Ive chartered (actually most was
trade time) about 9 weeks in the
Virgin Islands, about 6 in St. Martin and about 6 in the Abacos and have sailed my previous boat there even more. The Abacos of course in not quite in the
Caribbean, but close enough to consider if you are interested in
Caribbean locations.
I think each has it's pluses and minuses:
The BVIs offer very beautiful sailing which for the most part usually consists of circumnavigating Tortola while stopping at the many islands that surround it. You can easily pick up a
mooring every night if you don't like
anchoring, but it's easy to
anchor every night if you prefer as well. (mooring costs can add up). The snorkeling is good and most of it is protected. The sailing is easy with few obstructions to worry about. It's hard to find places to yourself. Some
anchorages are prone to back winding.
English is the spoken language. It's the home base of The Moorings and their new showers are way swanky. Something much appreciated at the end of a charter.
St. Martin along with
Anguilla and St. Barths can provide a cultural difference. The french wines are inexpensive. Most beaches are topless and there's even one famous nude beach there. The normal exit from
Oyster Pond may provide an exciting start, but they'll give you a
captain to help you out if you wish. Visiting St. Barths, normally the home to the rich and famous, by boat may be the only affordable way to see it.
Anguilla features a nice national park with good snorkeling. Although their are few hazards to worry about, there are fewer surrounding islands, so you are a bit more exposed than in the BVIs. Although much of the area is french speaking,
English is understood and spoken by most. I did feel the chart briefings were not a through as in the BVIs, so agree the BVIs are a bit more beginner friendly. However, St. Martin is where I did my first ever charter and found it quite easy. The Moorings has recently put a few of my favorite locations off limits for over night anchoring/mooring. I find going to St. Martin, is an opportunity to enjoy the french flavor without many of the negatives.
The Abacos: Sailing on the banks and in the Sea of
Abaco offers some of he most protected sailing you will find anywhere, but sailing in shallow
water can take some getting used to. Mid January to early March is considered off season, so it can provide an economical
winter escape. However, the reason it's off season is that the cold fronts can make it a bit windy a cool - possibly too cold for snorkeling. The snorkeling is some of the best I've seen, but much of the really good snorkeling is a bit less protected from
weather than in the BVIs. I love that even on a charter, it's fairly easy to have an anchorage completely to yourself. You don't find that in many places anymore. It's easy to
anchor out for free, but some of the sounds offer excellent protection with moorings available. One thing I love about the Abacos is the diversity. Almost every night you can choose between a secluded anchorage, a fun town, or a resort/marina. Oh, and the
winter is lobster season. yum yum. (Early summer is also lower season and warm, usually with less wind) The shallower water often forces you to anchor farther from shore, but you'll never have to worry about back winding. I have many photos of the Abacos charter area in my website listed below.
I've also heard great things about some of the islands further south in the Caribbean, but can't speak to them from personal experience.
If you choose The Moorings, 2 recommendations:
1. Take advantage of their friendly
skipper. Even if you are a competent and comfortable, they know the boats and the area inside out. You can learn a lot from them.
2. Consider
provisioning yourself. In the BVIs, you can get a complimentary cab to a local supermarket. It's not only less expensive, but you can choose what you want. The one time I did their
provisioning I wasn't too thrilled with it. Grocery stores are also convenient in St. Martin and the Abacos.
A lot of great
advice and options in this thread. I certainly agree it's hard to go wrong with the BVIs. You can also keep going back there and find more to do. You can find more out of the way areas as well as increase your cruising area to include the USVIs and/or Spanish VIs.
Have a great charter what ever you choose.