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Jolly Sailing

Address: 655 Pensacola Beach Blvd., Pensacola Beach, FL 32561
Phone Number: +1 850-723-6142
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Certificate of Excellence 2014
Owner description: Choose your own adventure! Sailing, dolphin cruises, snorkeling, stand up paddleboarding, sunset...
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Attraction details
Hours:
Sun - Sat 8:00 am - 9:00 pm
Owner description: Choose your own adventure! Sailing, dolphin cruises, snorkeling, stand up paddleboarding, sunset and dinner cruises aboard JollyDayz, a classic 34' Pearson Yacht, or Jolly'Ventures, a 26' custom power Tritoon, 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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102 reviews from our community

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Date | Rating
  • English first
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English first
Omro, Wisconsin
Contributor
18 reviews 18 reviews
10 attraction reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed January 27, 2015 NEW

They were very accommodating. The Captain took us out on a perfect day for sailing. He and his wife were very knowledgeable about the area. We learned a great deal about the boat and the features on the shores. The cruise was informative, relaxing and exciting. We would go with them again.

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Fort Lauderdale, Florida, United States
2 reviews
5 of 5 stars Reviewed January 25, 2015 NEW

This boat trip with Jolly Sailing has me sold forever on this type of entertainment. The hospitality and care extended were excellent. The captain is very knowledgeable about the different forts and military installations in the area, and his stories are entertaining and funny. We were able to watch the dolphins frolic close to the boat and the warm, cordial... More 

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1 review
5 of 5 stars Reviewed January 18, 2015 via mobile

Shown a great time by the crew on our dolphin cruise!!! Lots of Dolphins to see and we had a great relaxing time!!! We would definitely recommend Jolly Sailing the next time anyone wants to do something like that.

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

Thanks so much for your review! We really enjoyed having you and your family aboard, and happy to hear that you had such a great time. More 

Pensacola, Florida
Contributor
11 reviews 11 reviews
6 attraction reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed December 23, 2014

I took my family for an afternoon sail on the Jolly Days, and it was great! We ate salmon, cheese, grapes, and crackers; and we drank bubbly and listened to 40's jazz. My dad was allowed to take the helm, while my wife took a nap on the deck. We talked and laughed with Captain Jim about history and boats... More 

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your kind words! Glad you enjoyed your trip, we truly appreciate you! More 

1 review
5 of 5 stars Reviewed October 31, 2014

My first time sailing and it couldn't have been better. Our captain took us on a fantastic ride and we were able to see some dolphins. We were also out there on a perfect day which adds to the experience. We will definitely sail with them again.

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jollysailing, Owner at Jolly Sailing, responded to this review

Thank you so much for posting a review! Happy to hear your first sailing experience was good..we love those dolphins, always wonderful to see them. Thanks again for coming out with us! More 

Pensacola, Florida
1 review
5 of 5 stars Reviewed October 21, 2014 via mobile

Capt Jim was warm & friendly. A truly enjoyable family sailboat cruise! We appreciAte you, Jim! The dolphin siting at end of trip was the best!

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks for your feedback! Happy to hear your trip was enjoyable. We appreciate you! More 

Pace, Florida
2 reviews
5 of 5 stars Reviewed October 13, 2014

Our first sailing experience and we LOVED every minute of it Happy Sailing from The Humphreys Family

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jollysailing, Owner at Jolly Sailing, responded to this review

Thank you for your review! Glad your first sailing experience was a memorable one. We look forward to seeing you again, next time you might like a Gulf sailing adventure! Beautiful pictures, thanks for sharing! More 

1 review
5 of 5 stars Reviewed October 8, 2014 via mobile

Captain Jim was very nice and informative. Clean comfortable boat. We took the 2-1/2 hour powerboat cruise. Saw many dolphin, one stingray, and the ultimate; two sea turtles. Very easy to book and very accomodating. Highly recommend!

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your review. We appreciate you coming out, and really happy to hear you had a great time! More 

1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 1, 2014

This was my highlight of the trip! Beautiful sunset, super friendly captain, and we got up close and personal with dolphins! Great price for a great time.

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jollysailing, Owner at Jolly Sailing, responded to this review

Thanks so much for your kind review! Happy to hear you enjoyed the trip. More 

1 review
5 of 5 stars Reviewed September 15, 2014

We spent a few days after our wedding in Pensacola and the highlight of our trip was our night out sailing with Jolly Sailing! They coordinated everything we needed and stayed in constant communication about weather and on-board dinning options. Very reasonably priced and an excellent experience! We're excited to go back to Pensacola and take another trip with them!

Review collected in partnership with this attraction

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

Hi Bob! Thanks for coming out with us, so pleased that you enjoyed the experience. Would love to have you back anytime! Congrats and best wishes to you both. More 

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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?
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