Captain and crew


Jolly Sailing is a family owned company established in 2011 in Pensacola Beach, Florida. It all began with the Jolly Mon, our 27′ American Mariner Sailboat, on which we offered sailing, snorkeling and sunset tours that inaugural year.

Over the last few years, we have added JollyDayz, our 34′ Pearson sailing yacht, Jolly’Ventures, a 26′ power tritoon, and Jolly Roger, a 26′ power catamaran. Soon, we will be adding a 42′ power tritoon to the fleet, on which we will be able to accommodate larger parties. Follow our Facebook page for updates on this new vessel! We now offer a wide variety of excursions, both private and shared, for our guests to enjoy.

We have been pleased to welcome several experienced, friendly and informative Captains and crew members to our team. Together we strive to provide fun, safe, relaxing and entertaining excursions for our guests. It’s not just a job, it’s a lifestyle that we enjoy sharing with visitors to Pensacola Beach and residents of the Pensacola Bay Area.

Whether you’re looking for a sunset cruise in Pensacola, dolphin cruise, dinner cruise, snorkeling or stand up paddleboard adventure, you will be sure to enjoy a memorable excursion with Jolly Sailing.