Hilton Head Sailing Tours & Charters

Hilton Head’s sailing excursions offer an interesting and often quieter alternative to the dozens of tours of the area available on powered boats (thematically, the sailing tours are the same — nature and sightseeing, sunset cruises and trips coinciding with the island’s weekly summer fireworks displays).

Sailboats range from very small recreational sailing boats, through family-sized sailed yachts, to large vessels able to accommodate dozens of people. You can choose either a tour or a charter for your trip.

Tours are generally open to the public and priced on a per-person basis. Charters are for your own group only, and can offer more flexibility than a public trip, in addition to a private and more intimate experience. If you have a group of five or six people, the price of a private charter is often comparable to a public tour.

→ Hilton Head weather by month: January, February, March, April, May, June, July, August, September, October, November, December

!Tour or charter availability may vary by season, and activities may be changed or withdrawn without notice. Please check all details directly with the relevant company before planning your trip.

Small Sailboats

Tours

– Sailing Tour, with H20 Sports
1hr30. 6 people max. $49 per person, or $285 for a private tour.
Sailing tour of Calibogue Sound. Call 843-671-4386 or book online. More details

Charters

– Flying Circus Private Dolphin Watch Trip, with Hilton Head Island Sailing
2hrs+. 6 people max. 2hrs $300, plus $150 per additional hour.
Private dolphin tour on a sailed catamaran. Call 843-686-2582 for reservations. More details

Large Sailboats

Tours

– Afternoon Sail, with Vagabond Cruise
1hr30. 30 people max. Adults $44, children (12 and under) $22.
Yacht tour of the waters near Hilton Head. Call 843-363-9026 or book online. More details

– Pau Hana Dolphin Watch Trip, with Hilton Head Island Sailing
2hrs. 43 people max. Available daily in season. Adults $45, children (11 and under) $25.
Catamaran sailing tour of the waters near Hilton Head, from Palmetto Bay Marina. Call 843-686-2582 for reservations. More details

– Afternoon Sail, with Cheers Charters
2hrs. 24 people max.
Yacht tour of the waters around Hilton Head, out of Broad Creek Marina. Call 843-671-1800 for information and reservations. More details

Charters

– Pau Hana Private Charter, with Hilton Head Island Sailing
43 people max. Available daily.
Private boat charter on a sailed catamaran. Call 843-686-2582 for information and reservations. More details

– Private Sail, with Cheers Charters
24 people max.
Private charter of a sailed yacht, out of Broad Creek Marina. Call 843-671-1800 for information and reservations. More details

– Sailing Charter, with Island Water Sports
Afternoon sailing charter out of Hilton Head’s South Beach Marina. Call 843-671-7007 for information and reservations. More details

Sunset Sails

Tours

– Sunset Sailing Tour, with H20 Sports
2hrs. 6 people max. $65 per person, or $375 for a private tour.
Sunset sailing tour of Calibogue Sound. Call 843-671-4386 or book online. More details

– Sunset Sail, with Cheers Charters
2hrs30. 24 people max.
Sunset yacht tour of the waters around Hilton Head, out of Broad Creek Marina. Call 843-671-1800 for information and reservations. More details

– Sunset Sail, with Vagabond Cruise
2hrs. 30 people max. Adults $55, children (12 and under) $33.
Sunset yacht tour of Calibogue Sound and vicinity. Call 843-363-9026 or book online. More details

– Pau Hana Sunset Dolphin Watch Trip, with Hilton Head Island Sailing
2hrs. 43 people max. Available daily in season. Adults $45, children (11 and under) $25.
Sunset catamaran sailing tour of the waters near Hilton Head, from Palmetto Bay Marina. Call 843-686-2582 for reservations. More details

Charters

– Flying Circus Private Sunset Dolphin Watch Trip, with Hilton Head Island Sailing
2hrs+. 6 people max. 2hrs $300, plus $150 per additional hour.
Private dolphin tour on a sailed catamaran. Call 843-686-2582 for reservations. More details

– Sailing Charter, with Island Water Sports
Sunset sailing charter out of Hilton Head’s South Beach Marina. Call 843-671-7007 for information and reservations. More details

Fireworks Sails

Tours

– Pau Hana Summer Fireworks Cruise, with Hilton Head Island Sailing
2hrs. 43 people max. Seasonal tour, Tuesday evenings. Adults $45, children (11 and under) $25.
Catamaran sailing tour of the waters near Hilton Head, from Palmetto Bay Marina, to coincide with the Shelter Cove Harbor fireworks. Call 843-686-2582 for reservations. More details

Charters

– Flying Circus Summer Fireworks Cruise, with Hilton Head Island Sailing
2hrs. 6 people max. Seasonal tour, Tuesday evenings. $325.
Private boat tour on a sailed catamaran, to coincide with the Shelter Cove Harbor Fireworks. Call 843-686-2582 for reservations. More details

Sailed Boat Rentals

– Catalina Capri Rental, with H20 Sports (Harbour Town Yacht Basin, 149 Lighthouse Road)
2hrs $170, $85 per additional hour.
22-foot Catalina Capri rental. Experience required, sailing instruction available for an additional fee. Call 843-671-4386. More details

– Hobie Cat Rental, with H20 Sports (Harbour Town Yacht Basin, 149 Lighthouse Road)
1-2 people max. 2hrs $120, $60 per additional hour.
14-foot Hobie Cat (small sailed catamaran) rentals. Experience required, sailing instruction available for an additional fee. Call 843-671-4386. More details

Sailing Lessons

– Sail Boat Lesson, with H20 Sports (Harbour Town Yacht Basin, 149 Lighthouse Road)
1hr30. $75 per person, 2-person minimum.
Sailing lessons on a 22-foot sailboat. Call 843-671-4386. More details

– Sailing Lesson, with Hilton Head Island Sailing (Palmetto Bay Marina, 86 Helmsman Way)
6 people max. Daily.
Sailing lessons on a 27-foot sailed catamaran, call 843-686-2582 for information. More details

More Things To Do In Hilton Head, SC

– Hilton Head events
– Sunset boat tours
– Creek Cat tours
– Kayaking
– Paddle boarding
– Pinckney Island National Wildlife Refuge
– Hilton Head water sports