Wind and Wine Music Sail with Caleb

🍷⛵ Wind & Wine Music Sail with Caleb Hogan
📅 Saturday, September 5, 2026
⏰ 6:30–8:30 PM
📍 Danger Charters · 255 Front St, Key West
Set sail into the evening aboard a historic Key West schooner for one of the most refined—and relaxed—experiences on the water.
Consistently ranked among the best sunset sails in North America, Danger’s Wind & Wine experience offers a quieter, more elevated way to take in the island. 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.
This isn’t a party cruise—it’s something more intentional. A chance to slow down, take in the breeze, and enjoy the company around you as the light fades.
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 the early Key West years to life through music and storytelling, Caleb adds a personal, intimate layer that fits perfectly with the setting.
As the sails fill and the sun dips below the horizon, 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.
📝 Need to Know
— Departs from the Historic Seaport (exact check-in details provided upon booking)
— Boarding begins prior to 6:30 PM departure
— Approximately 2-hour sunset sail aboard a historic schooner
— Fine wines, beer, and hors d’oeuvres included
— Intimate, relaxed atmosphere (not a party cruise)
— Live acoustic performance by Caleb Hogan
— Comfortable, casual attire recommended; dress for the breeze on the water
— Must be 21+ to consume alcohol
⚠️ Limited capacity—advance booking recommended.
🌴 All are welcome · Come as you are · Be part of the story
“Aʟʟ ᴇᴠᴇɴᴛs ɴᴏᴛ ᴀꜰꜰɪʟɪᴀᴛᴇᴅ ᴡɪᴛʜ ᴏʀ ᴇɴᴅᴏʀsᴇᴅ ʙʏ Jɪᴍᴍʏ Bᴜꜰꜰᴇᴛᴛ’s Esᴛᴀᴛᴇ ᴏʀ Mᴀʀɢᴀʀɪᴛᴀᴠɪʟʟᴇ Eɴᴛᴇʀᴘʀɪꜱᴇ”