Our 4-Point Lodging Strategy

Way back in primary school social sciences, I remember once having to memorize a list of humankind’s basic necessities to sustain life. Shelter, food, and water were on the list. I don’t remember the rest of this list, but nowadays I imagine it includes good bandwidth and Netflix.

The one topic we invested the most research and thought into in regards to this nomadic lifestyle was lodging, a more comfortable euphemism for the first of that list, shelter. After all, we didn’t imagine living under a lean-to of palm fronds whilst visiting London and Paris. That research paid off (as all research tends to do), and we now have the benefit of nearly 2½ years of practice and refinement. For us—and presumably for anyone interested and with the wherewithal to apply what we have learned—it has come down to these four approaches for identifying and affording having palm fronds overhead (so to speak).

We’ll blog in more detail on each of these categories in the coming weeks as we strive to answer the most common question we get asked, “How do you do it?”

Privately Owned Lodging

The geeky term for this aspect of our lodging strategy is “peer-to-peer” lodging. Basically other private real estate owners like you rent out anything from their vacation homes and condos to spare bedrooms in their house. AirBnB.com has commanded the travel industry’s attention in the past few years, but the phenomenon has been around for a while. Years back we used A1Vacations.com, but there was also VRBO.com (Vacation Rentals By Owner)—both have been gobbled up by the venerable HomeAway.com. AirBnB blew past HomeAway a few years back with a better-looking site, better search options, social features and reviews, as well as in-site booking and payment handling. But HomeAway has caught back up with AirBnB and stands toe-to-toe with them in terms of functionality.

With either AirBnB and HomeAway, a factor working in favor of longer term travel (staying a month, for example) is that home owners love the idea of not having to worry about bookings and check-ins and check-outs for a month. Both sites will calculate longer-term stay rates with discounts, and sometimes those discounts can be 40% or more off the normal nightly rate. Rule of thumb: the longer you can stay, the deeper the discount. Also, negotiating is possible with both sites, though a bit easier with HomeAway: just use the “contact owner” feature before you use “instant book”, and simply ask if they’d take…and name your price. If we wanted to book a place in the Caribbean for 3 months, we’d expect to get at least 50% off the daily booking rate, even more if we are visiting outside of high season.

What both sites lack, however, are loyalty programs. Hey AirBnB and HomeAway, are you paying attention??

House Sitting

If big discounts to stay in someone else’s condo for a month or so aren’t enough, how about staying in their house while they go on vacation…for free?

House sitting used to be a business: you would have to pay a service for someone to come stay in your home, take care of your lawn and garden, and take care of their pets. But with the advent of digital nomadism, people—like us—volunteer to house and pet sit for free. It’s a win-win-win for the traveling house sitters, the homeowners, and the homeowner’s pets.

House sitting comes at the sacrifice of flexibility: you land housesits where and when the homeowners need you, not necessarily when and where you want to go. That’s not to say there aren’t house sits available in great locations like London or Paris at high season, but supply and demand dictates that you’ll probably be one of a couple of hundred applicants to such juicy assignments. Instead, especially as you are just getting started in house sitting, look for more out-of-the-way but still interesting places, like small English country villages or US States you’ve not visited before.

In addition to the obvious advantage of free lodging (including being able to cook and wash clothes for ourselves), we’ve found a few other wonderful advantages to house and pet sitting. First, it forces you to go outside the travel box and visit places you might not otherwise have thought to visit. Second, you get to be “pet grandparents”, loving on someone else’s pets for a little while, spoiling them rotten, and then handing them back. Third—perhaps best of all—you’re going to make great friendships with homeowners as you go.

Here are our three favorite house sitting websites:




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Our AirBnB Apartment in Budapest, January 2016

Home Exchanges

We actually started our full time travel life by doing home exchanges. Like house sitting, it’s a “free lodging” strategy with a simple premise: we want to go where you are, you want to come where we are, so let’s trade homes for a couple of weeks. If you have a vacation home or condo, then you’ve got two locations you can offer and if any of your homes are in an interesting location—like Florida or Italy—you can just about pick anywhere in the world you’d like to go.

An advantage of home exchanging over house sitting is the inherent flexibility. Your partner home owner is a peer in the transaction with you, so you both have the opportunity (and right) to negotiate dates and other conditions like using your vehicles or taking care of your pets and plants. And like house sitting, you’ll make friends through your travels.

The big disadvantages are that you (obviously) have to have some real estate to exchange. If, like us, you’ve gone entirely nomad, you lose your bargaining chip, but one day in the future we plan to “come in for a landing” somewhere, and that somewhere will be a place with high home exchange value.

There are a couple of home exchanging and swapping websites out there, but our experience has been limited to www.homeexchange.com, a great site in terms of functionality and availability of listings.

Conventional Lodging

While the majority of our lodging is in the first two methods above, we—like most travelers—enjoy the comfort and amenities of a nice hotel every now and then. We look forward to a few nights in a 5-star hotel sleeping in a nice king-sized bed, soaking in a hot tub, or sweating out some of the local cuisine in a sauna. The two keys to our hotel lodging strategy are to pay attention to the average per-night cost (a “few nights” in a 5-star hotel are ok, but if we need a place for a couple of weeks we’ll look for something more modest), and to always take advantage of the hotel rewards programs.

There are a billion or so blogs out on the interwebs on hotel (and credit card) points programs. Any strategy boils down to one real key: consistency. It will do you no good to participate in thirty different hotel loyalty programs. We recommend picking a single multi-brand program and concentrating all of your lodging reservations, from 1-star to 5-star, with that service. And for us, that service is Hotels.com.

For over two years now, all of our hotel reservations have been made on Hotels.com and have taken advantage of their rewards program. That program seems simple at first glance: stay 10 nights on Hotels.com bookings and stay an 11th night free. There’s a little more to it than that, as the value of that 11th night is the average of those 10 previous nights. So if you stay 10 nights in a discount hotel at $50 a night, your “free” night is really only a $50 discount. We prefer to think of it this way: every night you stay on a Hotels.com booking, you bank 10% of that stay which you can use after 10 stays. The math is the same, but it just seems to make a bit more sense to us that way.

An interesting aspect of the Hotels.com rewards program is that it (usually) supplements the hotel’s own rewards program, meaning you can often earn both Hotels.com rewards and the hotel’s own loyalty points. I say usually and often because sometimes the great rates you book through Hotels.com are discounted because the hotel doesn’t grant rewards credits for those bookings. You probably won’t know when you book at Hotels.com if this is the case, but every time you check in ask the front desk clerk if you can give them your hotel rewards number. Not only have we earned a dozen-plus free nights on Hotels.com, but we’ve accumulated a nice bank of Marriott, Hilton, and Intercontinental (Holiday Inns) points that we use from time to time.

For us, hotel lodging is our “gap” lodging option. We use hotels to fill gaps in the anchors of our travel, a few days here, a few days there. But with consistent bookings through Hotels.com and doubling up on rewards, sometimes those stays are free.

Honorable Mention: Couch Surfing

You might think couch-surfing is something the millennial crowd does (check out CouchSurfing.com), but the reality is it’s been around ever since Cain and Abel got their own houses and one came to visit the other (until they had that little spat). We all go stay with family and friends from time to time, and since we love visiting (and since we don’t have a house) it can’t be denied as a part of our travel strategy. The more we travel, the more friends we make and the more we get invited to visit. And it never ceases to amaze us how many people have invited us to stay in their condos or vacation homes when they’re not otherwise in use, an offer that we’ve never availed ourselves of (yet) but that we think is a wonderful commentary on people’s natural generosity to share their palm frond lean-tos.

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