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Ultimate 8-Day Hilton Head Island Itinerary Itinerary
Last updated: 2024 Jun 14Island Welcome and Sunset Cruise
Morning
Begin your Hilton Head adventure with a delightful breakfast at A Lowcountry Backyard Restaurant. Afterward, take a stroll on the picturesque Coligny Beach and explore the shops at Coligny Plaza.
Afternoon
Savor a sumptuous lunch at Skull Creek Boathouse, known for its waterfront dining. Spend your afternoon with an interactive Hilton Head Island Self-Guided Kayaking Tour, exploring the island's waterways and spotting local wildlife.
Evening
As the sun sets, enjoy a magical experience on the Hilton Head Island Sunset Dolphin Cruise. Witness dolphins playfully swimming in the golden light, accompanied by live commentary, and indulge in a memorable dinner onboard.
Bedtime
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Mango's Tropical Café
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Hilton Head Island 1.5-Hour Guided Small-Group Kayak Tour
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Hilton Head Island Sunset Dolphin Cruise
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Historic Tours and Gourmet Dining
Morning
Start with a delicious breakfast at The Crazy Crab Jarvis Creek. Then, embark on a journey to the past with the Hilton Head Island Historic Bike Tour. Explore the island's rich history and beautiful landscapes.
Afternoon
For lunch, head to Coast Oceanfront Dining and enjoy a meal with breathtaking views. Afterward, take a leisurely drive to the neighboring city of Beaufort for the Beaufort Historic City Tour by Bus. Explore the antebellum architecture and learn about the area's history.
Evening
Dine at Frankie Bones Restaurant & Lounge, a local favorite with a unique atmosphere and delectable menu. Conclude your evening with live jazz music at The Jazz Corner, known for its vibrant entertainment and excellent drinks.
Bedtime
Find amazing hotels in Hilton Head Island.
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Beaufort Historic City Tour by Bus
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Hilton Head Island Dolphin Nature Cruise
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Nature's Wonders and Culinary Delights
Morning
Enjoy a delightful breakfast at Charlie's L'Etoile Verte. Then, spend your morning on the Hilton Head Island Dolphin Watching Guided Tour by Boat, observing these magnificent creatures in their natural habitat.
Afternoon
Have lunch at WiseGuys, where the menu is filled with creative offerings. Afterward, take a serene Hilton Head Island Nature Lovers' Guided Kayak Tour, exploring the island's hidden waterways and spotting local wildlife.
Evening
Dine at Michael Anthony's Cucina Italiana for an elegant Italian dinner. Cap off the night with a visit to Hilton Head Island Sunset Dinner Cruise, enjoying a luxurious meal with stunning views of the water.
Bedtime
Find amazing hotels in Hilton Head Island.
Popular
Hilton Head Island Dolphin Watching Guided Tour by Boat
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Popular
Hilton Head Island Sunset Dinner Cruise
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Relaxation and Savannah Excursion
Morning
Start with a delightful breakfast at Old Oyster Factory Restaurant, known for its waterfront dining. Then, prepare for a day trip as you take the Hilton Head Island Round-Trip Ferry Ticket to Savannah. Explore the charming streets, historic sites, and vibrant culture of Savannah, Georgia.
Afternoon
Enjoy a delicious lunch at Santa Fe Cafe Hilton Head Island SC, a Southwestern-inspired eatery. After returning from Savannah, relax on the beautiful Hilton Head Island Beaches or explore the shops and galleries at Harbour Town.
Evening
For dinner, savor the flavors of the sea at Hudson's Seafood House on the Docks. End your night with a leisurely stroll and some live entertainment at Shelter Cove Harbour.
Bedtime
Find amazing hotels in Hilton Head Island.
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Hilton Head Island Round-Trip Ferry Ticket to Savannah
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Mango's Tropical Café
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Scenic Views and Daufuskie Island Exploration
Morning
Begin with breakfast at OMBRA Cucina Rustica - Hilton Head Island, SC., offering a taste of authentic Italian cuisine. Then, take to the skies on a Hilton Head Island Scenic Helicopter Tour, admiring the breathtaking aerial views of the island and surrounding waters.
Afternoon
Have lunch at CQ's Restaurant at Harbour Town Golf Links, where you can enjoy a meal with views of the golf course. Afterward, embark on the Hilton Head Island Round-Trip Daufuskie Island Ferry and spend your afternoon exploring the unique culture and history of Daufuskie Island.
Evening
Dine at ELA'S On the Water for a sophisticated waterfront dining experience. Conclude your day with a peaceful Hilton Head Island Sunset Kayaking Tour, gliding through the calm waters as the sun paints the sky.
Bedtime
Find amazing hotels in Hilton Head Island.
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Hilton Head Island Scenic Helicopter Tour
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Popular
Hilton Head Island Round-Trip Daufuskie Island Ferry
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Popular
Hilton Head Island 1.5-Hour Guided Small-Group Kayak Tour
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Dolphin Discoveries and Gullah Heritage
Morning
Enjoy breakfast at The Salty Dog Cafe, a Hilton Head classic. Then, set out on the Hilton Head Island Dolphin Cruise & Nature Tour to witness the playful dolphins and learn about the island's ecosystem.
Afternoon
For lunch, head to Red Fish Hilton Head Island and indulge in their fresh, contemporary Lowcountry cuisine. Afterward, immerse yourself in the rich Gullah culture with the Beaufort Gullah Heritage Tour in the nearby city of Beaufort.
Evening
Dine at Poseidon Coastal Cuisine and Rooftop Bar for a sophisticated meal with ocean views. Return to Hilton Head and enjoy the rest of your evening with a live performance at the vibrant Tiki Hut.
Bedtime
Find amazing hotels in Hilton Head Island.
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Hilton Head Island Dolphin Cruise & Nature Tour
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Beaufort Gullah Heritage Tour
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Hilton Head Island Dolphin Nature Cruise
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Leisurely Biking and Savannah's Charm
Morning
Start with a hearty breakfast at Lucky Rooster Kitchen + Bar, known for its innovative dishes. Then, spend your morning on the Hilton Head Island Self-Guided Bike Tour, exploring the island's beautiful landscapes and hidden gems.
Afternoon
Enjoy a leisurely lunch at The Wreck of the Salty Dog, where you can dine with views of the marina. Afterward, head back to Savannah for a relaxed afternoon of exploring the city's unique shops and boutiques.
Evening
Dine at Skull Creek Boathouse for a memorable meal with waterfront views. Conclude your night with a visit to Hilton Head Island Sunset Dolphin Cruise, where you can enjoy the island's natural beauty and the playful dolphins.
Bedtime
Find amazing hotels in Hilton Head Island.
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Hilton Head Island Sunset Dolphin Cruise
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Farewell to Hilton Head
Morning
Have a delightful breakfast at Frankie Bones Restaurant & Lounge, known for its upscale diner atmosphere. Then, take a peaceful morning walk at the Hilton Head Island Coastal Discovery Museum, exploring the cultural and natural history of the Lowcountry.
Afternoon
Enjoy a final lunch at Old Oyster Factory Restaurant, savoring the flavors of the sea. Spend your afternoon at the Hilton Head Island Shopping Locations, picking up some last-minute souvenirs and enjoying the island's retail offerings.
Evening
For your farewell dinner, choose The Jazz Corner for its intimate setting and outstanding cuisine. Reflect on your Hilton Head adventures over a gourmet meal, and perhaps enjoy a final drink while listening to live jazz music.
Bedtime
Find amazing hotels in Hilton Head Island.
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Hilton Head Island Dolphin Nature Cruise
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Hilton Head Island Dolphin Nature Cruise
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