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Sailing in Grand Cayman

Hobie Cat & Small Catamaran Sailing

Hobie Cats and similar small sailboats are available for rent from some resorts on Seven Mile Beach and from White Sand Water Sports in East End. The Sailing Club in Red Bay offer lessons and also rents out Optimisits, Fevas, Picos, Bytes and J/22s.

Sailing Charters

  • Point Blue Sailing offers exclusive private charters aboard their 46-foot sail boat. You can build your own itinerary and choose from full day, sunset or dinner cruises.
  • Red Sail Sports (Tel: (345) 946 3362) has four 65-foot catamarans that offer half-day group snorkelling trips into North Sound to feed the stingrays. They also do a sunset sail off Seven Mile Beach.
  • The Jolly Roger offers a daily ‘Pirate Adventure’ sailing trip for two hours. The cruise features traditional pirate antics, including a pirate’s trial, sword fighting and walking the plank and a swim stop. The boat departs from George Town Harbour at 2pm, however check-in is at 1.45pm sharp, and is fun for both adults and kids.

Group Sunset & Dinner Sailing

Red Sail Sports (Tel: (345) 946 3362) offers group evening sails on their 65-foot catamarans. The sunset sail leaves on Fridays at 6pm (from the Westin on Seven Mile Beach) and costs KYD$15 for locals, but you must pay 24 hours in advance to receive this rate. Do call ahead and make a booking as these trips are very popular. The sail takes you out for a very relaxing two-hour ride along Seven Mile Beach and includes light appetisers. Drinks are available from the bar. Call for information on dinner cruises, which are also scheduled during peak season. Red Sail also offers a free catamaran ferry to Rum Point for dinner every Tuesday through Saturday. This sail departs from the Safehaven Dock at 5pm (Tue-Thu) and 6pm (Friday & Sat).