Sail Pass

Committed to sailing but not ready to buy a yacht? Try Sail Pass. Sail Pass offers you the most flexible way to get out on the water sailing in the US, Caribbean, and the Mediterranean, with the largest fleet and the most exciting destinations available in a single offering.

Our annual passes offer great value compared to the average prices for high and low-season charters. With Sail Pass you can sail up to three times within 12 months for one annual price. 

Choose your Pass

Sail Pass

Sail up to three times within 12 months – 2 weeks x low season + 1-week x high season – or three weeks for one annual price (some restrictions apply). All you have to do is choose your yacht type and size. Easy!

Sail Pass Maxi

Sail 3 weeks x high season and 3 weeks x low season within 12 months (some restrictions apply to depend on the Pass you choose, Extensive or XL). Choose any yacht type and size for one annual price. Anchors away!

How it works

  • Choose your pass – Sail Pass or Sail Pass Maxi – some exclusions apply for dates and destinations.
  • Choose your yacht type and size, and schedule an appointment with one of our trip planners.
  • Start planning your dream vacation knowing you got a great deal!
We are here to help you!

Sail Pass - Monohulls

Monos up to 41
Sail Pass - Monos up to 41 ft.


Sail Pass - Monos 42-46 ft.


Sail Pass - Monos 47-52 ft.


Sail Pass - Catamarans

Sail Pass - Cats up to 40 ft.


Sail Pass - Cats 41-43 ft.


Sail Pass - Cats 44-47 ft.


Sail Pass - Maxi

Maxi Pass


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Destinations reviewed

“Boat great. Beautiful beaches, helpful base –
thanks for everything!”

Peter, Maya Riviera charter, Jan 2021

“Outstanding service and excellent base manager. Professional and great attitudes.”
Lynn, Key West charter, Jan 2021

“We just got off your Lagoon 52F. We had the trip of a lifetime cruising around St. Thomas and St. John!” 
Megan, USVI charter, 2020

“Amazing staff and incredible sailing location in the Exumas. The friendliest base staff I’ve ever encountered.”
Mike, Exumas charter, Jan 2021