Cayman Islands Sailing Charters

Cayman Islands Sailing Charters

If you’re dreaming of the perfect day on the Caribbean Sea, Cayman Islands Sailing Charters delivers it with ease and island charm.  Step aboard, Be Happy, you have your choice of a 46 foot Leopard Catamaran or a 37-foot Prout sailing catamaran, and let Captain Ben and his friendly crew show you the very best of Grand Cayman from the water.  Known for his easygoing personality, deep local knowledge, and genuine Cayman hospitality, Captain Ben customizes every trip to fit your mood—whether that’s a romantic sunset sail, a private family adventure to Stingray City, a snorkeling escape at Coral Gardens, or a day of pure relaxation at Starfish Point.  Guests love how personalized each charter feels. Small groups (up to 20 guests) enjoy plenty of space to lounge on deck, paddleboard in calm turquoise waters, and snorkel among colorful reef fish—all with refreshments, smiles, and great island vibes included.  For a truly memorable day on the water, Cayman Islands Sailing Charters makes you feel like the boat is yours for the day.  From the first friendly “Ahoy!” to the last golden-hour view, Captain Ben ensures you’ll sail away Be Happy—and be ready to book your next adventure before you’ve even docked.  Passenger Pick Approved!