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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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Awesome Experience

Awesome couple running sailing trips that offer supplied beverages on the trip, very friendly & well worth every penny of the very reasonable rates they charge!

5 of 5 starsReviewed August 1, 2015
Greg N
,
Cincinnati, Ohio
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129 Reviews from our TripAdvisor Community

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Date | Rating
  • English first
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English first
Cincinnati, Ohio
Level Contributor
3 reviews
5 of 5 stars Reviewed August 1, 2015 NEW

Awesome couple running sailing trips that offer supplied beverages on the trip, very friendly & well worth every penny of the very reasonable rates they charge!

Was this review helpful? Yes
Glenmoore, Pennsylvania
1 review
5 of 5 stars Reviewed July 24, 2015

Captain Jamie was a pleasure to meet and spend time with. He was knowledgeable of the area, funny and entertaining. Highly recommend over other dolphin cruises.

Was this review helpful? Yes
Sparta, United States
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed July 13, 2015

We took a Dolphin tour on the Jolly Ventures (their pontoon boat) - we are a family of 5 (girls 4, 7, 10) and thought a small boat might be better - and we were right! Our Captain Randy was excellent and knew a lot about the area. He worked hard to find our dolphins - the first group was... More 

Was this review helpful? Yes 1
Pensacola Beach, Florida
Level Contributor
3 reviews
5 of 5 stars Reviewed July 7, 2015

Jim and Cindy are the sweetest hosts ever.. I've been on the sunset sailboat cruise and the snorkeling trip and I had the best time on both! They're super accommodating with wine and snacks, as well as great knowledge of the local area and where to go on the water :) highly recommended! <3

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Cumming, Georgia
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed July 4, 2015

My wife and our four kids (18, 13 and 12 year old boys, and our 6 year old girl) took the Jolly Roger out on the bay for a 2 1/2 hour float to see the dolphins and watch the Blue Angels. The white sand dunes and turquoise water were intoxicating. We saw dozens of dolphins, and we enjoyed the... More 

Was this review helpful? Yes
Pensacola Beach, Florida
5 of 5 stars Reviewed July 2, 2015

Randy was truly amazing! He went above beyond to make our trip memorable! We will tell everyone we know go visit this place and ask for Randy

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Level Contributor
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
common_n_attraction_reviews_1bd8 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
Level Contributor
26 reviews
common_n_attraction_reviews_1bd8 5 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
Level Contributor
41 reviews
17 attraction reviews
common_n_attraction_reviews_1bd8 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 

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Additional Information about Jolly Sailing

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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Questions & Answers

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?