The past few years, I’ve been traveling about once per month. I’m starting to get a little embarrassed because I’m getting a lot of questions about it. How do I pull this off? I’m not a trust fund baby or a travel hacker or a frequent flier. But a lot of people have been asking how I manage to do it so I wanted to share my strategy and show you how it’s possible.
In 2014, I’ve already been to New York, Dallas, San Francisco, Denver, and Cancun. I’ve still got Alaska, Minneapolis, another New York trip, Philadelphia, and an anniversary trip to a yet unknown destination in the works. We scratched Oktoberfest in Germany because there was just too much traveling going on, and it would have been pricey for such a short trip. Also, we want to save up for a BIG trip next year like an African safari or Machu Picchu. We’re leaning toward safari.
I probably sound crazy after talking like that. But here’s how I do it:
1. I visit friends and family who live in cool places and stay with them for free.
I pick places where my friends live (this year’s free stays include New York, Dallas, SF, Denver, Alaska, and Minneapolis), which means lodging is free — and sometimes they feed me for free as well. All of those places involve visiting bridesmaids, friends, and family who flew in for my wedding last year. If they made the trip, I’m returning the favor. So travel is not just about having new experiences, it’s about having new experiences with the people you love and miss.
2. I fly on off days like Tuesdays, Thursdays, and Saturdays.
I’m lucky enough to have a flexible schedule where I can fly out on Thursdays and fly in on Tuesdays. Even when we plan a week-long trip, we might book a Saturday through Saturday flight to save a few bucks and have a day to recover before going back to work. Also, Thursday night after 5 PM still counts as a Thursday night price. So sometimes you don’t even have to take too many days off work to save the money. As long as you’re in your hotel bed by midnight, it will feel great to wake up fresh in a new city. The same philosophy goes for Tuesday morning at 5 AM — if you’re okay with going straight to work.
3. I travel off-season (read: not in the summer).
Paris is actually beautiful in February — and not that cold. And we were still able to snowboard in the mountains of Denver in early April instead of during the peak snow season. Sometimes just a week can make the biggest difference ever. We backpacked Europe in June instead of July, and boy did it help. We visited Disneyland on a supposed rainy day in January and walked onto every ride. We’re visiting Alaska in May, just days before tourist season kicks off. Many people forget that “travel” does not have to mean “summer vacation.” Summer is when travel is expensive and places are crowded. Plus, summer in Chicago is awesome so why would we leave? We’re staying put — with the exception of a couple quick trips.
4. I mostly take weekend trips instead of week-long vacations.
Travel doesn’t have to be a week-long commitment. I’ve seen plenty of cities in only three or four-day weekend trips. In fact, I prefer to take more shorter trips than fewer longer trips. There are few cities in this world where I feel I need an entire week to truly experience it. If I’m staying anywhere for a full week, there’s a 99.99% chance I’m visiting at least two different cities, if not three and I’m probably out of the country. Plus, shorter trips = fewer days spent paying for a hotel. (Another tip I’ve used: if you or your spouse get sent on a business trip, try to extend it into a weekend trip on the front end or the back end and at least one of your flights and maybe even a night in a hotel will be paid for.)
5. Weekend trips don’t have to be close to home.
A lot of “weekend destinations” in your area still probably require you to spend money on a hotel, and time and money on traveling by car. And because they are touristy destinations, the food won’t be cheap. In the Chicago area, great examples would be Door County or Mackinac Island. Why not spend just a tiny bit more — or sometimes less! — and fly somewhere? That’s my two cents. Just because a place is closer to home does not mean it’s going to be a cheap travel experience.
6. I join the rewards program at any hotel I stay at or airline I book with.
I’m trying to get better with this. For example, we flew to Thailand on Cathay Pacific and totally dropped the ball and didn’t sign up for their Asia Miles program. Often you can join late and still add miles from previous flights, but the deadline was six months after my flight. And I missed it. CRAP. That was a huge missed opportunity. In other news, I’m trying to become more loyal to Starwood Hotels and Southwest Airlines so the points add up faster. My loyalty would falter if I found a much cheaper deal somewhere else, but if we’re talking about a $20 difference, it might be better to book with a specific brand and get the rewards.
7. I have a credit card with a great travel rewards program.
I went with the Chase Sapphire Preferred after hearing rave reviews about it. I basically put everything on there, pay it off each month, and reap the rewards. (Our flights to Anchorage and Juneau were free and those were some EXPENSIVE flights.) There are people like The Points Guy who can help you maximize this kind of stuff, but I’ve yet to dive into all that.
8. I hate paying more than $250 for a flight, and I will take a 6 AM flight if it saves me lots of money.
Sometimes a crappy flight time is worth it. For our Alaska trip, we depart Anchorage Sunday night at 11 PM and get in to Chicago at 8 AM Monday morning. Yes, it was our only option, but also sometimes red eyes or early morning flights are worth it. It depends on how much you’re willing to sacrifice for travel. I’m pretty much willing to sacrifice it all. But I hate the idea of leaving at 6 AM on a Sunday when you’ve just had a fun Saturday night. I won’t do that. I’d rather leave at 10 PM Sunday night, which is probably just as cheap.
9. I’m not afraid to use public transportation.
I’ve taken a cab a couple times in New York City and once in Paris. Oh, and all over Thailand because cabs were about $3 USD. Every other city I’ve ever been to has been traversed 100% via a bus or a train. I took a 40 minute $3 bus ride in New Orleans from the airport into the city to avoid the $30 cab ride. I take SuperShuttle to and from the airport in cities that don’t have a cheaper option. (P.S. SuperShuttle is now in New Orleans. I am a frequent SuperShuttle user — you can always find discount codes on Retail Me Not.)
10. I love eating at the best “cheap eats.”
The bigger the city, the more super cheap options you’ll find. Try ethnic eats, dive bars, food trucks, unique grocery stores, delis, farmer’s markets, and the like. Because I’m obsessed with food, we often find ourselves casually “grazing” and sharing dishes throughout the day (so we can try more) instead of sitting down to big, fancy meals. Don’t get me wrong — we love a good meal and will pay a pretty penny for an experience that’s worthy. But one of my favorite things to do when traveling is to find that cheap delicious place the locals love.
11. I generally don’t fork over cash for museums or zoos and instead just experience the city itself.
I know I sound like a culture-hater for saying this, but I’ve really avoided museums lately. I’d rather walk around the busiest street or campus or park or library and people watch. Basically, in every city we visit we just neighborhood hop. Walking around and experiencing the city has proven to be more eye-opening — and cheaper — than locking ourselves in a building. I also have come to despise shopping — it’s all the same and can be bought online anyway — unless it’s a really cool outdoor market or an authentic local experience.
12. I don’t have a dog.
Besides the fact that I’m allergic, not having a dog is directly related to the fact that I like to travel. I’m not paying for my pet to go to a doggie hotel while I’m gone and I’m also not incurring extra expenses that come with dog ownership that could be spent on travel. Basically, I prioritize travel when it comes to how I spend my money.
And that’s basically it. We also cook at home a lot, I don’t buy clothes a lot, I don’t get my hair or nails done often, my gym membership is only $50 a month, we’re a one-car family, and the inside of our house is pretty minimalist — at least for now. Some people like to spend their money on fashion or expensive workout classes or their home or cars or their dogs or going out. I like to spend it on travel. The end.
P.S. I occasionally update my travel blog at travelpology.com.
P.P.S. If you want to feel instant wanderlust, watch this video and you’ll want to hop on a plane immediately. And notice, there are no museum shots here!