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

    Sail Pensacola Bay with a licensed captain, with time to swim or snorkel and spot wildlife.

    From$450

    Duration

    4 hours

    Ideal For

    Up to 6 people

    Includes

    Captain, Beverages, Taxes & fees

    Highlights

    Set sail aboard the 27' Jolly Mon for a relaxed 4-hour cruise across Pensacola Bay, Santa Rosa Sound, and the Pensacola Pass. Take the helm or unwind on cushioned seating, with an optional swim or snorkel stop and chances to spot dolphins and seabirds.

    • Cruise scenic National Seashore and bays
    • Learn or practice sailing at the helm
    • Watch for dolphins, seabirds, rays and turtles
    • Relax under shade with onboard restroom
    • Enjoy complimentary beverages aboard
    • Bring food or drinks; coolers welcome

    What's Included

    • Licensed captain
    • Complimentary bottled water and beverages
    • All taxes and fees

    Things to know

    Guests must be physically agile to board; the boat is not wheelchair accessible, though limited mobility may be accommodated. Children under 18 must be with a parent or guardian; children 6 and under must wear life jackets onboard. Glass containers are not permitted; guests 21+ may bring alcohol in cans or wine with plastic cups.

    FAQs

    Should I worry about seasickness?
    We cruise in protected waters where conditions are usually favorable. If you are prone to motion sickness, consider Dramamine or Bonine before the cruise.

    Is there an age requirement?
    All ages are welcome. Life vests are accessible, and children 6 and under must wear life jackets onboard.

    What should I wear or bring?
    Wear comfortable clothing and shoes. Jackets are recommended in cooler months, as it feels cooler on the water.

    Are alcoholic beverages allowed?
    Guests 21+ may bring beverages. Please bring cans instead of glass; a bottle of wine is acceptable with plastic cups. Portable coolers are allowed.

    Is there a restroom on the boat?
    Yes, there is a marine restroom onboard. 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 weather and water conditions. If cancelled, we will reschedule or refund.

    What is your cancellation policy?
    Cancel at least 24 hours in advance to avoid charges. Cancellations within 24 hours and no-shows are not refunded; allow extra time for traffic and parking.

    Are dogs allowed?
    Dogs are allowed on private cruises only. Service animals are permitted on all cruises and must be well behaved and leashed.

    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.

    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 #4UJWGK

    Private Trip

    $450

    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

    Meeting location

    655 Pensacola Beach Blvd., Pensacola Beach, FL 325661

    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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