Florida Keys – Learn to Sail – Fall Travel 2009

DESINATION: Flordia Keys



“Rail meat”: the regatta term for the sailors who throw their body weight against the rails of a ship to prevent capsizing. In all my (limited) sailing experience, I’ve only ever been rail meat: It’s the best job to give the clueless. To avoid such physical punishment again (and validate those docksiders in my closet), I headed to the Florida Keys, where sailing-world darlings Doris and Steve Colgate run an Offshore Sailing School, for an intense three-day course. After some classroom time, I stepped upon a slick sailboat with my instructor, Lori, and a group of fellow nautical novices. Turned out I was a natural at the helm, finding the balance of tension on the wind and steering into it, loving the loud crack of the sails as my classmates jibbed to my shouted “Jib ho!” Getting to give the orders — I could get used to that.

Offshore Sailing School’s three-day “Learn to Sail” package starts around $1,235 per person and includes a textbook. (Take a look before your first class meeting.) The days are divided into classroom and on-boat teaching (above). At the end, you’ll earn your Day Sailing Certification, and you’ll even get a free practice sail — sans instructor. The deal also includes a room for three nights at Hawks Cay. Offshore Sailing School, 800-221-4326, offshore-sailing.com/­florida-keys.asp.

Hawks Cay sits on a 60-acre Florida Keys island called Duck Key. (Offshore Sailing School docks at the resort’s marina.) The upscale-but-casual resort underwent a $35 million reno just over a year ago, and everything on the property feels brand-new — five swimming pools, five restaurants, Playstations in the room. Rooms start at $175, and private villas at $225. Hawks Cay, 305-743-7000, hawkscay.com

Hawks Cay is all about the water, and there are plenty of non-sailing activities. Board a boat of a different kind — say, a 40-foot powerboat — and head out in the Atlantic to catch tuna, yellowtail, snapper or mahimahi; chartered fishing expeditions leave from the on-property marina and start at around $600 for half a day. There’s also the more hands-on spearfishing, scuba diving, and swimming around with dolphins in a lagoon at Dolphin Connection ($155). Or, if you’ve got a car, Key West is a beautiful 60-mile drive south. Dolphin Connection, 888-814-9154, dolphinconnection.com.

Hawks Cay has five restaurants with everything from poolside chicken fingers to super-fresh seafood. Have an alfresco beachside lunch at the Beach Grill. (Order the local fish favorite, wahoo.) Alma’s modern design matches its trendy global/Latin menu. With rum flights on offer, what could go wrong? At the marina, Tom’s Harbor House is a casual restaurant that serves the freshest catches of the day — don’t miss the grouper — hauled in by local fisherman. Hawks Cay, 305-743-7000, hawkscay.com

After the three-hour flight from PHL to Miami, enjoy the beautiful 95-mile drive to Hawks Cay in a rented convertible. If you don’t want to rent a car (you really don’t need one once you’re at Hawks Cay), the resort runs an airport shuttle (reservations required, 888-765-9997).

Comfort rules — you won’t see high heels poolside at Hawks Cay, even at the finer-dining spots. For sailing, you’ll need non-slip white-soled shoes, comfortable but not baggy clothes, gloves and Croakies. If you go in late summer, don’t forget the bug spray.

Back in Philly: Keep your sea legs steady by studying (on the Delaware!) at Liberty Sailing School (303 North Front Street, 215-923-7245, libertysailingschool.com). ­Classes — on everything from docking to foul-weather sailing — start around $250.