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Jolly Sailing

#2 of 39 Tours in Pensacola Beach Features Animals
655 Pensacola Beach Blvd, Pensacola Beach, FL 32561-6805
+1 850-723-6142
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Review Highlights
STILL JOLLYFIED!!

It's been three weeks since we went sailing with Captain Glen and we are still JOLLYFIED! Thanks so... read more

Reviewed 6 days ago
Sdrillot
,
Atlanta, Georgia
Back in Pensacola, back to Jolly Sailing!

We visited Pensacola the first time in Aug 2016. We loved it so much that we returned in Aug 2017... read more

Reviewed 1 week ago
JBizzle76
,
Houston, Texas
Read all 380 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' 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!
  • Excellent96%
  • Very good3%
  • Average1%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain jim” (39 reviews)
“sunset sail” (31 reviews)
“sailing trip” (17 reviews)
Closed Now
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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 (380)
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1 - 10 of 379 reviews

Reviewed 6 days ago

It's been three weeks since we went sailing with Captain Glen and we are still JOLLYFIED! Thanks so much for a great sail, we look forward to seeing you again! Our sunset cruise was very relaxing and pleasant. Very easy to book, very easy to...More

Thank Sdrillot
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 5 days ago

Hello, thanks for stopping by to share your Jollification! Happy to hear your sail with Capt Glen was so enjoyable for you. Thank you for sailing with us, hope to see you back again sometime.

Reviewed 1 week ago

We visited Pensacola the first time in Aug 2016. We loved it so much that we returned in Aug 2017. Given I have recently taken Basic Keelboat Sailing 101 in Clear Lake, I was anxious to get out on the water. We sailed on their...More

Thank JBizzle76
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 5 days ago

Hello, thanks for taking the time to leave your review! Really pleased the weather worked out for at least one cruise during your visit; it's been a volatile summer. Glad you and your family had a memorable time with Capt. Glen and John. Thanks for...More

Reviewed 2 weeks ago

My daughter and I decided at the last minute to try this evening sail. Perfect evening skies and water. We couldn't have had a better crew they took great care of us. Can't wait to do this again! Thanks again Jolly Sailing!More

Review collected in partnership with this attraction
Thank betteann1
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 5 days ago

Hi Betteann, thanks very much for your review. Great to hear that you had a nice evening for a sunset sail with us, and that it was a fun time for you and your daughter. Hope to see you again, and thank you for sailing...More

Reviewed 2 weeks ago

Simply Awesome! We had the most amazing time on the water. We are from here, but we had friends visiting us and wanted to get them out on the water. We had kids ages 3-11 with us as well, and everyone was thrilled. Jim and...More

Thank Jduncan2000
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 2 weeks ago

Hello! Thanks much for your kind review. We truly enjoyed having your family aboard for the sunset dolphin cruise with beach stop. What a beautiful night with a great crew! Thank you for your recommendation, and for cruising with us! We hope to see you...More

Reviewed 3 weeks ago

My family came to visit me in Pensacola & I wanted to show them the best of our area so I called Jolly Sailing to help me! My husband & I have done romantic sunset dinner cruises on their lovely Sailboat & it is always...More

Review collected in partnership with this attraction
Thank Deborah621
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 2 weeks ago

Hi Deborah, thanks for taking the time to leave your detailed review! We always enjoy having you and your family and friends out with us. Glad to hear your group had a fun time out on the Jolly Dolphin, thanks for helping us shake it...More

Reviewed 3 weeks ago via mobile

Capt Jim and Cindy are fantastic hosts! We spent about 2 hours on the beautiful waters of Pensacola Bay headed right into the sunset. Every detail was attended to, even the "beverage delivery hatch"! I recommend this trip for couples, families or groups of friends...More

Thank Gregory B
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 2 weeks ago

Hi Gregory! Thanks much for your kind review. We enjoyed having y'all aboard, and so happy you two had a good time. Thank you for your recommendation, and for sailing with us! Look forward to future cruising with you!

Reviewed 3 weeks ago

Me. David was knowledgeable and patient. We probably asked too many questions like a tourist but he was very patient and engaging answering our questions and showing us dolphins. Mr. David himself is like he's part of the view. We got to know the history...More

Review collected in partnership with this attraction
Thank junehua300
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 2 weeks ago

Hello June, thank you for stopping by to leave your review. So pleased to hear your dolphin cruise with Capt. David was a great time for you. Thanks for cruising with us!

Reviewed 4 weeks ago

Jim was our tour guide and he was awesome! We enjoyed every minute of it and cannot wait to return. He had drinks and refreshments and made sure we were comfortable. We weren't able to see any dolphins but we had the time of our...More

Review collected in partnership with this attraction
Thank Leta09
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 3 weeks ago

Hi Leta! Thank you for leaving your review about your cruise. We're happy you enjoyed the trip with Capt. Jim and appreciate your recommendation. Though we do spot dolphins on the majority of our cruises, they are wild animals, and cannot guarantee a sighting. We...More

Reviewed 4 weeks ago

No complaints except that the sailboat was old. Crew was great! My wife and I had a private dinner cruise to celebrate our 5th anniversary.More

Review collected in partnership with this attraction
Thank 694scottn
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 4 weeks ago

Hello, and thank you for taking the time to write a review about your sunset dinner cruise with us. Glad to hear your anniversary trip was a good time for you. The sailboat is a 34' Pearson Yacht, built in 1984, very well regarded as...More

Reviewed 15 July 2017

Amazing views. Great weather. Crew was fantastic. Will do again next time we are in town. Very relaxing.

Review collected in partnership with this attraction
Thank annegE8069HX
jollysailing, Owner at Jolly Sailing, responded to this reviewResponded 4 weeks ago

Hi Anne, thanks for stopping by to leave your review. Happy to hear you enjoyed your sunset sail. We look forward to seeing you next time! Thank you for sailing with us.

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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
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xMissKimx
24 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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