Sailing The Lowcountry
OUR STORY
Otter Sailing Adventures pairs two of the most beautiful things on earth, sailing and the low country's waterways in and around Beaufort.
We are locally owned and operated, based on Saint Helena Island SC about half way between Beaufort and Hunting Island State Park. Our goal is to help you have an immersive experience into this world that will be unforgettable.
Our sailing charter adventures are customizable!
Whether you're looking for an engaged hands on experience or just taking in the view while sitting back and relaxing, let us know your preference and will help you have a great time.
All trips are captained by the owner, Barry Gupton, a licensed US Coast Guard Charter Captain. The sailboat used on all charters is the "Traveller" a Catalina 275 Sport. The Catalina 275 Sport is a high-performance "pocket cruiser" and dayboat designed by Gerry Douglas for Catalina Yachts. Awarded Cruising World's Best Pocket Cruiser, it blends the easy handling and speed of a sportboat with the basic comforts required for weekend cruising. Her home port is a private dock on Saint Helena Island.
MEET THE CAPTAIN
BARRY GUPTON
Born and raised in the Carolinas, Barry has been sailing in the Southeast and Caribbean his entire life, first captaining a sailboat by himself for a month long voyage in the Caribbean at the age of 17. He learned how to sail and explore from a young age thanks to his parents who were great sailors and adventurers. Barry and his family have called Saint Helena Island home for the last several years. Together with his wife, Stephanie, and 5 children (Eliza, Arch, Abner, Ada and Wiley) they own and operate Otter Sailing Adventures, where they love to share and teach others the joys of sailing and going on adventures in one of the most beautiful places on Earth.
SAIL AWAY WITH US
TRAVELLER - CATALINA 275 SPORT
Traveller is a Catalina 275 Sport, a modern 28-foot performance sailboat designed to be both easy to handle and exciting to sail. Whether you're stepping aboard for your very first sailing lesson or you're an experienced sailor looking for an exhilarating ride, Traveller delivers an unforgettable experience.
Her spacious, open cockpit features responsive tiller steering and a self-tacking jib, making sailing comfortable, engaging, and accessible for all skill levels. On light-wind days, we can hoist the colorful spinnaker to add an extra burst of speed and excitement.
Below deck, you'll find comfortable seating, a galley table for relaxing out of the sun or weather, and a private head (restroom) for your convenience.
Whether you're looking to learn the fundamentals of sailing, unwind with a peaceful cruise, or experience the thrill of a performance sailboat, Traveller is the perfect vessel for your Lowcountry adventure.
EXPLORE WITH US
CREEK FREAK - BOSTON WHALER 17
A recent addition to Otter Sailing Adventures, the Creek Freak is a classic 17’ Boston Whaler Powerboat. Although there’s nothing flashy about this skiff, Boston Whaler has perhaps the best reputation in the industry for making tough and solid boats. She was actually used in the commercial fishing industry here in the low country before being converted into a tour boat. This addition to our fleet allows us to offer powerboat charters for those not interested in sailing. This boat can cover more water, as we can go much faster, and a wider range of environments, due to its size, plus it’s a good option for the rare day when there’s no wind for sailing. The Creek Freak has a very shallow draft, which allows us to explore creeks and small tributaries that would be impossible in larger boats (hence the boat name).
FIND US
93 Rose Island Rd,
Saint Helena Island, SC 29920
CONTACT US
