Tips for the Smart Traveler: A Holiday Strategy

There are many resources out there like ShuttleWizard or ParkingHunt that make your travels frictionless.

We received a lot of good feedback on Rebecca’s guest post on parking at the airport that we wanted to share more tips on airport travel. For this holiday season, we have Alex from to give us some tips on traveling during the holidays. Enter Alex. 

We all know national holidays are the holy grail for delayed flights, overbooked reservations, angry customers, bad weather, sky high parking rates, etc. We’ve made a list of things you need to know to avoid the crowds and travel stress free.

I’m traveling right before the holidays. How can I avoid the crowds?

You can’t. You better learn to manage the crowds and manage the lines. Here are a few tips you can follow. Firstly, book your airport transportation in advance. You can find the cheapest rates at If you are traveling on a budget book an airport shuttle. If you are planning on calling an airport taxi, its actually cheaper to book an airport car service. Also, make sure you check-in in advance online. This way you will save waiting in line. Travel light and carry everything on your carryon. Book a front seat so you can board quickly to find a spot for your carry-on. Once you arrive at your destination, you will be the first one to leave and you won’t need to wait for your luggage. If traveling internationally, these techniques will save you around 10 minutes of waiting through customs. You can also save money and time by booking your off airport parking in advance at We have used this service before and love it. It saves you a lot of time from searching and getting quotes from dozens of lots. Its an easy way to search through all of them and save time and money.

Why is traveling during Christmas and New Years always so expensive? How can I avoid paying the high fees?

Christmas and New Years is the most popular travel season. Combining that fact that both parents get work vacations, kids are off school, relatives are in town, and that Christmas and New Years are simply really cool holidays you get a conglomeration of people throughout the country moving from one place to another. Everyone knows it’s a hassle to travel during those holidays. Hotel companies and airlines know that too and the simple uplift in demand with a steady supply causes increases in prices.

For special deals during these holidays you need to look where other travelers are not looking. Traveling a few days before or after the holidays is extremely cheap. In fact, visiting cities like Las Vegas for example the week before New Years can give you access to drop bottom hotel room rates. Staying there on New Years Eve might cost you 5x the price. You can find the best hotel deals during the first week of January. If you job is flexible you can volunteer to look after the office during the holiday season and take extra days off in early January. You will skip the lines and pay rock bottom fares.

For airline travel, the best deals can be found by searching for air travel between point A and B using the +/- 3 days feature. I like to use’s because it’s the easiest. Doing so, you will find that flying on Christmas or on New Years can be half the price than flying a few days before.

When are the least expensive dates to travel?

The second and third week of January have historically shown to be the best times to travel. The crowds are gone and hotel/flight rates are historically low. During these times, hotels normally announce last minute deals. My advice is to wait for these deals or call hotels directly and ask for them.

Should I fly or take the train?

If you are already considering both, probably taking a train is better. Remember that in most cities train station are located in downtown area with many of them having direct access to subway systems. Also, when calculating times make sure you include plane loading and unloading times. When traveling via train, you can arrive just a few minutes before departure, you don’t need to check in your luggage, and you don’t have to get pat down by TSA officials. Once you arrive at your destination is the same drill, you just grab your luggage and off you go. I have personally calculated that you save on average 3.5 hours by traveling via train versus airplane. Additionally, by traveling via train you don’t have to worry about weather delays, cancellations, or changing your departure times.

How can I avoid being grounded during the holiday seasons?

Firstly, book the earliest possible flight. In case of any delays and/or cancellations, you are most likely to be taken care of first. Secondly, whenever possible book only non-stop flights. This will remove from the equation any problems at the connecting city. If you have to pick a connecting airport pick a southern city. These cities are much less likely to have delays or cancellations due to weather conditions. And lastly, in case you do end up waiting hours on the airport for your flights, make sure you bring with you in advance extra food, snacks, and entertainment. You don’t want to get nickeled and dimed by the airlines while you sit around waiting to get to your destination.

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