The last cruise of the day, our dolphin sunset cruise departs approximately two hours before sunset. Come join us for the best part of the day on the water!
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.
Please arrive a few minutes early for boarding. Detailed directions will be included in your confirmation email.
All trips are subject to the captain’s approval of weather and water conditions. In the event a trip is canceled, we will attempt to reschedule the trip on another day. If this is not possible, guests will not be charged. If you need to cancel, we require a 24-hour notice prior to your scheduled trip. If you cancel within 24 hours, you will be charged half of the total booking fee.