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Fair Wind Sailing offers a relaxed and personalized way to experience the stunning waters of Bermuda. Based in historic St. George’s, Fair Wind Sailing provides private sailing charters that allow guests to explore Bermuda’s coastline at their own pace while enjoying the comfort and tranquility of a private boat experience.

Led by experienced sailors Captain Chloe and Serge, who bring a combined 30 years of experience in the sailing and charter industry, Fair Wind Sailing is dedicated to creating memorable experiences on the water. Guests can enjoy a scenic sail around St. George’s Harbour, admire the historic town from the water, or venture farther out toward Castle Roads and Bermuda’s South Shore for a more adventurous experience.

The company offers flexible charter options that can be customized around your schedule and interests. The popular 2-hour Harbour Sail is ideal for sightseeing and relaxing, while longer 3-hour trips can include time for swimming. For guests looking to explore farther, Castle Roads excursions require at least four hours.

Fair Wind Sailing is licensed for up to 10 passengers and can accommodate beverages, snacks, or lunch onboard, making it an excellent choice for couples, families, friends, celebrations, and private groups.

From $600

per person

Free cancellation up to 24 hours before the experience starts (local time)
Reserve Now and Pay Later – Secure your spot while staying flexible
Book ahead!

On average, this is booked 23 days in advance.

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Cancellation Policy

Free cancellation

100% refund
No refund
July 29 July 30

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience's start time.
  • If you cancel less than 24 hours before the experience's start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience's start time will not be accepted.
  • Cut-off times are based on the experience's local time.
Learn more about cancellations

Select Date

July 2025
Prices shown in USD ($)

Select Travelers

Traveler (Age 7-75)
Minimum: 2, Maximum: 15
5
Price varies by group size

Cancellation Policy

Free cancellation

100% refund
No refund
July 29 July 30

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience's start time.
  • If you cancel less than 24 hours before the experience's start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience's start time will not be accepted.
  • Cut-off times are based on the experience's local time.
Learn more about cancellations

Reserve Now & Pay Later

We'll reserve your spot today, and you can cancel up to two days* before your experience without making a payment. Secure your spot with ease, stay flexible, and never miss out.

How it works

1
Find your experience

Choose the experience you want knowing you can secure your spot without being locked in.

2
Make a reservation

Reserve now and pay later to secure your spot, commitment-free.

3
Choose when to pay

Come back to pay once your plans are set, or let auto-pay kick in two days* before your experience.

4
Enjoy your experience

Now you're all set! Have a great time.

Frequently Asked Questions | Terms & Conditions
*Up to 9 days depending on the booking/product