Call or text! (850) 706-1046
Our private sailing experiences are truly one of a kind in the Pensacola and Emerald Coast area. Gather up to six guests for a memorable day of sailing, snorkeling, and paddleboarding—or escape together on an intimate cruise for two, where breathtaking sunsets paint the perfect ending to an unforgettable experience.
Vacations are about slowing down—not squeezing in. Skip the crowded tours and make Wine Down your private yacht for the day. Sail your way, on your time. You deserve this.
Our Experiences Include:
- Licensed Captain
- Clean bathroom (known as a head on a boat)
- Organized galley (kitchen) and storage
- Cabin area with salon seating (in case of a Pensacola pop-up shower)
- Ample shade in our generous covered cockpit area or get some sun on the foredeck
- Bluetooth (play your own tunes or let the captain take over the playlist)
- Life jackets
- Refrigerator (for your snacks and beverages – you can also bring your own soft cooler)
- Paddle boards, snorkel gear and water floaties
- Water and soft drinks provided (BYOB and any snacks you may want)
- Sunscreen
A Few Of Our Cool Moments
CALL OR TEXT (850) 706-1046 FOR MORE INFO!
Frequently Asked Questions
How many people can we have in the group?
No more than a total of six guests per our Coast Guard certification.
Will we see dolphins?
While we can’t guarantee dolphin sightings, 80% the time we do encounter them.
Is this a private sailing experience?
Yes. All Sailing Experiences are 100% private. When you book, the entire sailboat is reserved exclusively for you and your guests — no shared trips, no strangers.
How long is the Sunset and Day Sailing Experiences?
Our Sunset and Day Sailing Experience lasts approximately two hours, giving you plenty of time to relax, sail, explore, and enjoy being on the water without feeling rushed. We can also add on another hour if more water therapy is required!
How long is a Full Day sailing experience?
Our Full Day Sailing Experience lasts approximately six hours, allowing for a more immersive day on the water with extended sailing time and flexible routing.
Will we sail in the Gulf?
No. Typically our sailing takes place on Pensacola Bay. However, areas near Perdido Key may also be explored. Your captain selects the best route for comfort, scenery, and wind.
What activities can we do during the sail?
Depending on conditions and your preferences, experiences may include:
- Sailing under wind power
- Relaxing and sightseeing
- Swimming or floating
- Snorkeling
- Paddleboarding
Your trip is flexible and tailored to your group.
Is sailing experience required?
Not at all. These experiences are perfect for first-time sailors and seasoned boaters alike. Your captain handles everything unless you’d like to participate.
Can we help sail the boat?
Yes. Guests are welcome to help trim sails, steer, or learn basic sailing techniques — or simply sit back and relax. It’s entirely up to you.
What should we bring on a sail?
We recommend:
- We furnish water and soft drinks so any specialized drinks or snacks or a light meal on the 6 hour experiences.
- Sunglasses, cameras and/or phones
- Comfortable clothing and soft-soled shoes
- A light layer, depending on weather
Can we bring alcohol on board?
Yes. Guests are welcome to bring their own alcoholic beverages. Please enjoy responsibly while on the water. No smoking allowed though.
Is this experience family-friendly?
Yes. Our experiences are great for families, couples, and small groups. Safety is always our top priority.
What happens if the weather isn’t suitable?
If conditions aren’t safe or comfortable for sailing, we’ll work with you to reschedule or discuss available options.
Will we sail the whole time or use the engine?
Whenever wind conditions allow, we sail for a smooth and peaceful experience. The engine may be used for maneuvering or timing purposes as needed.
Can we customize the experience?
Absolutely. One of the biggest advantages of a private sail is flexibility. Let us know what kind of day you’re hoping for, and we’ll do our best to make it happen.
Are your sailing experiences good for special occasions?
Yes. Our experiences are ideal for:
- Birthdays
- Anniversaries
- Weddings
- Photo shoots
- Family gatherings
- Small celebrations
- Relaxed group outings
How far in advance should we book?
Availability is limited, especially during peak season. We recommend booking as early as possible to secure your preferred date.
Where do we meet for our sail?
We depart from Day Break Windward Marina in Pensacola.
Why choose a private experience instead of a group charter?
A private sailing experience offers:
- No crowds
- Personalized attention
- Flexible timing and activities
- A calm, unhurried atmosphere
It’s your boat, your group, and your day on the water!
Learn More About Us!
Pensacola Private Sunset Sail Cruises! 