Winter Escape: Big Pine Key


Jan 5, 2010
Outside Magazine
Florida Keys

Scouting your Florida Keys playground

An important lesson my grandfather Herb taught me: Sun and sand are good, but they're even better when you add bistec de Palomilla and stone crab. The best spot to enjoy this combo stateside is the Florida Keys, and if you head for Big Pine Key, you can mix in some adventure while dodging the notorious local schlock. First, make a beeline for the Deer Run Bed & Breakfast (from $225; The eco-minded inn serves delicious vegan breakfasts (hey, Herb liked veggies, too) and provides kayaks on its Atlantic-facing beach. When you're ready for serious paddle exploration, mosey seven miles north to Big Pine Kayak Adventures ( Owner Bill Keogh literally wrote the book on kayaking here—2004's Florida Keys Paddling Guide ($18;—and offers four-hour tours winding around wild mangrove islands ($125 per person). Saturday night is for bistec, and I promise the 45-minute drive to Key West will be forgotten the moment you smell the Cuban food at El Siboney (elsibo­ney­ The next morning, snorkel the shallow reefs of Looe Key Marine Sanctuary with Strike Zone Charters ($35 per person;, which launches catamaran-based trips ten minutes from Deer Run. On your drive back to the mainland, complete Herb's recipe with fresh stone crab at the Keys Fisheries Restaurant (, on Marathon Key. NEAREST AIRPORT: Fort Lauderdale or Miami, three hours.