So many places to see, so hard to pick which one deserves your hard earned vacation time. As a frequent traveler, I find that one of the hardest elements of travel is figuring out "where". Sure, it's easy to get a few ideas, but there are lots of factors which make a trip possible, such as flight and hotel costs, and there are more factors which make it worthwhile. Here are a few cool tools to plan the perfect trip...


When you just "wanna get away", sometimes you just have a theme in mind like "beach", "skiing", "live music" or "cultural city". Hipmunk offers a really fun and flexible app which allows you to see the cheapest destinations around the world, broken up into categories just like that. You can enter a wide date range of more than a couple months and see the cheapest places for flights and or hotels with whatever "vibe" you have in mind. 

Google Destinations

Google Destinations is a true game changer in how we consider our travels and it all takes place right on your phone during a Google search. You can be as vague as selecting a region or continent, and the service will show you average flight costs, hotel costs, meal costs and itinerary costs by city. For example, you could enter "Caribbean destinations". Essentially, if you want to go to the Caribbean, but you're not sure where, it'll show you the relative costs between each place as well as the most popular attractions and how highly they're rated. Go play around...

Get "Inspiration" (Ideas) From An Itinerary...

A great trick to sift through the rubbish in any city or destination is to look up a professional tour company's suggested guide or itinerary. I like to (steal) inspiration from companies like Jacada Travel, Abercrombie & Kent and others which have experience in curating the best of each location. You can generally learn enough from their online guides to get a feel for the area you're visiting and then go piece it together yourself, or if you prefer, let them, the pros, handle everything.

Secret Flying + The Flight Deal

For most travelers, cheap is the operating word. Fortunately, Secret Flying and The Flight Deal both offer invaluable resources, which highlight the lowest fares from every city around the world to all the cities around the world. Not every deal will float your boat, but from time to time you'll see something so mouth watering that you dive in. The deals are so good that they typically don't last more than a few hours, so be sure to get it while it's hot.

Conde Nast Traveler

I'm very lucky to write for Conde Nast Traveler in addition to all of my musings here, but frankly I also use it for inspiration too. I find the "50 Best Beaches" style posts which are everywhere on the site to help sharpen my eyes to what I absolutely need or want to do on my next trip.