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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
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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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Great Snorkeling!

The crew is amazing, friendly and quite knowledgeable. They took us on a 2hr tour and knew the best places to see great marine life. Best part is one of the crew was a marine... read more

5 of 5 starsReviewed September 2, 2015
Erica W
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136 Reviews from our TripAdvisor Community

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Date | Rating
  • English first
  • Russian first
  • Any
English first
Level Contributor
5 reviews
5 of 5 stars Reviewed September 2, 2015 NEW

The crew is amazing, friendly and quite knowledgeable. They took us on a 2hr tour and knew the best places to see great marine life. Best part is one of the crew was a marine biologist! She snorkled with is and showed us crabs and other cool things. we even booked only the day before. A perfect tour!

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Gulf Breeze, Florida
Level Contributor
3 reviews
5 of 5 stars Reviewed August 31, 2015 NEW

Captain Jim made our sailing adventure fun and exciting! We learned how the sailboat worked, and he even let us all captain the sailboat. We enjoyed his knowledge and experience of the area and sailing. We loved seeing the sea life especially the dolphins and beautiful jellyfish. Jim and Cindy made scheduling the tour easy, and they helped us find... More 

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Baker, LA
Level Contributor
3 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed August 19, 2015

We had the best time on our 2 hour sunset cruise with Captain Jim and Cindy! They are excellent hosts and crew! We went for moms 80th birthday and she just loved it! Drinks and snacks provided. A great family and friends experience and we will definitely be back!! Thanks Jim and Cindy!

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

Thanks so much for your review. We are happy your Mom enjoyed her birthday sail. We appreciate you for coming out with us. Look forward to seeing you back again! More 

Florida Panhandle, Florida
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed August 11, 2015

Everyone was super friendly and accommodating! Jim & Cindy treated us like old friends even tho we just met. Loved seeing the dolphins, and relaxing on their beautiful boat. Don't miss out on the most fun sailing and dolphin cruises on Pensacola Beach!

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks for your feedback. We're glad you were able to join us for a relaxing sail! Hope to see you again in the future. More 

Level Contributor
22 reviews
common_n_attraction_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed August 9, 2015

Captain Randy and deckhand Jacob made our two hour adventure fun. They showed us how to find puffer fish, crabs and toad fish. We even got a quick dolphin show.

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

Thanks so much for writing a review. Happy to hear that your experience was a great one, and that our captain and crew showed you a wonderful time. Thank you for snorkeling with us! More 

Hattiesburg, Mississippi
Level Contributor
3 reviews
5 of 5 stars Reviewed August 8, 2015

Amazing time with Captain Randy on the 2.5 hr dolphin cruise. He kept us entertained, and we had a blast. Highly recommend.

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jollysailing, Owner at Jolly Sailing, responded to this review

We appreciate your feedback. Really glad that you had such an amazing time with Captain Randy on the dolphin cruise. Thanks for cruising with us! More 

hattiesburg, United States
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed August 4, 2015

We have sailed with Capt. Jim and Cindy many times....from celebrating birthdays to anniversary to I just need to be on the water....they are the best....Love...love...love them and they know what hospitality is all about!!....you won't regret this sailing adventure!

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your kind words! We appreciate you and your family for joining us for so many adventures over the years. We look forward to seeing you again soon! More 

Cincinnati, Ohio
Level Contributor
3 reviews
5 of 5 stars Reviewed August 1, 2015

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!

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your review. Pleased you had a great experience. Thank you for coming on our sailing excursion. Hope to see you again! More 

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.

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jollysailing, Owner at Jolly Sailing, responded to this review

Thank you so much for your review. We're glad that you enjoyed your dolphin cruise with Captain Jamie. We strive to provide a unique and personal experience, and we appreciate your recommendation. More 

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
jollysailing, Owner at Jolly Sailing, responded to this review

Thank you for your review! Glad your family had such a great time on the dolphin cruise with Captain Randy. Better than Disney and Blue Angels, that is something else! Thanks for cruising with us. More 

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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?