- 5 h
- 6 max
+$60pp (max 16)
Total
from
$ 1550
• Wind-dependent availability
- 5 h
- 6 max
+$60pp (max 16)
Total
from
$ 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
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 just $ 253 deposit
• Limited slots — confirm early
Not sure this is the right option?
• Balance payable on the day
High season note
This is a private charter operated by an individual boat.
Once your booking is matched to a specific captain and vessel, that boat can only run one charter per day.
During high season, private boat charters around St Maarten / St Martin often book several days in advance, particularly for weekends and calm sea days.
After you request your date, we confirm live availability with the captain operating your charter.
You’ll receive confirmation before paying anything beyond the initial deposit.
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)
Total
from
$ 695
• Very limited daily slots
- 2 h
- 8 max
+$20pp (max 16)
Total
from
$ 695
• Very limited daily slots
Different Experience
- 2 h
- 8 max
Price per jet ski
Total
$ 200
• Confirmed with captain
- 2 h
- 8 max
Price per jet ski
Total
$ 200
• Confirmed with captain
Based on the island. Here to help.
Local expertise
Direct support
7 days a week
We know the island and help you choose what actually works while you’re here.
Contact us anytime via bookings@explr.sx or WhatsApp +1 721 526 1049.
We’re available 7 days a week.
Already on the island?
If you’re planning something for today or tomorrow, we can sometimes help with last-minute private boat charter options.
Guest Reviews
Our activities turn dream days into real memories — hear from guests who’ve lived it!
"Our boat day out with EXPLR.SX was the highlight of our trip. Raymond made everything easy. Easy planning and great local tips. Highly recommend."
"So glad we booked our boat tour through EXPLR.SX. It felt personal, not touristy, and the whole day went smooth and was a lot of fun"
"EXPLR.SX delivered exactly what we wanted: a private boat trip with a fantastic captain. We explored hidden spots we’d never have found on our own."
"Best decision of our vacation. The boat was perfect, the crew was great, and we got to avoid the crowded tours. We’ll definitely book again."
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Compare Boat Options & Island Transfers
Compare the best boat options, transfers, and experiences in St Martin and Anguilla. These guides help you choose the right option based on your trip, group size, and preferences.
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