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 ...

Latest Blog Posts

  • Look What's Been Happening at Sail Connections

    Look What's Been Happening at Sail Connections

    Rob's Boat Build: a Covid lockdown project where Sail Connections' Robert Cross sets out to build an 11.5m plywood composite sailboat going solo (within reason): a real DIY boatbuilding project if ever there was one

  • Welcome Back to the World of Charter Sailing

    Welcome Back to the World of Charter Sailing

    Covid-19 vaccinations are rolling out, and countries dependent on the tourist dollar are now well-equipped to manage their borders. So while the pandemic is impacting communities still, there's no question that your next sailboat vacation is getting closer every day.

  • Whiting Sailing: NZ's Seachange Experience

    Whiting Sailing: NZ's Seachange Experience

    We are pleased to get behind Whiting Sailing, and their latest sailboating service out of Auckland, home of the America’s Cup. In the Whitings, NZ has a family of sailors who place the joy of sailing and shared experience first and foremost

  • Personal Care on Charter Part II: Evading Insects & Sunburn

    Personal Care on Charter Part II: Evading Insects & Sunburn

    Some more advice on protecting your body while on your sailing holiday charter. using products that are good for the natural environment too. Also explaining our free Charter Pack offer available on every charter sailing holiday booked with Sail Connections.

  • Personal Care on Charter Part I: a Message and a Free Offer

    Personal Care on Charter Part I: a Message and a Free Offer

    Some advice on protecting your body from environmental factors while on your sailing holiday charter. Recommendations that are good for the oceans and the planet too. And a free offer to demonstrate our case, available on every Sail Connections boat charter booked.

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.

Get in Touch

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.

Download Guide

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