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2 Hour Sightseeing Sail

Quick Details

Child Under 12 Years Old
Adult 10am Sail
Child 10am Sail
Private Trip Up to 2 passengers
Private Trip 3-6 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, with consistent afternoon sea-breezes.

On our vessels, you can experience a sailing adventure just like the early explorers. Learn about sailing, help hoist the sail and take the helm, or just sit back, relax and enjoy the scenery. Sailing is a unique experience that can be 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 hour shared or 2 to 8 hour private excursions. Skip the crowds and join us for a relaxing, personal experience.

Options include Jolly Mon, our 27′ American Mariner adventure sailboat, the boat that started it all 13 years ago! This vessel is perfect for families and groups up to 6 people. The unique style of this boat allows for anchoring in shallow waters, to enjoy a swim or snorkel stop as part of your excursion if desired. Great for sunset cruising too! NEW for 2024 Enjoy a luxury style sailing excursion with our affiliate aboard S/V Infinity, a beautiful 38′ Beneteau sailing vessel.