Wind and Wine Music Sail with Caleb

Set sail into the evening aboard a historic Key West schooner for one of the most refined—and relaxed—experiences on the water.

Danger’s Wind & Wine Sunset Sail is consistently ranked among the best in North America, and once you’re aboard, it’s easy to see why. Under full sail and open sky, you’ll drift through the backcountry enjoying a curated selection of fine wines from around the world, complemented by upscale beers and a generous spread of hors d’oeuvres designed to match the setting.

This isn’t a party cruise—it’s something more intentional. A quieter, more elevated way to take in the sunset, the breeze, and the company around you.

Adding to the experience, special guest Caleb Hogan—star of A Pirate Looks Back—joins the sail with a live, stripped-down performance. Known for bringing Jimmy’s early Key West years to life through music and storytelling, Caleb adds a personal, intimate layer that fits perfectly with the setting.

As the light fades and the sails fill, this is the kind of evening that doesn’t need much else—just good wine, good music, and the feeling of being exactly where you’re supposed to be.