Hilton Head Island Parasailing

Which Hilton Head Parasailing Trip Is Best for You

• Staying in Sea Pines or near the south end: H2O Sports, the only parasail boat in Harbour Town, and the shortest trip.

• Bringing someone who won’t fly: Island Head is the only one that lets you book an observer seat ahead.

• After the biggest height: Sky Pirate, at 500 feet.

• A family or group of up to 12: book the whole boat with Island Head or H2O Sports.

• Staying mid-island or at the north end: Sky Pirate at Broad Creek Marina or Island Head at Hilton Head Harbor.

Parasailing from Harbour Town

Harbour Town has one parasail boat, run by H2O Sports from its booth beside the lighthouse. You are over Calibogue Sound within minutes, with the lighthouse, the yacht basin and Daufuskie Island below. Getting into Sea Pines by car means the resort’s gate fee unless you are staying inside; our Harbour Town guide covers parking and what else is on the harbour. Island Head’s and Sky Pirate’s flights also circle over Calibogue Sound with Harbour Town in view, but they leave from marinas outside Sea Pines.

What a Hilton Head Parasailing Adventure Is Like

Everyone boards the boat together, and the crew flies two or three people at a time. You sit in a harness on the flight deck at the back, the canopy fills, and the winch lets the line out until you are hundreds of feet up. Takeoff and landing are both on the deck, so nobody has to swim. The flight itself is quiet and smooth: eight to ten minutes over the water, often with dolphins in the sound below. Island Head and Sky Pirate let you choose a dip in the water near the end or a dry flight. Then the next group goes up while you watch from the boat.

Wear a swimsuit with a T-shirt over it, and bring sunscreen, sunglasses with a strap, a hat, a towel and water. Check in 30 minutes before the trip.

Ages, Weights and Flying Together

All three boats take flyers from age 6, and H2O Sports and Sky Pirate ask that anyone under 12 flies with an adult of 18 or older. Two or three people go up at once, with a combined limit of 450 pounds. H2O Sports also sets a 200-pound minimum for a tandem or triple flight, so a light pair of children flies with an adult. The captain decides the pairings on the day, depending on the wind and everyone’s weight.

Weather and When to Go

The captain decides on the day whether the wind and weather are safe for flying. Summer afternoons often bring quick thunderstorms, so a morning flight is the safest bet, and the weather at one end of the island can differ from the other. H2O Sports waives its cancellation charge when it calls a trip off for weather. The water is warmest from May through September, if you plan to dip. Summer trips fill up, so book ahead; the rest of the year, check each booking calendar for dates. Monthly weather is on our Hilton Head weather guide.

Cancelling: H2O Sports refunds in full up to 24 hours ahead and charges half inside that. Sky Pirate gives no refund inside 24 hours or for a missed trip.

More Water Sports on Hilton Head

Sky Pirate and Island Head also pull tubes and skiers; see our tubing guide and water skiing guide. For banana boats, jet skis, kayaks and paddleboards, see our Hilton Head water sports guide. For a slower trip on the water, see our Hilton Head boat charters.