Island Sailing

Island Dreams is the only boat in the fleet offered bareboat, a 31-foot Catalina with a roller-furling main and jib, a colour chart plotter, autopilot, VHF with a cockpit microphone, a bimini and a swim platform, taking up to six. The qualification is a checkout rather than a certificate: whatever your sailing résumé, a first-time bareboat customer books a three-hour captained charter once to be checked out on the boat. After that she goes out for a four-hour half day, an eight-hour full day timed to have her back half an hour before sunset, or overnight. An 11-foot RIB with a 25hp outboard can be added with 48 hours’ notice, and linen and towels are included.

The third product is a club, which is rare in this directory outside the fractional franchises. A skipper pays for a four-hour checkout sail with a captain to demonstrate handling and docking, then buys days in blocks of five or ten, to be used inside eighteen months. On a club day the skipper owns the boat: setup, systems checks, responsibility for vessel and crew, and securing and cleaning her at the end, with the boat available all day and the option to sit aboard at the dock well after sunset. Membership is deliberately capped so members can actually get dates.

Capt. Rob and Rachel were customers before they bought Island Sailing in 2015. Rob learned on dinghies and a 27-foot Catalina and lived aboard a 45-foot Island Trader ketch in the Bahamas with his father, and still sails Bahamian water most other summers, which is where the company’s longer captained trips go. Capt. Mark holds a 50-ton master’s licence and is a certified scuba instructor who will build diving into a sailing trip; Capt. Marty has been sailing since 1966. The dock is on 12th Avenue South at the Naples City Dock.