Travel sites make cobbling a vacation together easy, but a superlative itinerary requires the kind of time and access not possessed by the typical Priceline user (sorry, Shatner). Let the pros sort it out, with an emphasis on flossiness: In The Know Travel
Not your shuffleboard-scheduling travel planners, ITK's a juiced up agency with concierge-service touches, started by two inveterate globetrotters (worked for Robb Report, savvy with the nightclubbing circuit, frequently seen riding in mahogany carriages perched atop lustrous elephants, etc). To start, complete a survey focusing on possible destinations, activities, and any access or services you might want, from chartered superyachts to, VMA tickets to, deep-sea-fishing with Hulk Hogan (seriously -- but he keeps the fish). They augment your itinerary with thoughtful personal touches, like stocking your room with your booze-of-choice/need -- and they're on call if you run into problems (from, say, pounding that whole handle of Midori)
While ITK's connections can have you soaking your bunions in the Playboy Mansion grotto, they do have limits: whether you can pay or not, Richard Branson's space plane'll probably leave you standing on the tarmac, next to a morose Shatner delivering his most halting version of "Rocket Man" ever.
You and a Dozen Friends Can Rent This Towering Beachfront Mansion