Captain Blacks Tours 

5.0
(1 review)
 58 Well Road, Cole Bay, Sint Maarten–

Captain Blacks Tours 

Cole Bay, Sint Maarten
–
31 feet
8
5.0
(1 review)

Explore the Caribbean with Captain Blacks Tours

Depart from Cole Bay with Captain Blacks Tours and experience the beauty of the Caribbean through unforgettable island adventures. Led by the experienced Capt. Dilan Penn, each trip is designed to showcase the best of Sint Maarten and its neighboring islands.

Whether you’re looking for an exciting island-hopping excursion, a scenic coastal cruise, a snorkeling adventure, or a relaxing day on secluded beaches, every charter is customized to create an unforgettable experience. Swim in crystal-clear waters, discover vibrant marine life, or simply unwind while taking in the breathtaking Caribbean scenery.

For an even more enjoyable day on the water, optional add-ons such as drinks, lunch, snacks, and snorkeling equipment are available to enhance your experience.

Captain Blacks Tours welcomes families, couples, and groups. Children, pets, alcohol, and swimming stops are all welcome, giving you the freedom to enjoy your adventure exactly the way you want.

Your safety is always our top priority. Every tour is operated with essential safety equipment onboard, including GPS navigation, VHF radio, life jackets, and other required safety gear, ensuring a safe and worry-free experience from start to finish.

Book your adventure with Captain Blacks Tours today and discover the thrill, beauty, and freedom of exploring the Caribbean’s most stunning waters.

Explore the Caribbean with Captain Blacks Tours

Depart from Cole Bay with Captain Blacks Tours and experience the beauty of the Caribbean through unforgettable island adventures. Led by the experienced Capt. Dilan Penn, each trip is designed to showcase the best of Sint Maarten and its neighboring islands.

Whether you’re looking for an exciting island-hopping excursion, a scenic coastal cruise, a snorkeling adventure, or a relaxing day on secluded beaches, every charter is customized to create an unforgettable experience. Swim in crystal-clear waters, discover vibrant marine life, or simply unwind while taking in the breathtaking Caribbean scenery.

For an even more enjoyable day on the water, optional add-ons such as drinks, lunch, snacks, and snorkeling equipment are available to enhance your experience.

Captain Blacks Tours welcomes families, couples, and groups. Children, pets, alcohol, and swimming stops are all welcome, giving you the freedom to enjoy your adventure exactly the way you want.

Your safety is always our top priority. Every tour is operated with essential safety equipment onboard, including GPS navigation, VHF radio, life jackets, and other required safety gear, ensuring a safe and worry-free experience from start to finish.

Book your adventure with Captain Blacks Tours today and discover the thrill, beauty, and freedom of exploring the Caribbean’s most stunning waters.

Dilan Penn
Captain
Dilan Penn
responds within an hour

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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4 Hr – Sint Maarten Sunset Cruise
FREE Cancellation 3 days notice
4 hour trip starts at 3:00 PM
US $500
Private tour: up to 8 people
4 Hour – Sint Maarten Adventure
FREE Cancellation 3 days notice
4 hour trip starts at 9:00 AM
US $600
Private tour: up to 8 people
4 Hour – Anguilla Island Adventure
FREE Cancellation 3 days notice
4 hour trip starts at 8:00 AM
US $700
Private tour: up to 8 people
6 Hour – Sint Maarten Adventure
FREE Cancellation 3 days notice
6 hour trip starts at 8:00 AM
US $800
Private tour: up to 8 people
4 Hour – St. Barths Adventure
FREE Cancellation 3 days notice
4 hour trip starts at 8:00 AM
US $900
Private tour: up to 8 people
6 Hour – Anguilla Island Adventure
FREE Cancellation 3 days notice
6 hour trip starts at 8:00 AM
US $980
Private tour: up to 8 people
6 Hour – St. Barths Adventure
FREE Cancellation 3 days notice
6 hour trip starts at 9:00 AM
US $1,000
Private tour: up to 8 people
8 Hour – Sint Maarten Adventure
FREE Cancellation 3 days notice
8 hour trip starts at 9:00 AM
US $1,100
Private tour: up to 8 people
8 Hour – Anguilla Island Adventure
FREE Cancellation 3 days notice
8 hour trip starts at 9:00 AM
US $1,200
Private tour: up to 8 people
8 Hour – St. Barths Adventure
FREE Cancellation 3 days notice
8 hour trip starts at 8:00 AM
US $1,500
Private tour: up to 8 people
There is 1 person looking at this charter.

Customer reviews

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Rating

5.0
(1 review)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (1)

Showing 1 – 3 of 3 reviews
Zoe Glanville
Zoe Glanville
us
Chicago, IL, US
•
Member since 2026
The captain canceled
September 5, 2026
Trip was supposed to happen on September 5, 2026

The charter operator canceled on trip date. This is an automated posting.

Kirsten Drumea
Kirsten Drumea
Repeat customer
us
Tennessee, US
•
Member since 2025
•
2 trips
5.0
Verified
Amazing Sunset Cruise
4 Hr – Sint Maarten Sunset Cruise on May 2, 2026 • 8 adults

From the beginning of the booking until we returned from our cruise, Captain Dilan was amazing! I’m a travel agent and I booked these guys for my group of 8! The captain answered all of my questions promptly. Carnival was extremely busy and we had a difficult time getting the pick up executed, but that was understandable bc of traffic he could not get to us but we jumped in a taxi and he waited patiently for our arrival. He took us over to the French side where we docked and watched the planes fly over the mountains. We swam, drank champagne and had the time of our lives watching the sunset! I give these guys a 10 out of 10! I’m definitely booking again

Dilan Penn
Response from Captain

Thanks so much Kirsten! We’re glad you and your group loved the sunset cruise with us. We appreciate you for the 10/10 and recommendation — can’t wait to have you back on board! 🌅

David Gross
David Gross
us
Texas, US
•
Member since 2025
The captain canceled
July 15, 2026
Trip was supposed to happen on July 15, 2026

The charter operator canceled on trip date. This is an automated posting.

FAQs about Captain Blacks Tours

Captain Blacks Tours offers the following trips to customers:
  • US $500 per group - 4 Hr – Sint Maarten Sunset Cruise (4 hours)
  • US $600 per group - 4 Hour – Sint Maarten Adventure (4 hours)
  • US $700 per group - 4 Hour – Anguilla Island Adventure (4 hours)
  • US $800 per group - 6 Hour – Sint Maarten Adventure (6 hours)
  • US $900 per group - 4 Hour – St. Barths Adventure (4 hours)
  • US $980 per group - 6 Hour – Anguilla Island Adventure (6 hours)
  • US $1,000 per group - 6 Hour – St. Barths Adventure (6 hours)
  • US $1,100 per group - 8 Hour – Sint Maarten Adventure (8 hours)
  • US $1,200 per group - 8 Hour – Anguilla Island Adventure (8 hours)
  • US $1,500 per group - 8 Hour – St. Barths Adventure (8 hours)
When you book a trip with Captain Blacks Tours, you can expect the following amenities onboard:
  • GPS
  • VHF Radio
  • Anchor
  • Wheel Steering
  • Life Jackets
  • Bimini
  • Audio System
  • Outside Speakers
  • Ice Box
Trips booked with Captain Blacks Tours include:
  • Snorkeling Equipment
  • Snacks
  • Drinks
  • Lunch
Captain Blacks Tours offers the following activities:
  • Boat & Yacht Tours
  • Island Hopping
  • Snorkeling & Diving Tours
  • Sandbar Tours

Your operator

Dilan Penn
Dilan Penn

Cole Bay, Sint Maarten

3 Customer reviews
Response time within an hour
Member since January 2026

Capt. Dilan Penn is the experienced captain behind a Vendette Guepard G31 based in Cole Bay, offering unforgettable days on the water. He specializes in boat tours, island hopping, and snorkeling trips, guiding guests to some of the most beautiful spots and crystal-clear waters in the area. With a passion for the sea and local knowledge, Capt. Dilan ensures every trip is fun, relaxing, and memorable.

Our Team
Luis Enrique S.

Luis Enrique S.

Captain

Dilan Penn
Dilan Penn
3
reviews
2026
member since
~1h
response
Capt. Dilan Penn is the experienced captain behind a Vendette Guepard G31 based in Cole Bay, offering unforgettable days on the water. He specializes in boat tours, island hopping, and snorkeling trips, guiding guests to some of the most beautiful spots and crystal-clear waters in the area. With a passion for the sea and local knowledge, Capt. Dilan ensures every trip is fun, relaxing, and memorable.
The crew
Luis Enrique S.
Luis Enrique S.
Captain

What the boat is like

Boat category
Center console boats
Boat type
Center console
Boat manufacturer
Vendette Guepard
Boat Model
G31
Year built
2010
Restored in
2025
Boat length
31 ft
Capacity
8 persons
Engine model
Mercury
Max crusing speed
60 knots
Powered by
2 x 300HP
Engine Type
Outboard
Fuel Type
Gas
Boat category
Center console boats
Boat type
Center console
Boat manufacturer
Vendette Guepard
Boat Model
G31
Year built
2010
Restored in
2025
Boat length
31 ft
Capacity
8 persons

Which kind of activities are offered

Boat & Yacht Tours
Island Hopping
Snorkeling & Diving Tours
Sandbar Tours

Which amenities are available onboard

GPS
VHF Radio
Anchor
Wheel Steering
Life Jackets
Bimini
Audio System
Outside Speakers
Ice Box

What’s allowed on the boat

Child Friendly
No age limits.
Smoking
Alcohol
Glass Bottles
Shoes
Pets
Swimming
Red Wine
What's included in the trip price
Snorkeling Equipment
Snacks
All Trips included Snacks And drinks On Request Of Our Customers
Drinks
Our Guests Drink What Ever They Request For us To Get For Them
Lunch
Lunch Can Be provided by a private catering or local business

What additional terms you should be aware of

Security deposit of US $380 per tour is required

A refundable deposit of US $380 per tour is required at boat pick-up and will be returned to you when the boat is returned without damage. Security deposit is to be paid directly to the charter operator.


Fuel is included

Fuel is included in the price of the rental.

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 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 10% booking deposit, pay the captain the rest

When the captain confirms your trip, BoatBooker charges your credit card a 10% 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:

 PayPal

 Bank transfer

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/5
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