Experience the beautiful sights and sounds of the Charleston harbor and surrounding waterways aboard our 45-foot USCG certified power catamaran as Charleston’s unique skyline comes alive with peaceful and breathtaking views of s... More

Sail the Charleston Harbor, see dolphins, amazing sunsets or even participate in real sailing yacht regattas. Fate is not only the most demanded but also the largest and nicest sailing yacht available for Charter in Charleston, kn... More

Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More

Join us aboard the Charleston Princess for a fantastic evening cruise. We have partnered with a variety of local and regional musicians for a fantastic cruise featuring amazing live music, breathtaking views of the "Holy City" and... More

Depart from Island Head's newest location at Broad Creek Marina. Enjoy the evening on a private sunset cruise on the waterways surrounding Hilton Head Island. This cruise if private to your party and the captain will customize the... More

Step aboard the Palmetto Breeze for a breathtaking sunset sail through Charleston’s iconic harbor. As the sun sets behind historic landmarks like Fort Sumter and the Ravenel Bridge, you’ll enjoy a front-row seat to one of the ... More

Kick back and relax on your own private sunset cruise and experience Hilton Head in it's best light. Premium private tour accommodations are provided on board our new 23' Key West - you won't find a nicer charter boat available on... More

Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. #1 activity on Tripadvisor for over 12 years, our sailing yachts are the highest quality and op... More

The private sunset cruise is the perfect way to end a day on Hilton Head Island. There is nothing quite like a low country sunset, especially seeing one from the water were you can see the broad spectrum of colors such as vibrant ... More

This Private Sunset Tour will be an activity your family or friends will always remember! This 1.5 hour tour comes complete with a Licensed captain, full eco narration, up close dolphin sightings, picturesque sunset views, water/s... More

Our Sunset and Fireworks sail is a Hilton Head must-do!! Every Tuesday night during the heart of our peak season Shelter Cove puts on a fantastic fireworks show just after the sun goes down. Your evening starts with our relaxing S... More

Calling all Ladies! Mermaid Monday is the ultimate ladies’ night out on the water. Gather your girlfriends for an evening filled with laughter, cocktails, and incredible harbor views as the sun sets over Charleston. Our lively 5... More

Celebrate the island spirit aboard our Aloha Wednesday sail, where Charleston’s harbor meets tropical vibes. With complimentary beverages—including local beers, seltzers, and wine—this 2-hour sail is all about unwinding in s... More