Sail the Americas

Discover the Americas

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. 

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

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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Latest Blog Posts

  • Going Charter Sailing? Why you should use a Broker

    Going Charter Sailing? Why you should use a Broker

    Bareboat and crewed boat sailing holidays are growing in popularity the world over. Every year new destinations open up and more of the latest designs in catamarans, monohull yachts, powered and motorsailer craft come into service for charter. With this growth come more ways to arrange your charter sailing holiday.

  • Sailing in the Marquesas Islands: the Ultimate Escape

    Sailing in the Marquesas Islands: the Ultimate Escape

    The Marquesas Islands group is the sort of place dreams of a tropical island escape are made for. Dreams are one thing, but getting there and experiencing these remote and unspoiled volcanic islands is another. The Marquesas lie some three hours’ flying north from Tahiti.

  • Sailing Qualifications Required by Port Authorities

    Sailing Qualifications Required by Port Authorities

    As part of our charter broker service we ensure your skipper status is approved by local port authorities before we pass your deposit to the boat's operator. Lately certification requirements in some locations have been tightened and minimum qualifications are coming under scrutiny. Here's our latest information on this.

  • Huahine: Something Special in Tahiti's Society Islands

    Huahine: Something Special in Tahiti's Society Islands

    A sailing holiday charter in Tahiti offers up the idyllic Society Islands, where most charters are sailed from Raiatea return. Other options include a one-way charter from Huahine to maximise downwind sailing. Add a short land-based Huahine stay and get the very best out of your Society Islands charter.

  • Charter a Gulet: Luxury Cruising in Classical Style

    Charter a Gulet: Luxury Cruising in Classical Style

    For your next sailing holiday, particularly in the eastern Mediterranean but in some other surprising places as well, consider chartering a gulet. Today's gulet is now a modern charter boat built for a unique vacation experience enjoyed in complete passenger comfort and luxury living aboard.

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.