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![Ultimate 5-Day Charleston and Sullivan's Island Adventure](/ItineraryPage/nature-scene.webp)
Ultimate 5-Day Charleston and Sullivan's Island Adventure Itinerary
Last updated: 2024 Jun 14Historical Charleston and Harbor Cruise
Morning
Begin your day with a delightful breakfast at The Obstinate Daughter, known for its unique and delicious dishes. Afterward, embark on the Charleston Historical Downtown Tour by Horse-drawn Carriage to immerse yourself in the city's rich history and charming architecture.
Afternoon
For lunch, savor the flavors of the South at Halls Chophouse, a renowned steakhouse. Afterward, enjoy a Charleston Harbor Bar Pedal Boat Party Cruise for a fun and unique experience on the water.
Evening
Indulge in a luxurious dinner at FIG, a top-rated restaurant in Charleston. Afterward, take a leisurely stroll along the waterfront and enjoy the evening ambiance of the city.
Bedtime
Find amazing hotels in Charleston, South Carolina.
![Visit Charleston Historical Downtown Tour by Horse-drawn Carriage in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/63ab2d72dba42.jpeg/21.jpg)
4.78Charleston Historical Downtown Tour by Horse-drawn Carriage
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![Visit Charleston Historical Downtown Tour by Horse-drawn Carriage in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/63ab2d72dba42.jpeg/21.jpg)
Charleston Historical Downtown Tour by Horse-drawn Carriage
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![Visit Charleston Harbor Bar Pedal Boat Party Cruise in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/62e129d243906.jpeg/21.jpg)
4.93Charleston Harbor Bar Pedal Boat Party Cruise
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![Visit Charleston Harbor Bar Pedal Boat Party Cruise in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/62e129d243906.jpeg/21.jpg)
Charleston Harbor Bar Pedal Boat Party Cruise
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Plantations and Ghostly Tales
Morning
Start your day with a hearty breakfast at Home Team BBQ, a local favorite for authentic Southern barbecue. Then, embark on a journey to the Charleston Boone Hall Plantation Entry & Tour w/ Transport, where you'll learn about the history of the Lowcountry.
Afternoon
For lunch, head to The Boathouse at Breach Inlet, a waterfront restaurant with stunning views. Afterward, experience the Charleston Haunted Carriage Evening Tour for a spine-chilling exploration of the city's haunted past.
Evening
Enjoy a relaxing dinner at Dunleavy's Pub, a cozy Irish pub with a welcoming atmosphere. End your evening with a nightcap at a local bar and reflect on the day's adventures.
Bedtime
Find amazing hotels in Charleston, South Carolina.
![Visit Charleston Boone Hall Plantation Entry & Tour w/ Transport in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/3cd78fe53922c553.jpeg/21.jpg)
4.38Charleston Boone Hall Plantation Entry & Tour w/ Transport
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![Visit Charleston Boone Hall Plantation Entry & Tour w/ Transport in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/3cd78fe53922c553.jpeg/21.jpg)
Charleston Boone Hall Plantation Entry & Tour w/ Transport
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![Visit Charleston Haunted Carriage Evening Tour in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/63ab31164feb4.jpeg/21.jpg)
4.70Charleston Haunted Carriage Evening Tour
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![Visit Charleston Haunted Carriage Evening Tour in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/63ab31164feb4.jpeg/21.jpg)
Charleston Haunted Carriage Evening Tour
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Sullivan's Island Relaxation
Morning
Wake up to the sound of the waves and enjoy a leisurely breakfast at Poe's Tavern, a charming restaurant with a literary theme. Spend the morning relaxing on the beach or exploring the island's natural beauty.
Afternoon
For lunch, grab a bite at Mex 1 Coastal Cantina, a casual spot known for its fresh and flavorful Mexican cuisine. Afterward, take a stroll around the island and visit the historic Fort Moultrie for a glimpse into the area's military past.
Evening
Enjoy a seafood dinner at a local restaurant, such as The Obstinate Daughter, and watch the sunset over the water. Afterward, unwind with a drink at a beachfront bar and soak in the island's laid-back atmosphere.
Bedtime
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Charleston's Cultural Heritage
Morning
Start your day with a delicious breakfast at The Boathouse at Breach Inlet, then join the Charleston African-American History & Simmons House Tour to learn about the city's diverse heritage.
Afternoon
For lunch, try the fresh seafood at The Obstinate Daughter, then explore the Charleston Women and Wine Tour for a unique blend of history and wine tasting.
Evening
Enjoy a sophisticated dinner at Halls Chophouse, followed by a visit to a local jazz club or live music venue for a night of entertainment.
Bedtime
Find amazing hotels in Charleston, South Carolina.
![Visit Charleston African-American History & Simmons House Tour in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/c12b8e7fe55ec0e3.jpeg/21.jpg)
4.76Charleston African-American History & Simmons House Tour
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![Visit Charleston African-American History & Simmons House Tour in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/c12b8e7fe55ec0e3.jpeg/21.jpg)
Charleston African-American History & Simmons House Tour
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![Visit Charleston Women and Wine Tour in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/30b6c0ae669facff.jpeg/21.jpg)
5.00Charleston Women and Wine Tour
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![Visit Charleston Women and Wine Tour in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/30b6c0ae669facff.jpeg/21.jpg)
Charleston Women and Wine Tour
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Farewell to Charleston
Morning
Enjoy a final breakfast at Dunleavy's Pub, then take a Charleston Sightseeing Harbor Tour & Dolphin Watch to bid farewell to the city from the water.
Afternoon
For lunch, savor the flavors of the South at Home Team BBQ, then spend your last afternoon exploring the city's shops and galleries, picking up souvenirs to remember your trip.
Evening
Conclude your Charleston adventure with a memorable dinner at Halls Chophouse, where you can toast to the memories made and the experiences shared during your time in this historic city.
Bedtime
Find amazing hotels in Charleston, South Carolina.
![Visit Charleston Sightseeing Harbor Tour & Dolphin Watch in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/609c292dd928f.jpeg/21.jpg)
4.51Charleston Sightseeing Harbor Tour & Dolphin Watch
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![Visit Charleston Sightseeing Harbor Tour & Dolphin Watch in Charleston, South Carolina](https://cdn.getyourguide.com/img/tour/609c292dd928f.jpeg/21.jpg)
Charleston Sightseeing Harbor Tour & Dolphin Watch
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