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In the heart of South Carolina’s low country, it’s hard to discern whether Hilton Head Island is for the nature lovers, the beach goers, or the history buffs. Really, it’s for all three. The island is known, of course, for their beaches—particularly inviting because you can enjoy them in any season. But beyond the coastal salt marshes and soft sand, Hilton Head Island offers poignant history lessons, beautiful outdoor venues for championship golfing or wilderness hiking, and of course, an incomparable seafood scene. If you only have the weekend on this South Carolina island, follow the Departures 24-hour guide for the best things to do on Hilton Head Island.
8 a.m.: What better way to celebrate the fact that you’re on a coastal vacation than waking up and strolling along the beach with a cup of coffee? The stillness that comes with strolling the beach, before the crowds wake up and the tide comes in, makes a morning beach stroll one of the most underrated and relaxing things to do on Hilton Head Island. We recommend starting your walk toward the south end of the island at Coligny Beach. Before your stroll, grab a latte to go at The French Bakery.
9:30 a.m.: Your introduction to low country cuisine starts immediately, with a Southern-style breakfast at Plantation Cafe & Deli. A local favorite, this independently owned cafe has classic diner vibes and will certainly satisfy anyone looking for a hearty, low country breakfast. Try the country fried steak and eggs or Ellie’s Southern breakfast with fried green tomatoes. They have two locations, but we recommend you visit their original cafe on the south end of the island, which has been open since 1974.
11 a.m.: Hilton Head Island is one of those rare destinations where you can seamlessly combine your love of history and the outdoors. Case and point: Historic Mitchelville Freedom Park. This park is known as the first free village in the U.S. History tells us that a large population of West Africans enslaved in the Sea Islands went directly to the Union army station on Hilton Head Island following the Emancipation Proclamation. It was there that they set up a village where freedom reigned. While visiting Historic Mitchelville Freedom Park is primarily about exploring the rich and poignant history of the area, you’ll wind through the park on a trail that brings you to Fish Haul Beach Park. The park has an elevated wooded trail where you can walk right over the low country salt marshes, or you can post up on the beach—it’s quieter than some of the beaches toward the south end of the island—where you’re likely to spot some of the waterbirds Hilton Head Island is known for.
1 p.m.: A sojourn at Fish Haul Beach Park and Mitchelville Freedom Park brings you to the north end of Hilton Head Island. Stick around the north end—where you’ll find some of the best things to do on Hilton Head Island—to get a feel for this part of the island. Start by lunching at Hudson’s Seafood House on the Docks. The atmosphere at this waterfront restaurant, where the tables are set up on a picturesque dock, is exactly what makes Hilton Head Island so memorable. Right on the Port Royal Sound, you’ll dig into flash-fried soft shell crab, peel-n-eat shrimp, and oysters on the half shell—all caught that morning.
3 p.m.: Next up is Coastal Discovery Museum, where visitors can explore history, wildlife, and the great outdoors on a scenic 68-acre former plantation. The most memorable part of the Coastal Discovery Museum is how they play with indoor and outdoor space. With salt marshes underneath a boardwalk-style walking path, oak trees pouring shade over the property, and a Southern red cedar tree that’s been standing since 1595, the low country outdoor scenery is on full display here. But so too is the history and culture of the island. The Southern-style, 19th-century plantation houses have been reclaimed as a space for permanent and rotating exhibits that delve into the fostering of Gullah culture on Hilton Head Island and an exploration of 20th-century American history.
4:30 p.m.: As the late afternoon rolls in, it’s time to explore the wine and spirits culture of Hilton Head Island. And the north end of the island is the perfect place to do so. You have two choices (though, really, why choose when you can do both?): Hilton Head Distillery and Island Winery. Hilton Head Distillery—the first craft distilling venture on the island—exclusively distills small-batch rum. The family owned business is half-distillery, half-bottle shop, so in addition to sampling their wares, you can try other up-and-coming local spirits they stock. If you’re more of a wine advocate and less called to small-batch spirits, visit Island Winery instead, where you can enjoy a tasting (either al fresco or in their rustic-chic tasting room), or buy a bottle to enjoy on the patio. They produce only small batches of wine, including their signature whites (Sea Island White is perfect on a hot day), red blends, and low country specialty wines (including a wine made from apples and an elderberry honey wine).
8 p.m.: Venture back to the south end of the island to freshen up at The Inn & Club at Harbour Town, the island’s premier hotel within Sea Pines Resort. From the resort, dinner is close by at Alexander’s Restaurant & Wine Bar. An upscale seafood restaurant-wine bar hybrid (the name is really right on the money), Alexander’s does exceptional wine dinners, with a beautiful set menu and wine pairing. If you’re not able to reserve a wine dinner in advance, fear not, you’ll still be extremely taken with this restaurant. Set amid the lush, almost tropical-feeling scenery, brimming with coveted wine bottles collected from around the world, and serving fresh seafood with creative expression, Alexander’s is a must-visit while on Hilton Head Island.
Where to Stay
Sea Pines Resort is on 5,000 acres of gorgeous oceanfront property. With private stretches of beach, a 600-acre hiking preserve, a championship golf course, and seemingly endless family-friend activities, there is something for everyone here, whether you’re on a romantic weekend getaway or a multigenerational family vacation. Within Sea Pines Resort, your accommodation options range from vacation home rentals (which work for two to 12 guests) to the island’s finest hotel, The Inn & Club at Harbour Town. If you’re planning a getaway with another couple to The Inn & Club, we recommend the Fairway Suite, which has two gorgeous master bedrooms and a tastefully decorated living space perfect for entertaining.