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![5-day Trip to Hilton Head Island](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018bb974-695d-7b7d-a49f-17dec04e21cd/location502.jpg)
5-day Trip to Hilton Head Island Itinerary
Last updated: 2024 Jun 14Island Exploration
Morning
Start your day with a delicious breakfast at The Salty Dog Cafe. Afterward, embark on a Hilton Head Island Dolphin Watching Guided Tour by Boat to witness the playful dolphins in their natural habitat.
Afternoon
For lunch, head to Skull Creek Boathouse and savor their fresh seafood specialties. Afterward, take a Hilton Head Island Scenic Helicopter Tour to enjoy breathtaking aerial views of the island.
Evening
Indulge in a delightful dinner at Hudson's Seafood House on the Docks while enjoying the waterfront ambiance. End the day with a Hilton Head Island Sunset Dolphin Cruise to witness a stunning sunset over the water.
Bedtime
Find amazing hotels in Hilton Head Island.
![Visit Hilton Head Island Dolphin Watching Guided Tour by Boat in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e2b29ee5f480.jpeg/21.jpg)
4.79Hilton Head Island Dolphin Watching Guided Tour by Boat
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![Visit Hilton Head Island Dolphin Watching Guided Tour by Boat in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e2b29ee5f480.jpeg/21.jpg)
Hilton Head Island Dolphin Watching Guided Tour by Boat
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![Visit Hilton Head Island Scenic Helicopter Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/998f0135d44a8dc2b62910cec455d286511536f271b2171b9d870505637951ed.jpg/21.jpg)
4.88Hilton Head Island Scenic Helicopter Tour
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![Visit Hilton Head Island Scenic Helicopter Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/998f0135d44a8dc2b62910cec455d286511536f271b2171b9d870505637951ed.jpg/21.jpg)
Hilton Head Island Scenic Helicopter Tour
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![Visit Hilton Head Island Sunset Dolphin Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/8b5b3215ff3ca5d5e359ed928ca02593cbe97411019ee9b81ea4825a126eab71.jpg/21.jpg)
4.59Hilton Head Island Sunset Dolphin Cruise
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![Visit Hilton Head Island Sunset Dolphin Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/8b5b3215ff3ca5d5e359ed928ca02593cbe97411019ee9b81ea4825a126eab71.jpg/21.jpg)
Hilton Head Island Sunset Dolphin Cruise
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Historic Charm
Morning
Start your day with a Beaufort Historic City Tour by Bus to explore the rich history and charming architecture of Beaufort. Enjoy a quick snack at a local cafe.
Afternoon
For lunch, visit The Crazy Crab Harbour Town and savor their delicious seafood dishes. Afterward, take a Hilton Head Island America’s Cup Sailing Yacht Cruise and experience the thrill of sailing on a championship yacht.
Evening
Enjoy a delightful dinner at Fishcamp on Broad Creek while overlooking the scenic water views. Afterward, head to Beaufort Tipsy Tour for a fun and entertaining evening exploring the local bars and pubs.
Bedtime
Find amazing hotels in Hilton Head Island.
![Visit Beaufort Historic City Tour by Bus in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e2b4305584af.jpeg/21.jpg)
4.92Beaufort Historic City Tour by Bus
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![Visit Beaufort Historic City Tour by Bus in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e2b4305584af.jpeg/21.jpg)
Beaufort Historic City Tour by Bus
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![Visit Hilton Head Island America’s Cup Sailing Yacht Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6026a7d3999ca.jpeg/21.jpg)
4.83Hilton Head Island America’s Cup Sailing Yacht Cruise
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![Visit Hilton Head Island America’s Cup Sailing Yacht Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6026a7d3999ca.jpeg/21.jpg)
Hilton Head Island America’s Cup Sailing Yacht Cruise
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![Visit Beaufort Tipsy Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/649ab8bef0a1e.png/21.jpg)
5.00Beaufort Tipsy Tour
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![Visit Beaufort Tipsy Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/649ab8bef0a1e.png/21.jpg)
Beaufort Tipsy Tour
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Nature and Adventure
Morning
Start your day with a Hilton Head Island Dolphin Cruise & Nature Tour to observe the diverse marine life and beautiful coastal scenery. Grab a quick coffee at a nearby cafe.
Afternoon
For lunch, visit Black Marlin Bayside Grill and enjoy their delectable seafood dishes. Afterward, embark on a thrilling Hilton Head Island High-Flying Parasail Experience for panoramic views of the island.
Evening
Indulge in a delightful dinner at Old Oyster Factory while savoring their fresh oyster selection. End the day with a Hilton Head Island Sunset Dinner Cruise and enjoy a scenic dinner cruise along the coast.
Bedtime
Find amazing hotels in Hilton Head Island.
![Visit Hilton Head Island Dolphin Cruise & Nature Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/624333e015b60.jpeg/21.jpg)
4.71Hilton Head Island Dolphin Cruise & Nature Tour
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![Visit Hilton Head Island Dolphin Cruise & Nature Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/624333e015b60.jpeg/21.jpg)
Hilton Head Island Dolphin Cruise & Nature Tour
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![Visit Hilton Head Island High-Flying Parasail Experience in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e821823d0b05.jpeg/21.jpg)
4.90Hilton Head Island High-Flying Parasail Experience
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![Visit Hilton Head Island High-Flying Parasail Experience in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e821823d0b05.jpeg/21.jpg)
Hilton Head Island High-Flying Parasail Experience
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![Visit Hilton Head Island Sunset Dinner Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6033fd920fc24.jpeg/21.jpg)
4.44Hilton Head Island Sunset Dinner Cruise
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![Visit Hilton Head Island Sunset Dinner Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6033fd920fc24.jpeg/21.jpg)
Hilton Head Island Sunset Dinner Cruise
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Coastal Excursion
Morning
Start your day with a Hilton Head Island Round-Trip Ferry Ticket to Savannah and explore the charming city of Savannah, Georgia. Enjoy a leisurely breakfast at a local cafe.
Afternoon
For lunch, visit Poseidon Coastal Cuisine and Rooftop Bar and indulge in their coastal-inspired dishes. Afterward, take a Tybee Island Historical 2-Hour Bike Tour to discover the historical landmarks of Tybee Island.
Evening
Enjoy a delicious dinner at Red Fish Hilton Head Island while savoring their creative seafood dishes. Afterward, head to Hilton Head Private 2-hour Sunset Cruise for a private and romantic sunset experience on the water.
Bedtime
Find amazing hotels in Hilton Head Island.
![Visit Hilton Head Island Round-Trip Ferry Ticket to Savannah in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6026995144d3a.jpeg/21.jpg)
4.54Hilton Head Island Round-Trip Ferry Ticket to Savannah
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![Visit Hilton Head Island Round-Trip Ferry Ticket to Savannah in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6026995144d3a.jpeg/21.jpg)
Hilton Head Island Round-Trip Ferry Ticket to Savannah
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![Visit Tybee Island Historical 2-Hour Bike Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/af06d8ca8dcf4b2a.jpeg/21.jpg)
Tybee Island Historical 2-Hour Bike Tour
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![Visit Tybee Island Historical 2-Hour Bike Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/af06d8ca8dcf4b2a.jpeg/21.jpg)
Tybee Island Historical 2-Hour Bike Tour
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![Visit Hilton Head Private 2-hour Sunset Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/589f77407550ea09.jpeg/21.jpg)
4.92Hilton Head Private 2-hour Sunset Cruise
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![Visit Hilton Head Private 2-hour Sunset Cruise in Hilton Head Island](https://cdn.getyourguide.com/img/tour/589f77407550ea09.jpeg/21.jpg)
Hilton Head Private 2-hour Sunset Cruise
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Island Adventure
Morning
Start your day with a thrilling Hilton Head Island Mini Boat Dolphin Tour to explore the island's hidden coves and encounter dolphins up close. Grab a quick breakfast at a local cafe.
Afternoon
For lunch, visit Charlie's L'Etoile Verte and enjoy their exquisite French cuisine. Afterward, rent an electric bike from Hilton Head Half-Day Electric Bike Rental Options and explore the island's scenic bike trails.
Evening
Indulge in a delightful dinner at WiseGuys while savoring their mouthwatering steaks and seafood. End the trip with a Hilton Head Island Mermaid Photoshoot at an Indoor Beach to capture unique and memorable moments.
Bedtime
Find amazing hotels in Hilton Head Island.
![Visit Hilton Head Island Mini Boat Dolphin Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e2b12f5ccbe7.jpeg/21.jpg)
4.88Hilton Head Island Mini Boat Dolphin Tour
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![Visit Hilton Head Island Mini Boat Dolphin Tour in Hilton Head Island](https://cdn.getyourguide.com/img/tour/5e2b12f5ccbe7.jpeg/21.jpg)
Hilton Head Island Mini Boat Dolphin Tour
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![Visit Hilton Head Half-Day Electric Bike Rental Options in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6fae464928faeb85.jpeg/21.jpg)
5.00Hilton Head Half-Day Electric Bike Rental Options
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![Visit Hilton Head Half-Day Electric Bike Rental Options in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6fae464928faeb85.jpeg/21.jpg)
Hilton Head Half-Day Electric Bike Rental Options
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![Visit Hilton Head Island Mermaid Photoshoot at an Indoor Beach in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6245d70e40ff2.jpeg/21.jpg)
Hilton Head Island Mermaid Photoshoot at an Indoor Beach
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![Visit Hilton Head Island Mermaid Photoshoot at an Indoor Beach in Hilton Head Island](https://cdn.getyourguide.com/img/tour/6245d70e40ff2.jpeg/21.jpg)
Hilton Head Island Mermaid Photoshoot at an Indoor Beach
Book Now