Jolly Sailing

Best money spent all weekend. Booked the sunset cruise as an add-​on to a quickie weekend get-​a-​way and it turned out to be the highlight of the trip. The excursion was calm, relaxing and beautiful… plus we got to see dolphins! Bonus! Will definitely look to book with Jolly again in the future when we visit Pensacola next.

Had a great time sailing with Jolly Sailing in April 2016 w/​very experienced and comical guides! All three of my children had a good time captaining the boat for a short time, and trying on the different hats! Very entertaining experience — highly recommend!

Jolly Sailing snorkeling was an incredible experience. The staff is so professional and helpful. On our tour morning, the weather wasn’t good enough to make the snorkel trip, but when it cleared up in the afternoon, they rescheduled so we could go! They made my slightly nervous 7 year old son feel safe and secure. The captain had drinks and snacks, and the swab snorkeled with us, finding and bringing up different sea creatures for us to see. We highly recommended this experience. Nothing bad to say!

Fantastic people, amazing experience! We chartered a sunset sail and lucked into several dolphin sightings. We had such a wonderful experience and highly recommend booking with Jolly Sailing!

My BF had been talking a big game for a month prior to arriving in Pensacola about a «surprise». I patiently waited (rather than my usual way of trying to get it out of him) and when we walked up at the marina I realized we were going on a boat. I figured it was a party boat or a pontoon or something like that but it was a real sailboat! Since I can’t swim very well and am still a touch scared of the water (I call it «healthy respect for the water»), I am sure he was worried that I wouldn’t like it. But I had a great experience!
We got there and checked in and walked over to get us a bottle of wine at the liquor store next door. The nice thing is that they have beer/​wine on board but you can also bring your own. We were just glad that we would have back up if we drank the entire bottle (and when have we EVER not drank the entire bottle?!).
Cindy helped us board and told us we could sit up in the front of the ship since the other people were not there yet. They limit it to 6 guests but apparently the best spot is up front so first ones there get shotgun! It took me a minute to get my sea legs and get comfortable but once I was up there I was ready to go! Cindy served us wine and talked to us and gave me tips to help me be more comfortable when the boat started going.
Well, the other 4 persons were no-​shows and Captain Jim declared we were going sailing anyway. Inadvertent private cruise! He was awesome about telling us what he was doing with the sails and explained that the boat would lean to one side and the other so that I wouldn’t freak out too much. There was an engine to get us out into the water and then it was just sails only and with the good breeze were were going fairly fast. It was awesome! We sailed into the sun while sitting at the very front of the boat and drank our wine and generally acted like schmoopy lovebirds. Then Cindy brought out some seats where we could sit on the side of the boat which we did.
We didn’t see any dolphins on this trip but not for lack of looking. However, we DID get to see the Blue Angels coming back from a show. I was disappointed that I was leaving before I could see them practice so this was a special treat. They came in formation, then they split off one by one and landed and we could see the whole thing. It was the fucking coolest! We also got to see a beautiful sunset as we were sailing back.
Later on we moved where Captain Jim was so he could show us how the boat works, the navigation system, etc. Plus get our pic taken with some captain hats which was cheesy in the best way possible.
I understand the appeal of booze cruises and such and, trust me, I could rock a party boat like no one else. However, I can also get into this sailboat thing — it was quiet, chill, relaxed, romantic if you want it to be, exciting, interesting, and fun! I have never had an experience like this before and I am just glad I had Jolly Sailing as my first experience. You MUST GO when you are in Pensacola… that’s it, you MUST. See, I’ve helped you plan your vacay. You are welcome.

My group had a fantastic experience with Jolly Sailing on our vacation! We chose to do the sailboat dolphin tour and wasn’t disappointed. Our captain was extremely nice and informative throughout the cruise. We sailed along side of a full pod of dolphins while the other dolphin cruise boats missed it. The sailboat was extremely nice and it was great being able to hang off the edge while the dolphins swam along side of us. We will be back again for our next visit!

We had an outstanding cruise with Jolly Sailing! Everything was perfect! We loved our Jolly Roger boat (the yellow fast one). It was perfect for our girls trip. They limit the boat to 6 plus driver. It was new, very clean, fast with 2 canopies. Other boats were larger and had lots of tourists on them. We were happy to be the only people on our boat! Captain Randy was great and made our cruise really special. He even told us what to expect during the Blue Angels show. He could be one of the pilots. He took us to view Dolphins on the way out and stopped again on the way back. Cindy quickly handled my inquiry and answered all my questions via email and phone. She even suggested I order the Coconut Mocha at the Drowsy Poet coffee shop.

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. We were in Pensacola for vacation.
We had been given this sunset sail as a gift from our children for our birthdays and 25^th anniversary. Special instructions were given to the captain and he complied with every single one of them to make this truly a dream come true for us.
Very friendly, no pressure, just relaxing and sailing. During the sail we learned about the area.
Would go back in a minute and am very happy with the entire experience. Would recommend to family and friends.

We travelled to Pensacola for a week in October. I contacted Jolly Sailing at least a week prior to the day of our sailing trip to make sure we could reserve a spot. Jim & Cindy run a top notch vacation sailing trip. The Sunday that we had our trip planned, the winds were excessively high; Cindy called me to tell me the trip had to be postponed to the next day for safety reasons due to the 20+ knots of wind. Once we went out on our trip, Jim & Cindy could not have been more accommodating to our comfort. They offered us champagne on the trip that they provide to their guests (at no additional charge) but, since they allowed us to bring our own wine, Cindy served me my wine. My wife, Cindy (not Jim’s wife), has NEVER been on a sailboat & is prone to sea sickness. The trip was peaceful & we BOTH enjoyed the trip thoroughly. even had the opportunity to steer the boat during the trip. We look forward to looking up Jolly Sailing again next year.
Lastly, Cindy had offered us an opportunity to go out on their dolphin cruise later that week. I called the next morning to accept her offer but their boat was already full. Without prompting her to do so, Cindy (from JS) contacted another dolphin cruise ship to get us a reservation with them. Cindy called me back to let me know that she got us a reservation. Too cool! Cindy went above and beyond for us! Thanks Jim & Cindy!

Called day-​of about going out sailing for a couple of hours and they were super flexible. Went out on a nice afternoon and it was a ton of fun! Very relaxed. No dolphins were promised, but we had about 4 hang with us towards the end of the excursion.
Jim and Cindy were wonderful. They’re fun to talk to, plus they gave us a few local suggestions that made our stay a little more fun after sailing with them!

Jolly Sailing was amazing!
Warm, genuine, fun experience. Our family and even our 3 year old enjoyed himself. The sailboat was just the right speed to relax. Calm, soothing, great music. Thanks so much.

Probably the best part of our trip to Pensacola. We booked the 3 hour SUP/​Snorkel sail, and were so glad we did.
My boyfriend and I called the day in advance and were the only people so far attempting to book a group trip, so our ability to sail was contingent on others wanting to go out too, and Cindy said she would call back and let me know the plan. The next morning at breakfast, my phone rang and Cindy said that while no one else had inquired about sailing that day that we would be able to take the trip privately but at the group rate! Talk about customer service!
Captain Randy was wonderful and full of information about Pensacola and the gulf. It was my first time sailing and hopefully won’t be the last. I had a blast out on the water, and enjoyed exploring Pensacola’s water through my snorkel mask as well. I was less than successful at Stand Up Paddle, but there’s always next time right? We even saw a sea turtle! How cool is that?
We brought our own beer onboard, but the boat was also stocked with daiquiri fixings, so we partook in those as well. All in all a great activity at a great price for anyone who loves the water.

My family and I had a fantastic experience with Jolly Sailing.
We took a 2 ½ hour sail during our recent visit to Pensacola. Everyone from our near two year old to my mother in law thoroughly enjoyed the time on the water. I don’t remember a time when the whole crew was so relaxed after an excursion.
Captain Jim and Cindy took care of everything. It was just like sailing with friends. They told us interesting history tidbits, gave us tips on where to visit during our stay and in general carried on pleasant conversation.
The view of Pensacola Beach and Fort Pickens from the water puts a whole different perspective on things. I recommend starting your vacation with a sail because it tends to set the mood for the rest of your trip.
We will definitely visit them again next trip.

Captain Jim and First Mate Cindy are fantastic. They were very informative, responsive and wonderful at answering all our questions leading up to our trip. My husband and I did a half day sail. Captain Jim cruised us all around the harbor while sharing interesting things about the sites and area. We had a beautiful sunny day to go out. The boat was gorgeous and very comfortable. We were treated like friends and had smiles on our faces all afternoon. It’s always fun to get out on the water and see the area from a whole different view! I would recommend Jolly Sailing to anyone in the area. I have full confidence all their adventure trips are just as great!

Jim and Cindy are wonderful people. They made the biggest effort to accommodate my boyfriend and I. We did the sailing and dolphin watch and selected Jolly Sailings based on the reviews. From the moment we arrived Jim offered us drinks and snacks. They allowed us to bring in wine and provided us with all the utensils needed to eat and drink. By far we had a blast and it was the best part of our trip. The day we went out to sail on, the weather was amazing. In addition, there were not many tourists on site. Consequently, it created the most lax environment to be in. Strongly recommend for anyone in the area to include Jolly Sailings for their next vacation.

We were lost, late and frazzed. Then we were met with smiles and a glass of wine each as we were greeted to set sail into a beautiful calm sunny day. Everything was right in the world and we were treated like special guests in thier home. I can’t say enough other than to tell any reader to trust your first instinct. Book a trip and enjoy the day. You are in good, safe and hospitable hands.

If ANYONE and I mean ANYONE is planning a trip to visit Pensacola beach they must book a trip with Jolly sailing! Who can beat sailing with two of the best husband and wife teams on the Gulf Coast, also they offer complimentary mai tais, beer, and snacks! Plus I heard a rumor (shhhhh) that they are planning to offer dinner cruises very soon, and they are going to soon charter a bigger boat!

This was a fantastic trip! My lady surprised me with a sunset sailing cruise and now I want to do it every day! The boat was roomy and very comfortable, the owners were fun and knowledgeable and the trip was beautiful! We went in late July so you think it would be hot but it was perfect out on the water. There were four of us and a 6mo. old and everyone loved it. This is a great way to get away from the standard touristy stuff and enjoy what makes Pensacola beautiful. Oh yeah, we saw a ton of dolphins, too!

A perfect day on the water! Jim & Cindy provided great drinks and good times on the best sail I’ve had since my Key West adventures! If you are in the NW Florida area I would definitely recommend a trip with Jolly Sailing.