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Consider the Grenadines. A lot of folks who've enjoyed chartering in the BVIs have moved on to those lovely islands.
The Grenadines are more laid back and a lot less crowded than the BVI, but are similar in that you can sail from one beautiful anchorage to another in a half day or less, mostly in protected waters. The sailing is almost all reaching in the Tradewinds--no long beats to weather like you'd find sailing amongst the Leeward Islands.
The Grenadines are more about getting away from civilization than enjoying fancy restaurants and nightlife ashore, but if you want to plan a few nights eating at restaurants, it's certainly possible. Bequia and Mustique have some very nice choices. You can also enjoy a chicken and lobster barbeque on the beach in the Tobago Cays some nights, prepared by a local gentleman.
The Moorings has a big charter base centrally located in Canouan, and there are charters available out of Blue Lagoon on St. Vincent. Chris Doyle's Cruising Guide to the Windward Islands is a great resource for seeing what the opportunities are, and planning out your itenerary.
My wife and I spent a total of eight weeks or so in the Grenadines during our two years of cruising in the Lesser Antilles. It was our favorite cruising area.
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