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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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Simply the BEST

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... read more

5 of 5 starsReviewed May 24, 2015
DaveMBart
via mobile
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114 Reviews from our TripAdvisor Community

Date | Rating
  • English first
  • Russian first
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English first
1 review
5 of 5 stars Reviewed May 24, 2015 NEW 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 

Was this review helpful? Yes
Memphis, TN
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed May 20, 2015 NEW

My husband & I, along with another couple, made arrangements to do a private tour on the Jolly Roger to see the Blue Angels practice last week. It ended up being one of the true highlights of our 9 day stay in Pensacola Beach! Making the reservation with Cindy over the phone was a breeze, the cost was very reasonable,... More 

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Pleasant Hill, Louisiana
1 review
5 of 5 stars Reviewed May 17, 2015

I got a sailing trip with Jim for a birthday surprise, and I absolutely can't think of any way our experience with Jolly Sailing could have been any better. Went sailing with Jim, on a lovely, well maintained and well appointed Pearson 34. Exemplary customer service from Jim and Cindy. Jim's sailing knowledge and experience plus his great personality made... More 

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College Station, Texas
2 reviews
5 of 5 stars Reviewed May 13, 2015

We had a really great experience with Jolly Sailing. We used the site's email function to book our reservation and they responded right away. Then later when we called to add a person, there was no problem. Captain Randy was beyond wonderful. He was personable and friendly. And he made sure that we saw lots of dolphins and we got... More 

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Rochester, New York
Senior Contributor
24 reviews 24 reviews
4 attraction reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed April 30, 2015

We had a stellar day with Captain Randy at the helm! We had the power pontoon boat to ourselves and it was a bit of a cool day but that did not stop our Captain from giving us 100% attentive service, as we got to see the blue angels perform and wild dolphins both along the way and coming back,... More 

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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 

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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!!

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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!

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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 

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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?