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U Sail Castle Harbour at Rosewood Bermuda offers an exciting range of sailing and watersports experiences in the beautiful, sheltered waters of Castle Harbour. Operating in partnership with Rosewood Bermuda and Tucker’s Point Club, this family-run watersports centre welcomes resort guests, club members, and the local community for memorable experiences on the water.

Whether you are completely new to watersports or an experienced sailor looking to improve your skills, U Sail provides activities for a wide range of abilities. Guests can enjoy beginner sailing, windsurfing, kayaking, stand-up paddleboarding, rowing, and specialized foiling activities. Equipment hire is also available for visitors who prefer to explore Castle Harbour independently, while instructor-led sessions provide personalized guidance and skill development.

For beginners, taster sessions are an excellent introduction to sailing and watersports, allowing participants to learn in a safe and supportive environment. More experienced guests can take advantage of advanced sailing, windsurfing, and foiling sessions, while families and younger visitors can participate in youth programs designed to build confidence and practical skills.

U Sail is also an accredited Royal Yachting Association training centre, offering internationally recognized sailing and windsurfing courses. With beautiful surroundings, professional instruction, quality equipment, and calm waters, it is an excellent choice for families, couples, groups, and watersports enthusiasts.

From $40

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.