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    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

    5.0 stars• 1.7K reviews
    From$104

    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.

    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.

    FAQs

    We cruise protected waters where conditions are usually favorable. If you are prone to motion sickness, consider medication before the cruise.

    All ages are welcome. Children under 18 must be accompanied by a parent or guardian, and ages 6 and under must wear life jackets.

    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.

    Meeting details

    715 Pensacola Beach Blvd., Pensacola Beach, FL 325661

    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

    $104.17

    0

    Private Trip

    $380.36

    Up to 6 guests per boat

    0

    Private Cruise - 2 Passengers

    $321.83

    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
    1.7K 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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