivan's Island. Afterward, visit the Aiken-Rhett House to see a preserved urban plantation.
Evening
Indulge in a fine dining experience at Peninsula Grill, known for its romantic courtyard. After dinner, take a leisurely walk along the King Street to explore the local shops and galleries.
Bedtime
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4.85St. Michael's Church
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4.85St. Michael's Church
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4.76St Philips Church
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4.76St Philips Church
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Bridge and Maritime Adventure
Morning
Start your day with a hearty breakfast at The Ordinary, a seafood restaurant known for its oyster bar. Then, take a scenic drive over the Arthur Ravenel Jr. Bridge (Cooper River Bridge) for panoramic views of the city.
Afternoon
For lunch, enjoy the casual atmosphere and delicious sandwiches at Butcher & Bee. Afterward, visit the Patriots Point Naval & Maritime Museum to explore the USS Yorktown and other historic ships.
Evening
Dine at Halls Chophouse, a classic steakhouse with a lively atmosphere. After dinner, take a sunset cruise to see the city from the water.
Bedtime
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4.73Arthur Ravenel Jr. Bridge (Cooper River Bridge)
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4.73Arthur Ravenel Jr. Bridge (Cooper River Bridge)
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4.80Patriots Point Naval & Maritime Museum
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4.80Patriots Point Naval & Maritime Museum
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Plantation and Fort Day
Morning
Enjoy a relaxed breakfast at Slightly North of Broad (SNOB), a Lowcountry bistro. Then, take a day trip to Middleton Place, a historic plantation with stunning gardens.
Afternoon
For lunch, have a picnic at Middleton Place or dine at the on-site restaurant. Afterward, visit Fort Sumter National Monument to learn about the start of the Civil War.
Evening
Return to Charleston for dinner at Leon's Oyster Shop, a local favorite for its seafood dishes. After dinner, take a ghost tour to explore the city's haunted history.
Bedtime
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4.68Middleton Place
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4.68Middleton Place
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4.67Fort Sumter National Monument
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4.67Fort Sumter National Monument
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Beach and Relaxation Day
Morning
Take a scenic drive to Hilton Head and enjoy a leisurely breakfast at The Salty Dog Cafe overlooking the water. Spend the morning relaxing on the beach or trying water sports.
Afternoon
For lunch, savor the fresh seafood at Hudson's Seafood House on the Docks. Afterward, explore the local shops and galleries on the island.
Evening
Dine at Red Fish, a restaurant known for its innovative cuisine. Take a sunset walk on the beach to end your day.
Bedtime
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Final Charleston Day
Morning
Enjoy a leisurely brunch at 167 Raw, a popular spot for oysters and seafood. Spend the morning exploring the Charleston Scavenger Hunt, a fun way to discover the hidden gems of the city.
Afternoon
For your last lunch in Charleston, indulge in the Southern classics at McCrady's Tavern. Afterward, visit the Drayton Hall, the oldest preserved plantation house in America.
Evening
End your Charleston adventure with a memorable dinner at Fig, known for its seasonal cuisine. Take a historic walking tour in the evening to learn about the city's past.
Bedtime
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Charleston Scavenger Hunt
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Charleston Scavenger Hunt
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4.54Drayton Hall
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4.54Drayton Hall
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