Sailing Adventure in Pensacola Bay and Santa Rosa Sound
Difficulty
moderate
Duration
3 hours
Fitness Level
Suitable for moderate fitness; ability to move steadily on a sailboat deck is recommended.
Overview
Glide through Pensacola Bay aboard the 27' Jolly Mon sailboat, spot dolphins, and dive into refreshing Gulf waters. This 3-hour coastal sailing trip blends wildlife, relaxation, and adventure.
3 Hour Jolly Mon Sailing Adventure with Optional Swim Stop
Experience the Excitement of Sailing on the Gulf Coast!
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Adventure Photos
About This Adventure
Embark on an unforgettable sailing adventure aboard the Jolly Mon, a 27' sailboat, as you glide through the stunning landscapes of Pensacola Bay and Santa Rosa Sound. Experience the thrill of sailing, spot dolphins and other wildlife, and enjoy a refreshing swim stop, all while sipping complimentary beverages.
Climb aboard the Jolly Mon, our 27' sailboat, for a sailing adventure with optional swim stop!
During this cruise we will sail along the beautiful landscape of the National Seashore, Pensacola Bay, and/or Santa Rosa Sound. Sit back and relax, or take the helm to experience the real joy of sailing!
Enjoy the wind in your hair while you look out for dolphins, seabirds, stingrays, turtles and other wildlife. Though we cannot always guarantee a dolphin sighting, we do often spot them in the bay.
On this cruise, you can choose to stop and hop in the water for a refreshing swim.
Cruise includes complimentary beverages. Guests are welcome to bring food or drinks aboard.
PLEASE NOTE: GUESTS MUST BE PHYSICALLY AGILE IN ORDER TO BOARD THE SAILBOAT. Any questions or concerns, please contact us directly at 850-723-6142.
Adventure Tips
Check Weather Forecast
Pensacola Bay conditions can shift quickly; ensure calm winds for a smooth sailing experience.
Bring Swimwear and Towel
The optional swim stop is a highlight—pack swimwear and a quick-dry towel.
Use Reef-Safe Sunscreen
Protect yourself and local marine life by applying eco-friendly sunscreen before boarding.
Arrive Early for Safety Briefing
Arriving 15 minutes early ensures you won’t miss important safety and sailing instructions.
Local Insights
Wildlife
- Bottlenose dolphins
- Loggerhead sea turtles
History
Pensacola Bay has a rich maritime history dating back to the 16th century as one of the earliest European settlements on the Gulf Coast.
Conservation
Local efforts focus on protecting seagrass beds and water quality to sustain the vibrant marine ecosystem guests experience.
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Adventure Hotspots in Pensacola
Frequently Asked Questions
Recommended Gear
Light Jacket
Offshore breezes can be cool during spring excursions.
spring specific
Swim Gear
Essential for the swim stop in warm summer waters.
summer specific
Sunscreen
Protects skin during long exposure to sun on open water.
summer specific
Hat and Sunglasses
Helpful for glare reduction and sun protection while onboard.