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  • Planning Your 2027 Caribbean Charter: The Dates, Seasons, and Questions Worth Sorting Out Now 

    Planning Your 2027 Caribbean Charter: The Dates, Seasons, and Questions Worth Sorting Out Now 

    A Caribbean charter has its own rhythm, and it rarely begins the week you step aboard.  It begins months earlier, with a calendar open on the kitchen table and a rough idea of when the trade winds settle in, when the water clears, and when a particular week already has your name half-attached to it.   The Caribbean…

  • Seven Days in Belize: A Crewed Charter Trip Report 

    Seven Days in Belize: A Crewed Charter Trip Report 

    By Beth Kolich, Waypoints Yacht Charters  I’ve been on a lot of boats in a lot of places, but Belize kept surprising me. Part of what we do at Waypoints is stay close to the charter destinations we offer, so our team can speak to them firsthand rather than secondhand. This trip was exactly that. I spent a…

  • What’s in a Boat Name? The Rules, the Superstitions, and the Stories Behind Our Newest Fleet 

    What’s in a Boat Name? The Rules, the Superstitions, and the Stories Behind Our Newest Fleet 

    Naming a boat is one of the first things new owners do and one of the things they think about longest. It’s a decision that gets debated at kitchen tables, crowdsourced to family group chats, and occasionally inspired by a dog.  At Waypoints Yacht Charters, we’ve watched owners arrive at names through every possible route: a word in another language, a childhood memory,…

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