• Drift with the trade winds...

    From one white sandy cove to the next, plunge into the clear waters or swing from a hammock in the breeze; enjoy a little activity (if you choose) and a hefty dose of relaxation.

  • Just Kick-Back & Enjoy the sail... or...

    Participate in as much or as little as you like: from perfecting their knot vocabulary to peering knowledgeably at our charts. Whatever you chose, you crew will ensure that your every need is catered for.

  • Memorable Family events or Celebrations

    Allow Drake to create a memorable experience for your vacation or special event.

  • We can't wait to tell you all about our amazing trips!

    Just fill out our booking form now to reserve you place without making a formal commitment. Then let us manage your perfect sailing holiday of a lifetime! Booking Form...

Crewed Luxury Sailing No Experience Necessary Tailor Made Call or Book Now!

Welcome to
The Drake Academy

Drake Sailing

Crewed Yacht Charters in the Caribbean & Beyond

A Drake Sailing holiday is not simply the sum of it’s carefully crafted parts; the yacht, the location, the sailing, the skipper, fellow guests; the food, the laughter, the friendship, the bonding… it is all those, but more than that, it’s the symphony, the journey, it’s the small things - most of all it’s the memories.

Drake Sailing provide:

• Crewed Sailing Holidays

• Corporate Sailing Events

• Cabin Charters & Berth Charters

• Regattas

• Bareboat Charter holidays


Relax just as hard as you like...
with a Drake Sailing Holiday

Christopher J Lait  | Founder | Drake Sailing

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