There’s nothing quite like exploring the crystal-clear waters of Key West on a pet-friendly SUP. Just ask the folks at Lazy Dog. The company logo was inspired by Camillo, the original Lazy Dog who loved nothing more than paddleboarding in the Keys. Trace her footsteps through creeks and shallows, keeping an eye out for jellyfish, conch, sea cucumbers, stingrays, manatees and even the occasional shark! Tourists can join a two-hour guided tour or rent a paddleboard and head out alone. The staff will give you tips on how to get Fido on the board safely and equip you with a handy map to navigate your own six-legged adventure. SUP rentals start at $30 per person. Tours and an introduction to SUP are $50 per person, and private lessons are available for $75 per person. Dogs paddle for free, and doggy life jackets are provided.
Drift away with your dog on a pet-friendly houseboat in the Hunter Cherubini Sailboat, moored in a marina with access to a dog park on dry land. When you're feeling peckish, get a taste of the ocean at nearby Hogfish Bar & Grill, where they serve seared scallops, tuna tacos and more treats from the deep.