It's no secret that I love to travel, and travel a lot. Sometimes as a family, sometimes just with Porter, sometimes just with the baby, sometimes with just a friend. I'm very lucky. It's also my hobby and passion and when people ask How I make it happen, I say:
1. I Prioritize
I don't shop, and when I do I buy on clearance or at thrift stores (with rare exception). We don't go out to dinner so often, we go to movies barely ever. My car is almost 20 years old, Porter's is 10+ years old. I love traveling and it costs money so the money I have to spend on non-essentials, I try to keep budgeted toward trips.
While traveling, I employ what I call the Skimp-Save-Splurge Strategy. (I just made that up, but I'm pretty sure I'm going to copyright it). Basically, when we are in Europe we eat free hotel breakfast, baguettes, cheese, and salami throughout the day (and trail mix/granola bars I pack from home), so we can afford a few really shmancy meals where I don't have to sweat about the price tag. For hotels, we stay at cheap-o places most of the time and if possible, a few nights somewhere that feels luxurious. We walk and take public transportation more than is always my preference (no taxis, if possible), do fewer organized tours than is Porter's preference and skip shopping sprees (coworkers and children do not need gifts, they just don't). We've Couch-surfed (officially, through the website and literally, just stayed with friends) and camped and swiped free breakfast food to eat throughout the day - but have also eaten expensive meals and paid a lot for boats, guides, and keepsakes that felt important.
At home and while traveling I often go back to the mantra: Pay for it if you love it, but only if you love it.
2. Gaming the system (miles and points)
I also haven't paid for a plane ticket in over 5 years. Some of this is because I can fly standby (see #3), but mostly I play the game of credit card points and miles. I sign up for cards, meet the bonuses, pay off the credit card (always!), and rack them up. I'm partial to the Chase Ultimate Rewards program, but there are tons of other ways to do it out there. For the last two years we've had the Southwest Companion Pass, which means you can buy one ticket (with cash or with points) and your Companion can fly for free (plus taxes, $5.60). Add in that babies fly free and we've taken several trips where all three of us cost $11.20 total out of pocket (plus points, of course, which feel like funny money).
For a while I compulsively read blogs dedicated to the game (Million Mile Secrets, Travel is Free, The Points Guyn are some favorites) for tips and tricks, reminders about category bonuses and heads up about promotions. It can get overwhelming pretty fast, but if you pick a system/airline, you can can learn all the upcoming promotions for that system/airline and all the ways to maximize your points. Then booking isn't quite so daunting.
What also feels like gaming the system is we AirBNB our house whenever we can when we're gone. It's a hassle to clean and prep the house while also packing for a trip, and we don't always get bookings that cover the whole time, but usually it covers the cost of a specific tour we want to do or a few nights in a nice hotel.
Porter's mom was a flight attendant for United and I am currently listed as her +1, which gives me major flight benefits (standby flights and a lap child FTW!). She is also an avid traveler, and generous travel partner when we travel with her, and generous Nana/caretaker so we can leave Jamie behind sometimes. Porter also makes thousands of dollars of purchases for his business which makes credit card points easier to rack up than most everyday spending. Not everyone has these, I realize.