- 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
Begin your afternoon sailing from Simpson Bay on a private charter that blends a refreshing swim stop with a beautiful Caribbean sunset. With calm seas, open sails, and drinks flowing, this experience offers a relaxed and elegant way to enjoy the island from the water.
from
• Wind-dependent availability
Not sure this is the right option?
• Balance payable on the day
High season note
This sunset cruise is operated by an individual private boat.
Once assigned, that vessel can only run one sunset charter per evening.
Sunset charters are very popular year-round and often book several days in advance during high season.
After you request your preferred date, we confirm availability directly with the captain operating the cruise.
Your booking is confirmed before any remaining balance is due.
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 flexible cancellation policy.
Unless otherwise stated in the activity description, you may cancel up to 48 hours before departure for a full refund of your deposit.
For weather-related changes, as determined by the captain, we’ll assist with rescheduling or provide a refund without hassle.
Set sail from Simpson Bay in the afternoon and cruise toward scenic spots such as Little Bay or Baie Rouge for a refreshing swim and snorkel stop. With clear water and a relaxed pace, the first part of the journey is perfect for cooling off and enjoying the sea.
Back on board, sweet and savory snacks are served alongside a selection of drinks as the sails are raised and the boat glides smoothly along the coast. The atmosphere is calm and social, with plenty of space to sit back and unwind.
As the sun dips below the horizon, enjoy the glowing colors of the Caribbean sky and the gentle motion of the boat under sail. With calm seas, beautiful views, and an open bar, this private charter delivers a memorable and relaxing way to spend an island afternoon and evening.
Total
from
$ 695
• Very limited daily slots
Total
from
$ 695
• Very limited daily slots
Total
from
$ 70
• Confirmed with captain
Total
from
$ 70
• Confirmed with captain
Total
$ 109
• Confirmed with captain
Total
$ 109
• Confirmed with captain
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.
Our activities turn dream days into real memories — hear from guests who’ve lived it!




Total
from
$ 563
• Limited slots — confirm early
Total
from
$ 563
• Limited slots — confirm early
Total
from
$ 1000
• Limited slots — confirm early
Total
from
$ 1000
• Limited slots — confirm early
Total
from
$ 625
• Very limited daily slots
Total
from
$ 625
• Very limited daily slots
Total
from
$ 1585
• Confirmed with captain
Total
from
$ 1585
• Confirmed with captain
Total
from
$ 1250
• Weather-dependent availability
Total
from
$ 1250
• Weather-dependent availability
Total
from
$ 3125
• Weather-dependent availability
Total
from
$ 3125
• Weather-dependent availability
We use cookies and similar technologies to enhance your experience, deliver personalized content, and analyze site traffic. By clicking "Accept" you agree to the storing of cookies on your device. You can manage your preferences or withdraw consent at any time. For more details, see our Privacy Statement below.
No payment now — we’ll confirm availability and send you next steps.
🔒 No payment now. We’ll confirm availability first.
We’ll reply with available options and next steps.
No payment required.
⏱ We usually reply within a few hours.