"How do I travel like you?" Airbnb, Travel Hack, & Pet Sit, Oh my!

Drakes Seat, St Thomas, U.S. Virgin Islands

Drakes Seat, St Thomas, U.S. Virgin Islands

The other day (or back in March when I started this post), I was enjoying breakfast with some new friends at a riverside hostel in Central Guatemala. After the basic introductions, one of the women turns to me and says, “I want to learn to travel like you do”. I thought it was a good idea for a blog, so I’ll share some tips here:


First things first: Leverage What You Have

Take a look around you what can you share? Most of us live in a house right (airbnb) ? Do you own a car (turo)? Put that shit up for rent and enlist a friend to help you with it while you are traveling!


Do you have some unutilized space? Get creative!


Can your basement be turned into a rental? Grab a few pieces from a weekend garage sale or craigslist and get rocking. Even better if it has a separate entrance.


Do you own an RV, pop up trailer, airstream, or camper van? You can rent that out just parked in your driveway. The key is maximizing income streams. I have even seen people rent a pitched tent in their backyard. Add an air mattress and a bottle of wine and all of a sudden it’s a “glam-ping” experience! Stretch your mind to what’s possible.



Great, now you’ve got a little cash and some income streams for while you are on the road. Next!


Number 2: Travel Hack like the best of them.     



My friends at ThePointsGuy.com and TravelMiles101.com can give you a list of all the best mileage and points cards to get you flights to anywhere around the world for as little as $5.60 each way. Not too shabby, eh? Some even claim they travel for free, but the only way I have accomplished this is through buddy passes from flight attendant friends. The caveat is you need to have a good credit score to qualify for these, but you’re a finance savvy b***ch, right? Of course you are.


I personally open 2-3 credit cards a year for all the awesome freebies (miles, points, companion tickets, airport lounge passes, hotel points, global entry/tsa pre check, rental car insurance, etc.), you just have to make sure to use them or you’ll lose them. My rule of thumb is to never pay more than $300 for a flight and so far it’s working out! I was even able to use my points to buy my sister a birthday flight to Miami from Maui recently. So nice to share the wealth.


Don’t worry if you are a total novice to the game, those websites/blogs have all the step by step details to explain the awesomeness.  


Step 3: House/Pet Sit.



Man, oh man, is this one underrated! I’ve been preaching this gospel for years and I think people are just starting to take notice. This little gem has allowed me to live free (and sometimes even get paid) in Maui, Spain, New York City, Playa Del Carmen, and Boulder, Colorado to name a few. AND, I just booked 2 sits in St. Thomas this Summer! Wowie! Okay okay, so now you believe it’s possible, but how the heck are you supposed to find these grandiose opportunities?  


Again, what are your resources? The first place I always go for an ask from my community is Facebook. Sure people give Facebook a lot of flack and I agree that I can feel empty and soulless if I spend too much time on it, but using it like a worldwide community bulletin board is unbelievably powerful. It has a large reach with many people who know and trust me and it has the power to trickle down into the hands of friends of friends. Simple decide what you want, where you want to go and ask.


Of course, there are more official ways to go about things and yet, I admit that 100% of my gigs have come from friends, word of mouth, and Facebook.


This February, I found myself detouring in St. Thomas, Virgin Islands for a few days while I was waiting on a cruise ship. I was fortunate enough to be taken in by a friends cousin who let me stay with him. Not only did he have a dog, but so did his two friends that I met during my short stay. Once I realized that I was obsessed with the Virgin Islands (it didn’t take long), I started dropping the hints, I asked how much they traveled, what they usually did with their pups and let them know I am available and happy to return as a dogsitter. This is how I was invited back in June.


The best part about this form of advertising is that animal owners light up when they hear of your offering. I don’t know if you’ve ever had a pet, but it can be a real drag on your ability to travel. You quickly wear out your friends and relatives with favors, find out how expensive boarding is and either stop traveling or start paying people to watch your pets. Of course, you don’t have to do it for free, if people ask what I charge, I say I accept donations but I don’t have a set rate. A lot of times they pay you in food (“you can eat anything you want!”). If you did step 1 & 2 correctly, you have money coming in from your shareable assets and you didn’t spend much to get there anyway.


Pro tip: When I first started pet/house sitting, I used to accept any stay, now I only want to live in a home at the comfort level of my own or better, I want access to a car or be in a walkable location, and I generally want to be there 2 weeks or more if I’m traveling for the gig.


Another one of my favorite community sharing sites is Craigslist. This upcoming Oct-Jan I am hoping to be in Maui, I already have a confirmed October cat-sit and some stray dates elsewhere and yet I want to find some others to fill in my gaps. I threw up an ad in the Maui site and have gotten a few bites already. We’ll see how it shakes out.


I have been working with a website called: www.HouseSittersAmerica.com and yet, I haven’t had much luck yet, although I have two friends who have done sits through them in the Denver area.



I recently turned my friend, ThriftyGal  (www.thepowerofthrift.com), a 34 yr old, financially independent, full-time traveler, on to the concept and she’s totally hooked. She is personally a fan of the website: www.trustedhousesitters.com. There are a ton of them and most require a small membership fee to cover a background check.


Another friend of mine in Costa Rica said that they had a house sitter when they lived in Petaluma who had been doing it full time for 12 years, was well known in town and booked up way in advance. If you are looking for ways to boost your savings rate towards Early Retirement this is a rocking way to go about it.


Part 4: Stay in touch like you are Home.



One of the downsides of my business is that I have to be available at a moment's notice. Crisis rarely strikes, but when it does, guests expect it to be handled ASAP. With a regular phone plan, this would require me to pay loads for an international plan, scramble around for a local SIM card, or quickly hop from WIFI point to WIFI point. What a hassle!


My secret travel weapon is Google FI. Google has an incredible, relatively new, phone service offering that can’t be beat. For $20 you get unlimited call/text, and Data worldwide is only an additional $10/gig. I’ve had the service about 2.5 years and still haven’t found a country that they don’t cover. From the jungles of Costa Rica to the rainforests in Jamaica, I’ve been right there to answer guest questions, send a quick text off to employees, and feed my instagram babies with new content. All for between $35-45/mo.


Want to try it out? My link provides you with $25 towards your first month of service!



What are some creative ways you have used to explore the world? Share in the comments.


  • Create your Airbnb listing today (We earn a referral bonus for up to 5 new listings per profile)

  • Track your Net Worth (get $sign up, it’s free!)”20 when you