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Compliments of the season and ideas for your 2025 sailing holiday Learn More

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

  • Modern Consumer Tech on Sailing Charter: do we really need it?

    Modern Consumer Tech on Sailing Charter: do we really need it?

    When thinking about a sailing holiday, it’s natural to wonder whether to bring our modern gadgets along for the ride - or leave them behind entirely. Technology is so deeply woven into the fabric of our daily routines. So should we pack our tablets and smartphones or is a sailing charter the perfect opportunity to fully disconnect and reset?

  • Gulet vs. Catamaran: which is the Best Charter Boat for you?

    Gulet vs. Catamaran: which is the Best Charter Boat for you?

    Planning a sailing holiday in the Mediterranean is a dream come true for many, with its crystal-clear waters, historic ports, and sun-soaked islands. Once you’ve chosen your destination, there’s still a crucial decision to make: should you charter a classic Turkish gulet or opt for a modern catamaran? Both offer unique experiences, so let’s dive into a comparison to help you make an informed choice for your group’s holiday.

  • Chartering with a Crew: the Options and all the Advantages

    Chartering with a Crew: the Options and all the Advantages

    A sailboat charter that includes a paid crew can mean different things: a crewed bareboat with your party joined by freelance skipper and sometimes cook; a boat that must have a skipper included, and the full-service charter with permanent, professional crew attached.

  • Sailing charter versus resort stay: comparing the costs

    Sailing charter versus resort stay: comparing the costs

    A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

  • Charter catamarans for modest sailing holiday budgets

    Charter catamarans for modest sailing holiday budgets

    Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

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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 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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