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

End your Hilton Head day with the experience your family will talk about for years. Our two-hour private sunset cruises are built for just your group — no strangers, no rush — so you can relax together while the sky turns gold... More

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... 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

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

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

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

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

Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with complimentary drinks on board. Whether you're going with a big or smal... More

Relax and enjoy a refreshing beverage as we cruise the Charleston harbor, take in a history tour or enjoy a swim or do it all! BYOB or add catering.. All charters are private, only those you bring will be onboard, there is a capta... More

***Booking 1 person, is booking 1 boat for up to 6 people *** Experience a breathtaking private sunset dolphin tour on Hilton Head Island! Watch dolphins, stunning sunsets, and magical fireworks while cruising the scenic waterway... More

Aloha Wednesday Sunset Sail: Island Vibes & Relaxation on the Charleston Harbor Celebrate the spirit of the islands right here in Charleston with our Aloha Wednesday Sunset Sail. This midweek escape combines tropical charm with st... More

Enjoy two hours cruising the harbor on a private center console captained by a professional yacht captain. Stop at secluded island beaches for shark tooth hunting, shelling or just enjoy the sunset while looking at mansions along ... More

Discover the ultimate Hilton Head Island experience with our Sunset Mini Boat Dolphin Tour! Glide across the sparkling waters on a thrilling mini boat, perfect for an up-close and personal dolphin encounter. As the sun dips belo... More

Climb aboard at Palmetto Bay Marina and kick off your evening Lowcountry-style. This two-hour Sunset Lowcountry Boil Cruise mixes everything Hilton Head does best—good food, good views, and that salty “I’m on vacation” fee... More