Discover the Charm of Hilton Head Island: A 7-Day Coastal Retreat

Immerse yourself in the natural beauty and rich history of Hilton Head Island with this 7-day itinerary, featuring dolphin tours, exquisite dining, and serene beaches.

Hilton Head Island, nestled in the heart of South Carolina's Lowcountry, is a haven for nature lovers and history enthusiasts alike. Known for its pristine beaches and lush maritime forests, the island offers a perfect blend of relaxation and adventure. With a history dating back to the 16th century, Hilton Head has evolved from a quiet retreat to a bustling destination, while still preserving its natural charm.


Fun fact: Hilton Head Island is home to the iconic Harbour Town Lighthouse, a symbol of the island's rich maritime heritage. The island's unique ecosystem supports a diverse range of wildlife, including the playful Atlantic bottlenose dolphins that frequent its waters. Whether you're exploring the island's scenic bike trails or indulging in its culinary offerings, Hilton Head promises an unforgettable experience.

Before you embark on your journey, note that Hilton Head Island is easily accessible via Savannah/Hilton Head International Airport. The island's culinary scene is a delightful mix of Southern comfort food and fresh seafood, with local favorites like shrimp and grits and Lowcountry boil. Be sure to pack your sunscreen and a sense of adventure as you prepare to explore this coastal gem.

Hilton Head Island

Welcome to Hilton Head Island, a picturesque destination renowned for its stunning beaches, world-class golf courses, and vibrant wildlife. The island's laid-back atmosphere and natural beauty make it an ideal getaway for families, couples, and solo travelers. With over 12 miles of sandy shores, Hilton Head offers endless opportunities for relaxation and exploration.

For accommodations, consider staying at The Sea Pines Resort, known for its luxurious amenities and prime location. Alternatively, the Holiday Inn Express Hilton Head Island offers a comfortable stay with easy access to the island's attractions. For a beachfront experience, the Omni Hilton Head Oceanfront Resort is a top choice.

Traveling to Hilton Head Island is convenient with flights available through Trip.com and Kiwi.com. Once on the island, renting a bike is a popular way to explore its scenic trails and charming neighborhoods.


Day 1: Arrival and Beach Relaxation

Afternoon: Arrive at Hilton Head Island and check into your chosen accommodation. Spend your first afternoon unwinding on Coligny Beach, known for its soft sands and gentle waves. Take a leisurely stroll along the shore or rent a beach chair and soak up the sun.

Evening: For dinner, head to Skull Creek Boathouse, a local favorite offering fresh seafood and stunning waterfront views. Try their famous Lowcountry boil or the catch of the day. After dinner, enjoy a sunset walk along the beach to end your first day on a relaxing note.

Day 2: Dolphin Watching and Harbour Town

Morning: Start your day with a visit to Java Burrito Company for a hearty breakfast burrito and freshly brewed coffee. Then, embark on a Hilton Head Island Dolphin Boat Cruise to witness dolphins in their natural habitat.

Hilton Head Island Dolphin Boat Cruise on Viator

Afternoon: Head to Harbour Town, where you can climb the iconic Harbour Town Lighthouse for panoramic views of the island. Explore the charming shops and grab a light lunch at The Quarterdeck, known for its seafood and casual atmosphere.

Evening: Enjoy a leisurely dinner at CQ's Restaurant, offering a menu of Southern-inspired dishes in a cozy setting. After dinner, take a stroll through Harbour Town and enjoy live music at one of the local venues.


Day 3: Outdoor Adventures and Local Cuisine

Morning: Fuel up with breakfast at Palmetto Bay Sunrise Cafe, famous for its omelets and pancakes. Then, embark on a Hilton Head Dolphin Tour with Stop at Disappearing Island for a unique experience exploring the island's ecosystem.

Hilton Head Dolphin Tour with Stop at Disappearing Island on Viator

Afternoon: After your tour, enjoy lunch at Hudson's Seafood House on the Docks, offering fresh seafood with a view of the water. Spend the afternoon exploring the island's bike trails or visiting the Coastal Discovery Museum to learn about the area's history and wildlife.

Evening: For dinner, visit The Jazz Corner, a renowned spot for live jazz music and gourmet dining. Savor dishes like shrimp and grits while enjoying the vibrant atmosphere.

Day 4: Day Trip to Savannah

Take a day trip to Savannah, Georgia, with a Hilton Head to Savannah Round-Trip Ferry Ticket. Spend the day exploring Savannah's historic district, with its cobblestone streets and charming squares. Visit Forsyth Park, the Cathedral of St. John the Baptist, and enjoy lunch at The Collins Quarter, known for its Australian-inspired cuisine. Return to Hilton Head in the evening and relax at your accommodation.

Hilton Head to Savannah Round-Trip Ferry Ticket on Viator

Day 5: Golfing and Spa Day

Morning: Start your day with breakfast at Plantation Cafe & Deli, offering a variety of breakfast classics. Then, tee off at one of Hilton Head's renowned golf courses, such as Harbour Town Golf Links or Palmetto Dunes.


Afternoon: After a morning on the greens, treat yourself to a relaxing afternoon at the Heavenly Spa by Westin. Indulge in a massage or facial to rejuvenate your senses.

Evening: For dinner, head to Red Fish, a local favorite known for its creative seafood dishes and extensive wine list. End your day with a nightcap at The Rooftop Bar at Poseidon, offering panoramic views of the island.

Day 6: Kayaking and Sunset Cruise

Morning: Enjoy a leisurely breakfast at Watusi Cafe, known for its healthy options and cozy atmosphere. Then, embark on a 2-Hour Hilton Head Guided Kayak Nature Tour to explore the island's salt marshes and observe local wildlife.

2-Hour Hilton Head Guided Kayak Nature Tour on Viator

Afternoon: After your kayaking adventure, enjoy lunch at The Salty Dog Cafe, a beloved spot for seafood and waterfront views. Spend the afternoon relaxing on the beach or exploring the island's shops and galleries.

Evening: End your day with a Hilton Head Sunset Dinner Cruise, where you can savor a delicious meal while watching the sun set over the water.

Hilton Head Sunset Dinner Cruise on Viator


Day 7: Departure

Morning: On your final day, enjoy a leisurely breakfast at Southern Coney & Breakfast, known for its Southern hospitality and hearty dishes. Spend your morning visiting the Pinckney Island National Wildlife Refuge, where you can explore its trails and observe a variety of bird species.

Afternoon: Before departing, enjoy a final lunch at Fishcamp on Broad Creek, offering a menu of Southern classics and seafood favorites. Take in the views of the creek as you reflect on your memorable week on Hilton Head Island.

As your 7-day adventure on Hilton Head Island comes to a close, you'll leave with cherished memories of its natural beauty, rich history, and warm hospitality. Whether you spent your days exploring the island's scenic landscapes or indulging in its culinary delights, Hilton Head promises a vacation filled with relaxation and discovery.

Ready to book your trip?

Search Hotels
Search Homes

Traveling somewhere else?

Generate a custom itinerary