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    1. Local experiences/
    2. Pensacola Beach, FL/
    3. Water Activities/
    4. Sailing/
    5. Pensacola Beach Sunset Sail on the Jolly Mon
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    Pensacola Beach Sunset Sail on the Jolly Mon

    Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins

    From$89

    Duration

    2 Hours

    Ideal For

    Up to 6 people

    Includes

    Captain, Drinks, Taxes and fees

    Highlights

    Watch the sun set over Pensacola Bay aboard the 27-foot Jolly Mon sailboat. Help hoist the sails or relax on cushioned seating as you cruise calm waters and look for dolphins and seabirds.

    • Sail Pensacola Bay and Santa Rosa Sound
    • Take the helm or sit back and enjoy the ride
    • Enjoy complimentary water, sodas, and limited beer and wine
    • Ride with a licensed captain in small groups up to 6
    • Relax with shade, a restroom, and cushioned seating
    • Watch for dolphins, shorebirds, rays, and sea turtles

    What's Included

    • 2-hour sunset cruise
    • Licensed captain
    • Complimentary beverages
    • Taxes and fees

    Things to know

    Maximum 6 guests. Not wheelchair accessible. Children under 18 must be with a parent or guardian; ages 6 and under must wear life jackets. Dogs are allowed on private cruises only; guests 21+ may bring drinks, no glass.

    FAQs

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

    Is there an age requirement?
    All ages are welcome. Children under 18 must be accompanied by a parent or guardian, and ages 6 and under must wear life jackets.

    Are alcoholic beverages allowed?
    Guests age 21+ may bring beverages. Please use cans; a bottle of wine is acceptable with plastic cups. Coolers are allowed. Glass containers are not permitted.

    Is there a restroom on the boat?
    Yes, there is a marine restroom aboard. 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 conditions. If canceled, they will be rescheduled or refunded.

    Are we guaranteed to see dolphins?
    Sightings are not guaranteed, though they are often seen. A free return trip is offered if dolphins are not seen.

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

    Cancellation policy

    Cancel at least 24 hours before your trip for a full refund. Cancellations within 24 hours are charged and late arrivals or no-shows are not refunded. Trips canceled due to weather or conditions at 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 #WPQZQX

    Person

    $89

    0

    Private Trip

    $325

    Up to 6 guests per boat

    0

    Private Cruise - 2 Passengers

    $275

    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

    715 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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