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    5. 3-Hour Pensacola Beach Sailing Cruise With Swim Stop
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    3-Hour Pensacola Beach Sailing Cruise With Swim Stop

    Sail Pensacola Bay with an optional swim stop on a 27-foot sailboat

    5.0 stars• 1.9K reviews
    From$175/ personincl. taxes and fees

    Duration

    3 hour

    Ideal For

    Up to 6 people

    Includes

    Complimentary beverages, Sailboat

    Highlights

    Climb aboard the 27-foot Jolly Mon for a 3-hour sailing cruise along the National Seashore, Pensacola Bay, and/or Santa Rosa Sound. Relax on deck or take the helm, with the option to hop in for a swim.

    • Board a 27-foot sailboat for a 3-hour cruise
    • Sail along the National Seashore, Pensacola Bay, and/or Santa Rosa Sound
    • Take the helm or sit back and relax on deck
    • Look for dolphins, seabirds, stingrays, turtles, and other wildlife
    • Choose an optional stop for a refreshing swim

    What's Included

    • Complimentary beverages

    Things to know

    You must be physically agile to board the sailboat.

    Cancellation Policy

    Cancel 24 hours or more in advance for a full refund. Cruises cancelled due to weather or conditions per the Captain's discretion will be rescheduled or fully refunded. No shows/late arrivals will not be refunded.

    FAQs

    Yes. You must be physically agile to board the sailboat.

    Your cruise includes complimentary bottled water. You can bring food and drinks, including a small cooler. Alcohol is allowed for guests of legal drinking age (except on tours involving snorkeling). Do not bring glass.

    Bring a jacket in cooler weather.

    Meeting details

    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

    Report an issue

    Reference #9A5F9V

    Adult

    $175.72

    Ages 13 and Up

    0

    Private Trip

    $465.84

    Up to 6 guests per boat

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    1.9K reviews•Google Maps
    1,894
    32
    7
    2
    5

    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 had the BEST time with Capt Roger and 1st Mate Matt on our cruise! Both were engaging and entertaining and made the trip fun! The dolphins were fantastic, and we got to see the USCGC Eagle at the end of our excursion. Such a cool experience! We loved the whole tour and will definitely be back!

    Photo of Ashley P

    Ashley P

    May 23, 2026

    Review 1 of 1
    5/5

    We had the BEST time with Capt Roger and 1st Mate Matt on our cruise! Both were engaging and entertaining and made the trip fun! The dolphins were fantastic, and we got to see the USCGC Eagle at the end of our excursion. Such a cool experience! We loved the whole tour and will definitely be back!

    Photo of Ashley P

    Ashley P

    May 23, 2026

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