How travel planner Lindsey Wallace crafted the perfect trip (four nights in Hong Kong and eight in the Maldives) for our 2008 Dream Trip Contest winner.

When New York City-based event producer Wanwisa Posner won Condé Nast Traveler's 2008 Dream Trip Contest and the grand prize of a $25,000 custom-tailored vacation of her choosing, she didn't seem to need help from a travel agent. A meticulous planner and food enthusiast, Posner knew exactly where she wanted to go: Hong Kong for a dim sum spree, and then on to the Maldives for a relaxing island getaway and to try out scuba diving in the Indian Ocean. She knew exactly where she wanted to stay: The Peninsula Hong Kong, for its eye-popping harbor views and ESPA spa, and the One&Only Reethi Rah—"to spend some stress-free time with my husband while soaking in our overwater villa's infinity pool." And she knew exactly how she wanted to get there: She and her husband, Jason, who fly to Thailand annually using awards mileage, planned to redeem Starwood American Express points for transpacific business-class tickets. This would enable them to devote most of their $25,000 budget to over-the-top accommodations, cuisine that would make any serious foodie drool, and adventures from helicopter rides for aerial photography to private cooking lessons with local chefs.

Click here for a Google Maps rendition of the Hong Kong portion of their Dream Trip.

Wanwisa and Jason knew what they wanted, but my job in helping with the trip was to guarantee that it turned out perfectly, and for that to happen I knew they had to use the right travel agent—someone with the destination expertise to know which overwater villa has the best view and the calmest waves; someone with the airline connections to obtain business-class mileage-award seats on packed flights; someone with the pull to negotiate reduced rates and special perks for clients; someone who could swoop to the rescue should any unforeseen snag occur.

Luckily, I knew just the person: Lindsey Wallace of Linara Travel. Normally Wallace, who has made 17 trips to the Maldives and 7 to Hong Kong, spends much of his time matching clients to the right destinations and properties. With Posner that wasn't necessary, but what was necessary was fulfilling her goal of stretching her Dream Trip dollars as far as they could possibly go. The months when she could travel were March and June. June officially falls during the Maldives' rainy season, but it's also when Posner could get more nights for the money at her chosen hotels. When Wallace explained that rainy season means barely an hour's rain in the afternoon or evening, and that both months are equally good for learning to dive, the decision was made. Going in June meant that the Posners could afford four nights in Hong Kong, eight in the Maldives, and business-class airfare throughout.