We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

“Absolutely Incredible”
5 of 5 bubbles Review of Jolly Sailing

Jolly Sailing
Ranked #2 of 35 Tours in Pensacola Beach
Certificate of Excellence
More attraction details
Attraction details
Owner description: 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!
Useful Information: Bathroom facilities, Activities for older children, Activities for young children
Cape Girardeau, Missouri
2 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
“Absolutely Incredible”
5 of 5 bubbles Reviewed February 17, 2014

My girlfriend and I took a dolphin tour with Jolly Sailing Tours, and it was absolutely amazing. It was my first time taking a dolphin tour since I was single-digits old, and my girlfriend's first time ever being on the ocean. Anyway, the tours are run by a husband and wife who are extremely personable, friendly, and outgoing. We saw at least 10 dolphins while on our tour, three different pods, which actually ended up converging and playing together as they chased along our boat, investigating us and following us. We even got to see a number of breaches, and literally over a hundred total surfaces. One dolphin even surfaced, sat still, and clicked at us. The hosts even provided complimentary drinks (beer and wine) and had snacks. They let anyone steer the boat if they wanted to, and explained how everything works. They even offered to give us some extra time if we hadn't spotted any dolphins by the end of the tour (which wasn't a problem at all). We could not have been happier with the tour, it was the highlight of our entire trip.

Visited February 2014
1 Thank NatePonder
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

341 reviews from our community

Visitor rating
Date | Rating
  • English first
  • Russian first
  • Any
English first
Dallas, Georgia
Level Contributor
13 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
“Great fun”
5 of 5 bubbles Reviewed February 14, 2014 via mobile

Capt. Jim was great and very knowledgeable of the area and his boat. The cruise was very pleasant for it to been a cool, windy day.

Thank Gemini S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Birmingham, Alabama
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
“Family fun at Sea”
5 of 5 bubbles Reviewed December 2, 2013

We decided to take our family of six (Mom and Dad and 4 children) on a dolphin view trip. When we called Jolly, Cindy was very polite and told us our best option was to take a private group trip.

Both Cindy and the Captain Jim greeted us at the dock and were very polite. They were very accommodating to the four kids as they loaded the boat.

While on the trip again we were impressed with how great they were with the kids. The three older ones were all offered opportunities to drive the ship and learn and understand how to navigate on the open seas. As our 20 mnth old walked around the ship they were very understanding on how restless he was and made sure he enjoyed the boat just as much as the rest of us. They did a great job in putting us up close with the dolphins we spotted and made sure we all had time to see they up close. Never once during the entire trip did we feel like they just wanted to get us out and back. Made sure we all had drinks and snacks and kept offering time and time again. Not one of those other boats where they give you one drink and then avoid the conversation at all costs.

When we arrived back at the dock they both took time to make sure we were happy and enjoed every part our the trip. Never once did the mention of payment come up until I asked how they preferred to be paid. VERY IMPRESSED.

With out a doubt they will be our only contact when we are in the area for all things sailing and relaxing on the water.

Visited November 2013
1 Thank cameron566
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Pensacola, Florida, United States
Level Contributor
6 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
“The Good Guys”
5 of 5 bubbles Reviewed November 15, 2013

Jim and Cindy are wonderful humans that take you on a boat ride. Had a great time on the SUP boat. Thanks for the ride.

Visited September 2013
Thank Kaipo R
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Clinton, North Carolina
Level Contributor
23 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
“Jolly Sailing”
5 of 5 bubbles Reviewed November 13, 2013

Couldn't ask for a more enjoyable sailing day with Captain Jim and Cindy. They are so full of fun, accommodating and made sure your sailing trip will be a everlasting memory. Thank you Captain Jim and Cindy for making it an enjoyable day and will see you again.

Visited November 2013
Thank windyrising
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

Travelers who viewed Jolly Sailing also viewed

Pensacola Beach, Florida Panhandle
Pensacola Beach, Florida Panhandle
Pensacola Beach, Florida Panhandle
Pensacola, Florida Panhandle

Been to Jolly Sailing? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing