A Bucket List for your Winter Escape to Hilton Head Island

By Hilton Head Insider

Looking for the best things to do on Hilton Head Island this winter? Whether you're into seafood festivals, outdoor adventures, or relaxing spa days, we've rounded up 10 unforgettable activities to enjoy between December and March on America’s Favorite Island®.

Winter on America’s Favorite Island® is a treat, with breezy, sunny days that seem endless and nights filled with live music and holiday festivities. We’ve compiled a list of our top winter activities you have to try at least once, from outdoor activities like golf and kayaking to relaxing, laid-back experiences like spa days and drinks on the beach. Ease into your winter escape to the subtropical Lowcountry and see how many of these you can check off your list this season!

1. Stroll our 12 miles of white-sand beaches

The beach should always be at the top of your list when visiting Hilton Head Island. Go on a beach stroll in the warmer afternoons or pack a cozy sweater for an evening by the water. You might even get lucky and spot a dolphin from shore! The coastline of Hilton Head Island is sprawling white sands, tidal creeks and inlets, and incredible ocean views. Check out all of our sandy beaches and try to visit all of them during your stay.

2. Cozy up to the firepits at Tiki Hut

Sip on a seasonal cocktail by a crackling fire on the beach this winter. Sink your toes in the sand and enjoy a scrumptious drink or bite to eat around the firepits at Tiki Hut, Hilton Head Island’s only beach bar and an icon of the Island since 1977. Plus, enjoy live, outdoor music on the beach all year round, seven days a week. Open daily from 10:00 AM to 10:00 PM, this island legend features jam sessions year-round, along with endless rounds of frozen drinks, handcrafted cocktails, and nonalcoholic specialties.

3. Stay cool on the courts

Enjoy a crisp morning on the courts with a game of tennis or America’s fastest-growing sport: pickleball! Explore the prestigious facilities and instructional teams at Palmetto Dunes Tennis & Pickleball Center, The Sea Pines Racquet Club, or the Port Royal Golf & Racquet Club and ace your winter vacation. With daytime temperatures hovering around 60°F in December and January, it’s the ideal time of year to get your sweat on outside while staying nice and cool. Advantage, you.

4. Slurp your first (or hundredth) oyster

If you haven’t tried Lowcountry oysters, now’s the time. Breezy winter temperatures mean oyster season is in full swing, and the Oyster Festival kicks it all off November 7–8, 2025. Head over to Hudson’s Seafood House on the Docks, Crazy Crab Jarvis Creek, or The Old Oyster Factory for some tasty seafood selections and stunning views. And the great news is, if you’re not a big oyster fan, there are plenty of other fresh-from-the-sea options to sample.

5. Celebrate Gullah Geechee culture

Catch one or more of the awe-inspiring events being held during the 30th Annual Hilton Head Island Gullah Celebration throughout February. With features like an Ol’ Fashioned Gullah Breakfast at Historic Mitchelville Freedom Park, Arts Ob We People, A Gullah Geechee Art Exhibition, and a Gospel Concert at the Central Oak Grove Baptist Church, this is a month full of history, cultural celebrations, and learning. Step back in time and immerse yourself in the stories and ongoing legacy of the Gullah Geechee People from January 29 through February 21, 2026, put on by the Native Island Business & Community Affairs Association.

6. Crack into some local seafood

Attend the 20th annual Hilton Head Island Seafood Festival from February 23 to March 1, 2026. Indulge in the incredible array of fresh local seafood served up by talented local chefs, view impressive exhibitions of their culinary skills, and, of course, experience Southern charm at its finest. Go beyond the plate and connect with Hilton Head Island from a foodie’s perspective with events like Asado by the Sea at Beach House, The Daufuskie Island History Experience, and a roaring afterparty at Lincoln & South Brewery. This is an annual event we wait for all season long, and marks the end of winter with the crack of seafood and the clink of glasses.

7. Hit the links

Play a round (or two) of golf at one of our championship courses on the Island during the brisker weather. The crisp temperatures are perfect for golf all winter long, with breezier days keeping you cool as you take on 18 holes. Plus, find wide-open tee times to choose from during the off-season on our Island’s 23 acclaimed golf courses. From the PGA Tour’s Harbour Town Golf Links with the stunning 18th hole views, to our best-kept secret for intermediate golfers, Robber’s Row, there’s something here for everyone, whether you’re perfecting your swing or playing a casual round. Head over to the Heritage Golf Collection to view golf packages and seasonal offers and plan your winter golf getaway to America’s Favorite Island®.

8. Go on a peaceful winter paddle

Kayak through the winter marshes and take in the sights and sounds of the Island from the water. With fewer crowds and much of our foliage still intact in the winter, it’s the perfect time to get out on the warm water and take in the local wildlife. You might even be able to spot birds, white-tailed deer, and owls more easily as they will be less spooked by us humans during the quieter winter months. Rent kayaks once you arrive on the island, or book a guide and get a tour through a local’s eyes. Check out the tours from Kayak Hilton Head, Outside Hilton Head, and Sea Monkeys Watersports. Whichever option you choose, make sure that you reserve ahead of time for a tour or rental during the Island’s off-season.

9. Visit local protected wilderness areas

Explore the Sea Pines Forest Preserve or Pinckney Island National Wildlife Refuge. These incredibly vast and beautiful protected areas are an excellent option for exercise, wildlife spotting, and wilderness exploration throughout the winter months, as temperatures are perfect for long hikes or bike rides, and there is less human activity for wildlife observation and photography.

The Sea Pines Forest Preserve is 605 acres of natural beauty, bridle paths, wetland boardwalks, bridges, and fishing docks, which you can explore on your own or with guided tours, horseback rides, or fishing expeditions. Over 200 species of birds have been spotted in the Preserve, and this area has even been designated as an “Important Bird Area” by the National Audubon Society, so don’t forget your binoculars and camera. If you want to see something really special, head out at dawn or dusk and tread quietly for a chance at spotting the Hilton Head white-tailed deer, a unique subspecies slightly smaller than the mainland deer you might have spotted during your trip over to the Island.

Pinckney Island National Wildlife Refuge, located between mainland Bluffton and Hilton Head Island, has 14 miles of trails throughout 4,000 acres of wild, protected Lowcountry, and an abundance of wildlife to spot. If you’re a birder, look for white ibis, herons, egrets, wood storks, and bald eagles along the salt marshes and tidal creeks throughout the Refuge along its nine different marked trails.

10. Sink into a Southern spa day

After a few adventure-filled days, slow down with a salt therapy session or massage at Pure Salt Studios in Shelter Cove. If you’ve never heard of Halotherapy, you’re in for a treat at Pure Salt Studios. Breathe in the tranquil effects of Himalayan salt during a Dry Salt Therapy session. Sit back, relax, and unwind — winter wellness never felt so easy. They also offer yoga, massage, meditation, and sound healing, along with an infrared sauna for all your wellness needs!

Completing Your Winter Bucket List

Whatever your ideal winter escape looks like, we’ve got special winter offers, outdoor adventure, relaxation, accommodations, and plenty of events on our calendar. Get your destination guide and get planning your great winter escape today.