cheers charters


It's Time To SAIL

SAIL on a Hilton Head Island Classic…
SAIL with a Hilton Head Tradition!

Get out on the water, see dolphin and wildlife, and enjoy our beautiful island from a fresh perspective.

Sunset Sail

Our private signature sunset cruise is 2.5 hours long. 

Call 843-671-1800 for
pricing and availability

Daytime Sail

This is a typically warm and breezy 2.5 hour long private trip.

Call 843-671-1800 for
pricing and availability

Corporate Team Building

Enhance your Hilton Head Island Meeting or Conference with team-building activities and a private sailing. 

Call 843-671-1800 for group size and pricing


Cheers private sailing trips follow lovely Broad Creek out to the pristine waters of the Calibogue Sound. Wildlife abounds in these rich waters, including plenty of dolphins, pelicans, bald eagles, great blue herons, osprey, and egrets of all kinds.  See dolphins in the water, learn why you should visit our national wildlife refuges and Daufuskie Island, and take in the expansive vistas of salt marsh and the Lowcountry.   On Sunset trips, we take in the dolphins and scenery, relax with some music and cocktails, and marvel at the tremendous sunsets directly over the Intracoastal Waterway.  

We offer ample parking, modern and clean facilities for your whole family, no gate or parking fees, a convenient location, and safe and comfortable accommodations on Cheers, which is US Coast Guard-certified to carry up to 22 guests.  We operate from the popular local docks at Broad Creek Marina, offering walking access to the on-site Up the Creek Pub and Fish Camp.  Our captain and crew are highly trained and have decades of experience on the water and in making customers happy.

Onboard amenities include bluetooth speaker, clean full-sized restroom, comfortable deck cushions, and limited protection from inclement weather. We do not sell food or beverages and feel free to bring a soft-sided cooler with your own beverages and snacks.   

Come aboard, and become part of this established Hilton Head Island legend!

The Vessel

Join us for a morning or afternoon cruise, or celebrate the end of a beautiful day by toasting the sunset aboard the beautiful 45’ Morgan sloop Cheers. Cheers has had the honor of sailing out of Hilton Head for over three decades and is truly a Hilton Head Island classic. She is owner-operated, and the crew and staff are trained and experienced; their highest priority is your satisfaction. Relax, listen to the music, enjoy a cocktail, and join the friends who have celebrated their special moments on Cheers!