It is hard to beat the benign Lesser Antilles for first-time charters. I recommend the BVI, St. Maarten and the Grenadines, in that order. Then the tamer areas of the Med. And then Tahiti/Moorea/Bora Bora. After those, the sky is the limit, with New Zealand, Australia, Fiji, Tonga, New Caledonia, Thailand and the Philippines beckoning.