Things To Do In Hilton Head During This Winter

Hilton Head Island offers an incredible variety of activities year-round. While summer attracts larger crowds, winter reveals a quieter side of the Lowcountry, perfect for unwinding, enjoying outdoor adventures, and making meaningful memories. From ocean breezes and Southern charm to kayaking, historical tours, and outstanding dining, Hilton Head truly has something for everyone—even in the cooler months.

Is Winter a Good Time to Visit Hilton Head?

Winter on Hilton Head is ideal for visitors seeking a break from the ordinary. Here’s why:

For Snowbirds

Hilton Head in winter offers the perfect retreat for snowbirds seeking to trade snowdrifts for sunny shores and peaceful days. With mild temperatures, fewer crowds, and a variety of activities, the island provides endless ways to relax, reconnect, and enjoy Lowcountry charm.

Here are some ideas for how snowbird couples can spend their days on Hilton Head:

• Quiet Mornings on the Water: Seize the day with a serene kayak nature tour through Hilton Head’s calm waterways and marshes. Glide past local wildlife, such as dolphins and egrets, while enjoying the peaceful morning light. Perfect for couples looking to reconnect in nature.
• Relaxing Sunset Boat Tours: As the day winds down, book a sunset cruise. Watch the sky turn golden as you sip on your favorite drinks and enjoy the tranquility of the Lowcountry. This romantic setting is perfect for anniversaries, date nights, or simply celebrating time together.
• Exploring the Island by E-Bike: Take a leisurely ride along Hilton Head’s scenic paths on a guided e-bike history and nature tour. This low-effort activity combines fresh air, light exercise, and fascinating insights about the island’s history and ecosystems—great for active couples who enjoy learning and exploring.
• Dolphin Day Sail: Dolphins are active year-round, and winter offers some of the best opportunities to see them up close. Book a dolphin watch and sail trip to learn about these incredible creatures and enjoy an intimate outing on the water.

For Couples

In addition to the activities mentioned above, our winter temperatures (30s-60s°F) set the stage for cozy, romantic getaways. Picture peaceful walks along the beach and cozy evenings dining at Hudson’s Seafood House On The Docks, where the sunset pairs perfectly with locally inspired dishes.

For Groups

Hilton Head is an excellent winter destination for groups, whether you’re celebrating, reconnecting, or just taking time away together:

• Bachelor Party Highlights: Hit the greens at world-class golf courses or charter a shark fishing trip for a memorable day on the water. End with dinner and drinks overlooking the island’s beautiful waterways.
• Girls’ Weekend Favorites: Start the day with a private dolphin tour, then take a guided e-bike ride through scenic trails while learning about local history and nature. Finish the day with boutique shopping and a seafood dinner at a local hotspot.
• Custom Group Adventures: Outside Hilton Head specializes in private tours and custom excursions, making it easy to craft the perfect itinerary for your group.

Looking for Winter Boat Tours Around Hilton Head?

Hilton Head’s waterways offer some of the best ways to enjoy the Lowcountry in winter. Take a dolphin tour, join a guided kayak trip, or relax on a private charter to soak in the serene beauty. Looking for more? Venture beyond the island for even more unique experiences:

Savannah, Georgia

Just an hour’s drive from Hilton Head, Savannah combines historic charm with vibrant activities. Walk along River Street, explore the iconic squares, and take a Savannah Port Tour to witness the nation’s largest shipping port up close. Add boutique shopping and waterfront dining to round out your visit.

Palmetto Bluff in Bluffton, South Carolina

Palmetto Bluff offers a mix of relaxation and adventure, including kayak nature tours, private dolphin cruises, and the spectacular Sunset Hibachi Dinner Cruise. This two-hour experience features a chef-prepared hibachi meal, drinks from a full-service bar, and breathtaking views of the May River.

Don’t Wait! Plan Your Hilton Head Winter Adventure Today

Even in the quieter winter months, popular activities and tours can book up quickly. At Outside Hilton Head, we make it simple to reserve your spot, whether it’s a private dolphin tour, an e-bike adventure, or a group charter.

Choose your adventure today and let us help you make the most of Hilton Head this winter.