A Million Ways to Madrid
How to Start Planning Long-Term Travel
There’s something daunting about sitting in front of a screen and trying to discern what life will look like on another continent enough to make informed decisions about it.
The difference between two Airbnb listings could be the difference between two completely different perspectives on the town depending on what neighborhood you drop yourself into. That listing may have had a gorgeous photo, but can you get to it without a car? Is the area walkable? Are there markets? How far will I have to carry groceries? Is there public transit nearby and is it good? All this is safe, right?
There’s a rush of exhilaration that follows making the decision to travel full-time immediately followed by a flood of questions. It’s time to take all of those abstract ideas about traveling and whatever destination you’ve been dreaming of and find out all the practical things about it. Those photos may have been two pages apart in the guidebook, but they may be two days apart in reality. Here is the process we took in planning our first months of full-time travel and some of the resources we picked up along the way:
How to Pick a Destination
Start with the kind of experience you want. What does your ideal day look like? Are you waking up near the beach, in the city, in the mountains? Are you moving from place to place often or looking for some place to set up base camp for awhile? Do you have a car or are you traveling on foot? Answer these questions and use them as a filter when looking at potential destinations.
Hop on Airbnb and see what’s interesting. Set up filters with your price range and must-have amenities. Start with cities you think you might like or just drag the map around until you find something. I tend to make lists of potential places divided by country. Over time, you’ll discover places you’ve never heard of or would have never thought to consider.
Make a short list from your favorite Airbnbs. Jump on YouTube and see if there are any VLOGs about the location. Read guidebooks—but be aware that they’re geared toward vacations and vacation budgets. Reach out to friends to see if they know anyone who has been. Or, message guides and travel writers directly with specific questions. I’ve found that 90% of the time, they’ll take the time to write you back with an enthusiastic, first-hand response (Thanks Rick Steves!)
Double-check your work. What will it take to get there? Does it have the amenities I need (washer, internet, space to work, enough space to stay out of each others’ hair, an adequate kitchen, etc.)? Taking the time now to imagine what it’s going to be like finding food or having an off-day will help solidify if the studio with a sofa bed and a microwave is really a good idea for two people for an entire month.
Know that nothing is perfect. There is no one perfect place out there; there are always trade-offs. You’re going to make mistakes, things will go wrong. Do your homework as best you can and book it! You’ll know when you’re getting down into the weeds. You can deal with the rest in motion.
How to Get There
Look at all the options. Start broad and work your way down. Is flying the only option? Can I take the train? I like to start with Rome2Rio and just see all the different ways to go between two points on the globe.
Start working combinations. After flying for the airlines, I still can’t tell you too much about the rhyme or reason of pricing individual flights, but I can tell you some things to consider. Start simple and gradually add complexity. I like to jump on Google Flights and start with the two city pairs as a baseline. Can you direct? Are there layovers? How long (32 hours isn’t a connection, Frontier)? Sometimes, altering your departure airport can yield savings (i.e. Burbank vs LAX). Maybe there’s a subsidy there you don’t know about? Maybe there’s more competition? Or, maybe airlines are paying through-the-roof for landing slots or gates?
In our research for Spain, I found that adding a segment before our transatlantic flight was significantly cheaper than paying for the transatlantic alone. Why? Who knows. Try different combinations (airport pairs) and see what you can learn about the routes.
If you don’t need specific dates, fly on days that are cheaper…like Saturdays or whatever day is low-demand for that route. If you want to get fancy, you can also do things that time-limited vacationers don’t typically do: add a stopover. Maybe it’s cheaper to fly to an intermediate stop and stay for a day or two and fly on another cheap flight to your final destination than it is to fly directly same-day (i.e. Napoli-Venice-Split vs. Napoli-Split).
You can also consider booking two separate reservations (flying two different airlines), but bear in mind that the first airline has no obligation to get you to your final destination, so if you are delayed (maintenance, weather), you could miss your second flight and be stranded. (Adventure, right? Maybe not…) I only do this if I know something about the route and the time of year (storms, icing, air traffic control delays) AND if there’s enough time to take a significant delay. For our trip to Spain, we elected to fly Southwest from Nashville to Washington D.C. on one reservation before starting a separate trip on American over 5 hours later.
Also, if you are flying a budget airline, look up their bag fees and carry on sizes (they’re different in Europe).
Draw it all out! There’s no way you’re going to keep up with everything in your head—especially when you start factoring in local trains and ferries. While there are endless possibilities, you’ll notice when the new ideas start slowing to a halt. Again, consider tradeoffs. Maybe paying an extra $100 is worth not stressing about a connection. Or, maybe you want to spend $200 on three nights in an intermediate city rather than flying directly for the same cost.
Be sure to double check your dates, times, and connections. Look at a map and check your distances between airport and train stations and consider if you need to Uber or take local transit. Thinking through your day(s) start to finish will help factor in things like that as well as immigration checkpoints or meals.
Book it! Once you’ve gotten a good picture of the routes and have decided how you want to travel, book it!
Our Trip to Spain
Nashville (BNA) - Washington D.C. (DCA) 10:10 - 12:50 Southwest $136
Washington D.C. (DCA) - Boston (BOS) 18:00 - 19:32 American +
Boston (BOS) - Madrid (MAD) 20:50 - 9:50* American (Iberia) $235
Flight cost per person: $371
For our maiden voyage across the Atlantic, we elected to leave from Washington D.C. (DCA) because of the price and availability of connections. No matter what way we looked at it, an itinerary starting in Nashville and ending in Europe started at $800 one-way. For that reason, “leaving” from another airport made sense. If booked alone, our transatlantic flight from Boston would have been $700, but when combined with a flight from D.C., it was only $235 for the entire trip. Makes sense, right? That with the availability of affordable flights from Nashville made DCA a viable intermediate stop. Because our flight from Nashville left on a reliable airline, in the morning (before summer storms), and with over five hours of leeway, I felt comfortable booking two separate reservations.
From there we allowed 4 hours to deplane, clear customs, catch an Uber, and grab lunch before taking the high-speed train from the city center in Madrid to Sevilla. The train tickets cost $58 per person bringing the total to travel from Nashville to Sevilla to $429 for each of us.
THE VERDICT: Not for the nervous traveler.
Tips
Reach out to Airbnb hosts directly to see what the best price is for your dates (long stays).
Monthly stays on Airbnb are often heavily discounted.
Book train tickets in advance.
Use a VPN from an in-country server to book train tickets. RENFE declined all of my cards and would only accept PayPal. Oui SNCF would only display prices from a French server.
It’s cheaper to book a one-way ticket. 😎
