How to Plan a Trip

How to Plan a Trip

Of course there are many ways to properly plan a trip, but I wanted to take the time to share how I plan mine: choosing a destination, choosing travel dates, selecting airlines, selecting hotels, planning tourist sites, etc.

Have a running list of travel locations
In my notebook, which comes with me almost everywhere, is a running list of locations that I still want to visit. There are obviously places that I return to often (Vegas, Italy, Chicago, LA, San Francisco), but this list is for my aspirational/future spots. I have them separated into three categories: ASAP, soon, someday. My ASAP locations are places that are either luring me in an emotional or romanticized way, or places that are specifically cool during a certain time of year. My “soon” locations are places that I want to visit but probably need a reason to visit (great airfare, hotel special, etc). The “someday” spots are either places I’m in no rush to visit but clearly want to see or places that don’t necessarily serve me at this point in my life (family oriented locations, deeply romantic isolated tropical islands). Also included in this list are places that I’m in no way prepared to visit yet (Mount Everest, African Safari) or places that are in no way ready to have visitors (Iraq, Libya, etc).

Be Flexible with your Destinations if Possible
One major key to finding free or discounted travel is to be flexible about your destination. Sure there are places that you’re going to want to see no matter what, but for the times that the destination isn’t that important, you can save a ton of money. For example, if you want a warm, sunny, beach location for a vacation, be flexible among the many Caribbean or southern destinations. Punta Cana, Dominican Republic flights right now are averaging about $550 round trip for the summer, but Cancun flights are averaging less than $400. If you want to go to Europe on an award ticket in the summer, expect limited availability to hot spots such as Rome, Paris, Nice, or Barcelona. However you may be able to find extra availability to Seville, Spain or to Lyon, France.

The Power of Google Flights
My favorite first step in booking a standard ticket is to use Google Flights. Last year Google purchased ITA Matrix and has since fully incorporated this tricky, sometimes cumbersome flight search software into an incredibly easy, graphic search module ( You can use Google flights to perform standard flight searches, and you can filter the results by price, by number of stops, by airline, or by alliance, obviously a helpful feature for alliance loyalists like myself (Kayak also allows this). You can’t book flights directly through Google flights, and I have found some inconsistency in what they show versus what is actually available, but their search engine is very fast and it produces an extensive list of flight options. What I find most useful about Google Flights though is when I’m not sure of my destination, or when I really don’t care about the destination (mileage runs, quick weekend getaways, etc). If you set the dates you’re looking to travel, and then set the departure city but leave the destination blank, it will pull up a map of all airports in the world and how much it would cost to fly to that city. See below for an example:

This map shows a graphic of all flight options leaving from NYC (all airports), with flight dates of June 8-12, with no airline filter selected. You can zoom in on any region, and more city options will appear if there are flights available between NYC and that city. It shows the prices, but it does not show how many connections a flight may require, so if you want to avoid or to add connections for mileage purposes, then you can toggle that filter menu.

Once you decide on a destination, you can look at a graph that shows the price of flying to that destination by departure date. Some people don’t have date flexibility, but if you do, this is a great feature. For example, if you set the parameter for how many nights, you can see a month-plus long horizontal chart that shows the average price of the trip and the price for each departure date. This replaced the old ITA matrix that would show a month-long calendar with the price for departing on that specific day. You can still run the old Matrix calendar option, but this one is a little simpler.


Ok so after you have a destination and dates, you can select your airline although most loyalists will probably choose their destination and dates according to their airline/alliance of choice. Because of the added value given to me as perks of my frequent flier status, it is a rare, almost never, occasion that I would choose to buy a ticket on an airline with which I did not have elite status. To me, the elite miles, the free bags, the priority check in, and of course the chance for an upgrade are enough for me to justify paying more for a ticket on a specific airline. I have no problem connecting if necessary as long as I can fly on my airline of choice, but I do draw the line if the connections require an overnight or if the connections would cause me to miss an event.

My next post in this series will cover selecting a hotel. Thanks for reading!

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