Skip to primary navigation Skip to content Skip to footer

Pensacola Beach Sailing Tours

Quick Details


Set Sail in Pensacola!

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 many sailing excursions.

We are located directly on Pensacola Beach offering two and four-hour shared or private excursions. Skip the crowds and join us for a relaxing and more personal experience.