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    1. Local experiences
    2. /Things to do in Pensacola Beach…
    3. /Water Activities
    4. /Sailing
    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• 2.1K reviews

    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.

    Product ID: 9A5F9V

    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

    Related locations

    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 1-877-GREET-WELL

    Report an issue

    Adult

    $177.26

    Ages 13 and Up

    0

    Private Trip

    $469.91

    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
    2.1K 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 4
    5/5

    We had an awesome experience on the 6-passenger boat, the Jolly Ventures, with Captain Matt to see dolphins and then the Blue Angels practice. Matt was very personable and knowledgeable, especially about dolphins… he gave us many interesting facts about their lives and communication, etc. When we saw them, one of them actually swam partially under our boat and seemed to be leading us! Then we were taken to an island to watch the Blue Angels practice… what a spectacular treat!! Matt made it a point to engage with each passenger for awhile. He so obviously enjoys his job! And he seemed to take a lot of pride in keeping the boat clean and comfortable. Out of the many options for dolphin cruises, we are so happy and fortunate that we chose Jolly Dolphin.

    Photo of Susan Suggs

    Susan Suggs

    August 31, 2026

    Review 1 of 1
    5/5

    We had an awesome experience on the 6-passenger boat, the Jolly Ventures, with Captain Matt to see dolphins and then the Blue Angels practice. Matt was very personable and knowledgeable, especially about dolphins… he gave us many interesting facts about their lives and communication, etc. When we saw them, one of them actually swam partially under our boat and seemed to be leading us! Then we were taken to an island to watch the Blue Angels practice… what a spectacular treat!! Matt made it a point to engage with each passenger for awhile. He so obviously enjoys his job! And he seemed to take a lot of pride in keeping the boat clean and comfortable. Out of the many options for dolphin cruises, we are so happy and fortunate that we chose Jolly Dolphin.

    Photo of Susan Suggs

    Susan Suggs

    August 31, 2026

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