Sailing, Snorkeling Tours, & Powerboat Dolphin Cruises in Pensacola, FL

Choose Your Adventure on the Beaches in Pensacola, FL!

Featured Pensacola Tours!

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1.5 - 2 hours
All ages

Pensacola Beach Dolphin Cruise & Scenic Bay Tour

Take a scenic sightseeing tour of Pensacola by water. View dolphins and marine life by boat and iconic Pensacola sights along the way!

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From $65

2 hours
All ages

Go Snorkeling in Pensacola!

Visit one of our great snorkel spots in Pensacola Bay and Santa Rosa Sound. Snorkel in shallow water, about 3 – 4 feet deep. The trip includes snorkel gear and instruction. Trip may take place on our sailboat or powerboat, and lasts about 2 to 2 1/2 hours.

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From $75

2-4 hours
All ages

Jolly Mon Sailing Tours

A day or sunset sail is the best way to relax on Pensacola Bay. Treat yourself to a unique sailing experience at Pensacola Beach, featuring steady afternoon sea-breezes, smooth sailing, no worries, and Jollification!

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From $35

2-3 hours
All ages

Jolly Dolphin Boat Tours

Soak up the sights of Pensacola by water! We offer a variety of Jolly Dolphin scenic bay boat tours, dolphin cruises and more, private and shared, for up to 28 passengers.

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About Jolly Sailing Pensacola Bay Cruises

Come see dolphins play on a Pensacola Beach dolphin cruise in Pensacola Bay and Santa Rosa Sound. 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, with sailing, snorkeling, and sunset cruise.

We currently have several boat options to choose from, including Jolly Roger, a 24′ powerboat tritoon, Jolly’Ventures, a 26′ powerboat tritoon, and Jolly Dolphin, a 42′ powerboat tritoon passenger vessel that carries up to 28 passengers. COMING SOON FALL 2023 we are launching Pensacola Beach’s newest Dolphin Cruise boat, a brand new, custom built 49 passenger 38’catamaran! We offer a wide variety of excursions, both private and shared, for guests to enjoy.

Over the years, we have been pleased to welcome several experienced, friendly, and informative captains and crew members to our team. Together we strive to provide a safe, relaxing, and entertaining excursion 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. We love meeting guests from all over the world and sharing our knowledge of boating, dolphins and local wildlife, as well as Pensacola history and attractions with them. Join us on a tour today!