Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins
2 Hours
Up to 6 people
Captain, Drinks, Taxes and fees
Watch the sun set over Pensacola Bay aboard the 27-foot Jolly Mon sailboat. Help hoist the sails or relax on cushioned seating as you cruise calm waters and look for dolphins and seabirds.
Maximum 6 guests. Not wheelchair accessible. Children under 18 must be with a parent or guardian; ages 6 and under must wear life jackets. Dogs are allowed on private cruises only; guests 21+ may bring drinks, no glass.
Should I worry about seasickness?
We cruise protected waters where conditions are usually favorable. If you are prone to motion sickness, consider medication before the cruise.
Is there an age requirement?
All ages are welcome. Children under 18 must be accompanied by a parent or guardian, and ages 6 and under must wear life jackets.
Are alcoholic beverages allowed?
Guests age 21+ may bring beverages. Please use cans; a bottle of wine is acceptable with plastic cups. Coolers are allowed. Glass containers are not permitted.
Is there a restroom on the boat?
Yes, there is a marine restroom aboard. Do not throw anything into it; use the waste can provided.
What happens in case of bad weather?
Trips are subject to the Captain’s approval of conditions. If canceled, they will be rescheduled or refunded.
Are we guaranteed to see dolphins?
Sightings are not guaranteed, though they are often seen. A free return trip is offered if dolphins are not seen.
What should I wear or bring?
Wear comfortable clothing and shoes. Jackets and long pants are recommended in cooler months, and it often feels cooler on the water.
Cancel at least 24 hours before your trip for a full refund. Cancellations within 24 hours are charged and late arrivals or no-shows are not refunded. Trips canceled due to weather or conditions at the Captain's discretion will be rescheduled or fully refunded.
Discover what we've curated for you
715 Pensacola Beach Blvd., Pensacola Beach, FL 325661
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