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    1. Local experiences/
    2. Pensacola Beach, FL/
    3. Water Activities/
    4. Sailing/
    5. 3-Hour Jolly Mon Sailing Adventure with Optional Swim Stop
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    3-Hour Jolly Mon Sailing Adventure with Optional Swim Stop

    Sail scenic waters near Pensacola with an optional swim and a chance to spot dolphins

    From$100/ person

    Duration

    3 hours

    Ideal For

    Up to 6 people

    Includes

    Complimentary beverages, Swim stop

    Highlights

    Set sail aboard the 27' Jolly Mon for a relaxed cruise along the National Seashore, Pensacola Bay, and Santa Rosa Sound. Take the helm or unwind on deck as you watch for dolphins and other wildlife, with the option to stop for a refreshing swim.

    • Sail the National Seashore, Pensacola Bay, and Santa Rosa Sound
    • Take the helm to experience the joy of sailing
    • Watch for dolphins, seabirds, stingrays, turtles and more
    • Choose a stop to hop in the water for a swim
    • Enjoy complimentary beverages on board
    • Bring your own food and drinks if you like

    Things to know

    Guests must be physically agile to board the sailboat. Each passenger must complete a digital waiver before arrival.

    Cancellation policy

    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.

    Meeting location

    The Jolly Mon is located at Sabine Marina, behind the Sandbar/Frisky Dolphin Restaurant, 715 Pensacola Beach Blvd., Pensacola Beach, FL 32561.

    Experience provided by Jolly Sailing
    Experience provided by Jolly Sailing

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #9A5F9V

    Adult

    $100

    Ages 13 and Up

    0

    Private Trip

    $395

    Up to 6 guests per boat

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    Discover what we've curated for you

    5.0 stars• 1.7K reviews

    Review summary

    5.0
    Excellent
    1.7K reviews•Google Maps

    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.

    What people are saying

    Review 1 of 5
    5/5

    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.

    Photo of Martina Ambrosio

    Martina Ambrosio

    September 26, 2025

    Review 1 of 1
    5/5

    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.

    Photo of Martina Ambrosio

    Martina Ambrosio

    September 26, 2025

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