IT’S 11:26 a.m. in California and Tim Ferriss, who has turned his personal tactics for streamlining life’s chores and savoring its pleasures into best-selling books like “The 4-Hour Workweek” and “The 4-Hour Chef,” is timing himself to see how fast he can get from his house to his departure gate at San Francisco International Airport.


Using Uber, a cashless car service, and Clearcard, a fast-pass for airport security, he zipped from home to gate in 20 minutes. A friend making the same flight spent 33 minutes on the security line alone.


“I had lunch and polished off two conference calls before my friend even got his shoes back on,” Mr. Ferriss said.


If there are upsides to obsessive-compulsive behavior, traveling efficiently is one. I consider myself a nimble traveler, able to fold a dress into the size of a croissant and get out of the airport before most passengers can even find the baggage claim. But as I grilled Mr. Ferriss and a handful of his Silicon Valley peers, who have made a sport of stripping time and pain out of routine nuisances, it was clear that even I could learn a thing or two. (Like when to pack a starter pistol, but more on that later).


For a certain type of frequent-flying entrepreneur in and around Silicon Valley, travel is an art form — one that doesn’t require private jets and fat wallets. Rather, they have perfected the art of traveling comfortably, without anxiety or wasted time. I caught up with half a dozen of these travel aces from companies like Google, Klout, Yelp and LinkedIn and pumped them for pointers on how to make planning and taking vacations as effortless as shuffling an iPod.


Designing Your Trip


Oh, the monotony of cutting and pasting details from confirmation e-mails — plane tickets, hotel reservations, car rentals — into your online calendar. So what do the experts do? They turn to TripIt, a Web site and free app that allows users simply to forward those e-mails to plans@tripit.com and — bang! — everything is instantly organized into a digital itinerary that can be synced with calendars and shared with friends and family. (There is also an option to automatically import the e-mails from an in-box.) The itinerary, organized chronologically from flight to hotel and everything in between, includes all the essentials: addresses, reservation numbers, weather forecasts (notes can be added, too). When your flight lands, pull up your itinerary on your smartphone and tap “directions,” and maps, along with step-by-step instructions on how to get from A to B, will appear. No need to test your phone battery and your patience with GPS.


Minimalist travelers don’t schlep destination guides, especially now that there are Web sites like Wikitravel, a worldwide guide the travelers I spoke to say is particularly useful for figuring out how to get around a city. They also rely on apps from familiar brands like Lonely Planet, and start-ups like Trippy.com. A new social site and free app for the iPhone, Trippy (to which Mr. Ferriss is an adviser) enables users to “friendsource” their vacations by telling connections on social sites like Facebook, Twitter and LinkedIn where they are planning to visit. Those in the know can then offer recommendations about where to stay and what to do. Suggestions can be added with a click to a master list, which can then be consulted throughout a trip. A photo album in the app enables users to show friends in real time that their advice is being heeded.


Another handy, free app endorsed by some of the travel aces I spoke to is Room. “When you travel as much as I do,” said Miriam Warren, vice president of new markets for the consumer review site Yelp.com, “you start to forget your room number.” Room stores it on the home screen of your smartphone, along with hints like “east tower.”


Is your French rusty (Est-ce votre français rouillé)? When traveling internationally, Krista Canfield, a senior manager for LinkedIn’s corporate communications, relies on Google Translate, a Web site and free app that translates words and phrases between more than 60 languages.


Of course, part of planning a getaway is preparing for bumps in the road — like having your flight canceled. And the only thing worse than being stuck in an airport without a flight is being simultaneously stuck in a phone maze unable to reach a customer service representative. That’s why Mr. Ferriss and his peers use GetHuman.com, a Web site and free app that tells you the swiftest way to reach a live operator (for example: dial the 800 number, then press 1 and then 4). “Calling on the phone is always faster than getting in line at the customer service desk if there’s a problem,” he said.


Joe Fernandez, the chief executive and co-founder of Klout, a company that uses data from social networks like Twitter to rank from 1 to 100 how influential you are on the Web, suggests also installing the apps of the major airlines on your smartphone, keeping your accounts at your fingertips. “In the ride over to the airport I can make sure I’m all checked in,” he said. It can also pay to check the “perks” section of Klout.com, where users can learn if they rank high enough to reap certain benefits. For instance, recently San Francisco International Airport visitors who had Klout scores of 40 or higher and were using the site’s iPhone app were given free access to the Cathay Pacific Airways first- and business-class lounge, even if they weren’t passengers of the airline.


For overseas adventures, Chris Hutchins, a product manager at Google, recommends safeguarding yourself and your possessions with insurance from WorldNomads, which he said is more comprehensive than many other policies. It covers an array of sports and adventure activities, lost bags, health care, even necessities like food if your flight is delayed. You can get a quote on the Web site — for instance, a weeklong policy covering two people (under age 67) traveling anywhere in the world for a week beginning July 10 was $98. When his camera was stolen, Mr. Hutchins said “all I had to do was get a police report and send them the receipt, and they paid us back.”


Packing


Mr. Ferriss is not alone in feeling like he “would rather jump face first through a window than check luggage.” So it’s no surprise that young entrepreneurs flying without children prefer duffel bags or backpacks that can be squished into an overhead bin. Mr. Ferriss likes Victorinox backpacks because they are durable and can be used for hiking yet also have wheels.