Take the helm with a private, customizable keelboat sailing lesson
3.5 hrs
Up to 6 people
Private sailing lesson, water
Learn the fundamentals of keelboat sailing aboard a Catalina 275 Sport, whether you are sailing for the first time or building on existing skills. Shape your time on the water around the sailing skills and activities that interest you.
Free cancellation with at least 24 hours' notice. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.
Dress for current weather conditions, bring needed sun protection, and wear shoes and clothing that can get wet. Bring an extra layer in fall, winter, or spring, when it can be cooler on the water.
Yes. Use the bathroom below deck to change into or out of swim attire, and bring a beach bag or backpack with supplies such as towels.
3 Dulamobluff, Saint Helena Island, SC, US
My wife, daughter, and I enjoyed going out sailing with Barry on his sailboat during our vacation to Beaufort. Barry is a genuine down to earth guy with whom I really enjoyed talking with. I’ve never been on a sailboat, and wanted to learn the basics of how to sail, so Barry put together a beginners lesson. I highly recommend looking up Barry with Otter Sailing Adventures if interested in sailing or looking to go out on a private charter.
John MacKorell
July 18, 2026
My wife, daughter, and I enjoyed going out sailing with Barry on his sailboat during our vacation to Beaufort. Barry is a genuine down to earth guy with whom I really enjoyed talking with. I’ve never been on a sailboat, and wanted to learn the basics of how to sail, so Barry put together a beginners lesson. I highly recommend looking up Barry with Otter Sailing Adventures if interested in sailing or looking to go out on a private charter.
John MacKorell
July 18, 2026
Private sailing with dolphin sightings on Saint Helena Sound
Private sunset sailing with room below deck for passing weather
Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys
Cruise rural Beaufort waters while watching for dolphins and coastal birdlife
Paddle tidal waters to a remote sandbar and Boneyard Beach on a guided exploration
Paddle Downtown Beaufort to a local sandbar at low tide