We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Pensacola Beach, FL/
    3. Water Activities/
    4. Sailing/
    5. Jolly Mon 2-Hour Sailing Adventure
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    Personal concierge

    Real humans available to help before, during, and after your booking

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else

    Easy booking

    Reserve in minutes with flexible cancellation on most experiences

    Greetwell

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Gallery image
    Gallery image 2
    Gallery image 3
    Gallery image 4

    Jolly Mon 2-Hour Sailing Adventure

    Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages

    From$89

    Duration

    2 Hours

    Ideal For

    Up to 6 people

    Includes

    Beverages, Licensed captain

    Highlights

    Set sail on Jolly Mon, a 27’ American Mariner sailboat, and relax as you cruise Pensacola Beach with a cold beverage. Enjoy intimate small-group sailing for up to 6 guests with chances to spot dolphins and coastal wildlife.

    • Sail the scenic waters of Santa Rosa Sound and Pensacola Bay
    • Relax on cushioned seating with some shade and a restroom aboard
    • Enjoy complimentary water, soda, beer and wine for ages 21+
    • Watch for dolphins, shorebirds, rays and sea turtles
    • Choose a shared sail or book a private cruise
    • Cruise with a licensed captain as your guide

    What's Included

    • 2-hour sailing adventure
    • Licensed captain
    • Complimentary beverages
    • Taxes and fees

    Things to know

    Guests must be physically agile to board. Children under 18 must be accompanied by a parent or guardian; children age 6 and under must wear life jackets. The boat is not wheelchair accessible; guests with limited mobility may be accommodated at the crew’s discretion.

    FAQs

    Should I worry about seasickness?
    We cruise in the protected waters of Santa Rosa Sound and Pensacola Bay, and most guests do fine. If you are prone, consider motion sickness medication before the cruise.

    Is there an age requirement for the tour?
    All ages are welcome. Children age 6 and under must wear life jackets onboard.

    What should I wear or bring?
    Wear comfortable clothing and shoes. In cooler months bring jackets or long pants; it often feels cooler on the water.

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

    Is there a restroom on the boat?
    Yes, there is a marine restroom onboard.

    What happens in case of bad weather?
    Trips are subject to the Captain’s approval of weather and water conditions. If a trip is canceled, it will be rescheduled or refunded.

    What is your cancellation policy?
    Cancel 24 hours or more before your scheduled trip to receive a full refund. Late arrivals or no-shows are not refunded.

    Are dogs allowed on the boat?
    Dogs are allowed on private cruises only. Certified service animals may ride on all cruises.

    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 #PRP3EQ

    Person

    $89

    0

    Private Trip

    $325

    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

    Search all experiences

    Discover what we've curated for you

    Meeting location

    715 Pensacola Beach Blvd., Pensacola Beach, FL 32561

    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

    Nearby activities

    Thumbnail

    Pensacola Beach Dolphin and Scenic Tour

    From$30/ person
    Thumbnail

    Pensacola Beach 1.5-Hour Fun Cruise

    From$55/ person
    Thumbnail

    Pensacola Beach Sunset Cruise on a Floating Tiki Bar

    From$65/ person
    Thumbnail

    3-Hour Pensacola Beach Floating Tiki Cruise

    From$100/ person
    Thumbnail

    Pensacola Beach Lights on the Water Private Tiki Cruise

    $500
    Thumbnail

    3-Hour Jolly Mon Sailing Adventure with Optional Swim Stop

    From$100/ person