How We Travel so Often

As I type this, I am on my way to St Petersburg, Florida. It will be my 4th trip in 3 months & none of them have been work related.   Since December our family has spent 2 weeks in Michigan visiting family, a long weekend in Orlando meeting up with family & Mickey, Drew & I cruised the Caribbean together with my sister and brother in law, we saw Hamilton in New York City and over winter break we took 3 of our kids and went back to see Mickey for a longer stay.  


Drew and I have been married for almost 25 years.  We have 4 kids and we love to travel. Family is extremely important to us. We prefer investing in experiences over owning things. A couple years ago we started to get intentional about what we wanted our life to look like and how we could make that happen. We knew we wanted travel to be a huge part of how we spend our time. We began arranging our lifestyle to accommodate that vision.


The more I open our life up to the internet, the more questions I get on how we travel so often.  I thought I’d answer a few of those questions here.

How do you afford to travel so often?

Two and a half years ago we significantly downsized the size of our home.  I talk about it here and here. Doing so allowed us to no longer have a mortgage, with no other personal debt, that freed up a lot of finances.  With travel as a priority, we’ve allocated money that would have at one point gone to interest, now can be reallocated to more delightful locations.

Our approach at this time is quantity over quality.  In other words, we aren’t staying in 5 star luxury hotels. We are pretty low maintenance when it comes to accommodations.  That being said, my frugal husband is also an extremely great researcher and has found some excellent deals over the years.   

Who cares for your kids when you travel without them?

Two of our children are full-time college students who live on location.  The other two, in high school and middle school, are cared for by a small variety of people we love and trust.  My parents, Drew’s parents, and a dear friend have all helped us at one time or another. In addition, both of the college kids have {or have plans to} come home on a break to care for their siblings. It does help that our kids are at an age where they are quite self sufficient. We do feel blessed for the people who love our kids and are willing to take care of them.

Are you vacation professionals; how to you get so much time off work?

Drew and I are both self-employed.  Together we flip houses and Drew also owns a fire protection company. The small team of people that work for us are amazing and help keep things running smoothly while we are away. Access to a cell phone and the internet while we travel are also very helpful resources to keep us up to date and connected with work related progress or issues. We think of our travels more as adventures as opposed to vacations, so there are times when we “work” while we are away.

How often do you plan to travel?

We try to take a trip at least once a month.  Even if it’s just a weekend away, we schedule to get out of Georgia once a month. It may not always look like this, but for now that works with our schedule.  We are always planning and adjusting with our life seasons in consideration.

Do your kids love to travel as much as you do?

Our kids do enjoy traveling.  Some are way more passionate about it than others. We’ve noticed a trend, it often has to do with their stage of life. One of our children is in the life stage where his world is prioritized by which friend he is going to hang out with next.  He has been known to say on occasion, “Can’t we just stay home?” To which I respond, “So you can lay around and play FortNite? Nah. Get packing kid.” He always enjoys himself once he’s there. We recognize it as a season of his life and one that isn’t likely to last. Another one of our kids is quite self sufficient and recognizes the cost of adulting.  She’s been know to invite us to meet up with her somewhere {for example: on a sailboat in Florida}. We are fully aware we were invited because she knows we will pay for it. We are also fully aware our days are numbered and soon she will likely be working a 9-5 in another state and we won’t have this luxury of time with her on a sailboat.

My spouse and I  have a “traditional” job, but we would like to incorporate more traveling into our family life, what suggestions do you have to help us?

My first suggestion would be to take trips you can pay with cash.  The trip will be that much more enjoyable when it’s not coming back to visit with interest each month via your Visa statement. Perhaps you can do something extra {aka: a side hustle} that would be allocated to travel.  Some ideas that we have done are sell items on Ebay or Facebook Market Place and take on one extra day of work or an additional client once a month and put all that income toward the travel fund.

I would also suggest exploring places you can get to and enjoy over a weekend/long weekend.  That way you aren’t taking so much time off work, but you’re still able to explore and learn what your favorite types of family travel include {camping, skiing, water park, etc}.

One final thing to note, that I mentioned earlier, it doesn’t have to be 1st class travel and accommodations.  We have been known to cram all 6 of us in a Priceline hotel room and offer $5 a night bonus to the kids that are willing to use our packed portable mattresses and sleep on the floor.

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