- 5 h
- 6 max
+$60pp (max 16)
Reserve with $ 310 deposit
Total $ 1550
✓ Wind-dependent availability
- 5 h
- 6 max
+$60pp (max 16)
Reserve with $ 310 deposit
Total $ 1550
✓ Wind-dependent availability
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- HALF DAY — SXM Caribbean Breeze Sail
HALF DAY — SXM Caribbean Breeze Sail
- Private Boat Charter
- Simpson Bay
- 5 h
- 6 max
Overview
Private Charter
Small Group Adventure
Breezy Coastal Cruise
Swim & Snorkel Stops
Relax & Chill Vibes
Enjoy a private half-day sailing adventure along the coast of St Maarten that blends relaxed cruising, swimming, and scenic island views. Aboard a comfortable sailing trimaran, this experience offers an easygoing escape with time to unwind on the water.
From
$ 1275
+$60pp (max 16)
Secure with a $ 253 deposit
✓ Limited slots — confirm early
Balance paid on the day
Simple & transparent booking
How booking works
- We confirm availability with your captain after your request
- Pay the balance only once your booking is confirmed
Why you’ll love this experience
- You enjoy a personalized, small-group sailing experience.
- You relax on a spacious trimaran with cushioned seating and shaded areas.
- You swim and snorkel in calm Caribbean bays.
- You savor a freshly prepared lunch with drinks served throughout the trip.
- 5 hours
- 6 max
- Simpson Bay
- 56 ft Trimaran
- Private Boat Charter
- Private sailing charter with licensed captain
- Water, sodas, juices, beer, white wine, and rum punch
- Gourmet sandwich lunch
- Snack and tropical fruit platter
- JBL mobile speaker available
- Snorkeling stop and safety gear
To secure your charter, you’ll pay a small deposit online through our secure checkout powered by Stripe or PayPal.
We accept all major credit cards — Visa, Mastercard, American Express, and Discover — as well as Apple Pay, Google Pay, and PayPal for fast and flexible deposit payments.
The remaining balance is due on the day of the charter and may be paid by card in USD or in cash in USD.
All bookings are covered by our clear and fair cancellation policy.
You may cancel up to 48 hours before the scheduled departure time and receive a full refund of your deposit.
Bookings cancelled less than 48 hours before departure are non-refundable. The deposit secures the reservation of the boat, captain, and time slot specifically for your group.
If an activity cannot operate due to unsafe weather conditions, as determined by the captain, we will assist with rescheduling or provide a full refund.
Full activity terms and guest information can be found here: explr.sx/activity-terms.
Depart from Simpson Bay and settle into a relaxed half-day sail along St Maarten’s picturesque coastline. The spacious trimaran features open trampolines and comfortable seating, creating an inviting setting to enjoy the sea breeze and island scenery.
After a gentle cruise, drop anchor in a calm bay for swimming and snorkeling in clear Caribbean water. While you enjoy the water, a fresh gourmet sandwich lunch is prepared on board and served with a selection of drinks.
Following lunch, enjoy a leisurely sail back toward Philipsburg, drinks in hand, as the rhythm of the sea and warm trade winds set the tone for a laid-back and memorable island experience.
Not quite right? Consider these options
Closest match
Shorter option
- 2 h
- 8 max
+$20pp (max 16)
Reserve with $ 130 deposit
Total $ 695
✓ Very limited daily slots
- 2 h
- 8 max
+$20pp (max 16)
Reserve with $ 130 deposit
Total $ 695
✓ Very limited daily slots
Different experience
- 2 h
- 8 max
Price per jet ski
Reserve with $ 40 deposit
Total $ 200
✓ Availability confirmed
- 2 h
- 8 max
Price per jet ski
Reserve with $ 40 deposit
Total $ 200
✓ Availability confirmed
Already on the island?
If you’re planning something for today or tomorrow, we can sometimes help with last-minute private boat charter options.
Trusted by guests visiting St Martin & Sint Maarten
From first message to the day of the experience, guests consistently highlight how smooth and well organised everything feels.
“Everything was thoughtfully organised from start to finish, especially travelling with two young children. We felt completely looked after on the day, and the experience was both safe and unforgettable. Communication was excellent throughout, which gave us real peace of mind.”
- Chelsey
- March 2026
- USA
- Verified Guest
“Everything felt easy and smooth from booking through to the day itself. The experience was well planned but still flexible, which made it perfect for our group. We had an amazing time in Anguilla and would highly recommend it.”
- Kristen
- April 2026
- USA
- Verified Guest
“An incredible day on the water and one of the highlights of our trip. Everything was perfectly organised, with great attention to detail throughout — including an amazing meal and thoughtful care for dietary requirements. The whole experience felt effortless.”
- Stefani
- April 2026
- USA
- Verified Guest
“The highlight of our two weeks in St Maarten. We were a large group with kids and everything was incredibly smooth and completely stress-free. Communication was excellent and we felt looked after from start to finish.”
- Marcus
- September 2025
- USA
- Verified Guest
“Very professional and reliable from start to finish. The whole day was easy, well organised, and a lot of fun — exactly what we were hoping for.”
- Sara
- January 2026
- USA
- Verified Guest
“An absolutely amazing day and a perfect experience for our family. Everything felt smooth and effortless, and it’s something we’ll remember for a long time.”
- Lauren
- March 2026
- USA
- Verified Guest
Based on the island. Here to help.
Local experts
Direct support
7 days a week
You might also like
- 8 h
- 8 max
+$125pp (max 12)
Reserve with $ 469 deposit
Total $ 3125
✓ Weather-dependent availability
- 8 h
- 8 max
+$125pp (max 12)
Reserve with $ 469 deposit
Total $ 3125
✓ Weather-dependent availability
- 7 h
- 10 max
Reserve with $ 250 deposit
Total $ 1250
✓ Confirmed with your captain
- 7 h
- 10 max
Reserve with $ 250 deposit
Total $ 1250
✓ Confirmed with captain
- 5 h
- 6 max
+$60pp (max 16)
Reserve with $ 253 deposit
Total $ 1275
✓ Limited slots — confirm early
- 5 h
- 6 max
+$60pp (max 16)
Reserve with $ 253 deposit
Total $ 1275
✓ Limited slots — confirm early
Most Booked
- 7 h
- 12 max
Reserve with $ 430 deposit
Total $ 1720
✓ Weather-dependent availability
Most
Booked
- 7 h
- 12 max
Reserve with $ 430 deposit
Total $ 1720
✓ Weather-dependent availability
- 4 h
- 8 max
+$125pp (max 12)
Reserve with $ 225 deposit
Total $ 1125
✓ Limited slots — confirm early
- 4 h
- 8 max
+$125pp (max 12)
Reserve with $ 225 deposit
Total $ 1125
✓ Limited slots — confirm early
- 3.5 h
- 11 max
Reserve with $ 263 deposit
Total $ 1313
✓ Confirmed with your captain
- 3.5 h
- 11 max
Reserve with $ 263 deposit
Total $ 1313
✓ Confirmed with captain
Need help choosing the right charter?
Not sure if this is the right option?
We’re happy to help you choose based on your dates, group, and what kind of day you’re looking for.
Plan your boat day with confidence
Helpful guides to make planning easier.
→ Typical prices and what to expect for each option.
→ The best options for couples and small groups.
→ Ideal for quick access to Tintamarre, Pinel and calm waters.
→ Safety standards and what to look for.
