Why Now Is the Best Time to Book a 2026 Bachelorette or Group Trip
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…
January 28, 2026
Best Places to Watch the Sunset in Winter on Hilton Head
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…
January 28, 2026
Why Winter Is the Best Time to Visit Daufuskie Island
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…
January 21, 2026
Valentine’s Day with Island Head
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…
January 5, 2026