“There’s an amazing deal from Amsterdam to Tokyo”. “Who cares?” says just about anyone not living in Amsterdam. Everyone wants to travel more for less but most people don’t think about the creative ways to actually accomplish that goal. One consistent habit of savvy travelers is “nesting” a trip within a trip, leveraging great deals to random places into one big experience. Here’s how you can (and should) do the same…

a snow covered mountain in the background

So What Is Nesting?

Nesting is the act of creating a trip within a trip or a trip around a trip. Sometimes it’s totally spontaneous and purely based on exciting deals that pop up and other times it involves clever planning and timing to make the most of a region of the world. It can start with something like a planned round trip flight to somewhere you’ve had in mind with the goal of booking deals to see more interesting cities before your return flight home. It can also happen when you’ve found an incredible deal in a dreamy cabin from a place that’s not your home, but because you’d like to visit the place where the deal starts anyway it’s worth booking the far away deal and booking a separate deal using cash or points to get there.

a bed with a tv and a monitor in the back of a plane

Here’s A Real Life Example…

This week there was an incredible flat bed business class fare from Amsterdam to Tokyo for a mere $640 round trip. Most people living outside of Amsterdam wouldn’t have batted an eye at the deal, but those who recognized just how good it was began to create nested trips just to take part. Since I live in New York I have to fly to Amsterdam to get in on the deal, but for such an amazing offer to a place I love it’s a no brainer, especially for someone with miles. I’ll use miles to get from New York to Amsterdam, which is an awesome city anyway, spend some time there and then carry on to Tokyo on the separate amazing deal,  giving me more than 30 hours in a bed round trip. If I wanted to further nest the deal I could even build a trip before my flight home from Tokyo hitting cities like Seoul and Osaka while i’m there before returning to Amsterdam, before returning from there to New York…

a red pagoda with a bridge over water

Here’s When Nesting Is Best…

Most people can’t travel all the time and most people don’t like flying super long distances. Nesting is at it’s best when you use it to get a comprehensive, multi city look at a faraway place you may never get the opportunity to go back to. If I plan three weeks in Tokyo, leaving myself enough time to pop over to Seoul for a few days, Kyoto for a couple days and maybe Osaka for a couple more I feel like I’ve then really experienced the region and don’t have a need to plan another expensive trip further down the line. For most people It all starts with a simple round trip and the intention to build in more trips within trips before returning home by taking advantage of clever deals or using miles, especially with airline partners.

a man holding two luggage

And Here’s Some Practical Advice For Nesting Deals…

If you’re nesting different deals into a big trip, you’ll want to give yourself some safety nets. Don’t book a flight too close to a separately booked deal in case things get delayed and you miss a flight on a different itinerary. If it’s safer to overnight somewhere do it.  Be sure to check baggage allowances for all parts of your trip, rather than just one part. If I’m on a business class deal my baggage allowance is likely going to be different than an economy deal I used to get into position and could prove costly if I bring too much. Finally, remember all the tools you have at your disposal and remember that the airline whose miles you hold have partners.

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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