Travel Roulette

I'm a fly by the seat of your pants kind of guy when it comes to pretty much everything, but especially when deciding what destination to explore next.

I recently traveled to Dubai from NYC, on a brand new Qatar Airways A350 XWB for less than the cost of a Louis Vuitton pocket organizer. I didn't plan on going to Dubai, I didn't plan the dates, and I definitely didn't expect to travel 7,000 miles on a brand new plane for that price. No reward miles were used, no "point" perks, no benefits... just resourceful travel roulette.

How does it work?

I set up automatic searches for the best travel deals and receive updates as they're available (I prefer text alerts instead of emails lost in an inbox swamp). A travel deal could be a few weeks, months, or even a year+ away. All you need to know is that you want to travel somewhere, sometime in the near future, to some destination you've never been. Unless you've visited all 196 countries in the world, you can most assuredly benefit from surprise deals that will make you say, "I totally didn't even know I wanted to visit [insert deal destination here]!" There are over 4,000 cities in the world with a population greater than 150,000... now just imagine how many there are if you include the cities with a population below 150,000. Basically, there is NO shortage of places to visit. Just set your departure destination and let the universe decide for you.

It's that simple. Here are my 3 tips for playing travel roulette:


This is my top pick, hands down. You receive text alerts with the newest, cheapest travel deals around the globe just by entering your mobile number. Set your departure location and let Dealray do the rest. You can also delegate preferred departure airports and priority destinations for more catered alerts.

As I'm writing this, one of the deals is a flight from NYC to Curacao for $244 round trip, anytime between April 2017 and March 2018. You can fly to this beautiful island for literally less than a couple pairs of jeans... and you have an entire year's worth of dates from which to choose.

Sign up here: the first month is free and each thereafter is $9.99. Receive two free months for every friend you refer; tell enough friends and it practically pays for itself (as if the money you save per trip doesn't already do that)!


Google Flights has come a long way since it's launch in September 2011. It has become one of my top sources for comparing travel dates and destinations because of how easy it is to explore airfare around the globe. See those red dots in the image above? Those are all cities and their respective airfare for the dates you select. For example, if you're interested in traveling to Europe but can't decide which country (because they're all amazing), let Google Flights help you determine which locations have the best prices. You can also save an itinerary and receive alerts when the price goes up or down (and yes, it actually does go down at times).

P.S. Google flights is great for intra-country travel as well. For example, I was recently in Madrid, Spain for 2 weeks and let Google Flights help me decide what other city to visit. Majorca was the best deal at the time, and I quickly found myself on one of the most beautiful islands in the Mediterranean for only $39.


This is a great trip-booking site if you have a specific destination or dates in mind. I have used this site when I knew exactly when I was able to travel, but wanted to leave the destination up to the deal. For example, I searched for the week of my birthday and found that most cities in Mexico were the cheapest at approx. $350 for a round-trip ticket.

You can search destinations from the Skyscanner home page for free.

When does this come in handy?

1. When you need to plan a birthday/honeymoon/anniversary/retirement/just for fun trip, this can be a great way to fly somewhere exotic for practically the same price you could fly across country.

2. When you have to book travel quickly. Using a site like Dealray or Skyscanner will assure you get the best possible price for last minute travel.

Follow these steps and this could be you:

Le Méridien Mina Seyahi Beach Resort & Marina

Le Méridien Mina Seyahi Beach Resort & Marina


Happy rouletting!