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Address: 655 Pensacola Beach Blvd, Pensacola Beach, FL 32561-6805
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, water taxi, sunset and scenic bay tours available. Our fleet includes JollyDayz, a classic 34' Pearson sailboat Yacht, Jolly'Ventures, a 26' custom powerboat Tritoon, and Jolly Roger, a 26' fast powerboat cruiser, leaving daily from Pensacola Beach Marina. Private or shared trips. 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 281 reviews
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  • 269
    Excellent
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    Very good
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Great Experience!

Excellent customer service. We were rained out on the initial reservation day so they slotted us the next morning. We will definitely be using Jolly Sailing again in the near... read more

Review collected in partnership with this attraction

5 of 5 starsReviewed yesterday
joelw45
,
Pensacola, Florida
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281 Reviews from our TripAdvisor Community

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Showing 280: English reviews
Pensacola, Florida
1 review
5 of 5 stars Reviewed yesterday NEW

Excellent customer service. We were rained out on the initial reservation day so they slotted us the next morning. We will definitely be using Jolly Sailing again in the near future.

Review collected in partnership with this attraction

Helpful?
Thank joelw45
Pensacola Beach, Florida
1 review
4 of 5 stars Reviewed 2 days ago NEW

It was fantastic! Captain Bob and his Wife were very friendly and accommodating. The weather was not the best for sailing but we still enjoyed the ride! Would highly recommend

Review collected in partnership with this attraction

Helpful?
Thank lisawT2632YI
1 review
5 of 5 stars Reviewed 6 days ago NEW

Our family of 6 had a great time sailing. Kids ages are 12,10,8,6. We all had a great time, got to pilot the boat, and even saw a baby dolphin. I would definitly reccomend Jolly Sailing.

Review collected in partnership with this attraction

Helpful?
Thank jlparker75
Houston, Texas
Level Contributor
72 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 129 helpful votes
5 of 5 stars Reviewed 1 week ago

We recently visited Pensacola Beach for a 10 day beach vacation. We spent most of our time at our beach house, but wanted to get out and do some sailing and dolphin watching on a couple of days. Cindy was fantastic in communicating with me before we got to Pensacola and while we were there; the weather turned bad on... More 

Helpful?
Thank JBizzle76
jollysailing, Owner at Jolly Sailing, responded to this review

Hello! Thanks so much for taking the time to leave us a detailed review! We're happy that you enjoyed your dolphin cruise and sailing excursion with us, glad the nasty weather didn't hang around too long. We'll look forward to seeing you again in the future Thank you for cruising with us. More 

Level Contributor
7 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 1 week ago via mobile

Capt Jack was a perfect tour guide and his excitement and knowledge about Pensacola made us want to plan a trip to see more next year. Our trip was the perfect outing for our 16,13,8 yr old kids! We saw at least 8 different dolphin pods. They got to see the beautiful green waters off Fort Pickens and we also... More 

Helpful?
Thank carterbrooke
jollysailing, Owner at Jolly Sailing, responded to this review

Wow, thanks for your review! Truly glad your dolphin and Blue Angels cruise with Capt. Jack was such a great time for you. Thank you for your recommendation, and for choosing Jolly Sailing! Look forward to seeing you next year. More 

Pensacola, Florida
1 review
5 of 5 stars Reviewed 2 weeks ago

The weather held out for a wonderful sunset cruise with wonderful friends. Capt. Bob and Caleb were great.

Review collected in partnership with this attraction

Helpful?
Thank F3215LDdeborahp
jollysailing, Owner at Jolly Sailing, responded to this review

Hi, really glad the weather held out and you enjoyed your sunset sail with Capt. Bob and Kaleb! Thanks for your review, and thank you for sailing with us. More 

Panama, Oklahoma
1 review
5 of 5 stars Reviewed 2 weeks ago

Captain Mike made this tour exciting and fun. He took us right to where dolphins were. We will definitely use him next time. He also was very helpful with things to do and see while we visit.

Review collected in partnership with this attraction

Helpful?
Thank vblack2684
jollysailing, Owner at Jolly Sailing, responded to this review

Hello, and thanks for taking the time to leave a review. Happy to hear your dolphin cruise with Capt. Mike was a great time for you. Thank you for cruising with Jolly Sailing! More 

Marietta, Georgia
1 review
5 of 5 stars Reviewed 2 weeks ago

We took two trips with Jolly Sailing, an evening sunset cruise and a sailing trip. Both were fantastic. I highly recommend Jolly Sailing.

Review collected in partnership with this attraction

Helpful?
Thank charlesgM991BX
jollysailing, Owner at Jolly Sailing, responded to this review

Hi, and thanks much for your review. Pleased to hear your sunset cruise and sailing excursion with us were a good time for you! Appreciate your recommendation, and thank you for cruising with us. More 

Columbia, Missouri
1 review
5 of 5 stars Reviewed 2 weeks ago

Capt Bob and his 1st mate made our sailing experience an excellent one! They were very knowledgeable and wonderful hosts! I would highly recommend a sail with them!!! We took a 2 hour sail and wished we would have taken a longer one because it was just so relaxing and peaceful!

Review collected in partnership with this attraction

Helpful?
Thank massmanv
jollysailing, Owner at Jolly Sailing, responded to this review

Hello, thank you for your review, and for your recommendation of our services. Pleased to hear that your sailing experience with Capt. Bob and crew was a good time. Thanks for sailing with us! More 

Nashville, Tennessee
2 reviews
5 of 5 stars Reviewed 2 weeks ago

Captain bob is the best!! Cindy in the office communicated great about potential options and keeping us informed about weather issues!!

Review collected in partnership with this attraction

Helpful?
Thank 703waynes
jollysailing, Owner at Jolly Sailing, responded to this review

Hi, thanks for taking the time to write a review of your experience with us. Really glad you enjoyed it, and thank you for choosing Jolly Sailing. More 

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Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Jolly Sailing and other visitors
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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?