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    1. Local experiences/
    2. Things to do in Pensacola Beach/
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    4. Sailing/
    5. Jolly Mon 2-Hour Sailing Adventure
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    Jolly Mon 2-Hour Sailing Adventure

    Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages

    From$107incl. taxes and fees

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    Discover what we've curated for you

    Duration

    2 Hours

    Ideal For

    Up to 6 people

    Includes

    Beverages, Licensed captain

    Highlights

    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.

    1. Sail the scenic waters of Santa Rosa Sound and Pensacola Bay
    2. Relax on cushioned seating with some shade and a restroom aboard
    3. Enjoy complimentary water, soda, beer and wine for ages 21+
    4. Watch for dolphins, shorebirds, rays and sea turtles
    5. Choose a shared sail or book a private cruise
    6. Cruise with a licensed captain as your guide

    What's Included

    1. 2-hour sailing adventure
    2. Licensed captain
    3. Complimentary beverages
    4. Taxes and fees

    Things to know

    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.

    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.

    FAQs

    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.

    Wear comfortable clothing and shoes. In cooler months bring jackets or long pants; it often feels cooler on the water.

    Guests age 21+ may bring adult beverages. Please bring cans instead of glass; a bottle of wine is acceptable with plastic cups.

    Meeting details

    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 #PRP3EQ

    Person

    $107.59

    0

    Private Trip

    $392.86

    Up to 6 guests per boat

    0

    Private Cruise - 2 Passengers

    $314.87

    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

    5.0 stars• 1.8K reviews

    Review summary

    5.0
    Excellent
    1.8K 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 4
    5/5

    What an incredible cruise ride! The Jolly Sailing company shared great info about dolphins and took the cruise around to many places to find dolphins. Everyone was very enjoyable, we had a great time!

    Photo of Samantha Smith

    Samantha Smith

    April 4, 2026

    Review 1 of 1
    5/5

    What an incredible cruise ride! The Jolly Sailing company shared great info about dolphins and took the cruise around to many places to find dolphins. Everyone was very enjoyable, we had a great time!

    Photo of Samantha Smith

    Samantha Smith

    April 4, 2026

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