The Perfect Hilton Head Island Weekend Itinerary

Hilton Head Island, renowned for its pristine beaches, world-class golf courses, and relaxed coastal vibes, makes for the ideal weekend getaway. Whether you’re seeking outdoor adventure, culinary delights, a serene retreat, or a bit of all three, this itinerary will help you experience the best Hilton Head Island has to offer in just a few days.

Start your weekend by checking into one of Hilton Head Island’s top resorts. For the idyllic Hilton Head Island experience, there’s no place better than The Sea Pines Resort, which offers over 400 stunning rental villas and homes, or the Inn & Club at Harbour Town. Both options offer the perfect jumping-off point to take in the splendors of Sea Pines while keeping the rest of the island's adventures easily within arms reach.

Those with a golf-centric weekend in mind should consider the Omni Hilton Head Oceanfront Resort, which offers access to Palmetto Dunes’ three resort courses: the Robert Trent Jones Course, George Fazio Course, and the Arthur Hill Course. Additional options include the Sonesta Resort Hilton Head Island and Marriott’s Grande Ocean Resort, each offering high-end accommodations with stunning Atlantic Ocean views.

Once you’ve settled in, head to Quarterdeck along Lighthouse Road in Sea Pines. The newly renovated, two-story restaurant in Harbour Town is the perfect place to catch your first Hilton Head Island sunset, drink in hand. Sip on a cocktail or a glass of wine while watching boats in the marina under a golden sky.

You can stick around for dinner at the Quarterdeck or head to Coast, Oceanfront Dining at the Sea Pines Beach Club, overlooking the Atlantic. The outstanding eatery blends upscale dining and casual coastal vibes with seafood that’s as fresh as it gets. The ahi tuna, seared scallops,  seafood tower, and local oysters are the highlights of the menu, perfectly paired with a selection from the extensive wine list.

Wake up early and embrace the peaceful atmosphere of Hilton Head Island’s most iconic beach, Coligny Beach Park. Soft sand and a gentle breeze provide the perfect backdrop for a morning stroll. The beach is expansive and adjacent to Coligny Plaza, the island's popular de facto downtown filled with boutiques, shops, and restaurants.

After your walk, fuel up with a delicious breakfast at The French Bakery in Shelter Cove. Their pastries, quiche, and fresh-brewed coffee make it the ideal spot to jump-start your day. Grab a table on the patio for views of the marina as you savor your meal.

Now you're ready for an adventure. Hilton Head Island is teeming with wildlife, and it's best experienced from the water. Rent a kayak from Kayak Hilton Head and paddle along Broad Creek, where you’ll likely spot dolphins, herons, and egrets. Hilton Head Outfitters can equip you with the necessary gear to navigate the 11-mile network of inland lagoons meandering through Palmetto Dunes.

Head to Hudson’s Seafood House on the Docks for a laid-back, local lunch. Overlooking Skull Creek and the Pinckney Island National Wildlife Refuge, its beautiful waterfront setting showcases a more sublime side of the island, and the seafood is among the freshest you’ll find in the Lowcountry.

Among the nation’s top golf destinations, golfers may choose to forgo Hilton Head’s many other outdoor offerings to hit the links as often as possible — and for good reason. A golfer’s paradise, the island boasts an array of strategic challenges and scenic layouts. In addition to the aforementioned Palmetto Dunes courses, Hilton Head Island also features Harbour Town Golf Links, famous for hosting the PGA Tour’s RBC Heritage, the stellar Atlantic Dunes by Davis Love III and Heron Point by Pete Dye at The Sea Pines Resort, and the under-the-radar Oyster Reef Golf Club at the north end of the island.

If pampering is more your style, opt for an afternoon spa treatment at one of the island’s standout retreats, including Namaste Spa at the Barony Beach Club or Grande Ocean locations. If you’re staying in The Sea Pines Resort, head to the nearby Le Spa of Sea Pines in The Shops at Sea Pines Center.

For an unforgettable dining experience, make a dinner reservation at Nunzio Restaurant + Bar, one of Hilton Head Island’s most celebrated high-end eateries featuring some of the best Italian dishes on the East Coast. If you’re in the mood for French-inspired fare, Charlie’s L'etoile Verte is a worthy alternative focusing on local seafood and “Lowcountry-to-table” dishes.

Regardless of your choice of cuisine, head across William Hilton Parkway and cap off your evening with live jazz at The Jazz Corner, one of Hilton Head Island’s most beloved entertainment venues. Smooth tunes and craft cocktails create the ideal atmosphere for a relaxing, sophisticated night out.

Sunday morning calls for a laid-back brunch at Lowcountry Produce Market & Café, where you can enjoy local favorites like shrimp and grits or a salmon or veggie and feta omelet. The café’s charming market setting offers a cozy and relaxed start to your day.

After brunch, rent a bike and explore the extensive trails. The scenic routes wind through ancient oak trees draped with Spanish moss, peaceful lagoons, and stretches of beachfront. If you’re feeling a bit more adventurous, stop by the Lawton Stables and book a 60-minute horseback trail ride through the 600-acre Sea Pines Forest Preserve.

Before you leave the island, enjoy one last dose of Hilton Head Island’s famous beaches. Head over to Driessen Beach Park, an absolute gem along the Atlantic that offers a quiet atmosphere for relaxing under the sun. The park provides access to Bradley Beach via a picturesque boardwalk and includes a picnic pavilion, playground, and nearby restaurants accessible from the sandy shores, including Sea Salts Beverage Company and Jamaica Joe’z.

With the perfect mix of relaxation and adventure, your Hilton Head Island weekend will certainly be one you won't soon forget. Whether you’re a fan of the beach, a foodie, or a golf enthusiast, Hilton Head Island caters to every traveler, making it the ultimate weekend escape.

If you want to explore more of Hilton Head Island's unparalleled luxury, outdoor recreation, and fine dining and make it a permanent part of your lifestyle, contact Karen Ryan to start your home search in one of the country’s most coveted locales. Whether you seek an oceanfront home or an estate with a golf course or harbor view, allow Karen’s experience and expertise to help you navigate this sought-after region.