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Experience Pensacola Bay the way it was meant to be enjoyed — under sail, with your favorite people, and without the crowds. Welcome aboard S/V Wine Down, a beautifully maintained 36-foot Catalina sailboat offering fully private sailing experiences for up to 6 guests. Whether you’re looking for a relaxing sunset cruise, a fun day on the water with friends, a romantic evening, or a customizable sailing adventure, your time aboard is designed around you. Unlike crowded “per-person” tours, every trip is completely private. When you book, the boat is yours. What To Expect Step aboard in Pensacola and enjoy: - Relaxing sailing on beautiful Pensacola Bay - Stunning sunset views - Dolphin sightings - A true sailing experience — not just a motorboat ride - A laid-back, personalized atmosphere - Flexible itineraries depending on weather and your preferences Want to take the wheel? You’re welcome to. Want to sit back with a drink and enjoy the view? That works too. Perfect For - Couples & date nights - Families - Friends outings - Anniversaries & birthdays - Proposals & special occasions - Visitors wanting a unique Emerald Coast experience Your Private Experience Includes - Licensed captain - Private charter for your group only - Bluetooth music onboard - Ice, bottled water, and sodas - Comfortable seating & shaded cockpit area - BYOB welcome Longer experiences may also include: - Paddle boards - Snorkeling - Beach stop options depending on conditions Trip Options Choose from: - Sunset sails - Day sails - Custom private charters Why Guests Choose Wine Down Sailing We focus on relaxed, personalized experiences rather than rushed group tours. Many guests tell us this becomes one of the highlights of their Pensacola vacation. If you’re looking for a memorable way to enjoy the Emerald Coast, we’d love to welcome you aboard and help you “Wine Down.”


Catalina 36 sailboat owner and licensed Coast Guard Captain.
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 5 days before your trip.
Your safety and enjoyment are our top priorities aboard S/V Wine Down. Charters may be delayed, rescheduled, or canceled due to unsafe weather conditions at the captain’s discretion. Light rain does not always require cancellation, but strong storms, high winds, or hazardous marine conditions will. Please arrive 15 minutes prior to departure. Late arrivals may shorten your experience, as charters typically return at the scheduled time. No-shows and last-minute cancellations may forfeit deposits. For safety reasons, the captain reserves the right to end a charter early if guest behavior, intoxication, or unsafe conditions become a concern. Bare feet are preferred while onboard, and all guests must follow captain instructions during the sail. Children are welcome with adult supervision. U.S. Coast Guard-approved life jackets are provided for all guests. Wine Down Sailing is a private sailing experience designed for relaxation, sightseeing, and making memories on Pensacola Bay. We appreciate your cooperation in helping us provide a safe and enjoyable experience for everyone aboard.