So, somewhere along the line, and this going back to a of couple years ago, (now almost 5!) I say aloud to my wife “I can’t get this one thought out of my mind. I don’t remember where I heard it, but somebody said ‘tomorrow is promised to no one’, and that feels so true to me.” Numerous examples exist in our life (family, friends, coworkers etc…) of people who reached a normal-ish retirement age in a state of health that’s not conducive to extensive traveling. Hell, for that matter people we know have died before ever reaching their retirement. We had already been thinking about cutting a couple years off our work time to retire early-ish, but as we talked it through, we came to agree that our plan to see Europe in our mid to late 60s suffered from an extreme case of optimism. Who knows if we’ll both be healthy in 10-15 years, or if we are then how much longer can we expect it to last? We’re only in “ok” health right now, and while we’re trying to take steps to improve that there’s no guarantee that it’s going to pay off. We could easily reach our 60s and find that we’re in no condition to do all the things we want to do. What, exactly, are we waiting for?

The answer to that question, of course, is basically “money.” I said earlier that the ability to move to Europe requires, first and foremost, the will to do it, and that’s true. The second thing it requires, though, is money. Not obscene money, but whatever number you thought you’d want to retire comfortably (or at least safely) in the United States is a reasonable starting place.

There’s actually a whole lot more to say on this subject. We’ve met people who have indeed immigrated on very modest means. You can live much more cheaply here – but you will be living much more cheaply if you take my meaning. If you’re prepared to live far from a city, in a small town or village where you can expect next-to-no English being understood, and eating a quite-simple diet, you could probably get your monthly budget to … I don’t even know. $500/month? I can find you a T0 or T1 in the sticks for +/- 200eu, utilities oughtn’t to be more than another 100, and then you’re feeding and entertaining yourself on the balance. (Note that you most likely would strongly consider having a car to succeed at this kind of lifestyle.) However simple a life that sounds, you’d at least be saved from the possibility of ruination via medical debt. So from that starting point, your available resources can push you closer to town, push you into nicer digs, push you into more restaurants, and so on and so forth. We’ll chewing on how to write more on this subject later, because we know if you’re anything like we are, this is the subject that gives you the most anxiety about potentially making the move. Hang in there.

Now where were we…

If our financial plan only works on the assumption that we’re working into our 60s, then trying to go any earlier could be super dangerous. Back to the financial advisor we went. “Kevin,” we said (for his name is Kevin; hi, Kevin!), “you know that financial plan we had worked out all nice and pretty? Wellll, what happens if we stop working sooner than we initially said?” He asks us how much sooner we’re talking about. “No no, you misunderstand. We want to know how early we can stop working and still be financially viable. You tell us.” So Kevin runs some different scenarios, and we work out our best estimates on what a monthly budget would look like, and he comes back to us and says “assuming average returns and no catastrophes, you can retire as soon as you can access your retirement accounts without penalties.” (Small clarification here: he never framed it as in “so long as there are no catastrophes” in the sense of recessions/depressions; any competently designed plan builds in some amount of risk management to get through lean times. What he meant was “so long as the basic underpinnings of the economy don’t disintegrate, like a catastrophic war, or similar.”) Great! That’s only 6-7 years away, way better than the 12 or so we were aiming for! We can almost taste the buffala mozzarella from there. We begin to shift from fantasizing to cautiously planning what retirement might look like. Do we own or rent a home? Which part of Italy do we want to live in?

A brief aside. Getting this news was actually far more emotional than I’ve described it to you. Neither Lisa nor I “come from means” as they say. Neither of us was actually dirt poor, but neither of us had a model of comfortable retirement in our lives. (This has since changed, but when we got together this was definitely true.) We had been doing what we had read we should do (fund the 401k, spend within your means, don’t try to keep up with the Joneses, etc.) but we weren’t financially literate enough to have a firm grasp of how we were doing. The moment we were told, by a professional with fiduciary responsibility towards us (that is, not trying to sell us anything, they get paid for knowledge not commissions) that we had, in fact, colored within the lines and were on track for a secure retirement, we had an intense shared moment of “we actually did it.” You tell yourself it’s going to work out, but part of living a moderate lifestyle is not having tangible feedback of financial success. And yes, greater financial literacy would have helped here. I’m not saying we’re geniuses, I’m saying this is what happened. Parents, teach your kids about money while you’re teaching them everything else; you’ve got nothing but time, right? :p

Aside over! We began to think of our future in very concrete terms of “when we move to Italy…”. What’s the rental market in Pieve al Toppo look like? How’s the grocery shopping? Ooo, which cities do we want to explore first? Do we maybe want to live in a city instead? Rome would be way too intense, and Florence looks kind of spend-y, but Siena looks like it’s in a sweet spot of culture and scenery and affordability. Yeah, that might work! Plus, we can never tell the story of accidentally driving onto the Piazza del Campo too many times, right? Do we want a car? We were excited by all the questions.

Except, soon we’re not so sure about Italy.

Many people know Sienna because of the opening scenes of the rebooted Bond series, A Quantum of Solace, or maybe just for the bi-annual horse race, the Palio. If you don’t know what I’m talking about, Rick Steves does a great job of capturing the magic of Siena (here).

We weren’t going to go at all. “Everyone” talks about how it’s a perfect example of a medieval city, and that’s a period of history we just aren’t all that interested in. Two people talked me into it (I blame C. and E. — you know who you are).

We would have been wrong to miss it.  If only because it gave us one of our best stories of the trip. We were using Google to get us to a parking lot on the outskirts of town (many walled cities don’t allow cars inside, or not during the day, or only for deliveries, or . . . it’s best to plan to park and walk). Fro most of it we were following other vehicles, until we made a left and found ourselves on a narrow street that opened . . . onto the Campo itself.

Yes, that Campo. Filled with pedestrians. Off limits to traffic. Aieeee!

So we took a quick left and turned down another street, this one lined with cafes. Our being lost must be regular events for the locals, the waiters just moved the chairs a bit out of our way. A local asked J. how the handling was on our car (a hybrid). And we slowly made our way back to safe roads.

Once we parked (legally) we were free to wander, and we had a great time.  Each of the seventeen “contrade,” or areas in which the city is divided, challenge each other in a passionate horse race, the Palio. The contrade are: the Eagle, Snail, Wave, Panther, Forest, Tortoise, Owl, Unicorn, Shell, Tower, Ram, Caterpillar, Dragon, Giraffe, Porcupine, She-Wolf and the Goose. As one walks through the streets of Siena it is easy to know in which Contrada you currently are in by observing the flags and emblems displayed along the street.

The Duomo is incredible. It’s a huge Gothic building filled with treasures by Pisano, Donatello and Michelangelo as well as frescoes by Pinturicchio. The exterior of the cathedral is pretty impressive, and if you don’t have a lot of time in Siena, you might not even go inside and just enjoy the outside. The exterior and interiors are decorated in white and greenish-black marble in alternating stripes, black and white being the symbolic colors of Siena. I’m told the interior of this Duomo puts the (more famous) one in Florence to shame.

I do know that the pavement is decorated with the art of mosaics (using various techniques) to create storytelling masterpieces. They are superb. My camera did not capture all that I would have liked (it was a bit too dim, and I avoid flash to preserve the works). Furthermore, the Piccolomini Library is a gaudy collection of manuscripts and frescoes by Pinturicchio. In the middle of the room, take a few moments to admire the beautiful copy of The Three Graces from Roman times, based on the more ancient original that dates back to the Hellenistic period.

We picked up our annual holiday ornament here, and headed out to find the secret square on the side of the Duomo.

It was time for an aperitif by then, so we found a table facing the Torre del Mangia — town hall. The red brick subtly changed color over the hours we sat watching the people and telling stories to one another (and shamelessly listening in on other’s conversation!).

We had a lovely time.