Jamaica Sailing Adventures

out of 5 stars from 1 review See review
Sunset Drive
Montego Bay, Jamaica

Jamaica Sailing Adventures offers the most unforgettable sailing, fishing and snorkeling trips in Jamaica. You will enjoy every minute of your trip and leave with amazing memories that will last a lifetime. They are unique as to the type of fishing trips they offer because they have a sailboat that you can troll on using fishing rods under sail.

Your trip will take you out to the reefs too, where you can bottom fish or try your luck at spearfishing. The ultimate goal is to enjoy the day, whether you catch fish or snorkel or just relax.
The targeted species will be Mahi Mahi, King Mackerel, Jacks, Whiting, Bonito, Tuna, and Barracuda.

Fishing and sailing will take place aboard the Deja Vu, which is a 40 foot Endeavour sloop rigged sailboat. It was built in Largo, Florida and can sleep 6-8 guests in 3 separate cabins. The boat is spacious with a stateroom which also sleeps 2 persons, and features ensuite bathroom with a stand up shower stall. The boat also boasts air-conditioning, an MP3 stereo system, a full kitchen with a stove, barbecue, a fridge and freezer, and all the safety equipment you might need.

This vessel is powered by a 56 HP Yanmar engine which is maintained continuously. It contains a GPS and a fishfinder, a dual emergency VHF radio, and an AIS (Automatic Identification System).

Jamaica Sailing Adventures will provide you with the fishing gear, and also serve cool drinks and snacks so all you have to bring is sunscreen. You’ll also enjoy the shade provided by the T-Top, and the music onboard. Come and enjoy your Jamaican sailing adventure aboard a beautiful boat with an experienced captain who will go above and beyond to make your trip a lasting memory.

Select date to see available trips and rates:

  • Private trip
    Full Day Trip - Sail, Fish, Snorkel
      FREE Cancellation 14 days notice
    8 hours trip, starts at 7:00 AM
    US$ 700
    up to 6 persons
    + US$ 75
    each additional person
    On the full day trip, you will have plenty of opportunities to troll under sail, targeting Mahi Mahi and other species. Afterward, you will stop at a reef for bottom fishing or snorkeling. Maximum 20 people.
  • Private trip
    Half Day Trip - Sail, Fish, Snorkel
      FREE Cancellation 14 days notice
    4 hours trip, starts at 8:00 AM
    US$ 550
    up to 6 persons
    + US$ 50
    each additional person
    On this trip, you will sail around the Island, while trolling with lures. Then, you will stop at a reef for a chance to spearfish. Maximum 20 people. You will target Mahi Mahi, Marlin and other species that swim in the local waters.
There are 3 people looking at this charter.

About this listing

Targeted Species

Dolphin (Mahi Mahi)
King Mackerel (Kingfish)
Tuna (Yellowfin)

Boat Specs

Endeavour (Other) originally built in 1981, and restored in 2014. Powered by a 56HP Yanmar engine, with a maximum cruising speed of 7 knots.

40 ft
8 persons

Types of Fishing

Offshore Fishing
Reef Fishing

Fishing Techniques

Heavy Tackle


Life Jackets
Snorkeling Equipment
Spearfishing Equipment
Ice Box
Life Jackets
Snorkeling Equipment

Trip Includes

Rods, reels & tackle
Catch cleaning & filleting


FREE Cancellation
You can cancel or change your booking free of charge up to 14 days before the trip date.
Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
No Smoking
You Keep Catch


Book with 15% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.
Pay remaining balance to captain
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:

About the Captain

Christopher Pinto
Montego Bay, Jamaica
Member since November 2016
Captain Chris is a fully licensed captain with over 25 years of experience and holds a 100 ton US Coast Guard license. He is also a PADI rescue diver, so he knows CPR and is able to advise on boat handling, navigation and has even taught sailing at the Caribbean Maritime Institute. He is a fun and relaxed person who loves the sea and taking his guest sailing.
Response time: 2 hours
Response rate: 100%

Montego Bay Fishing Calendar

Customer Reviews

5 out of 5 stars from 1 review

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Our family enjoyed spending half of our day with Capt. Pinto and Wanda.  The snorkeling was amazing at two different locations.  Sadly, we did not get a single bite on the fishing line.  Capt. Pinto took very good care of us with water and sodas as well as Jamaican snacks; they were very informative about other excursions in Montego Bay as well as other parts of the island (like Ocho Rios).  We were especially thankful that they gave us advice to go to the Progressive supermarket to buy spices and Jerk sauce we wanted to take home for ourselves and as souvenirs—-MUCH MUCH cheaper at the Progressive.  Overall, it was a gorgeous day spent with a very nice couple!  We would definitely do this again and recommend sailing with Capt. Pinto to anyone interested in snorkeling and fishing!

Fished December 21, 2017
Christopher Pinto (The Captain)
Replied to this review on December 24, 2017

Thanks for the wonderful review and it was a pleasure to meet you all.Thanks for choosing Jamaica Sailing Adventures. Hope to see you again soon.Capt Chris and Wanda.

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  • Crew
  • Overall