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Five Questions to Answer Before Your First Abaco Yacht Charter 

The Sea of Abaco has been drawing sailors for a long time, and the reasons are as clear as the Abaco water is: sailing that welcomes all experience levels, distances between cays that make island-hopping feel manageable, and small settlements with genuine character rather than resort infrastructure.   Waypoints Bahamas operates from Boat Harbour Marina in Marsh Harbour […]

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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 […]

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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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Dine on the Dock: The Waypoints Guide to Waterfront Eating in Annapolis, Maryland 

There are few dining experiences on the East Coast quite like eating on the waterfront in Annapolis, Maryland. A steaming pile of Old Bay-dusted blue crabs spread across brown paper, a cold Orange Crush in the summer heat, and the masts of sailboats swaying gently in the harbor just beyond your table. That’s a Tuesday night in Annapolis.  Tucked […]

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Seven Places to Sail with Your Kids This Summer (and Everything They’ll Learn Along the Way) 

There is a version of your kids’ summer that looks like this: a screen, a sofa, a slowly emptying bag of snacks, and a child who has technically been on holiday for six weeks but could not tell you a single interesting thing that happened.   Then there is another version, one where they come home […]

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