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Jolly Sailing

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655 Pensacola Beach Blvd, Pensacola Beach, FL 32561-6805
+1 850-723-6142
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Review Highlights
Sunset cruise with children and grandpa

My husband chartered a sunset cruise for our family and it was amazing. Cindy of Jolly Sailing made... read more

Reviewed yesterday
Gianinna C
via mobile
Family cruise on the Jolly Dolphin!

Visited Pensacola Beach for a mini family reunion, had a blast on the dolphin cruise with Jolly. We... read more

Reviewed 15 October 2017
Kim P
,
San Antonio, Texas
via mobile
Read all 391 reviews
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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' 28 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, church/civic/school groups, corporate excursions available. Come enjoy a memorable cruise with Jolly Sailing!
  • Excellent96%
  • Very good3%
  • Average1%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain jim” (41 reviews)
“sunset sail” (33 reviews)
“sailing trip” (18 reviews)
Open Now
All hours
Hours Today: 08:00 - 21:00
LOCATION
655 Pensacola Beach Blvd, Pensacola Beach, FL 32561-6805
CONTACT
Website
+1 850-723-6142
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Reviews (391)
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1 - 10 of 390 reviews

Reviewed yesterday via mobile

My husband chartered a sunset cruise for our family and it was amazing. Cindy of Jolly Sailing made sure to pick the best day and the weather was rather agreeable for November. They had plenty of snacks and beverages and our two hours flew by....More

Thank Gianinna C
Reviewed 15 October 2017

Visited Pensacola Beach for a mini family reunion, had a blast on the dolphin cruise with Jolly. We enjoyed every minute of this cruise around the bay for some dolphin watching (saw several pods), a beautiful sunset, and added the beach stop, which was really...More

Thank Kim P
Reviewed 11 October 2017 via mobile

We had a wonderful trip to view the Blue Angels and Dolphins. Cindi did a great job booking the trip and promptly called us. Capitan Jim and 1st mate were over the top accommodating. We were impressed by their historical knowledge of the forts in...More

Thank Susan L
Reviewed 25 September 2017

When we booked this attraction, I was under the impression it would be more to it. We basically got a boat ride with a total of 6 people and 4 people were in our party. We were told at Margaritavilla that the boat was full...More

Review collected in partnership with this attraction
Thank Veronica P
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 9 October 2017

Hi Veronica, we appreciate you taking the time to leave your feedback. We're sorry for any confusion about the nature of your cruise and for any misinformation you may have received from the hotel. At the time of your cruise, we had 2 powerboats boats...More

Reviewed 24 September 2017 via mobile

My four friends and I booked a Jolly Sailing sailboat this weekend for a bachelorette trip activity and it was smooth sailing! The words we would use to describe our experience include hospitality, informative and friendly. Captain Cindy greeted us on the dock with a...More

Thank cameronkayla55
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 9 October 2017

Hi Kayla, thanks for stopping by to leave your review. What a fun time with you lovely bachelorettes! Pleased to hear your sail with us was a good time for you, hope your photos turned out great, it was a perfect day for it! We...More

Reviewed 23 September 2017

The Sunset Sail was lovely. Professional staff and complimentary drinks and snacks. The sail was gorgeous and we were able to take some lovely photos. Would definitely do this again.

Review collected in partnership with this attraction
Thank sisk_pam
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 9 October 2017

Hello, thank you for taking the time to write a review. Really pleased to hear that your sunset sail with us was enjoyable. Hope to see you again sometime, thanks for sailing with us!

Reviewed 20 September 2017

We booked a private sunset cruise Sept. 20, 2017, and it was fantastic!! Captain Jim and his wfe(first mate) Cindy were awesome!! The 5 of us, me, my daughter, sister, and 2 sisters-in-law felt like part of their family and they really made the experience...More

Thank Jackie H
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 9 October 2017

Hey Jackie, thank you for your review. Happy to hear you enjoyed the sunset sail with us, we had a blast with y'all. Thanks so much for your recommendation, and for cruising with us.

Reviewed 20 September 2017

Everyone at Jolly Sailing was wonderful, from Cindy making sure that we were taken care of for our reservation, to the captain of our little boat making sure that we saw dolphins. It is mating season and we saw at least 10 dolphins in a...More

Review collected in partnership with this attraction
Thank divatravelqueen59
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 9 October 2017

Hello, thanks for stopping by to leave your review...we're so glad your dolphin cruise with us was fun for you, and the dolphins were in a frisky mood! Thank you for cruising with us.

Reviewed 18 September 2017

Our family (My dad, wife, me and two little kids) had great time with this sailing trip and felt it worth every penny. I booked this trip with Cindy who is extremely patient with me. She answered all my questions in very detailed manner. I...More

Thank mix95
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 9 October 2017

Hi there, thank you for your detailed review. Happy to hear that your extended sunset sail with Capt. Glen and First Mate John was an enjoyable time for you. Great tips also regarding the kids...they do have a tendency to get a little antsy after...More

Reviewed 31 August 2017

Taking a sunset sail was on our bucket list and the evening with Captain Jim and Cindy was fantastic. They went out of their way to assure that everyone on the cruise had a great time and memorable experience. They really made it a personal...More

Thank 911davev
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 13 September 2017

Hi Dave, thanks for your review and recommendation! We enjoyed having y'all aboard, and glad your sunset sail with us was a memorable experience! Thank you for sailing with us, hope to see you again sometime.

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Ask a question
Questions & Answers
laserne h
1 July 2017|
AnswerShow all 3 answers
Response from jollysailing | Property representative |
Hello, thanks for your inquiry...at this time we are permitted to take up to 6 passengers. We do have a larger boat that will be certified for more than six, but it will not be available until August.
0
Votes
Gloria P
3 June 2017|
Answer
Response from jollysailing | Property representative |
Hi Gloria! Currently it is $45 per person for a 2 hour daytime cruise, $55 per person for the sunset cruise, or $60 per person for the Extended dolphin cruise with beach stop or dolphin and Blue Angels cruise. This would... More
1
Vote
xMissKimx
23 May 2017|
AnswerShow all 4 answers
Response from jollysailing | Property representative |
Hi everyone! Thanks for all the great descriptive answers! xMissKimx I am so sorry to be late with a reply, never saw your inquiry until now. The dolphin cruise does include beverages and snacks, including beer and wine... More
1
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