Freestyle Sailing Experience 

3.0/5 (1 review)
 Jimmy Cliff Boulevard, Montego Bay, N/A, Jamaica

Freestyle Sailing Experience 

Montego Bay, Jamaica
52 feet
50
3.0/5 (1 review)

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!

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!

Freestyle Sailing Experience
Charter Operator
Freestyle Sailing Experience

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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2 Hour – Private Chartering
FREE Cancellation 30 days notice
2 hour trip starts at 10:00 AM
US $1,000
Private tour: up to 10 people
2 Hour quick sunset cruise
FREE Cancellation 30 days notice
2 hour trip starts at 4:00 PM
US $1,000
Private tour: up to 10 people
3 Hour – Private Chartering
FREE Cancellation 30 days notice
3 hour trip starts at 9:00 AM
US $1,500
Private tour: up to 10 people
3 hour sailing and snorkeling
FREE Cancellation 30 days notice
3 hour trip starts at 12:00 PM
US $1,500
Private tour: up to 10 people
3 hour Sunset Cruise
FREE Cancellation 30 days notice
3 hour trip starts at 3:00 PM
US $1,500
Private tour: up to 10 people
4 Hour – Sailing and Snorkeling
FREE Cancellation 30 days notice
4 hour trip starts at 9:00 AM
US $2,000
Private tour: up to 10 people
4 Hour Sailing and Snorkeling
FREE Cancellation 30 days notice
4 hour trip starts at 12:00 PM
US $2,000
Private tour: up to 10 people
8 Hour – Private Charter
FREE Cancellation 30 days notice
8 hour trip starts at 10:00 AM
US $4,000
Private tour: up to 10 people
There are 2 people looking at this charter.

Customer reviews

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Rating

3.0
(1 review)
3.0
Boat & equipment
3.0
Captain & crew
3.0
Experience

All reviews (1)

Showing 11 of 1 review
Jim Tucker
Jim Tucker
us
Maryland, US
Member since 2025
3.0
Verified
Keep looking
3 hour sailing and snorkeling on December 31, 20258 adults1 child

Sailed around in circles in the bay a hundred yards off the beach. Snorkeling was mediocre and literally same spot as ScubaCaribe, preplanned light tackle fishing as part of the experience, it was one hand line and little concern if there were any fish in the area. Kids had fun jumping off the boat. Drinks/snacks were available. I get it’s a touristy thing and it’s probably redundant doing it over and over again but don’t expect anything more if you barely provide the service.

FAQs about Freestyle Sailing Experience

Freestyle Sailing Experience offers the following trips to customers:
  • US $1,000 per group, additional US $100 per person after 10 guests - 2 Hour – Private Chartering (2 hours)
  • US $1,000 per group, additional US $100 per person after 10 guests - 2 Hour quick sunset cruise (2 hours)
  • US $1,500 per group, additional US $150 per person after 10 guests - 3 Hour – Private Chartering (3 hours)
  • US $1,500 per group, additional US $150 per person after 10 guests - 3 hour sailing and snorkeling (3 hours)
  • US $1,500 per group, additional US $150 per person after 10 guests - 3 hour Sunset Cruise (3 hours)
  • US $2,000 per group, additional US $200 per person after 10 guests - 4 Hour – Sailing and Snorkeling (4 hours)
  • US $2,000 per group, additional US $200 per person after 10 guests - 4 Hour Sailing and Snorkeling (4 hours)
  • US $4,000 per group, additional US $400 per person after 10 guests - 8 Hour – Private Charter (8 hours)
When you book a trip with Freestyle Sailing Experience, you can expect the following amenities onboard:
  • VHF Radio
  • Depth Finder
  • Anchor
  • Dinghy
  • Wheel Steering
  • Life Jackets
  • Wheelchair Accessible Advance request necessary.
  • Bow Sundeck Deck & 2 Bow Nets.
  • Aft Sundeck All Deck and Mid Ship.
  • WiFi
  • Audio System
  • Inside Speakers
  • Outside Speakers
  • Ice Box
Trips booked with Freestyle Sailing Experience include:
  • Snorkeling Equipment
  • Snacks
  • Drinks
  • Lunch
Freestyle Sailing Experience offers the following activities:
  • Sailing, Catamaran & Gulet Tours
  • Sunset Dinner Cruises
  • Booze Cruises
  • Snorkeling & Diving Tours
  • Whale & Dolphin Watching

Your operator

Freestyle Sailing Experience
Freestyle Sailing Experience
Freestyle Sailing Experience

Montego Bay, Jamaica

1 Customer reviews
Response time 6 hours
Member since June 2025

Capt. Chokey Taylor leads the Freestyle Sailing Experience aboard the stunning 51' sailing yacht Freestyle in Montego Bay. With a passion for the sea and years of expertise, he offers unforgettable catamaran and sailing tours, snorkeling adventures, and breathtaking sunset cruises. Join Capt. Chokey for a true taste of Jamaica's beauty and warm hospitality on the water.

1 Customer reviews
Response time 6 hours
Member since June 2025

Capt. Chokey Taylor leads the Freestyle Sailing Experience aboard the stunning 51' sailing yacht Freestyle in Montego Bay. With a passion for the sea and years of expertise, he offers unforgettable catamaran and sailing tours, snorkeling adventures, and breathtaking sunset cruises. Join Capt. Chokey for a true taste of Jamaica's beauty and warm hospitality on the water.

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
Engine model
Perkins
Max crusing speed
12 knots
Powered by
1 x 95HP
Engine Type
Inboard
Fuel Type
Diesel
Number of cabins
5 cabins
Number of berths
5 berths
Number of heads
1 head
Number of toilets
1 toilet
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

Which kind of activities are offered

Sailing, Catamaran & Gulet Tours
Sailing and Snorkeling on request.
Sunset & Dinner Cruise
Request for Dinner on Request.
Booze Cruises
O
Snorkeling & Diving Tours
Snorkeling & Swimming. No tank diving.
Whale & Dolphin Watching
We see them sometimes in the wild.

Which amenities are available onboard

VHF Radio
Depth Finder
Anchor
Dinghy
Wheel Steering
Life Jackets
Wheelchair Accessible
Advance request necessary.
Bow Sundeck
Deck & 2 Bow Nets.
Aft Sundeck
All Deck and Mid Ship.
WiFi
Audio System
Inside Speakers
Outside Speakers
Ice Box

What's included in the trip price

Snorkeling Equipment
Included.
Snacks
Included.
Drinks
Included.
Lunch
On Request with additional cost.

What’s allowed on the boat

Child Friendly
Any age.
Smoking
Equipment is onboard.
Alcohol
After watersports activities.
Glass Bottles
Handled by the bar tender in the Galley.
Shoes
Must be removed when boarding.
Swimming
At snorkeling stops.
Red Wine
On request.

What additional terms you should be aware of

Security deposit is not required

A refundable deposit is not required by the charter operator.


Fuel is included

Fuel is included in the price of the rental.

How cancellations work

Free cancellation up to 30 days prior to trip

You can cancel or modify your booking up to 30 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

How you can pay

Reserve with a 15% booking deposit, pay the captain the rest

When the captain confirms your trip, BoatBooker charges your credit card a 15% booking deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Cash

 Visa

 Mastercard

 American Express

 PayPal

 Bank transfer

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/5
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