Travel Hacking, Work, and Embracing Fast Travel

The great thing about getting into the world of credit cards and travel hacking is just how much it opens up the world to you, not just with where you can travel, but also with how often you can do it. Inspired by traveling attorneys like MVMT blog and Jen on a Jet Plane, I’ve been on a bit of a mission to get in as much travel as I can this year while also working as a full-time attorney without a lot of vacation time. 

So far, things are going well. I’ve gone on six trips since the beginning of the year, with more planned in the coming months (I basically define a trip as any time I take a plane to go somewhere – I don’t travel for work, so a plane trip is still a special event for me). As I punch this post out, my wife and I just got back from a four-day trip to Iceland for the Memorial Day weekend – a European destination that surprisingly isn’t that far away. The weekend before that, I went to Las Vegas to celebrate a friend’s graduation from law school. And last month, my wife and I traveled every weekend around the country to visit friends and family. 

For most people, travel (at least plane travel) is a big deal – something that has to be planned out, saved for, and completed over a long(ish) period of time. From a personal finance and value perspective, this makes sense. If you’re going to spend hundreds or thousands of dollars on flights and hotels, you don’t really want to spend all of that money just to hop on a return flight a few days later. You need to make your flight worth it, which often means that travel is something you can only do once you’ve saved up the money or, more likely, once you’ve saved up the vacation days.

But when you’re sitting on a ton of points and miles (and accumulating more points and miles every few months), destinations suddenly become much closer than you think. Instead of having to wait to travel, traveling becomes possible even without a lot of time, money, or vacation stored up. Despite all of the travel I’ve done this year, I still haven’t paid for a flight yet. And I’ve only had to use one vacation day this entire year.

Embracing Fast Travel in 2018

Having this big stash of points and miles is pretty nice. So far in 2018, I’ve traveled to the following places, all using the points and miles I’ve accumulated from the past year of travel hacking:

• February = Arizona to visit Saguaro National Park and enjoy some warm weather
• April = Atlanta to visit friends; Chicago for our 1-year anniversary; DC to visit family
• May = Las Vegas to hang out with friends; Iceland just for fun 

Along with free flights, I’ve also been able to avoid paying for hotels during this travel spree.

• In Arizona, I paid for our hotels using points.
• We stayed with friends and family in Atlanta and DC.
• In Chicago, I used points to book us a room downtown.
• And in Las Vegas, I used points to book me and my friends a last minute room on the strip (the value wasn’t too bad either since there was some huge music event going on that weekend that resulted in really high hotel prices).

The only place I’ve paid for lodging so far is this recent Iceland trip, where my wife and I opted to go with the Airbnb route. Hotel options weren’t that great and we had a few hundred bucks of Airbnb credit to use from being Airbnb Superhosts.

Later this summer, I’ll fly to South Dakota for a wedding – a surprisingly expensive flight when paid for with cash. It’s a Friday wedding, so for the rest of the weekend, my wife and I will hike to Harney Peak (the highest point in South Dakota), hit up Mt. Rushmore, and then probably try to swing by Wind Cave National Park or Badlands National Park before we return home on Sunday evening. In July, we’ve got another wedding to go to in DC, so we’ll be back out that way again for a weekend.

Since my wife and I have the Southwest Companion Pass, we’re sticking to domestic travel in 2018 (if you don’t know, the Companion Pass is basically the best perk you can get if you want to do a ton of trips with your significant other like I’m trying to do).

I’d like to try to get another international trip in over a long weekend or holiday – somewhere in the Carribean would be nice, especially since it’s not that far away. We’ll see how things shake up with our free time. Ideally, I’d love to do 10 to 12 trips by the end of the year. With 6 trips already in the books, plus another 2 planned, I think I can get there.

Appreciating the Advantages of Fast Travel

Naturally, slow, longer trips would be preferable – I’d love to be able to spend a week or two in a place before having to leave. But the problem is, I’m not financially independent and my job isn’t that great on the vacation front. I only get two weeks of vacation each year, plus holidays. That doesn’t leave a lot of time for me to go on extended trips.  

What embracing fast travel does is that it makes travel possible for someone like me. I’m just a regular working stiff. I need to make travel work with my lifestyle. And while traveling to exotic, really far-off destinations can be fun, there are advantages of opting for the quick, weekend trip, including:

You Get To See Your Friends And Family. Probably the best thing about accumulating all of these points is that it lets me see friends and family that I otherwise wouldn’t see because I can’t afford the flight. I flew to Las Vegas a few weekends ago to celebrate a friend’s graduation from law school, and given my work schedule, I arrived on Saturday morning and left Sunday night. There’s no way I would have paid for that kind of flight if I had to use cash – it wouldn’t have felt worth it to me to drop the dough for such for such a short trip. But when you’ve got points, who cares? A three-hour plane ride and I was able to be there in Vegas celebrating with my friend. 

You Save Your Vacation Days. I wish we were like other countries that had more vacation days, but sadly, this isn’t the case here in the US. I only get a measly two weeks of vacation per year. What I do get though are weekends and holidays. By taking advantage of this fact, it’s possible to travel a lot without having to burn through your vacation days. For my trips, I try to leave on Friday evening and return on Sunday evening. Most of the time, my employer doesn’t even know I went anywhere. And it’s usually enough time for me to explore a place, at least for a little while. 

Travel To Recharge Your Batteries. Traveling can be stressful for some people, but for whatever reason, it’s never really stressed me out. I always feel invigorated once I get back. If you’re like me, this is a great way to recharge your batteries and do better at work.

It’s Fun. I’ve been having a ton of fun looking at a map and figuring out random places I can go to for free over a weekend or long weekend. Since I live in Minneapolis, a lot of places are only a few hours away from me, so I’ve got a lot of options for places to go.

Travel Hacking Makes Fast Travel Possible – Take Advantage Of It

For a lot of people, travel hacking is something that requires travel to far-off, exotic places – that’s all you’ll see in the blogosphere, in any event.

Unfortunately, my situation doesn’t really work with that type of travel. But it doesn’t mean travel is out of reach. By travel hacking and using points and miles, I can hop on a plane whenever I have the time, visit a place over a weekend, and be back at work on Monday, all without having to feel like I’m not getting the full value out of my plane ticket. 

If you’re thinking about embracing this fast travel lifestyle, here are some things to think about:

Don’t Underestimate Domestic Travel. We live in a huge, varied country, and I think a lot of us forget that. I’ve been in the Midwest for a while now and the way things look here is totally different compared to other parts of the country. I’d never really thought about desert locations until I went to Arizona this past winter. I was in Atlanta in 80-degree weather while a foot of snow dropped on Minneapolis. And there are many more places in this big country that I’d like to check out. Domestic travel is legit travel – don’t forget that.

Nearby International Destinations. It’s actually interesting just how many international destinations aren’t really that far away. Iceland was only a 6-hour flight from Minneapolis – easy enough to do for a long weekend. Places like the Carribean or Mexico aren’t very far away either. And any city in Canada is easy enough to get to from anywhere in the US. 

Keep Accumulating Points (And Actually Use Them). One thing that a lot of travel hackers do is constantly hoard points and miles, waiting for that perfect, optimal use for them. This is totally fine, but in my view, points and miles aren’t really that hard to come by. You’ll always spend your points and miles, but you’ll just keep getting more of them.

Marvel At How Far You Can Go

I still get amazed whenever I step off a plane and realize that I’m hundreds or thousands of miles from where I started a few hours before. It used to take people months or years to make those trips – now we do it in hours. It’s pretty incredible when you think about travel in that way. 

If you want to embrace this fast travel lifestyle, playing the credit card game is where it’s at. It’ll allow you to fly for free, so you won’t feel like you’re not getting your money’s worth. I keep adding more and more cards to my collection (currently sitting on 15 credit cards now), and at the moment, I pretty much have more points than I even know what to do with. I don’t think I’ll have to pay for a flight for at least another year or two – and that’s assuming I don’t keep adding more points and miles to my stash.

There’s a lot that goes into the travel hacking world, but if you want a starting point for your travel hacking journey, consider starting with the Chase Sapphire Preferred or Chase Sapphire Reserve. If you want to do it the best way possible though, you’ll want to snag them both at once (read my post about the One Sapphire Rule to understand the process of getting both cards and make sure you understand the 5/24 rule). And if you can get it, the Southwest Companion Pass is probably the best thing you can ever have when it comes to fast travel.

Or consider starting off your travel hacking journey with a business credit card like the Chase Ink Preferred (and read my post on business credit cards to understand why they’re the ultimate travel hacking tool).

Travel is attainable, even if you don’t have a lot of free time on your hands. You just need to understand the ways you can do it and figure out how you can fit it into your lifestyle.

How do you fit travel into your world?