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

  • The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering

    The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering

    A peak season cabin-share sailing holiday with skipper in glorious Croatia in August. Chartering a 2020-model 47 foot sailboat for just 175€ per person per day! This is the reality aboard the Sun Loft Monocat 47: a whole new concept in group charter with friends or extended family.

  • Bareboat Luxury at an Affordable Price: Crunching the Numbers

    Bareboat Luxury at an Affordable Price: Crunching the Numbers

    In 2019 the Bali 5.4 catamaran entered charter fleets with the bareboat option added. Until now such a large boat was only available with paid skipper and crew. This is a significant development in yacht chartering: it continues a recent trend towards larger boats progressively coming into charter on a self-skipper basis.

  • Whale Watching on Charter in New Caledonia

    Whale Watching on Charter in New Caledonia

    Winter is the season for spotting humpback whales in New Caledonia’s southern lagoon. The calves are starting to learn the ways of the ocean while still safely under mother’s watchful eye. The lagoon offers the perfect location for observation, whale watching a highlight of any New Caledonia boat charter

  • 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.

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.