What's Happening

January/February is planning season. It’s the time when calendars reset, goals are set, and trips start turning from ideas into actual plans. If a bachelorette party, birthday celebration, or group getaway is on your 2026 vision board, now is the best moment to start booking. Especially when it comes to private sailing experiences, early planning…

Winter on Hilton Head Island brings cooler air, less crowds, and beautiful sunsets. With calm waters and quiet evenings, it’s one of the best seasons to enjoy a sunset — especially from the water. Whether you’re on land or on a private boat, Hilton Head offers stunning vantage points for nature’s daily show. But for…

Every season is great on Daufuskie Island, but winter brings a quieter, more relaxed kind of magic. With fewer visitors, cooler temperatures, and a slower pace, it’s the perfect time to experience the island at its most peaceful. The natural beauty feels more untouched, the days feel unhurried, and the island’s charm truly shines. Fewer…

Valentine’s Day is about connection — and nothing creates lasting memories quite like time spent on the water. This year, skip the predictable gifts and surprise your person with an experience they’ll remember long after February 14th. At Island Head, we specialize in turning moments into memories. Whether you’re celebrating love, planning a surprise, or…

Summer usually comes to mind when you talk about Hilton Head Island — busy beaches, warm water, and packed calendars. But those who know the island best will tell you a secret: winter is one of the most underrated and rewarding times to experience Hilton Head, especially from the water. From peaceful waterways to active wildlife and…

At Island Head, we operate ferries to Daufuskie every single day of the year except Christmas Day, making your island experience simple, reliable, and unforgettable. Whether you’re planning a quiet day trip, visiting family, or traveling with a large group (and lots of luggage!), we offer two options to get you there smoothly: our Public…

There’s something special about life on the water — the way the breeze hits just right, the sound of the sails, and the sight of Hilton Head glowing in the sun. On Rosé, Island Head Sailing captures that magic every single day. Whether you’re planning a laid-back morning, a perfect sunset celebration, or a private sail…

Private sails designed for smaller groups and meaningful moments If you’re looking for a more intimate way to explore Hilton Head’s waterways, Salt Marsh Sailing delivers the perfect blend of peace, scenery, and authentic island charm. This 6-passenger private sailboat offers an experience that’s both personal and unforgettable. Every sail with Salt Marsh is completely…

Your private event, elevated. When it comes to hosting an unforgettable celebration, nothing compares to taking it out on the water. Island Head’s Bonjour, our spacious luxury catamaran, brings together comfort, style, and that signature Hilton Head charm — all with room for up to 35 guests. Whether it’s a birthday bash, corporate outing, wedding…

A DAY TRIP OR A LONGER ESCAPE — YOU DECIDE Daufuskie Island is one of the Lowcountry’s best-kept secrets: rich in natural beauty, full of coastal charm, and just far enough away to feel like a true escape. Just a short ferry ride from Hilton Head, it offers a refreshing, off-the-grid experience that feels worlds…

Soar Above Hilton Head’s Breathtaking Coastline for an Unforgettable Adventure There’s no better way to experience Hilton Head’s natural beauty than from the sky. Island Head Parasailing offers a thrilling yet peaceful adventure that lets you glide above the Atlantic waters, taking in panoramic views of the island’s beaches, marshes, and waterways. Whether you’re seeking…

Bachelor and bachelorette parties that go beyond the ordinary! When it’s time to raise a toast to the bride or groom, there’s no better way to celebrate than out on the water. Island Head offers a lineup of private boat experiences perfect for bachelor and bachelorette parties—each one offering its own kind of fun, from…