How To Charter A Boat In The Tropics (Part 1)

There’s nothing better than sitting in front of a roaring fire when the wind is whipping, and the snow is flying, and the temps hovering in the teens up here in the Northeast…except charting a boat in the tropics when the wind is whipping, and the snow is flying, and the temps are hovering in the teens in the Northeast!

What would you rather do? Shovel snow or open a fresh coconut on the stern of a charterboat in the tropics?
What would you rather do? Shovel snow or open a fresh coconut on the stern of a charter boat in the tropics?

In fact, I believe we all feel “The Call of the Caribbean” (i.e. a physical, emotional, and spiritual compulsion to escape the bitter reality of the northern winter aboard a romantic and restorative boat–both sail or power–in a warm and exotic location). But, as I’m often reminded by some of my non-sailing friends, not everyone knows what’s required to skipper a charter boat, or where the best places to go are, or how much it costs or quite frankly where to begin their quest to find the unique rest, rejuvenation, and even the challenge, that a winter bareboat charter in the tropics makes possible.

Ahhh. You need a boat to get a beach like this all to yourself.
Ahhh. You need a boat to get a beach like this all to yourself.

Now, we all know that every worthwhile quest begins with some googling so, my goal is to me help you save some steps. And we’ll start with the basics:

You can see the world from the desck of a chatrerboat. This was our "Waterfront home" for 10 days in the hopelessly exotic Seychelles.
Charter boats provide the best water view available.

The question(s) I get asked most frequently are some variation of: How much do you need to know, or how good of a sailor do you need to be, or how much experience do you need to charter a boat?

Now, I might get in trouble for saying this but…chartering a boat is not really that hard. But, don’t start calling the safety police on me. I’m not saying that someone who’s never sailed before can waltz up to a charter base and captain a bareboat charter boat. And I’m not saying that charter companies will charter a boat without being assured that their customers are competent sailors, or that there are not real skills you need to be the captain of a charter boat.

Bikini babe on deck of boat
Sailing between tropical islands is a pretty awesome way to get a suntan, no?

But I am saying that none of those requirements are all that hard to achieve.

So, if you’re an experienced sailor (but have never chartered before) you’ll have to demonstrate that you have the skills and experience to handle all the responsibilities (and liabilities) of charting. In most areas (except for several Mediterranean destinations), no formal certification is required, but you will need to be able to prove that you can operate a chartplotter, and dock and pick up a mooring in addition to being capable of sailing and maintaining what ever size boat you are interested in. Most charter companies require charterers to complete detailed “sailing resumes” so they can understand your experience and the size boat that you can handle.

captian caroline

So, most charter companies will ask you to describe your basic sailing experience including:

How many days you’ve been the “captain” of a boat?

How many days you’ve been the “crew” of a boat?

How many days you’ve chartered before and where?

How many offshore miles you’ve sailed/raced and where?

Your general experience with docking, sailing, operating an engine, and navigating, etc.?

And what sailing courses have you completed?

And if you’re an aspiring charterer, the best way to gain experience is to charter with others…

Most join more experienced friends, but many charter companies allow you to “book a berth” on boat (with a professional captain) too.


There are lots of “crewed” charters available. And most companies also offer captains that can join you for one or two days of your cruise. Hiring a captain is a great way to ease into chartering in that it allows you learn from (and fall back on) a pro until you are comfortable. Then you can experience all the freedom and satisfaction that comes from running the boat yourself.

But the best way to learn all you need to know is to take a course. They’re as fun as they are informative where you not only learn to charter but gain valuable confidence too.

There are even online courses that allow you to gain valuable knowledge and experience at home.

But this is only the beginning. Stay tuned for more insider info on what courses to take, what are the best charter companies, where to go, what to bring, how much it costs, and even where you can find the best deals in future posts.

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  1. says: Geoff Smith

    I am a contract Bareboat Briefer in the Whitsundays, Qld, Aus. 32 deg C at the moment.
    Because we don’t require qualifications the bureaucrats require a comprehensive brief that takes about 4hrs with a crew with a little experience.
    We have plenty of power cats in the charter fleets as well and I would recommend one to zero experience people.
    Most of our nice anchorages are only an hour or two apart so you don’t need to sail. Especially as you need 3hrs motoring every day to keep your batteries charged!
    If you don’t sail well, don’t sail, motor. You are on holidays you don’t need the stress. You only sail for pleasure, not to save money.