Friday Five: 5 Tips to Travel More Often

acropolis and parthenon in greece

Let’s start the long weekend off right by talking about one of my favorite things to do. Travel. When we left for Greece last Thursday, I got asked how Matt and I travel so much. This isn’t the first time so I thought I’d share my tips for traveling “so much” when you have a full time job!

1. Plan ahead.

To get the best deals, plan far in advance. We got caught not doing this for our trip to Thailand (when we didn’t know when Matt would move to Chicago) and a little for Greece (work has been killing me lately). And we really felt it. Financially. It’s amazing how many deals you can find if you give yourself ample time to plan. And I’m not talking about studying points programs or anything crazy like that. Yawn. Just set up some Kayak alerts for the destination you’d like to go to and use to tell you what deals are available. We take advantage of’s buy 10 nights, get one free reward regularly (and are using one in Greece!).

Planning ahead also makes for a less stressful experience overall in my opinion. I like having time to think about what I want to see and do research. While this may seem like a no brainer, I’ve talked to so many people who look up flights a month or so out, only to be disappointed with how expensive they are. To put it in perspective, I’m going to start planning our 2018 travel as soon as we get back!

2. Maximize long weekends.

If you look back at where we’ve been this year (and when), you’ll notice that most of our trips happen over long weekends. Since we both have full time jobs, it makes it a lot easier to plan a trip that doesn’t feel rushed. Since flights and hotels are usually more expensive over these long weekends, book as early as you can.

While I wish I could take off 2 weeks or more at a time, it’s not very realistic for my type of work. That’s why we are (again) traveling over a long weekend with Labor Day coming up. I’m only using 4 vacation days for this trip believe it or not (and 1 summer Friday). If you’re planning a longer trip, try to include at least 2 weekends in the dates that you’re traveling. Book flights that leave right after work so you are literally maximizing your time off. Also, minimize the number of stops. While nonstop flights at ideal times might be a little pricier, you can usually find some that are affordable if you plan ahead.

Fun Fact: Matt hates layovers and red eyes so when we met, that was the end of my bargain flights with awkward times!

3. Get rewards for traveling.

You know my day job (finance) had to play a part somehow! Matt and I spend the most on food and travel categories which is why we opted for the Chase Sapphire card. I talked more in detail about the credit cards we have here. They make a huge difference. Traveling is expensive. But a strong rewards program paired with planning ahead can make anything feasible. Remember, you can have anything – you just can’t have everything. Prioritize and ask yourself what you want most.

One of the other programs that has let us travel so much this year is the Southwest Companion Pass. We randomly checked for rewards in the app last year to find out they were offering an amazing deal for SoCal residents. We only had to fly 5 round trip flights in 3 months to get it. That means that Matt flies with me for free until the end of the 2017. Usually, you have to fly 100 flights which we would never do so it was an amazing deal! We (obviously) didn’t earn it in 2017 (although I am A-list now) so we are wondering what we will do for 2018. Booking through Chase’s Ultimate Rewards program is at the top of the list right now.

4. Don’t let any vacation go unused (if you don’t live in CA).

Statistically, you’re a better employee when you take vacation. When you’re starting out in your career, you might feel guilty using these days. Heck, I did. Don’t. You deserve it – it’s like your paycheck. Time off is another form of compensation!

Vacation was something that played into every one of my job decisions. I know I need a company that provides this flexibility for my own job satisfaction. Everyone has their own priorities though whether it’s flexibility to work from home or monetary compensation. If travel is something that’s important to you, make sure your next job offers a healthy amount. And if it doesn’t, try to negotiate.

Using my vacation was never a problem in California because vacation rolls over each year. In Illinois, that’s not the case. I’ve been tracking my days off more closely this year to make sure I don’t lose a bunch at the end of the year.

5. No excuses. 

You guys aren’t the only ones to ask me how I travel so much. My coworkers do it too. While everyone’s situation is different, my last tip is to not have any excuses (assuming you really want to travel). I don’t care if you just bought a house. Plan ahead and save up. If you have a family and are dying for a girls’ weekend, ask your husband or family to help you out for a few days. Making excuses for why you can’t go somewhere results in one thing: you not going. Obviously, there is always a situation where you truly can’t go but be honest with yourself. Can you really not go? Is there a compromise? If you want something bad enough, you’ll make it happen.

I hope these tips help. Now, start planning that trip!

13 thoughts on “Friday Five: 5 Tips to Travel More Often

  1. I started traveling a ton for work, which means I’ve racked up the points and I’m so excited (and grateful) to get to use them to do some travel on my own! I almost never take a full week off – it’s usually just a day here or there and sometimes it’s just to stay home and work on homework or blog work. So I am SO excited to take a real vacation!
    – Katherine
    Engineering In Style

  2. love these! now that my husband is back in school we’re all about the long weekend trips!

Let me know what you think!