Hacker Kid

The Ultimate Guide to Traveling Obsessively (Part 2): 6 Tips for Planning Your Trip Like a Boss

Free martinis, fold-flat massage seats, and Champagne bubble baths at the hotel might be the norm for Warren Buffett and the 1%-ers, but the rest of us are lucky to survive our trips without having a complete meltdown. With pay-toilets on the airplane, $30-a-day hotel Wi-Fi, and this lady at the check-in counter … these days, travel can royally suck.

Vagabondish is reader-supported. When you buy through links on our site, we may earn a small affiliate commission. Read our disclosure.

But it doesn’t have to. You just need to retake control of your travel destiny. Call it: “being a Control Enthusiast“. In this three-part series, we reveal our favorite tips for doing just that …

“Better travel planning through technology.” That’s my personal motto. These days, there’s a smarter, faster, and better way to plan everything. I mean ev-er-ee-thing. And when you’re a Control Enthusiast, that means being able to plan your entire trip exactly how you want. Here are my favorite tips for obsessive travelers looking to plan every trip like a professional travel hacker:

Book Like a Travel Ninja

Hacker Kid
© Donnie Ray Jones

Orbitz, Travelocity, Expedia … that’s where your nana books her summer trips to Dollywood. These days, travel pros know that it’s all about the metasearch. That means finding one site that swiftly and accurately searches dozens — even hundreds — of other sites to find the best travel deals. Kayak and Skyscanner are great places to start. But you know that already, don’t you? Of course you do.

… and Plan Like a Hacker Too

Travel — actually getting from point A to point Z — is often the hardest part of travel. Simply determining the cheapest, most convenient, and/or shortest routes with a side-by-side comparison can seem like a Herculean task. Look to a comprehensive metasearch site like Rome2Rio to help plan your route.

Rome2Rio Travel Planner

Plug in where you’re traveling from and where you wish to go, and the site concisely displays all possible transport routes — including buses, trains, planes, cabs, rental cars, etc. — and the corresponding prices and travel times.

Stay on Course

Pocket Earth Mobile App

Getting lost is fun … until it isn’t. At home, it’s easy to pull out your smartphone and ask Google where the hell you are. But that’s not always possible in a foreign country where internet access may be slow or nonexistent.

Look into a solid offline map app to keep you on track at all times. For less than an airport latte, Pocket Earth does just that by combining public map data with open source travel guides. Before you head out, simply launch the app whenever Wi-Fi is available, tell it where you’re headed, and download the appropriate map for your area. Even with your smartphone in airplane mode, the GPS locator still works so you’ll never get lost again.

Create a Bulletproof Backup System

Backup Button

Paperless travel courtesy of electronic tickets has made the entire travel experience infinitely easier. But batteries die, phones sometimes like to take a swim, or the internet connection you desperately need to pull up that airline e-ticket suddenly isn’t available. Which is why you should always have paper printouts and backups of your most important documents.

Use a mobile scanning app to snap photos of your printed documents, passport, ID cards, travel schedules … anything essential for your travels. Then store them in the cloud (Dropbox and OneDrive are both excellent) for easy access from your smartphone or tablet whenever you need them. Likewise, print hard copies of any tickets, itineraries, hotel reservation confirmations, etc. Again: you just never know.

Show Your Loyalty

Loyalty programs for hotels, airlines, and car rental services are an invaluable way to save boatloads of time on your trip. Many major hotel brands offer expedited check-in for loyal guests and most car rental companies do the same.

National Car Rental’s Emerald Club, for example, allows travelers to bypass the rental counter entirely at many major U.S. airports. You don’t even need to find your “assigned” rental car – just pick any ride from their Emerald Aisle and drive away. Oh, and it’s free to register.

Pack (Almost) Everything

Luggage Cart Piled High
© @sage_solar

Every unprepared traveler has at least one piece of kit that they’re constantly forgetting to pack. Which is why it pays to be prepared. That could mean going old school with a printed list (the checklists at OneBag.com are a good place to start) or stepping up your game with a dedicated packing app like QuinnScape’s Packing Pro. Whatever your poison, create a single master list that includes everything you would ever want to pack for every type of trip you might take. Work through it every time you travel and you’ll never forget to pack a single thing.

Founding Editor
  1. Some great tips there Mike. Having print outs of essential items can prove invaluable. Phone functionality is often limited when away from home but something that can easily be overlooked.

Your email address will not be published. Required fields are marked *

Let's Make Sure You're Human ... * Time limit is exhausted. Please reload CAPTCHA.

Subscribe to Our 'Under the Radar' Newsletter
If you love travel, you're gonna love this!