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Address: 655 Pensacola Beach Blvd., Pensacola Beach, FL 32561
Phone Number: +1 850-723-6142
Website
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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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TripAdvisor Reviewer Highlights

Read all 108 reviews
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What a great time

Hat's off to Capt. Jim for providing a great sailing experience. This was not one of those engine powered "sails" but a real sail with just wind. Capt. Jim was explaining the... read more

5 of 5 starsReviewed April 16, 2015
shov76
,
New England
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108 Reviews from our TripAdvisor Community

Date | Rating
  • English first
  • Any
English first
New England
1 review
5 of 5 stars Reviewed April 16, 2015

Hat's off to Capt. Jim for providing a great sailing experience. This was not one of those engine powered "sails" but a real sail with just wind. Capt. Jim was explaining the ropes/rigging and the basic how to while he was doing it. Satellite radio provided some great sailing tunes and the weather was great. Chilled beverages were provided. There... More 

Was this review helpful? Yes
1 review
5 of 5 stars Reviewed April 12, 2015

Had an amazing time, It was the best part of our trip. Took my two teenagers and my mom to see the blue angels perform and got to see dolphins along the way. I definitely recommend booking a cruise with them!!

Was this review helpful? Yes
Clinton, North Carolina
Reviewer
4 reviews 4 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 12, 2015

Captain Jim and first Mate Cindy were awesome, did several trips with them. Very accommodating, brought us out to all the beautiful sites of the bay and Ocean....seen dolphins. Very awesome, highly recommend to go "Jolly Sailing"

Was this review helpful? Yes 1
Winter Garden
Senior Reviewer
7 reviews 7 reviews
13 helpful votes 13 helpful votes
5 of 5 stars Reviewed March 26, 2015

A perfect way to spend 2 hours if the water is too chilly to swim! We got a chance to see the Blue Angels practicing too and our kids (6 and 4) loved it. Bring a jacket!

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

Thanks so much for your feedback! That is a great tip, in the spring and winter seasons especially you never know how cool it will be on the water. Thank you for choosing Jolly Sailing! More 

Lubbock,
Senior Contributor
25 reviews 25 reviews
7 attraction reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed March 9, 2015

We were looking to relax get on the water and see some dolphins while staying in pensacola, jolly sailing did not disappoint! We did a 2 hour tour and had a great time! Our captain was very friendly and knowledgeable about Pensacola and the sights we were seeing. We were able to see lots of dolphins and had a beach... More 

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

Hi Katie! Thanks for sharing your feedback about your dolphin cruise with us! Happy to hear it was a good one. What a beautiful spring day on the water. Appreciate you and your group taking a trip with Jolly Sailing. More 

Maroa, Illinois
Senior Reviewer
10 reviews 10 reviews
3 attraction reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed February 12, 2015 via mobile

It was our first time sailing and we will be back! They were Soooo accommodating and pleasant and the boat is very comfortable. Smooth ride an they both know a lot about the area. Great bang for your buck.

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

Hello, we really appreciate you taking the time to write us a review. We are happy that your first sailing experience was such a good one. Thanks again for coming on a trip with us! More 

Omro, Wisconsin
Senior Contributor
39 reviews 39 reviews
19 attraction reviews
20 helpful votes 20 helpful votes
5 of 5 stars Reviewed January 27, 2015

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.

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

Thank you for your review! Enjoyed having you and little Cruizer onboard. Glad to hear you had a great trip, thanks again for coming out with us. More 

Fort Lauderdale, Florida, United States
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed January 25, 2015

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 

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

Thank you for your kind words! We appreciate you joining us for a dolphin cruise, so happy to hear you had a good experience. Would love to have you back out another time, next time you'll have to try the sailboat! More 

1 review
5 of 5 stars Reviewed January 18, 2015

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
13 reviews 13 reviews
7 attraction reviews
9 helpful votes 9 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 

Was this review helpful? Yes 1
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 

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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?