Curator’s statement
Hilton Head Island is where Southern charm meets coastal adventure. It's an easy drive from most places in the Southeast and equally easy to access by plane. With its pristine beaches, world-class golf courses, great tennis and a laid-back yet luxurious atmosphere, it’s the perfect destination for a long weekend escape. Hilton Head is a place that blends relaxation, history and adventure seamlessly. Whether you're here for the golf or tennis, the beaches or the incredible seafood, this island has something for everyone. This itinerary is designed to help you experience the island’s best, from sunrise beach walks to sunset cocktails.
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Day 1: Arrival
Welcome to Hilton Head! After traveling, you’ll likely be ready to grab a bite before starting your adventure.
Lunch or late afternoon snack
Head to Skull Creek Boathouse for a relaxed waterfront lunch with fresh seafood, sushi and Lowcountry classics. The outdoor patio overlooking the marina is perfect for unwinding.
If you prefer something light, stop by The French Bakery & European Café for a croissant and iced coffee before exploring.
Afternoon activities
Stroll along Coligny Beach Park, where you can dip your toes in the Atlantic and get your first taste of Hilton Head’s famous wide, sandy beaches.
Rent bikes from Hilton Head Outfitters and explore the island’s 80 miles of scenic bike trails.
Stop by Harbour Town to see the iconic Harbour Town Lighthouse and enjoy boutique shopping.
Evening
Grab a sunset cocktail at Coast Oceanfront Dining with stunning beach views.
End the night with fresh seafood at Hudson’s Seafood House on the Docks, where the catch of the day is straight from local waters.
Day 2: Nature exploration
Plan to explore nature and hit the water! Pinckney Island National Wildlife Refuge is a hidden gem for nature lovers.
Morning
Kayak or paddleboard through Pinckney Island National Wildlife Refuge, a serene spot teeming with birds, dolphins and lush marshland. Rent gear from Outside Hilton Head.
Afternoon
Spend the rest of the afternoon at Driessen Beach Park, a more secluded, locals’ beach with soft sand and calm waves.
Evening
Enjoy dinner at The Jazz Corner, where live jazz music and gourmet Lowcountry cuisine create an unforgettable night. Reservations are a must!
Day 3: Golf or tennis & sunset sail
Hilton Head is well known for its award-winning golf courses and tennis facilities. Even if you are a beginner, and regardless of your age, you can enjoy group or individual lessons.
Morning golf
Tee off at one of Hilton Head’s championship golf courses, such as the Robert Trent Jones Course at Palmetto Dunes or Harbour Town Golf Links.
Mid-morning tennis lesson
Head to the Smith Stearns Tennis Academy or Palmetto Dunes Tennis & Pickleball Center for a private or group lesson with a pro. Hilton Head has been ranked one of the top US tennis destinations, so it’s the perfect place to improve your game!
Afternoon
Indulge in a spa treatment at The Heavenly Spa by Westin for the ultimate relaxation experience.
Evening
Take a sunset dolphin cruise with Vagabond Cruise and watch the sky turn pink over Calibogue Sound. End with a romantic waterfront dinner at Poseidon, where the rooftop bar offers breathtaking sunset views.
Day 4: Relax at Burkes Beach
Before you go, spend a peaceful morning at Burkes Beach. It's one of Hilton Head’s quieter beaches, making it the perfect spot to soak in the last of the island vibes.
Morning
Spend a lazy beach morning at Burkes Beach, one of the island’s most peaceful spots. Rent a cabana and soak up the last of Hilton Head’s sunshine.
Brunch & departure
Wrap up your trip with brunch at Lowcountry Produce Market & Café, known for its house-made jams and Southern specialties.
Travel Advisor
Tracy Nicholson
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For more inspiration and insider recommendations, visit our Hilton Head page.