Freestyle Sailing Experience 

 Jimmy Cliff Boulevard, Montego Bay, N/A, Jamaica
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Jimmy Cliff Boulevard
Montego Bay, Jamaica

Set sail with Chokey Taylor, renowned Jamaican songwriter and musician, aboard his 51’ sailing yacht Freestyle for an unforgettable adventure in Montego Bay Marine Park. Explore 17 miles of lush coastline and vibrant marine life on your private sail and snorkel tour, sunset cruise, or special celebration. Whether it’s a birthday, anniversary, bachelor's or bachelorette party, or even a wedding and reception, Freestyle is the perfect venue.

Your tour includes a stop at a stunning snorkeling spot where you can swim and snorkel with provided gear under the watchful care of our certified Jamaican lifeguards and rescue divers. Onboard, enjoy an authentic Jamaican bar stocked with Red Stripe beer, rum, gin, vodka drinks, rum punch, fruit punch, juices, sodas, and water. Indulge in local snacks like sweet bread and cheese, Jamaican jam on crackers, banana chips, Solomon Gundy, Jamaican cookies, and rum cake. Additional premium drinks and food can be arranged with advance notice.

Relax or dance to the rhythms of Jamaican music on 1500 sq. ft. of deck space. Upon request, your tour can include stops at Margaritaville or Doctor’s Cave Beach. Freestyle is fully equipped with essential safety gear, life jackets, a depth finder, VHF radio, and wheel steering.

Bring your towel, sunglasses, and sunscreen, and get ready for the adventure of a lifetime. Flexible departure times available – contact us to customize your perfect day on the water. Book now to experience true Jamaican vibes under sail!

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Trip availability and prices

Trip Date:
Days:
Group Size:
Trip Date:
Days:
Group Size:
Almost there...
2 Hour – Private Chartering
FREE Cancellation 30 days notice
2 Hour Trip, starts at 10:00 AM
Seasonal trip Jan 1 - Dec 1
Price for up to 10 people
US $1,000 
3 Hour – Private Chartering
FREE Cancellation 30 days notice
3 Hour Trip, starts at 9:00 AM
Seasonal trip Jan 1 - Dec 1
Price for up to 10 people
US $1,500 
4 Hour – Fun Sailing
FREE Cancellation 30 days notice
4 Hour Trip, starts at 9:00 AM
Seasonal trip Jan 1 - Dec 31
Price for up to 10 people
US $2,000 
8 Hour – Private Charter
FREE Cancellation 30 days notice
8 Hour Trip, starts at 10:00 AM
Seasonal trip Jan 1 - Dec 31
Price for up to 10 people
US $4,000 

Customer reviews

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FAQs about Freestyle Sailing Experience

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What the boat is like

Boat category
Catamarans
Boat type
Catamaran
Boat manufacturer
Norman Cross
Boat Model
Motor Sailer
Year built
1994
Restored in
2019
Boat length
52 ft
Capacity
50 persons
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