Morning Star Sailing Charters is the longest-running sail and snorkeling charter operation in the Florida Keys. Founded by Captain Rick Winters, it spent 30 years running unmatched oceanside snorkeling trips and sunset sails aboard the 50' yacht S/V Morning Star, six private guests per trip.
Captain Rick has since retired and sold Morning Star Sailing Charters to Paul Keever, owner of Key Lime Sailing Club and Cottages, which also houses the American Sailing Academy. Paul has expanded the fleet with several vessels — S/V Toby (a 36' C&C performance cruiser), S/V Karnack (a 33' Morgan Out Island), and S/V Endless Summer (a 47' Lagoon eco-friendly all-electric catamaran) — for bay and oceanside sailing, snorkeling, sunset sails, and private rentals from day trips to week-long charters.
Trips are capped at 6 guests, though a Demised Bareboat Charter (your own vessel or captain) can accommodate up to 12. Rates stay affordable: sunset sails from $65/person ($325 private for up to 6), full moon and snorkel sails from $75/person ($390 private). Bayside Catalina 22's are $250/day for qualified sailors, easy to handle around Buttonwood Sound, Manatee Bay, and the Everglades — including float plans like the Nest Key mud bath and the Mangrove Jungle sailing-and-kayaking adventure.