Step aboard Wine Down Sailing’s Locals Island Charter for a rare glimpse of Pensacola Bay’s serene islands, guided by Captain Steve’s expert hands. Enjoy an intimate, personalized sailing experience framed by Florida’s stunning Gulf Coast.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; minimal physical exertion required
Wildlife
History
Pensacola Bay has been a critical naval and trading hub since the early 16th century, with deep ties to Gulf Coast maritime culture.
Conservation
Wine Down Sailing emphasizes low-impact boating and maintaining the pristine condition of Pensacola Bay’s fragile ecosystems.
Wine Down Sailing
Step aboard Wine Down Sailing’s Locals Island Charter for a rare glimpse of Pensacola Bay’s serene islands, guided by Captain Steve’s expert hands. Enjoy an intimate, personalized sailing experience framed by Florida’s stunning Gulf Coast.
Wine Down Sailing is a Pensacola, Florida sailing company offering private yacht charters and guided sails in Pensacola Bay and the surrounding coastline. The business runs a range of trips including The Quietwater Beach Sail, The Locals Island Charter to Ft. McRee, Sunset Sails from Bayou Chico, Fun Sails past the Bay Bridge and NAS Pensacola, and the Blue Angel Practice Sail anchored for overhead rehearsals. Trips vary from multi-hour charters to targeted experiences such as a 9:30 am Blue Angel Practice anchoring and a five-to-six-hour Quietwater Beach outing that includes lunch. Guests can expect opportunities for swimming, paddleboarding, dolphin watching, sightseeing, and enjoying local sunsets. Selected trips include light sandwiches, lunch, and beverages; the Locals Island Charter and Blue Angel Practice Sail specifically note provided food or drinks. Wine Down Sailing operates in and around Pensacola Bay and Quietwater Beach and visits historic points like Ft. McRee during island charters. Scheduling details, departure points, and included amenities vary by trip, and bookings are available for private charters.
Reservations accommodate private groups and small parties with tailored itineraries and flexible departure times. Guests should check trip details for duration, included items, and meeting locations. Wine Down Sailing emphasizes clear, location-specific offerings so visitors can choose the exact Pensacola sailing experience that matches interests and schedules, and online booking options available.
Location
Pensacola, Florida
Sails around Pensacola Bay
Tours Offered
5 unique sails
Quietwater, Locals, Sunset, Fun, Blue Angels
Max Duration
Up to 6 hours
Five- to six-hour charters available
Amenities
Light food & drinks
Lunch or sandwiches on select trips
Reserve a Quietwater Beach Sail, Ft. McRee charter, sunset cruise, Fun Sail, or Blue Angels practice outing with Wine Down Sailing — availability varies by season.
Book Ahead for Sunset Trips
To secure a prime spot for the sunset sails, reserve your trip in advance, especially during weekends and peak seasons.
Bring Layers
Evenings on the water can cool quickly after sunset; pack a light jacket or windbreaker for comfort.
Mind the Seasickness
If you’re prone to seasickness, consider preventative measures before boarding the sailboat as motion can be noticeable in open water.
Hydrate and Snack
Though drinks are available, bring water and light snacks to stay refreshed during your outing.
Windbreaker Jacket
Protects against sudden breezes and cool post-sunset temperatures.
spring
Sunscreen
Necessary to guard against prolonged sun exposure on open water.
summer
Comfortable Non-Slip Shoes
Provides secure footing aboard the boat during movement and docking.
Reusable Water Bottle
Helpful for staying hydrated during your trip.