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How to Charter a Yacht in the Caribbean

Have you ever thought about chartering a yacht?  They are surprisingly affordable if you gather a few fun friends!  It helps if you know a travel professional who has a relationship with a great wholesale charter company like Carefree Charters (.com!)  Considering that a 6-night cruise with your captain and chef can sleep 6-10 or even 12 and costs from $17,000 to about $30,000 for deluxe catamarans or mono-hulls, you can see the value and the possibilities!

Once you choose the beautiful vessel that most fits your needs, the additional costs will include gratuities for the staff and your airfare and transfers.  If traveling in the winter, you will also want to reserve at least one night pre-cruise in your destination; you know, just in case your flight is delayed or cancelled due to a weather event.  Most of the vessels that Carefree charters will have an embarkation port in either St. Thomas or Tortola.  This is an easy short hopper flight from San Juan, making it possible to connect from any city in the US and Canada.

Carefree Yacht Charters

What They Do:  Straight from their website (photos courtesy of Carefree YC)

Carefree Yacht Charters® is a boutique yacht charter company distinguished by service, quality charters, and client experience. We specialize in luxury crewed catamaran charters in the BVI, USVI, Bahamas and other Caribbean destinations. The majority of our luxury crewed catamaran charters are all inclusive, starting at around $15,000 per week and up to $65,000 per week, plus tip. Learn more about our crewed yacht charter costs.”


A catamaran is a great choice because it has wider spaces, forward trampolines, typically 3-5 staterooms, and has great stability under sail.  Feel free to browse the different options on the website to find your perfect match.

Power Catamarans

You will love the power catamarans and motor yachts for their popular fly-bridge , lux appointments and superb stability.  Browse here for your own!

Monohull Sailboats

“Classic sailing experience: Guests will feel the true power of the wind aboard a monohull sailing yacht. These yachts heel over while sailing, providing an adventurous and exhilarating sailing experience.

Traditional features: These yachts offer their guest wonderful character and charm, plus typically traditional features and amenities.

Owner/Operators: A large majority of our monohull sailboat charters are crewed by the owners of the yacht, which in some cases can provide guests with an added level of attention.”

Ready to plan?    Gather your friends or family and let’s choose your favorite together soon.

Peace, Bobbie