Hilton Head Island was the nation’s first resort community designed to preserve the ecology of its site. Its developer, Charles Elbert Fraser, designed the resort town in the 1950s, and he saw the island’s abundant canopy of oaks and pines, miles of beaches, and coastal animal habitats as natural assets, not obstacles to be bulldozed. Today, even as one of the nation’s most popular destinations for golfers and beachgoers, the 12-mile-long island is home to three nature preserves; restaurants and storefronts seem to hide behind the tree canopies; and strict town ordinances prohibit high-rises and streetlights that might obstruct visitors’ beach views by day or spoil their stargazing at night.
Check out the recently renovated Westin Hilton Head Island Resort & Spa, with three outdoor swimming pools, four restaurants, and a deck bar that overlooks the Atlantic. Parents can drop the kids at the Westin Family Kids Club and escape to the spa for a massage. The Omni Hilton Head Oceanfront Resort is another kid-friendly option, with tennis and pickleball courts, an elevated pool, and suites with kitchenettes. For a more intimate vacation, try The Inn & Club at Harbour Town. This boutique hotel overlooks the first tee of the famed Harbour Town Golf Links, one of the most famous courses in America. A stay here includes private beach access at the Sea Pines Beach Club and food and drink service under one of its signature orange umbrellas.
Head to Nunzio Restaurant + Bar for authentic Italian fare. The chef grew up in the Puglia region of Italy and focuses on homemade pasta and seafood. Skull Creek Dockside is a family-friendly spot with waterfront views and addictive bacon hush puppies and lobster deviled eggs. For cheap eats, try Sea Shack, which admits it’s “not fancy, just good!” Order at the register and get anything fried, blackened, or grilled. (There’s usually a line, but it moves fast.) New to the island is Lulu Kitchen, an intimate date-night spot with great cocktails and Southern food with a twist. Lucky Rooster Kitchen + Bar is another local favorite, thanks to their extensive cocktail list and a selection of wines divided into categories like “Still Tasty After All These Years” and “Not Your Parents’ White Wine.”
Rent a kayak, paddleboard, or jet ski through H2O Sports and get out on the water, or sign up for a guided tour and look for dolphins from a catamaran. If you’d rather stay on land, explore the island’s 60 miles of bicycle trails or visit one of Hilton Head’s more than 23 championship golf courses. History buffs can visit the National Register-certified Stoney-Baynard Ruins, the remains of a late 18th-century house that was seized and used as a Union headquarters during the Civil War before it burned down soon after. See the 600-acre Sea Pines Nature Preserve on horseback via Lawton Stables or by boat on a nature tour at the Sea Pines Resort.
Looking for more outdoor adventure? Book a guided boat tour at The Sea Pines Resort, a 5,000-acre gated community on the southern tip of the island. Cruise the freshwater lakes of the Sea Pines Forest Preserve and get a close-up view of the island’s wildlife. The Alligator & Wildlife Boat Tour is a one-hour, family-friendly ride where you learn about the island’s plant and animal life. For an adults-only outing, reserve a spot on the Alligator Wine & Cheese Boat Tour and look for alligators at happy hour. If reptiles make your blood run cold, explore Calibogue Sound and the waterways surrounding Daufuskie Island by boat during a dolphin tour.