Tuesday Tools and Tips

Tuesday Tools and Tips: Staying Organized When Booking Travel

Welcome back to Tuesday Tools and TipsThis is a series to help the traveler and runner with various tools and tips that will help to make your training and traveling easier. If you have suggestions or questions that would apply to this weekly series, feel free to contact me and let me know and I will work it in!

Staying Organized When Booking Travel

When it comes to booking travel – paid or award – one really does need to be organized throughout the process. I am not the most organized person in all aspects of life, but when it comes to travel my fortunate memory helps to make up for that to make me be better organized with travel. I have learned a lot (mostly by experience!) when booking travel over the last 15 years and hopefully some of these tips will help you avoid the pitfalls that can come when booking travel! Please note: this is the process that I use to stay organized when booking travel but it is not necessarily the best way. Feel free to leave your comments on your process.

1) Make a list of what needs to be done – I know, this sounds simple and mundane but if you sit down and take note of the reservations that need to be made, you will be better prepared when the reservations are moving fast. Some things on the list would be: Airplane reservation(s), car rental, hotel, race entry (if it is for a race), visa application (if traveling internationally), passport/passport card (if traveling internationally), etc.

2) Start with the award tickets – If you are booking award tickets, start your travel booking with the award tickets. You may need to be flexible to secure your award tickets so it makes for a logical place to begin so you can see what dates/times you have at your disposal. This is also the time that you get to see which of you award programs will help you to get to where you are going. For example, when I went to Fargo for the Fargo Marathon a couple of years ago, I first looked at booking tickets with my Delta Skymiles. I didn’t really want to because it was requiring 40,000 miles and there were two layovers, but I had more Skymiles than I had other miles and I would (more than likely due to my high status) be upgraded. However, it only took 25,000 US Airways miles to book with only one layover, so I ended up booking that way.

Another reason to begin with the award ticket is that you may often need to book separate tickets (like if you are booking a Singapore Airlines route but your home airport is a regional, not a city serviced by your award airline). For an example, I was booking my Singapore Airlines ticket for my return to the US and I needed to shift the dates slightly due to availability.

Be aware of cancellation terms for the award tickets – many airlines will allow you to cancel within 24 hours (or more), but it is smart to know if your airline offers that before booking.

3) Book your connecting ticket (if applicable) – Now that you have the hard ticket booked, you can continue with the connecting tickets. You may need to exercise some additional flexibility with this stage as you will need time to connect with your long-haul ticket (especially if it is international) so check for different times/airports with this step.

4) Book your hotel(s) – You should now have your airline tickets secured. At this point, you can move on to the booking of your hotel(s). If you booking a hotel room with points, it is most likely that your points are fully refundable until close to your arrival date. If you are staying in different locations, take careful note of your arrival and departure dates for the hotels! This sounds simple, but you can’t imagine how many people actually leave themselves with one night of no hotel or double up with hotels. Check your confirmation e-mails for the dates and put them on a calendar to be certain – it will help!

5) Secure your rental car – Car rentals (unless booked through Priceline/Hotwire/airline portals) are typically one of the easiest travel components to book. You do not have to enter a credit card and you can make multiple reservations if you find better deals (and want to make the new one before deleting the old one). Make sure you book your rental car right away! You can continue to look for better prices later but this way you will definitely have a rental car in case you cannot find a cheaper price.

6) Apply for visas – With all of your travel secured, now is the time to see what the visa requirements (if traveling internationally). In fact, for any visa that you need to send to apply for, you will need travel documents before you apply. Get this done sooner rather than later since some countries can take a long time to process the application!

7) Use TripIt! I have talked about TripIt before (and will have a dedicated post about the features next week) but it is an invaluable tool to in helping you to stay organized when booking travel!

*Extra Tips – Go ahead and get your race entry in. This can be difficult sometimes about whether to submit the application before or after your travel booking. If the event sells out fast, just go ahead and apply for the race. If it is not a race that fills the cap quickly, then book all of your travel first to ensure that the trip will work out before submitting your non-refundable race payment. When booking your travel, one of the things that can really help you to stay organized is to map out your arrival airport, hotel, and race location. You can save significant travel time by doing this and it gives you a better perspective of the area.

Case Example: For my return to the US, I had to buy/ticket several segments to make it work. I am going from Greece to Rochester but am using Singapore Airlines for the long-haul. The first thing I did was to book the Singapore Airlines segment – Frankfurt – New York City – because availability for the First Class Suites was spotty. After I had that, I moved on to my flight from Greece to Frankfurt. Aegean Airlines does not have a free cancellation period, but the change fee is so small that it worked ok for me to book this one next even if I had to change things later. After those two flights were booked, I went ahead to find a ticket from JFK-Rochester. The problem was that I arrive in NYC at 11AM and did not want to hang around NY for many hours since I want to get home and see my family. The early tickets were ridiculous prices, so I had to get a flight to Buffalo instead. I made sure I booked it after midnight EST (it was Delta) so that gave me almost 48 hours to cancel if I found something cheaper. Sure enough, today I found a cheaper flight to Rochester (thank you, JetBlue!) and booked that one so I can fly into the more convenient of the two airports.

After I had my flights done, I went to the hotels. I knew which hotel I wanted to stay at in Frankfurt (I have an over-night before my Singapore flight) since I love how convenient it is, but I had to be able to secure it with Cash&Points (it is a SPG hotel). If that was not available, I would move on to something else. But, it was available, so I booked it and am now all set!


As you can see, it can get complicated when booking travel. There have been a few times when I have messed something up or forgot to book a segment thinking I already had. This is why staying organized when booking travel is so important – if you forget one component, the cost for that oversight could be huge when you finally realize what you have done. Stay organized and have safe travels!

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About the author


Charlie has been an avid traveler and runner for many years. He has run in marathons around the world for less than it would cost to travel to the next town - all as a result of collecting and using miles and points. Over the years, he has flown hundreds of thousands of miles and collected millions of miles and points.
Now he uses this experience and knowledge to help others through Running with Miles.