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Seamanship Article Index

Chartering in the Caribbean

Fractional Boat Ownership


What does it take to charter a boat?

Winter is approaching and you’re planning to get some skiing in.  But what if the snow just doesn’t live up to expectations this winter?  And what happens in early March when it starts raining - that cold dark dismal time.   Maybe it’s time to recharge by heading down to get some time in the sun.  Chartering in the Caribbean can be the ticket to rejuvenation!

Crewed or Bareboat? Will I qualify to bareboat?

All it takes to charter a boat with captain and crew is a vacation.  This is truly a decadent way to sail, with someone taking care of all the details including passage planning, boat handling and maintenance, provisioning, and meal preparation.  You can do as much or as little as you choose.  It’s really not that expensive if you have two or three couples sharing a boat.  Between the room charges and food costs in a hotel, you’ll find that it’s pretty comparable. 

But if you want to charter bareboat, with you as the skipper and your crew backing you up, then you’ll need to do a bit of preparation in advance.  Chartering in the islands takes the same basic seamanship skills as handling your own boat at home.  You need to know navigation, sail trim and boat handling, anchoring and mooring, and basic trouble shooting. You do not need special licenses or certifications outside of the EU, although those do help if you’re arranging your first charter.  What you do need is to show experience as the skipper of a vessel the same length as the one you wish to charter.  It also helps to have a prior charter – say a weekend on the Chesapeake Bay – on record.  

You will need to provide a sailing resume – a list of all the courses you’ve taken, and all the vessels you’ve sailed (what, where, what capacity, and for how long).  Essentially, if you have owned a boat and you have documentation of ownership, that’s proof.  Most reputable charter companies will interview you and check you out (go along for a short sail with you) if it is your first time with them or if they need to be made comfortable about your boat handling skills. If after the check out, they are still not comfortable with your ability, they may insist on putting a licensed captain onboard at your expense. Once you have chartered with a company like the Moorings, you will be in their system, check in becomes routine, and you even get discounts for repeat bookings.

If you want to be really sure you will qualify, there are several sailing schools offering bareboat certification courses.  They will provide you with a “license to charter”, which does not substitute for time at the helm.  You will still have to show that you skippered a vessel on your own in the size range you wish to charter.  In addition, US Sailing has just introduced a Bareboat Certification program that will assist American sailors who wish to charter bareboat in the Mediterranean

Bareboat Charter Certification Resources

How can I find the right charter boat?

There are essentially three ways find a charter vessel in your desired destination.  You can work with a broker or booking agent who represents multiple charter companies.  These folks will often handle all the details for you, much like a travel agent, but they specialize in boat charters. One of the longest operating booking agents is Ed Hamilton.  They even offer a form online to help assess if your sailing resume will qualify you for chartering bareboat. 

The second way to charter is to go directly to the charter companies.  There you have the option of many charter companies, some of whom specialize in bareboat, others in crewed charters only, and still others that offer the option.  There are also individual boat owners who charter – typically with crew – as well.  There are benefits and drawbacks to each type.



Brokers/Booking agents

(crewed or bareboat)

  • Know all the boats, the charter companies, the locations, and the issues
  • Will find you a boat in your desired destination and time frame with minimal hassle
  • Some handle all the details including travel arrangements
  • May not get discount for repeat charter
  • Opinions can be biased toward select charter companies and locations they represent

Charter Company

(crewed or bareboat)

  • Professionally maintained fleets
  • Services such as provisioning, rescue/replacement in case of failure
  • Maintain records of clientele making it easier to repeat and often provide discounts for repeat business
  • Less comprehensive/ personal service
  • Limited locations

Individual boat owner

(crewed in all likelihood)

  • Highly personal experience
  • May be willing to teach and share knowledge and responsibilities
  • May be very experienced in the cruising territory
  • May be lower priced than similar charter company arrangements
  • May not have backup in case of failure
  • May not have the training in service aspects of business
  • Boat may not be in top charter condition

Some additional items to consider: the reputable charter companies will provide charts, walk you through the main aids to navigation, show you your route options, establish clear procedures for where to go, when to check in, and what to do in the event of a problem, and show you where everything is on your boat and how to operate it.   They will also offer provisioning options, and we seriously recommend taking at least the basic provisioning.  You want to spend your time sailing not shopping, especially when you do not know the territory.   

You may also be able to negotiate staying aboard the night of your arrival for a nominal extra fee to avoid the cost of staying in a hotel.  That way, you’ll be settled in and ready to go in the morning. 

Choosing your destination

Where you go may have a direct relationship with how much time you have and how comfortable you are chartering.  Some of the islands are a little more difficult to reach. Others are a snap with daily direct flights from the US .  Some of the islands have gentle winds, calm seas, and easy navigation.  Others offer greater challenges.  Some offer plenty of activities, others only beaches. First time charterers often choose the Virgin Islands because they offer easy access, gentle breezes, line-of-sight navigation, and plenty of variation.  Let’s examine some of the options.  Click below to learn more about these destinations.

Chartering in the Caribbean & Bahamas (click here)

  • British Virgin Islands
  • US Virgin Islands
  • St Lucia and Martinique
  • St. Vincent and the Grenadines
  • Guadeloupe
  • Belize
  • The Abacos, Bahamas

Click here to view a map of the Caribbean.

Visit T2P for an informative, free on-demand online viewing of Paradise Found, a Gary Jobson production on chartering in the BVI through Sunsail.


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