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Jolly Sailing


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

Choose Your Adventure on the Beaches in Pensacola, FL!

Featured Pensacola Tours!

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 the Original Jolly Mon! In addition, we have added 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 guests. COMING SOON SUMMER 2024 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!

Cruise Into Our Five-Star Dolphin Cruise in Pensacola!

So Much Fun

I have been coming to Pensacola for many many years and I've been on almost every dolphin Cruise in this area. We had a blessed time. So many dolphins and a beautiful sunset. Captain Mike was funny and knowledgeable and his first mate Paul was on point with drinks and very friendly.

– Marcy B. | TripAdvisor
Perfect Cruise

We took the sunset dolphin cruise which exceeded our expectations. There were plenty of dolphins, a great sunset, and the crew was enthusiastic and fun. The price was more than reasonable, the seating comfortable. Overall the experience was a very relaxing excursion. Highly recommend Jolly Sailing.

– Davis R. | TripAdvisor
Amazing Experience

Excellent trip. Great information received on the dolphins we watched frolicking in the ocean. Captain Mike and Riley were full of information with great humor and refreshing "beverages" that made the trip even more enjoyable. Highly recommend. Great price!

– Karen V. | TripAdvisor
Great Cruise

This was a great trip and an amazing dolphin encounter that exceeded my expectations. Captain Mike shared lots of interesting dolphin facts in an entertaining fashion. First Mate Riley was friendly and made us feel welcome. I highly recommend this cruise!

– Laura S. | TripAdvisor