Are You Ready to Wine Down?
Step aboard our 36-foot Catalina sailing yacht, S/V Wine Down, and enjoy a relaxing sail on beautiful Pensacola Bay. With so much stunning water surrounding Pensacola and Perdido Key, there’s no better way to experience the area than from the deck of a sailboat — away from the crowds and at your own pace.
We specialize in private sailing experiences, meaning it’s just you and your guests on board. Each sail offers the chance to unwind, enjoy the breeze, spot dolphins and other marine life, and learn a little about the history of Pensacola from the water. Select experiences also include time to swim or paddleboard when conditions allow.
From peaceful day sails and unforgettable sunsets to a cool dip and paddle board fun at anchor , every experience is designed to help you slow down, relax, and truly Wine Down.
CALL OR TEXT (850) 706-1046 FOR MORE INFO!
Day Sail
A Great Introduction to Sailing!
This private sailing experience is $490 and includes up to six guests. Your choice of afternoon or morning sailings and gives you two relaxing hours on the water. We’ll cruise Pensacola Bay, keep an eye out for dolphins, and you may even catch a glimpse of Pensacola’s own Blue Angels during practice days.
Soft drinks and water are provided. Feel free to bring your favorite beverages and snacks (BYOB). Sunscreen, life vests, and towels are also included.
Note: An additional hour may be added for $100.
Sunset Sail
Our Most Popular Experience!
This private sailing experience is $520 and includes up to six guests. We’ll depart from Bayou Chico two hours before sunset and sail through beautiful Pensacola Bay, taking in the scenery, keeping an eye out for dolphins and other marine life, and sharing a bit of local Pensacola history along the way. As the sail winds down, you’ll enjoy one of Pensacola Bay’s spectacular sunsets from the water.
Soft drinks and water are provided. You’re welcome to bring your favorite beverages and snacks (BYOB). Sunscreen, life vests, and towels are also included — just relax and enjoy the sail!
The Locals Experience
Island Hop and Swim!
Island-hop aboard your own private sailing yacht for a full day on the water. This six-hour experience is $1,400 and includes up to six guests.
Sail like a local as we cruise to Fort McRee, anchoring near the historic fort and a secluded beach accessible only by boat. While anchored, you’ll have plenty of time to swim, snorkel, paddleboard, explore the shoreline, or simply relax and take in the views. Dolphins are often spotted along the way.
Soft drinks and water are provided. You’re welcome to bring your favorite beverages (BYOB) lunch and snacks. Paddleboards, snorkel gear, sunscreen, life vests, and towels are all included — just show up ready to enjoy the day!
Wine Down Merch
Before you hit the water, stop by our merch shop and grab our fan-favorite rash guards, hats, and T-shirts—perfect Florida vacation keepsakes and a lasting reminder of the unforgettable time you’ll have aboard Wine Down.
Gift Certificates
Ask about our gift certificates. Give more than a gift—give an experience. Wine Down gift certificates make a thoughtful, unforgettable present for birthdays, anniversaries, or just because.
CALL OR TEXT (850) 706-1046 FOR MORE INFO!
- Small soft coolers allowed on all charters.
- Boarding the boat requires steps from the dock to the deck of the boat. Please let us know if an easier boarding experience is required.
Cancellation Policy: 48 hour notification for full refund of deposit. If weather doesn’t permit the charter and a reschedule is not possible, full deposit is refunded.
Call or Text (850) 706-1046 for more information!
Pensacola Private Sunset Sail Cruises! 