Where to Start?
The first question you should ask yourself is where am I starting and where am I going. That seems absurd, but it isn’t and here’s why: unless you’re flying out of New York-JFK, Los Angeles, London-Heathrow or the like, you probably won’t have a plethora of airline options or destination choices. So, let’s start with an example for a vacation to Bolivia flying out of Savannah, Georgia on September 18, 2019 and flying home September 29, 2019.

Freezing in Alpine Bolivia
Our destination will be Uyuni, Bolivia so we can see the salt flats and alpine lakes.
Start Here!
The first step is to google your starting airport. From the link, I can view each direct destination from Savannah, focusing on the most likely airport with a direct near my final destination. Bolivia is in South America, so the direct flight from Savannah to Miami looks like a winner. Next, google the destination airport, Uyuni, Bolivia.

From the link, I see that Uyuni has flights to three cities, but I want to focus on the flights from La Paz and Santa Cruz, as they’re the two biggest cities in Bolivia. I’ll run a SkyScanner search to make sure the information is correct, and that these flights really exist. From my search, I see that there isn’t a direct flight from Santa Cruz to Uyuni on my date, so I’ll focus on flights to La Paz, but keep Santa Cruz in mind.
Next, use a little google *trick* before I run my first search on SkyScanner. I go to google and type in “MIA LPB flight time” and “MIA VVI flight time” and view the results.
*NOTE, MIA, LPB, and VVI are airport the airport codes for Miami, La Paz, and Santa Cruz, which can be found through googling them. It’s a far more effective *trick* if you use airport codes. From my *trick*, I note that there are directs from Miami to Santa Cruz, but not directs to La Paz. Here are the results to La Paz, and here are the results to Santa Cruz. WOW, they’re super affordable, but we need our “feeder flights” to get us to and from Miami, and then on to Uyuni. *NOTE, we won’t be staying in Uyuni for the whole trip, but it’s where we’re starting in this example.

Next, I run a SkyScanner search for a roundtrip from Savannah to Miami. *NOTE* Keep in mind when your long-haul flight is overnight! Here are the results. Then, I’ll look at flights to Uyuni from La Paz. Here are the results.
I also see that American Airlines flies from Savannah to Miami, and on to Santa Cruz. I can check to see if it makes sense to buy a roundtrip from Savannah to Santa Cruz by looking on aa.com. Check to see about flying from Savannah to La Paz, as I know that the only direct flight to Uyuni on my date leaves from La Paz.
If you’ve run all the searches and clicked on all the links, you’ll see why I’ve chosen this example, and why I suggest running ALL of these searches for a flight itinerary!
There is more than one way to do this, but running a thorough search is EXTREMELY important. Here, the QUICKEST way to get from Savannah to Uyuni is: SAV-MIA on American Airlines flight AA3375 leaving 5:36 pm arriving 7:11 pm, connecting (and re-checking in) to for the MIA-VVI on Boliviana de Aviation flight OB767 leaving 11:00 pm and arriving 5:45 am on the 19th, and catching Amaszonas flight Z8103 from VVI to LPB, leaving at 8:35 am and arriving at 9:40 am, and connecting to Amaszonas flight Z8304 from LPB to UYU leaving at 1:30 pm and arriving at your destination, Uyuni, at 2:20 pm.

Note, the quickest flight may not necessarily be the BEST flight for you. First, in our example, it requires three separate check-ins, which is a hassle for most travelers. Second, the flights are on separate tickets. If the first flight is severely delayed, you run the risk of having to purchase all new tickets. (This would be rare, but possible with the proposed flights.)
Therefore, in my opinion, the SAFEST flight itinerary with the most reward value for this proposed trip is: SAV-CLT on AA5534 leaving at 9:25 am arriving 10:45 am, CLT-MCO on AA561 leaving 1:00 pm arriving 2:39 pm, MCO-LIM onAA7683 leaving 5:16 pm arriving 10:35 pm, LIM-LPB , on LA2400 leaving 12:25 am and arriving 3:25 am, and finally, LPB to UYU on Z8300, leaving at 7:15 am and arriving at 8:05 am.
WHERE DID THIS OPTION COME FROM?
This option was ONLY available since we searched American Airlines website, aa.com. The itinerary did not exist on regular search engines! Why do I think this is the safest? It allows enough layover time if something goes wrong, like weather. The American South has tons of thunderstorms on proposed date, so I don’t want cramped layovers. Plus, if something does go wrong, I’m booked on one ticket all the way to La Paz, so I’ll only have to re-purchase the Uyuni flight.
The most important lesson is to be thorough in your searches!
I know it seems like a lot of work. Trust me, it’s worth it. You can save yourself countless hours wasted in airports and hundreds of dollars of your hard earned money by spending a little time playing around with the various tools I’ve described.
TO SUMMARIZE:
- Check all direct flights from your starting airport
- Check all direct flights from your destination airport
- Make sure these flights exist on your dates
- Use the google trick “XXX to YYY flight time” to check directs
- Play around on SkyScanner–it’s a useful search engine!
- Check round trip destinations from your home airport to the closest major city to your destination–it just might work!
- Check airline websites, sometimes they come up with itineraries that don’t appear on search engines
- If at all possible, book on airline sites with a travel rewards credit card!
- If you have any questions, leave me a comment!