Weekending in Hilton Head Island, South Carolina

Harbour Town Lighthouse / Photograph courtesy of Hilton Head Island VCB

With its laid-back charm, walkable trails, and mix of nature, history, and beachfront fun, Hilton Head Island packs a lot into its small footprint. Here’s how to make the most of a long weekend there.

Day One on Hilton Head Island

Beach bumming on Hilton Head Island / Photograph by Navadise Media

This island might clock in at only 12 miles long, but there’s plenty to see and do, whether you want to soak up the sun or explore — or a bit of both. Check in to an ocean-view room at Beach House Hilton Head Island (rooms from $334), located in the buzzing downtown district, then head to the newly renovated pool deck, outfitted with year-round heated water and swanky cabanas.­ And be sure to hit the property’s adjacent Tiki Hut for a toes-in-the-sand experience. This outdoor bar is open to the public and has been a cornerstone of the area since the late ’70s. Later, catch a ride to Hudson’s Seafood House on the Docks, a casual neighborhood joint on the northwestern part of the island, to watch the sunset and indulge in fresh catches.

Day Two on Hilton Head Island

Bike riding on the beach in Hilton Head / Photograph via Getty Images

Much of the island is walkable and bikeable, with various trails and bike rental shops. Spend an afternoon at one of the wildlife refuges, like the 50-acre Audubon Newhall Preserve or, for a small fee, the private Sea Pines Forest Preserve, where visitors can fish or ride horseback. Or stroll along the shore with a wine smoothie from the Carolina Tasting Room.

Day Three on Hilton Head Island

Quarterdeck / Photograph courtesy of the Sea Pines Resort

Need a break from the sun? Treat yourself to a body wrap or pain-relief massage at the Moor Spa. And you can’t leave the island without a visit to the Harbour Town Lighthouse — walk the 114 steps to the top — and the surrounding marina. Follow that with dinner at the nearby Quarterdeck. You’ll want that second order of oysters; I certainly did.

Must-Do Activities to Round Out Your Trip

A cocktail at Hilton Head Distillery / Photograph by Steven Blackmon

1. Harbour Town Golf Links, a public course and PGA tour stop, will reopen later this year after a massive reno. Its clubhouse, grill, and shop are remaining open.

2. Book a two-hour cocktail-making class or a tour of the production facility at Hilton Head Distillery, the island’s only distillery. Take home a bottle of rum or whiskey.

3. Bring home some trinkets from Binya, a gift shop focused on the region’s Gullah Geechee culture — think candles, apparel, and educational books on history and traditions.

4. Have the kids in tow? The Coastal Discovery Museum, a partner of the Smithsonian, offers family-friendly activities such as sweetgrass basket making.

Published as “Escaping to Hilton Head Island, South Carolina” in the May 2025 issue of Philadelphia magazine.