The choice of an area can be at first a little tricky because it will result from: your sailing experience, your climatic preferences and your budget. There is no really simple way to do this, because your decision will have to combine those 3 elements. We provide you with sailing area charts that will show you weather and cost components for the main sailing areas of the world. You should print them to facilitate your decisions.
1. The time of the year is the first thing to sort out because it is probably the element you have the less control on (school vacations, job constraints etc.). But it is very important because depending on the area, the timing will influence your budget. If you have tight financial constraints, you can find excellent deals and discounts in some areas at low season. For example, the BVI in July still offer great sailing, but at a 40% discount compared to March for example. In the Med., May or September can be delightful and are much cheaper (and much less crowded) than July or August.
2. Your party's weather preferences. Do you like very hot weather, or more temperate climate? The Bahamas are much cooler (and cheaper) in February than in May.
3. Your experience. Regardless of your skills, if this is your very first charter in open waters, we strongly suggest you choose an easy sailing area.
Here are two suggestions (if you like the Caribbean, that is!) that are guaranteed to provide you with the most delightful first charter experience.
The British Virgin Islands (a.k.a. B.V.Is): Located next door to the US Virgin Islands, on top of a magnificent scenery, incredible beaches and snorkeling, the BVI are also phenomenal sailing grounds. Island hopping is done in line of sight, and the islands layout is such that most little "crossings" are short (2-3 hour sail on average) and well protected. Winds are most of the time an ideal and sustained E/SE 12/15 knots. This idyllic description does not mean you cannot get in trouble though, as the conditions can get harsh (remember, this is the ocean). But if you apply good seamanship rules, and listen religiously to the weather forecasts, as any cautious skipper should, you will be fine. Besides, the BVI have a large amount of mooring balls so you can do an entire cruise without anchoring!
View the detailed BVI classic itinerary.
The Sea of Abaco (Bahamas): The Abacos are the northern-most islands of the Bahamas. The Sea of Abaco is roughly defined as the relatively shallow water between the islands of Little Abaco and Great Abaco. The Sea of Abaco has many of the same ideal attributes for first-time charterers: Well-defined bounds, reasonably calm waters, easy line-of-sight navigation, relatively free of hazards and easy anchorages. You just have to watch your depths carefully.
View the Sea of Abaco detailed charter itinerary.
Lastly, some other elements have to be taken in account like: do you want to enjoy an active night life during your cruise? do you want to go shopping? do you like to fish? Those are important considerations, but they should be weighted only after you have resolved the 3 main issues above.