The best trips let you spend all of your time chilling out, eating, and drinking, but planning them can be almost impossible, what with you being the kind of person who's always chilling out, eating, and drinking. Get someone else to plan your debauchery, at Fortnighter.com.
FN's a just-launched service that'll provide you with a custom itinerary for the destination of your choosing, relying on their staff of nearly 100 seasoned travel writers (each of whom worked at top pubs like Fodor's and the NYTimes, and spent years in their respective lands of expertise) to give your visit a local touch, perhaps quite literally if you're headed to Southeast Asia...or Amsterdam...or anywhere with women, really. Getting a tailored experience starts by answering a series of questions sussing out your style, from how you want to travel (solo, couple, friends), to activities you're into (museums, cocktails, walking...), to your preferred lodging conditions, which can run from "utility" to "high design", which, considering it usually leads to garden-gnome totem pipes, definitely isn't focused simply on utility. Info in hand, your personal planner'll pump out detailed daily itineraries chock full of bullet-pointed tips on how to get to the best places, where to eat the most interesting foods, and local secrets, e.g., when in Prague "look for the 554-year-old U Medviku pub, which serves their 'X-33' super strong beer on the pub's second floor", so U Medviku is probably the best college ever.
Each itinerary also comes with travel essentials including the time difference, the tipping culture, numbers for a reliable cab company, and the local currency, which hopefully you can use to pay someone to read all this stuff for you.