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!
Jolly Mon Sailing Tours
- Private Cruise
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 Jollymon, our sporty custom 27’ American Mariner sailboat, you can experience a sailing adventure just like the early explorers. Your Captain will be happy to show you the ropes, and even let you steer the boat, or you can just sit back, relax, and enjoy the scenery. The Jollymon is certified for 6 passengers, most comfortable for families or smaller adult groups. Cruises range from 2 to 4 hours and may include snorkeling, in season. This boat is best suited for private cruises, at an affordable rate. Sailing is a wonderful experience that is relaxing and exciting at the same time.
New for 2021, we offer premium sailing tours through our affiliate Travelin’ Light, aboard the S/V Sapphire, a beautiful 37′ Hunter Cherubini. Many options are available aboard the Sapphire, from 2 to 8 hours, enjoy a romantic sunset sail, day sail, Gulf sailing adventure, dinner cruise or custom cruise. Private and shared trips available. Please call us at 850-723-6142 for further details.
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 at the Sabine Marina, behind the Frisky Dolphin Sunset Oyster Bar & Grill, and The Sandbar. Skip the crowds and join us for a relaxing and personalized 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.