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Windward Side, Saba Boat Rentals

Ferry to St Barts Round Trip onboard 62' High Speed Wave Piercer in
Travel in Simpson Bay · 62 guests

Ferry to St Barts Round Trip onboard 62' High Speed Wave Piercer in

New
$100person
Cruising Catamaran Charter for Up to 65 People in St Maarten
Sailing in Simpson Bay · 65 guests

Cruising Catamaran Charter for Up to 65 People in St Maarten

New
$1,800day
Charter the 40' Santino Center Console in Simpson Bay, Sint Maarten
Powerboats in Simpson Bay · 12 guests

Charter the 40' Santino Center Console in Simpson Bay, Sint Maarten

New
$1,200day
Rent SeaGlass a 28' Mako Private Boat to Explore the Beautiful St Maarten!
Powerboats in Simpson Bay · 8 guests

Rent SeaGlass a 28' Mako Private Boat to Explore the Beautiful St Maarten!

New
$1,250day
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500day
Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends
Sailing in Simpson Bay · 20 guests

Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

5.0
Best of 2023
$1,944day
Spacious 55ft Motor Yacht perfect to discover Anguilla with your family
Events in Simpson Bay · 12 guests

Spacious 55ft Motor Yacht perfect to discover Anguilla with your family

5.0
$270hour
Powerboat Charter in Cole Bay
Powerboats in Cole Bay · 10 guests

Powerboat Charter in Cole Bay

New
$200hour
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Sailing in Simpson Bay · 16 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

New
$1,500day
Immerse yourself in paradise on Earth!
Sailing in Simpson Bay · 8 guests

Immerse yourself in paradise on Earth!

New
$1,350day
Full day around St Maarten/St Martin with Donzi 38ZF
Powerboats in Simpson Bay · 10 guests

Full day around St Maarten/St Martin with Donzi 38ZF

New
$1,512day
HALF DAY around St Maarten/St Martin. DONZI 38
Powerboats in Simpson Bay · 10 guests

HALF DAY around St Maarten/St Martin. DONZI 38

New
$1,188day
2hours SUNSET cruise St. Maarten/St. Martin
Powerboats in Simpson Bay · 10 guests

2hours SUNSET cruise St. Maarten/St. Martin

New
$270hour
Full day from Anguilla around St Barth.
Powerboats in Simpson Bay · 10 guests

Full day from Anguilla around St Barth.

New
$2,700day
Full Day from Anguilla around St. Maarten/St. Martin
Powerboats in Simpson Bay · 10 guests

Full Day from Anguilla around St. Maarten/St. Martin

New
$1,944day
Full Day from Anguilla around Anguilla Donzi 38
Powerboats in Simpson Bay · 10 guests

Full Day from Anguilla around Anguilla Donzi 38

New
$1,836day
Full Day around Anguilla. Donzi 38
Powerboats in Simpson Bay · 10 guests

Full Day around Anguilla. Donzi 38

New
$1,728day
2 Hours Terres Basses BOAT TOUR
Powerboats in Simpson Bay · 12 guests

2 Hours Terres Basses BOAT TOUR

New
$297hour
MoonDance 36' Catalina
Sailing in Simpson Bay · 6 guests

MoonDance 36' Catalina

4.7
$1,000day
Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
Sailing in Simpson Bay · 10 guests

Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

5.0
$1,150day
Private Charters In Simpson Bay or Philipsburg
Sailing in Simpson Bay · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300day
The Best Day Sail in St. Maarten
Sailing in Simpson Bay · 30 guests

The Best Day Sail in St. Maarten

New
$129day
Luxury Catamaran Trips in St Maarten and Surrounding Islands
Sailing in Simpson Bay · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0
$215person
Deep Sea Fishing Charter in St. Maarten with Captain Rudy
Fishing in Simpson Bay · 6 guests

Deep Sea Fishing Charter in St. Maarten with Captain Rudy

New
$169hour

Windward Side Reviews

  1. Mark

    Mark

    Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

    Communication could have been a little better with the captain before our trip but once on board David and Stephanie were awesome. Definetly 5 star service. The snacks and wide variety of alcohol and soft drink choices were excellent. Would book again for sure!

  2. James

    James

    Mambo 40ft Sail Catamaran

    Great experience and value. Snorkelling equipment for every member of our party! We stopped multiple times for snorkelling and to get food and the crew are amazing. They happily topped up drinks for us throughout the day and were full of energy. Highly recommend

  3. AW

    Angela

    Luxury Catamaran Trips in St Maarten and Surrounding Islands

    Choose this boat!!! I booked an 8 hour PRIVATE charter to accommodate 18 people to celebrate my husband's 50th birthday. Upon booking, Captain Neal was immediately in contact and worked to meet all of my needs. A few things to note... * If you need transportation to the dock, the Captain can recommend * The catamaran is large, to board you'll arrive by a small shuttle boat * The boat is as pictured. There is a large upper deck, under shade, with lots of seating and a lounge pad that I did not see in the pictures when I booked. It was a welcomed surprise * The food was AMAZING!!!!!!! Literally everything prepared was delicious. No one asked for additional seasoning or condiments. Everyone had seconds. I belive we had Chef Andrew. One of the best meals of our trip. * Our mate was Anna. Excellent service. She kept a drink in everyone's hands at all times without having to be asked. Pro tip... bring tumblers for your drinks to avoid spills and melting ice. * Alcohol was premium, not rail * We were able to connect our devices to the speakers on the boat. Good sound system that you can hear all over the boat. Overall excellent charter. I highly recommend and would book again.

  4. FC

    Fallon

    Luxury Catamaran Trips in St Maarten and Surrounding Islands

    I cannot say enough about our experience. When I say top notch service, captains, food and all the amenities…it was AMAZING! Book this boat if you are looking. Worth every penny. Unbelievable day on the water! This is the best way to see SM in just a day trip!

  5. SS

    Shalonda

    Luxury Catamaran Trips in St Maarten and Surrounding Islands

    Capt. Neil and his crew made my 35th Birthday yacht ride one to remember. We were able to play our music, take plenty of pictures and videos, get in the water and relax. Lunch was AMAZING😋. Everything was so good. I could not have asked for a better experience🧡🧡🧡🧡

  6. SG

    Stephanie

    Luxury Catamaran Trips in St Maarten and Surrounding Islands

    Neil was an adept captain and this was the highlight of our experience during this trip to St Marten! Neil and Anna and Bob were very helpful and accommodating during our trip, even letting us DJ for a bit of the ride. Bob is a great chef and the food was incredible for lunch (which included barbecue ribs, roasted veggies, a seafood paella, and mahi mahi) while Anna kept our drinks full. The itinerary was well timed and kept the day moving right along. This would be a great addition to anyone’s itinerary, in particular for people looking for a more mellow and relaxing day trip.