In 2019, I planned a trip to French Guiana, Suriname, and Guyana with a friend who also loves flying weird airline routes and visiting less-visited countries. We planned the trip because we wanted to fly Air France’s Caribbean Island Hopper from Miami (MIA) to Cayenne, French Guiana (CAY).

This worked out great for me because after that I was meeting up with friends in Peru and ultimately needed to make my way to Cusco (CUZ). Our plans were to travel overland from French Guiana to Guyana and fly out of Georgetown, Guyana (GEO).

Aerial panorama of Willemstad on Curacao island

How I Booked My Flights

Unfortunately, flights from Georgetown to Cusco were expensive no matter how you looked at it: Cash prices were an outrageous $800+ in economy and the best option with miles I could find was 40,000 United miles and $88 in taxes/fees for business class on a narrow-body jet with multiple long layovers.

I didn’t love those options for so many reasons. I didn’t want to drop that much cash for a one-way flight in economy and I knew that there were much better uses of my United miles than a terrible itinerary with an unimpressive business class product.

I had two weeks of buffer time in my schedule before I needed to be in Peru, so I was open to other options — and I found a pretty amazing one.

I started by looking at where I could fly from Georgetown, noting that Georgetown actually has two airports — GEO and OGL. From OGL, my only options were to fly to Trinidad or Barbados (outside of other destinations in Guyana and Suriname).

Downtown area of Port of Spain in Trinidad and Tobago. Caroni sanctuary on the background behind the city center.

From GEO, I could fly to Trinidad or Panama (plus destinations in Suriname or the United States). I wasn’t interested in visiting Panama again, so I started by considering my options if I went to Trinidad or Barbados.

Flights out of Barbados were not great with cash or miles, but Trinidad looked promising. A flight from OGL to Port of Spain, Trinidad (POS) only cost $103. And while a flight to Cusco from POS was still expensive, I found a flight to Curacao for $157 and then a flight from Curacao to Cusco with a reasonable itinerary for only 12,500 United miles + $58.


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I knew that if I was visiting Trinidad, I would also want to visit Tobago. A round-trip flight between POS and Tobago (TAB) would cost $60.

In the end, it came down to two options:

  1. Spend 40,000 United miles + $88 to fly from Georgetown, Guyana (GEO) to Cusco (CUZ) in domestically configured business class with two overnight layovers; or,
  2. Spend 12,500 United miles + $378 to fly from Georgetown, Guyana (OGL) to Cusco (CUZ) with four nights in Port of Spain, Trinidad, four nights in Tobago, and a week in Curacao.

For me, time was not a limiting factor, so this was a completely viable option for me even though it wouldn’t be for everyone. Not to mention, I was interested in visiting Trinidad and Tobago and Curacao. So the question came down to, was I willing to pay an additional $290 to save 27,500 miles?

The answer for me was a resounding YES!

Beautiful colorful buildings of the district of Punda in Willemstad, the capital city of Curaçao, an island in the southern Caribbean Sea.

I typically value my United miles around 2 cents each because I like to redeem them for premium cabin travel. And, since I travel nearly full-time, I have to be stingy about redeeming my miles. Even though I have a considerable stash, if I used my miles for every single flight I take, I could easily blow through them in under a year without a way to replenish them quickly enough.

I went through quite a few steps to determine whether or not it was possible to piece together an itinerary where I stopped in more places without spending more money.

Here are steps you can follow to create something similar for your next trip where the options aren’t great:

  • Look up Cash and Miles Prices for Your Ideal Airports

Before you start doing anything fancy, look up the simplest things you can: cash prices and award prices (with whatever miles you have available to you). If those options seem reasonable and you don’t want to spend a bunch of time hacking something else together, go ahead and book! But, if the options aren’t reasonable or there are no options available at all, continue on.

  • Use CleverLayover to Pull up a Cash Itinerary With a ‘Clever Layover’

While I’ve never actually booked something on CleverLayover, I regularly use it to get ideas — and sometimes it spits back some really good options. Even if you don’t have extra time to extend your trip, sometimes CleverLayover will offer you an itinerary where you need to book two separate tickets.

If this is something you consider doing, keep in mind that you need to leave yourself a long enough layover in case your first flight is delayed, and you do so at your own risk! I personally would not use CleverLayover unless I had an extra day to spare at my clever layover destination.

Similarly, Kiwi will offer separate tickets that can be booked together, and they do offer coverage in case you miss your connection. These are both tools that I always check.

  • Use Wikipedia to Find Flights

Some small airlines won’t show up on online travel agent (OTA) searches. Likewise, even with Kiwi or CleverLayover, there will be more options out there. I like to look at an airport’s Wikipedia page in the “Airlines and Destinations” section.

This is how I can find out when there’s an airline or a destination that I haven’t been considering. This is how I found that I could fly from Georgetown (OGL) to Port of Spain, Trinidad (POS). And also how I found out I could fly from POS to Curacao (CUR) on Surinam Airways — an airline that’s not even based in one of those two countries.

  • Repeat as Necessary

Depending on how much spare time you have, you can repeat the above as necessary until you are about to find a reasonable fare from wherever you end up to your final destination. For me, it took two stops — one in Trinidad and one in Curacao — to find a reasonable price to get to Cusco. I added a trip to Tobago because it was cheap and I wanted to, although that detour was totally unnecessary and cost me an additional $60.

The National Academy for the Performing Arts, Lord Kitchener Auditorium in Port of Spain Trinidad and Tobago

Bottom Line

Outside of the box thinking will sometimes can really help you to save money or miles, and you might even be able to visit a couple of extra destinations without paying more! In my case, I paid an additional $290 to save 27,500 United miles and I was able to visit Trinidad, Tobago, and Curacao along the way.

Even if I hadn’t had time to spend at my stops, I would have been tempted to book this way because I value my United miles around 2 cents each. Be creative and see where your miles can take you!