Planning Guides
5-Day Hilton Head Itinerary
The best of the island — beaches, water activities, dining, and golf — in five days.
Five days on Hilton Head Island is the sweet spot — enough time to experience the best beaches, get on the water, eat well, explore the communities, and still feel like you've had a proper vacation. This itinerary is built around what locals actually recommend, not just the tourist highlights.
Day 1
Arrive, Settle In, Explore Coligny
Check In & Head to Coligny Beach
After checking in, head straight to Coligny Beach Park — the island's most accessible public beach. Spend the afternoon getting your bearings, swimming, and walking the shoreline. The beach faces southwest, so the afternoon light is beautiful.
💡 Arrive by 3pm to get a good spot before the afternoon rush.
Dinner at Skull Creek Dockside
Head to Skull Creek Dockside for your first Hilton Head waterfront dinner. The Lowcountry shrimp and grits are the move, and the sunset views over the Intracoastal Waterway are unmatched.
💡 Reservations recommended, especially on weekends.
Drinks at Skull Creek Boathouse
Walk or drive to the nearby Skull Creek Boathouse for a nightcap on the water. Live music most evenings, and the outdoor deck is one of the best spots on the island after dark.
💡 The bar gets busy after 8pm — arrive early for a good seat.
Day 2
Dolphin Tour & Harbour Town
Dolphin Tour from Shelter Cove
Book a morning dolphin tour with Lowcountry Watersports from Shelter Cove Marina. Hilton Head's bottlenose dolphins are incredibly active in the morning, and sightings are near-guaranteed. The 90-minute tour covers the creeks and open water.
💡 Book in advance — morning tours sell out fast in peak season.
Explore Harbour Town
Drive or bike to Harbour Town in Sea Pines. Climb the 114-step lighthouse for panoramic views of Calibogue Sound, browse the shops, and have lunch at The Quarterdeck on the water.
💡 Non-Sea Pines guests pay a $10 gate fee — worth every penny.
Dinner at Michael Anthony's
Michael Anthony's is one of the island's best fine-dining experiences — creative Lowcountry cuisine in a warm, intimate setting. Reserve ahead.
💡 Ask for the chef's tasting menu if you want the full experience.
Day 3
Beach Day & Water Activities
Full Morning at Driessen Beach
Driessen Beach is one of the island's most beautiful and least crowded public beaches. Arrive early, set up for the morning, and enjoy the wide flat sand and calm Atlantic water.
💡 Bring your own chairs and umbrella — rentals here book up fast.
Jet Ski Rentals or Kayaking
Spend the afternoon on the water. H2O Sports at Palmetto Dunes rents jet skis and kayaks with access to the 11-mile lagoon system — one of the best kayaking experiences on the island.
💡 The lagoon is calmer than the ocean and great for beginners.
Sunset Cruise
End the day on the water with a sunset cruise from Shelter Cove Marina. Lowcountry Watersports and Vagabond Cruise both offer excellent sunset tours. The views across the sound are spectacular.
💡 Book the 6:30pm departure for the best light in summer.
Day 4
Lowcountry Boil & Shopping
Bike the Trails
Rent bikes near your accommodation and explore Hilton Head's 60+ miles of paved bike paths. The Sea Pines Forest Preserve loop is a local favorite — 8 miles through maritime forest with wildlife sightings.
💡 Rent from a local shop rather than a resort — rates are 30–40% lower.
Shopping at Coligny Plaza & Shelter Cove
Spend the afternoon browsing Coligny Plaza's 60+ shops and Shelter Cove Towne Centre's waterfront boutiques. Hilton Head Vibes at Coligny Plaza is the best spot for locally-made beach apparel.
💡 Coligny Plaza has free parking — arrive before noon in peak season.
Lowcountry Boil at Sweetwater Steamer
Tonight's dinner is a Lowcountry boil at Sweetwater Steamer — shrimp, crab, corn, potatoes, and andouille sausage, all cooked together in a seasoned broth. Order online for pickup and enjoy it back at your rental.
💡 Order by 3pm to guarantee your order for the evening.
Day 5
Golf, Spa & Farewell Dinner
Golf at Harbour Town or Palmetto Dunes
If you play golf, your last full morning is the time to tee off. Harbour Town Golf Links is the bucket-list choice — the Pete Dye design is one of the most celebrated in American golf. Palmetto Dunes' Arthur Hills course is an excellent (and more affordable) alternative.
💡 Tee times at Harbour Town book out weeks in advance in peak season.
Spa or Final Beach Time
Non-golfers: spend the afternoon at the Westin's spa or simply back at the beach. The Westin's spa is one of the best on the island — book a massage or facial as a trip finale.
💡 The Westin spa is open to non-guests with a day pass.
Farewell Dinner at The Sage Room
End your trip with dinner at The Sage Room — one of Hilton Head's most beloved fine-dining restaurants. The filet and the crab cake are the standouts. Make a reservation and dress up a little.
💡 Ask for a window table if you're celebrating a special occasion.
Book Before You Arrive
The most popular activities sell out weeks in advance in peak season. Secure your spots now.
