Ultimate 5-Day Hilton Head Island Adventure Itinerary

Enjoy a relaxed morning with breakfast at Santa Fe Cafe Hilton Head Island SC, known for its Southwestern cuisine. Afterward, take a Hilton Head Island Scenic Helicopter Tour to admire the beauty of the island from above.

For lunch, savor the flavors of the coast at Coast Oceanfront Dining. In the afternoon, experience the Hilton Head Island America’s Cup Sailing Yacht Cruise for a taste of sailing history.

Dine at ELA'S On the Water for a waterfront dining experience, watching the sunset over the harbor.

Start your day with a peaceful breakfast at Old Oyster Factory Restaurant with a view. Then, immerse yourself in nature with a Hilton Head Island Dolphin and Nature Tour to learn about the local ecosystem.

Enjoy a leisurely lunch at Red Fish Hilton Head Island and spend the afternoon at the beach, relaxing and soaking up the sun.

For dinner, indulge in Italian cuisine at Michael Anthony's Cucina Italiana in a cozy setting.

Take a morning ferry to Daufuskie Island and have breakfast at Marshside Mama's upon arrival. Explore the island's unique culture and history, visiting sites like the First African Baptist Church and the Daufuskie Island Rum Company.

Enjoy a Lowcountry lunch at Daufuskie Crab Company and spend the afternoon relaxing on the beach or taking a Hilton Head Island Self-Drive Pontoon Boat Rental around the island.

Return to Hilton Head for a dinner at Hudson's Seafood House on the Docks, known for its waterfront dining experience.

On your last day, have a luxurious breakfast at Skull Creek Boathouse with a view of the water. Then, set out on a Hilton Head Private 2-hour Sunset Cruise for a private and intimate experience.

Enjoy a final lunch at OMBRA Cucina Rustica - Hilton Head Island, SC. and spend the afternoon at leisure, perhaps shopping at the Shelter Cove Towne Centre.

Conclude your Hilton Head adventure with a memorable dinner at Charlie's L'Etoile Verte, known for its French and Lowcountry fusion cuisine.