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Jolly Sailing

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Address: 655 Pensacola Beach Blvd., Pensacola Beach, FL 32561
Phone Number: +1 850-723-6142
Website
Today
8:00 am - 9:00 pm
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Hours:
Sun - Sat 8:00 am - 9:00 pm
Description: Choose your own adventure! Sailing, dolphin cruises, snorkeling, stand up...
Choose your own adventure! Sailing, dolphin cruises, snorkeling, stand up paddleboarding, sunset and dinner cruises aboard JollyDayz, a classic 34' Pearson Yacht, Jolly'Ventures, a 26' custom power Tritoon, or Jolly Roger, a 26' fast power cruiser, leaving daily from Pensacola Beach Marina. All vessels have an enclosed restroom/changing area, and plenty of seating in sun and shade. Safe, comfortable, and fun for all ages. Complimentary beverages and snacks included with all trips. Use of snorkel gear and stand up paddleboards, along with instruction, included with snorkel and paddleboard trips. Special occasion trips such as birthdays, anniversaries, graduations, proposals, or wedding vow renewals available. Come enjoy a memorable cruise with Jolly Sailing!
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We booked a private snorkeling & paddle board trip. The night before Cindy called to suggest we depart earlier to take advantage of better water conditions. We were fortunate to... read more

5 of 5 starsReviewed June 24, 2015
April J
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123 Reviews from our TripAdvisor Community

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English first
2 reviews
5 of 5 stars Reviewed June 24, 2015

We booked a private snorkeling & paddle board trip. The night before Cindy called to suggest we depart earlier to take advantage of better water conditions. We were fortunate to enjoy several unexpected extras. On our way out Captain Jayme spotted dolphins and took us in beside a large pod including a new born calf. We also got a nice... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks for your feedback. Pleased that the conditions were just right for your adventure, We do our best to show our guests the best experience possible. Appreciate your family joining us for the trip! More 

Knoxville, Iowa
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 22, 2015

This was an absolute amazing experience! Captain Jamie was so knowledgeable about the area and the dolphins. He could answer all of our questions. We were able to see so many dolphins!!! They try really hard to work with other boats to find the dolphins. I was so very happy with the experience! Two thumbs up!!

Was this review helpful? Yes 1
jollysailing, Owner at Jolly Sailing, responded to this review

Thanks for taking the time to write a review! Happy to hear your dolphin cruise with Captain Jamies was a great time for you. Appreciate you for joining us on the trip. More 

Dallas, Texas
Senior Contributor
24 reviews 24 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed June 20, 2015

We had an outstanding cruise with Jolly Sailing! Everything was perfect! We loved our Jolly Roger boat (the yellow fast one). It was perfect for our girls trip. They limit the boat to 6 plus driver. It was new, very clean, and fast with 2 canopies. Other boats were much larger and had lots of tourists on them. We were... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks for your feedback. Happy to hear you had such a wonderful time on the Blue Angels Practice and Dolphin Cruise with Captain Randy. Appreciate you for choosing Jolly Sailing for your personalized adventure! More 

Nixa, Missouri
Senior Contributor
41 reviews 41 reviews
17 attraction reviews
19 helpful votes 19 helpful votes
5 of 5 stars Reviewed June 18, 2015

We were so happy with our experience in 2013, we came back for our new family vacation in May 2015 only with more people this time! We had a total of 10 people from toddler to adult. We took two boats to our snorkeling spot. The crew was fantastic with the kids. They were very helpful, knowledgeable and funny! We... More 

Was this review helpful? Yes 1
jollysailing, Owner at Jolly Sailing, responded to this review

We appreciate your feedback! Pleased to be able to accommodate the whole party of 10 between our two boats. Thanks for joining us for an adventure again, and we look forward to seeing you in the future! More 

Lancaster, Pennsylvania
2 reviews
5 of 5 stars Reviewed June 16, 2015

This was by far one of the best sailing experiences we've ever had! Captain Jim and his wife were very gracious and eager to please their guests! They are well experienced sailboaters and made sure that all 6 of us felt comfortable. The music, boat drinks and scenery made this a memorable trip! The two hour cruise was well worth... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your review! What a fun crew, we enjoyed having you onboard. Glad that you had a great experience with us on the sailboat. More 

1 review
5 of 5 stars Reviewed June 14, 2015

Everything was easy, accommodating and fun! Reservations were quick, requests honored and Captain Jamie at our service. Great sunset cruise!

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your review! Really happy to hear that your family had such a great time with Captain Jamie and enjoyed the dolphin cruise. More 

2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed June 3, 2015 via mobile

We decided to do an impromptu boat ride around the gulf during our Pensacola vacation, and this company was the first one Google recommended, and it was great! Capt. Jamie took me, the hubs, and our 4 and 6 yr old kids out to see dolphins and he was a friendly and knowledgeable tour guide! Definitely recommend this company if... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thank you for taking the time to write this review. Glad to hear that your family had such a great experience on the dolphin cruise! More 

Pensacola, Florida
1 review
5 of 5 stars Reviewed May 31, 2015

I was treated to a sunset cruise and the captain went above and beyond to find us dolphins! We expected a beautiful sunset, but we got to see dolphins, a sea turtle, and even a rainbow. The Captain gave us history of the areas in which we were seeing and was entertaining and even took pics for us. Five stars!... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thank you for your feedback. Glad you enjoyed the sunset powerboat cruise. Appreciate you coming out with us! More 

Senior Reviewer
6 reviews 6 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed May 28, 2015

From the initial phone call to the determination to see what we came for-dolphins! I was more than pleased to sail with Jolly Sailing! There were several landmarks and attractions to see along the way to find the elusive dolphin. Just when I was beginning to think that we would never see a wild dolphin is when the captain pulled... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your review. We are happy to hear that you enjoyed your dolphin cruise. Thank you for sharing your appreciation of the nature of our trips. We do our best to provide a most personal experience in a small group, private atmosphere. More 

1 review
5 of 5 stars Reviewed May 24, 2015 via mobile

Read This Review: Jolly Sailing is number one rated for a reason : they are simply the BEST in Pensacola. Being a business owner myself for 26 years there is an expectation that I have anytime I open my wallet. Jolly Sailing far exceeds any expectation I had. Been on their twice now. Once as a family and now just... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Wow! Thanks so much for your kind review! Happy we could help bring a little peace and serenity to your day. Really enjoyed having y'all aboard and look forward to having you back out with us. More 

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Additional Information about Jolly Sailing

Address: Address: 655 Pensacola Beach Blvd., Pensacola Beach, FL 32561
Phone Number: +1 850-723-6142
Location: United States  >  Florida (FL)  >  Florida Panhandle  >  Pensacola Beach
Open Hours:
Sunday 8:00 am - 9:00 pm
Monday 8:00 am - 9:00 pm
Tuesday 8:00 am - 9:00 pm
Wednesday 8:00 am - 9:00 pm
Thursday 8:00 am - 9:00 pm
Friday 8:00 am - 9:00 pm
Saturday 8:00 am - 9:00 pm

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  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
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