This is the way to do southwest Florida—from a crewed, floating B&B loaded with kayaks, limes, rum, and five of your closest paddling buddies to split the cost. The Mirage, a shallow-draft 70-foot outrigger catamaran, cruises through the barrier islands of Pine Island Sound, dropping your gang off at a new location each morning along the just expanded Great Calusa Blueway, a 190-mile marked canoe and kayak route. A loose itinerary leaves room for spontaneity and takes into account the skill level and ambition of the group. Poke around the grassy fringes of Sanibel’s J.N. "Ding" Darling National Wildlife Refuge, where manatees roll in the dark green water; paddle through the chop with a posse of dolphins to the empty beaches of Cayo Costa State Park; or cut through a channel to play in the Gulf of Mexico on the islands’ western shores. And if you simply want to drift, that’s cool too. "Sometimes we just let the kayaks float along the edges of the flats and watch the roseate spoonbills fish," says Elke Thuerling, co-owner of Kayak Voyagers. After dinner, take a moonlight swim, then stretch out on the deck and count the stars.
The Lure: Boating, kayaking
Vitals: Kayak Voyagers, six nights, doubles from $1,375, December–May; nps.gov/wicakayakv.com