Jolly Sailing & Dolphin Cruise
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Jolly Sailing & Dolphin Cruise
Take a scenic sightseeing tour of Pensacola by water. 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! The waters of Pensacola Bay and Santa Rosa Sound offer the perfect venue for sailing and cruising.

Join us for a sunset or day sail, or a sail and snorkel adventure on a 27' sailboat! Soak up the sights of Pensacola by boat! We offer a variety of Jolly Dolphin boat tours, private and shared, for up to 28 passengers. Come see dolphins play on a Pensacola Beach dolphin cruise in Pensacola Bay and Santa Rosa Sound.
Services
Explore Pensacola Bay and Santa Rosa Sound on a Pensacola Beach dolphin cruise, sailing tour, or snorkeling adventure!. We offer complimentary beverages (water and soda). Guests are allowed to bring alcohol, and coolers are welcomed. Our boats feature full shade, comfort cushioned seating, relaxed, uncrowded atmosphere, and all vessels have a restroom aboard.
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! Take a scenic sightseeing tour of Pensacola by water. The Blue Angels fly over the waters of Pensacola Bay and the Gulf of Mexico, offering an excellent view to boaters!
Combine two of our most popular activities! On this cruise, we will have time to explore the waters of Pensacola Bay in search of dolphins and other wildlife and stop for snorkeling. Soaking up the sun and beachcombing the sugar-white sands of Pensacola Beach are perfect ways to relax and enjoy your vacation.
Add a gourmet snack plate to your private cruise, starting at $25. Champagne may be added for an extra fee. Contact us for details and options. Hop on one of our dolphin cruise boats (Jolly'Ventures, up to 6 passengers, or Jolly Dolphin, up to 25 passengers) for a fun party cruise around Pensacola Bay and Santa Rosa Sound.
We sail in the protected waters of Santa Rosa Sound and Pensacola Bay, where conditions are quite favorable for boating. Seasickness is highly unlikely to occur while sailing, as it is generally a much smoother ride than on a powerboat. The sails stabilize the boat and keep it from rolling and pitching.
Reviews (10)
Lauren K.
Lauren K.
Dec 04, 2021
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Freddy and Mike had so much applicable knowledge to share-not only of the ocean life and local area but specifically about dolphins and the history behind the gulf coast and its military forts. Freddy is very accommodating towards every single customer, whether there’s 10 or 20. We were guaranteed dolphin spotting and weren’t let down! We saw a dolphin within 30 seconds of setting off! Definitely recommend.
Karen K.
Karen K.
Dec 01, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
Took this 2-hour cruise on 12/4/2021 and it was spectacular!! Fun, informative and more dolphin than I've ever seen before!! Fun crew, too! Note to self ... it's much colder on the water - wear long pants and take a jacket in December!!
Rachel Salerno
Rachel Salerno
Aug 31, 2021
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Freddy and Mike were great! It was a slightly overcast morning, so it ended up being a perfect temperature, with a light breeze.
The Blue Angels were back at base this week and out practicing! They made sure to head towards their maneuvers so we could have a front row seat to part of their practice!
Oh! And we saw plenty of dolphins as well.
Jesse Lawrence
Jesse Lawrence
Aug 27, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
We saw ten dolphins! Went to a preserve, heard silky jokes, danced to music, learned fun facts, laughed and snuggled on the way home. 2year old and 6 year old made it no problem. So fun. Worth every penny. Bring a tip. These people are awesome.
Joyful Family
Joyful Family
Aug 21, 2021
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We enjoyed our sunset dolphin cruise. We were able to locate two different sets of dolphin and were able to see them up close. We were completely satisfied after finding the first set of five dolphins but he took us further out and found another set of five. So fun! The boat was comfortable with cushioned seats and it was completely covered. The captain was professional as was the assistant. We felt safe, comfortable and saw lots of dolphins.
Tiffany Miller
Tiffany Miller
Jul 03, 2021
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We had the best time with Andrea & captain on our Dolphin Cruise. The cruise was clean, they offered us drinks & even took our families picture. They were fun & were interactive with us guests & made sure we were always in the right spot to see the dolphins responding! I 100% recommended Jolly’s sailing! You won’t be disappointed! It definitely was a highlight of our trip to Pensacola!!
Bo Bo
Bo Bo
Jun 26, 2021
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Spent the afternoon cruising and snorkeling, everyone had a good time. Two were first timers on the water and on snorkel, and all enjoyed it. Paul did a great job of seeking out things to see, found a few sharks, several rays, and a couple of dolphin pods.
We've been out with Jolly Sailing a few times over the years and will definitely be back again.
Lisa Breitbach
Lisa Breitbach
May 24, 2021
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The crew was amazing! Captain Mike and Freddie (the best host!) Just a fun, beautiful tour all around.
Angie Wolff
Angie Wolff
May 20, 2021
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Great experience. Captain Freddy and Riley were enthusiastic and entertaining. We saw several dolphins . I couldn't be happier with the choice we made to cruise with Jolly Sailing.
Deepak Gupta
Deepak Gupta
Apr 05, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
We were a group of total 16 members, including kids. We booked for Dolphin and sunset cruise (~5 PM ish) We really had a great time, watching Dolphins. The Captain was funny and his assistant was very humble. They both were quite professional.