The waters of Pensacola Bay and Santa Rosa Sound are renowned for sailing and cruising. Join us for a sunset or sightseeing sail!
- Child Under 12 Years Old
- Adult 10am Sail
- Child 10am Sail
- Private Trip Up to 6 passengers
Pensacola Sailing Charter
Sailing in Pensacola has been a tradition since 1559, when Don Tristan De Luna of Spain landed on the shores of Pensacola Bay, marking the first European Settlement in mainland America.
The waters of Pensacola Bay and Santa Rosa Sound are renowned for sailing and cruising, featuring steady afternoon sea-breezes, plenty of depth and easy anchorages.
On the JollyDayz, our classic 34’ Pearson yacht, you can experience a sailing adventure just like the early explorers. Help hoist the sails and take the helm, or just sit back, relax and enjoy the scenery. Sailing is a unique experience that is relaxing and exciting at the same time.
Sailing with dolphins on Northwest Florida’s Gulf Coast is a unique experience. Wild dolphins seem naturally attracted to sailboats, often swimming alongside us, crossing our wake, playing and feeding nearby. Though we cannot always guarantee a sighting, we do cross paths with dolphins on most sailing excursions.
We are located directly on Pensacola Beach offering 2 and 4 hour shared or private excursions. Skip the crowds and join us for a relaxing and more personal experience.