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Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$180
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$180
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$410
Sailboats
Set sail with these traditional wind-powered boats
$410
KI
Katie
Discover the Island's, South Paradise aboard our Bayliner 2659 Rendezvous Boat!!
We had the best day with CayTrips. Being out on the water with our own boat felt easy and fun from start to finish. It was just the three of us celebrating a birthday, and Captain Oscar and First Mate Allie made it special. They were warm, attentive, and genuinely cared about every detail - and were flexible with the itinerary. They had fresh fruit, drinks, and sandwiches ready for us. Then they surprised the birthday boy with cupcakes and got everyone singing. Such a thoughtful touch. The boat was incredibly spacious, more than enough room for our group and plenty of space for a larger group too. A perfect day on the water. We will be talking about this one for a long time.

Jacob
Private Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'
José and first mate were phenomenal! Seas were a little choppy on the ride over but the ride was very smoother as they had the bow trimmed up. Lunch, snorkeling, swimming, fishing - couldn’t ask for more for us and our four year old. They watched him and fished while my wife and I snorkeled.
RC
Rocco
Private powercat 40 around saint martin, pinel, tintamarre and anguilla
Our captain did an amazing job navigating the rough seas. Everyone felt comfortable and enjoyed the experience. His recommendations for beaches to visit and how to experience the most of our time at the Anguilla beaches was perfect. He also made a great recommendation for lunch as well. He was very accommodating to our request as well. Chloe, the first mate was incredible. She made fantastic drinks, maintained the boat and was always there to assist our group in any way. Thank you both for a great day.
JK
Joanna
44ft Sailing Catamaran Charter in Bridgetown, Saint Michael
If you are thinking about booking a trip with Kirk & Caroline DO IT, you won’t be disappointed. Communication was very easy. We went snorkeling and then set sail. Very accommodating and was the highlight of our cruise.
OZ
Osmar
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Great trip. Our party of 6 really enjoyed it. We asked for a food option and they made an incredible BBQ. The snorkel equipment was great and they were very attentive through the trip.

Jocelyn
PRIVATE POWERCAT 40 AROUND SAINT MARTIN, PINEL, TINTAMARRE AND ANGUILLA
If we could give Captain Joe and Chloe, 100 stars, we would. We had the best time with them on the boat, they showed us all around the island, their hospitality is unmatched. We enjoyed it so much, we ended up booking the boat for two days instead of one. I would highly recommend them for the best experience in Saint Maarten!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

June 07, 2023
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June 18, 2021
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December 12, 2019
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August 01, 2023
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November 23, 2022
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October 03, 2022
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