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Jolly Sailing

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Address: 655 Pensacola Beach Blvd, Pensacola Beach, FL 32561-6805
Phone Number:
+1 850 723 6142
Website
Today
08:00 - 21:00
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Hours:
Sun - Sat 08:00 - 21:00
Description:

Choose your own adventure! Sailing, dolphin cruises, snorkeling, water...

Choose your own adventure! Sailing, dolphin cruises, snorkeling, water taxi, sunset and scenic bay tours available. Our fleet includes JollyDayz, a classic 34' Pearson sailboat Yacht, Jolly Mon, a 27' American sailboat, Jolly'Ventures, a 26' powerboat tritoon,leaving daily from Pensacola Beach Marina; and *NEW for 2017, Jolly Dolphin, a 42' 19 passenger power tritoon with daily cruises leaving from Shaggy's Marina. Private or shared trips. Plenty of seating in sun and shade. Safe, comfortable, and fun for all ages. Complimentary beverages included with all trips. Use of snorkel gear, along with instruction, included with snorkeling tours. Special occasion trips such as birthday parties, bachelor(ette)parties, wedding/rehearsal cruises, family reunions, and corporate excursions available. Come enjoy a memorable cruise with Jolly Sailing!

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TripAdvisor Reviewer Highlights

Read all 330 reviews
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  • 316
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My Birthday Bucket Drop

Loved my trip. First time sailing, enjoyed every moment. They made sure we were comfortable and having fun. Amazing!

5 of 5 bubblesReviewed 3 days ago
Faith L
via mobile
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330 Reviews from our TripAdvisor Community

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Showing 329: English reviews
2 reviews
5 of 5 bubbles Reviewed 3 days ago NEW via mobile

Loved my trip. First time sailing, enjoyed every moment. They made sure we were comfortable and having fun. Amazing!

Helpful?
Thank Faith L
Pensacola, Florida
1 review
5 of 5 bubbles Reviewed 6 days ago NEW

Captain Jimmy certainly knows how to pack a lot of fun into a few short hours! Can't wait for the next trip!

Review collected in partnership with this attraction

Helpful?
Thank 958olgas
Bend, Oregon
1 review
5 of 5 bubbles Reviewed 3 weeks ago

We loved our Sunset Cruise on February 25th. It was so relaxing and the sunset was gorgeous. The captain and his wife were so accommodating and the wine and beer was a nice treat.

Review collected in partnership with this attraction

Helpful?
Thank Tammy P
Rochester, Minnesota
1 review
5 of 5 bubbles Reviewed 3 weeks ago

Captain and Cindy were great! They did everything they could to make sure we enjoyed it. Hope to return next year!

Review collected in partnership with this attraction

Helpful?
Thank bethjtaylor507
Atlanta, Georgia
1 review
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 17 February 2017

The captain of the boat on our trip was diligent in locating a group of dolphins. This was one of the best trips we have ever taken. Everything was pleasant, peaceful and relaxing. We were NOT disappointed in any way!

Review collected in partnership with this attraction

Helpful?
2 Thank Mark C
jollysailing, Owner at Jolly Sailing, responded to this review

Hello, and thanks very much for your review. Pleased to hear that your dolphin cruise with us was a great experience for you! Thank you for cruising with us. More 

Gulf Breeze, Florida
1 review
5 of 5 bubbles Reviewed 14 February 2017

We chartered Jolly's sail boat for a Valentine's Day sunset cruise and could not have been more pleased. The weather was questionable that morning and the Jolly staff were completely on top of the situation calling me with updates throughout the morning. The weather cleared and what a magnificent time we had! Smooth sailing along with Mimosas and a gorgeous... More 

Review collected in partnership with this attraction

Helpful?
Thank johnmI3704HG
jollysailing, Owner at Jolly Sailing, responded to this review

Hello, and thank you for taking the time to leave a review of your sunset sail with us. We're glad to hear that you had a great time with Capt. Jim and crew on the sailboat. Thanks for sailing with us, we hope to see you again! More 

Metairie
1 review
5 of 5 bubbles Reviewed 13 February 2017

This was my wife and I second time aboard and we loved it. Both trips were for our aniversary, which is a very romantic setting if you do the sunset cruise. You can't beat the price, which includes wine and the captain is very friendly.

Review collected in partnership with this attraction

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

Hi Keith, thanks very much for your review, and for being a repeat customer! We're glad we could help make your anniversary special on the sunset sail. We appreciate you and hope to see you again sometime, maybe on a powerboat adventure with the kids! More 

Pennsylvania
Level Contributor
18 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
5 of 5 bubbles Reviewed 11 February 2017

This evening we joined Captain Jim for a sunset cruise. We had a very enjoyable time. Captain Jim went out of his way to make us comfortable. Unfortunately we did not have the opportunity to see dolphins, but we had great fun getting to jnow the crew and other passengers. Would love to sail with Jolly Sailing again.

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

Hi, and thanks for stopping by to leave your review! Glad to hear your sunset sail with Captain Jim was an enjoyable time for you. We always recommend the powerboat cruise if your focus is wanting to see dolphins, as we cover a 20 mile round trip looking for them, and find some on almost every trip. We see them... More 

Tulsa, Oklahoma
1 review
5 of 5 bubbles Reviewed 16 January 2017

Jolly Sailing goes above and beyond to make your trip as relaxing and fun as possible. Their sailboat is the perfect size for a small group and has great seating on the bow for the best sunset and dolphin viewing. They pampered us with great service and even went a little over time to make sure we had the best... More 

Review collected in partnership with this attraction

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

Hi Brenda, thanks so much for taking the time to review your trip! So happy y'all had a fun time with us, look forward to seeing you next year. Thanks for sailing with us. More 

Anderson, South Carolina
Level Contributor
164 reviews
23 attraction reviews
common_n_attraction_reviews_1bd8 92 helpful votes
5 of 5 bubbles Reviewed 6 December 2016

From when we arrived to the dock, until we approached the dock after sunset, Captain Mike is the best host. He made the sail almost perfect. There were 6 on board, our four and a couple from Kentucky. Mike easily made sure we were all introduced and continued the conversational support until we were all openly talking and enjoying each's... More 

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

Thanks so much for taking the time to leave a review of your trip with us. We are happy to hear that Captain Mike showed you a great time. Appreciate your recommendation as well, thank you for cruising with us! 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?