Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages
2 Hours
Up to 6 people
Beverages, Licensed captain
Set sail on Jolly Mon, a 27’ American Mariner sailboat, and relax as you cruise Pensacola Beach with a cold beverage. Enjoy intimate small-group sailing for up to 6 guests with chances to spot dolphins and coastal wildlife.
Guests must be physically agile to board. Children under 18 must be accompanied by a parent or guardian; children age 6 and under must wear life jackets. The boat is not wheelchair accessible; guests with limited mobility may be accommodated at the crew’s discretion.
Should I worry about seasickness?
We cruise in the protected waters of Santa Rosa Sound and Pensacola Bay, and most guests do fine. If you are prone, consider motion sickness medication before the cruise.
Is there an age requirement for the tour?
All ages are welcome. Children age 6 and under must wear life jackets onboard.
What should I wear or bring?
Wear comfortable clothing and shoes. In cooler months bring jackets or long pants; it often feels cooler on the water.
Are alcoholic beverages allowed?
Guests age 21+ may bring adult beverages. Please bring cans instead of glass; a bottle of wine is acceptable with plastic cups.
Is there a restroom on the boat?
Yes, there is a marine restroom onboard.
What happens in case of bad weather?
Trips are subject to the Captain’s approval of weather and water conditions. If a trip is canceled, it will be rescheduled or refunded.
What is your cancellation policy?
Cancel 24 hours or more before your scheduled trip to receive a full refund. Late arrivals or no-shows are not refunded.
Are dogs allowed on the boat?
Dogs are allowed on private cruises only. Certified service animals may ride on all cruises.
Cancellations must be made 24 hours or more in advance of the trip in order to receive a full refund. Cruises cancelled due to weather or conditions per the Captain's discretion will be rescheduled or fully refunded.
Discover what we've curated for you
715 Pensacola Beach Blvd., Pensacola Beach, FL 32561
Dolphin sightings are practically guaranteed here, and you'll likely leave having seen plenty up close. The crew consistently gets praised for being knowledgeable and fun, sharing interesting facts about the marine life throughout the tour. Captain Roger and Matt seem to be frequent favorites, along with Mary and Captain Carson, and Paul also gets enthusiastic shoutouts. The boat is comfortable, and as a bonus, you might catch other sights like sea turtles or even the Blue Angels during your cruise. The atmosphere is educational without being dry, and the guides clearly love what they do. One reviewer felt the crew tried a bit too hard with commentary, but the overwhelming majority appreciate the engaging, informative approach. The sunset stop adds a nice touch to the experience. With smooth rides and reasonable pricing, this tour delivers exactly what it promises: a relaxed, enjoyable time on the water with dolphins and a crew that genuinely makes the trip memorable.
We took the Dolphins sightseeing tour this afternoon (9/26/25). Captain Roger and Bosun Matt were fantastic. Both were very engaging, professional and very knowledgeable about all things Dolphins and Pensacola history. My husband and I thoroughly enjoyed the tour. Captain Roger knew exactly where to find at least 20 Dolphins while Bosun Matt must have studied Marine Biology because he was so knowledgeable about Dolphins. Lastly, a big thank you to Ms. Cindy who kept us updated with schedule and reporting to the dock etc. We absolutely loved it and can wholeheartedly recommend Jolly Sailing! You won't be disappointed.
Martina Ambrosio
September 26, 2025
We took the Dolphins sightseeing tour this afternoon (9/26/25). Captain Roger and Bosun Matt were fantastic. Both were very engaging, professional and very knowledgeable about all things Dolphins and Pensacola history. My husband and I thoroughly enjoyed the tour. Captain Roger knew exactly where to find at least 20 Dolphins while Bosun Matt must have studied Marine Biology because he was so knowledgeable about Dolphins. Lastly, a big thank you to Ms. Cindy who kept us updated with schedule and reporting to the dock etc. We absolutely loved it and can wholeheartedly recommend Jolly Sailing! You won't be disappointed.
Martina Ambrosio
September 26, 2025