Plan With Me: How I Plan Vacations


One of the biggest questions that I get from people is: "How do you afford to travel so much."

The easy answer to that is that travel is a priority in my life. The lifestyle I have created for myself allows me to be able to drop everything and go. I understand that not everyone has the same priority as me, so I will share my research tips and tricks so that you can make the most out of your travels.

I will cover what websites I use to plan my vacation and try and answer the question of: "How do I know if I am getting a good deal?"

When I first started planning my vacations, I used to go the easy route and trust that Expedia was getting me the best deal. I was all about guided tours instead of piecing together a trip. As I became more and more comfortable with putting together an “a la carte” trip, the websites I used started to expand.

When to start planning

I typically like to start looking into flight and hotel costs of my next trip about 6 months early. I typically never book my trip that early, but getting a baseline cost is always a good idea. For the next few weeks, I will go back and check pricing to see if it fluctuates. If the flight looks to stay the same price over the few weeks I am checking, I begin to build out my budget based on that pricing.

How Do You Know if You are Overpaying for a Flight?

If you are newer to travel planning, then you really don't know what a GOOD deal is until you have the experience of just browsing flight prices. Below are some of the examples of my flight price max for some popular destinations:

Seattle to Las Vegas

  • I typically won’t pay more than $275

Seattle to Europe

  • I typically won’t pay more than $1100

Seattle to New York

  • I typically won’t pay more than $400

Sites used to track flight costs

Hipmunk – This is an app that will show flight costs from a bunch of airlines. While this app is similar to Expedia, I enjoy using it more due to the user interface and the home page of the app contains top flight deals if you are looking to be spontaneous as well as a bunch of different destination ideas

Hopper – This is the app I start with. It allows you to put in a destination with the dates of travel. It will let you know if you should book the flight now or wait. When you first download the app, it asks you to put in your personal flight cost preferences. For example, I said that a reasonable amount to pay to travel to Las Vegas is about $225 so on the predictor calendar it will show green for great price, yellow, orange and red each category getting more expensive. I will usually “watch” the trips I know I am going to take. I have been able to save about $100 by using this app and booking when it recommends.

Best Way to Use Airline Miles

I love my Alaska Credit card. Alaska Airlines is my favorite airline so I got their credit card last year and have been earning miles ever since. The great thing about the Alaska credit card is that you get a companion fare every year. That means buy a regular priced ticket, and get the second for $120 plus taxes and fees. Sure, there are a few stipulations to the companion fare, but I got two tickets to Maui last year and ended up paying $1050 total for two tickets. Sure, we paid more than we wanted, but we couldn’t be flexible on our flight dates. The companion fare was a life saver.

I recommend signing up for a credit card that fits your travel needs. A lot will give you bonus miles for signing up. The best bang for your buck is to use that card and gain about 60k total miles and cash them in for a high ticket trip - like Europe.

I signed up for the Alaska Credit card last year, got the 25,000 signing bonus miles, used my card like crazy for a year and between flight miles and charging the card, I got to that 60,000 mark. I cashed in those miles for a flight to Glasgow and a flight out of Paris. I only had to pay about 300 total for the flight!


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