Live yacht life the Caribbean

Group Membership
-Private weekly sailing for up to 4 people-

or

Flex Membership
-Individual membership to weekly group sails-

  • Enjoy Vieques from the water, without the maintenance of boat ownership

  • Flexible, community-oriented sailing — for locals, travelers, and seasonal guests

  • Sail weekly from Esperanza Harbor, all season (November through April)

  • Easy, single payment + seamless scheduling

Why Club Membership?

Sailing Life isn’t a day trip — it’s a rhythm.

At Esperanza Sailing Club, we believe in community.
Whether you’re traveling, vacationing, or living in Vieques — The Esperanza Sailing Club Membership makes it simple to sail regularly, share time with people who love the sea, and enjoy the beauty of the island from a unique persepective.

Membership Options

Private Group Membership — $5,000 / season

Private weekly sailing aboard Just Today, for your group (up to 4). Enjoy the freedom and intimacy of your own boat — without the hassle of ownership.

  • 1 private sail per week (up to 4 people)

  • flexible day selection, first priority on bookings

  • 10 guest passes included

Individual Flex Membership — $1,500 / season

Prefer sailing with a community? Join our weekly Club Sail and enjoy regular time on the water alongside other like-minded sailors. Shared boat, shared vibe — same salt-air, same island horizon.

  • One spot on our designated Weekly Club Sail (shared among up to 4 members)

  • Weekly Club Sail schedule chosen weekly based on weather and member surveys

  • Non-Member guest passes available for $125 per guest*

Only 1 more Group Membership Available!

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Only 12 more Flex Memberships Available!

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Events

Sign up for a Member Preview Sail Today!

Why join Esperanza Sailing Club?

– Consistent sailing, no long-term ownership commitments
– Easy, one-time payment before the season starts
– Access to the same boat and pier all season
– A small, trusted sailing community — not a crowded charter

How It Works:

  1. Choose your plan & pay the fee

  2. Schedule your sails
    — Full Members choose a day to sail each week
    — Flex Members book their seat on club sails scheduled weekly by the captain

  3. We sail together, safe and simple, all season long!

FAQs

What if I miss a week?

Memberships are built with a generous amount of sailing days included. As such, unused days do not roll over to future weeks and cannot be “banked”.

Can I bring guests if I’m a Flex Member?

Yes! A benefit of being a member is the ability to bring your guests along for a fraction of the price of a traditional charter. Flex Members get unlimited guest passes for $125 each. Passes are not to be resold or promoted commercially. See our Terms and Conditions for more information.

What if weather cancels a sail?

If the Captain deems the weather on a scheduled sailing day to be above sailable limits, the scheduled event automatically becomes a “Harbor Hangout”, where members have access to the boat and the water but the sailboat does not leave the mooring. For more information about our sailable limits and cancellations please see our “Weather and Motion Sickness Policy”

What’s included / not included

All memberships include access to the boat and safety gear while onboard. Personal gear such as towels, drinks, sunscreen, etc., are not included. We do provide a cooler to store any ice and drinks you would like to bring.