Sail the Americas

A New World of Holiday Sailing 

From Chesapeake Bay in the north to Costa Verde in the south, a wide range of American sailboat charter locations await. From ports of call as diverse as urban Annapolis, remote and spectacular desert island landscapes in the Gulf of Cortez, idylic western Caribbean cays along the world's second largest barrier reef, and the Atlantic rainforest of Serra da Bocaina National Park, there are plenty of safe, secure and reliable offerings for avid sailors to seek out adventure on bareboat and crewed charters in North, Central and South America. 

Year-Round Sailing, with Two Continents to Choose from 

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

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The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

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The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.