Daren’s Perspective – esterinaanderson.com

Becoming Figlinese: Taxes, Pet Passports, and the Perfect Gelato

Posted on 04/12/202605/06/2026 by Esterina Anderson

This was an important week for us. No grand excursions, no Michelangelo, no thousand-year-old walls or frescoes. Instead, we focused on the more mundane, but essential, tasks of daily life: registering our dog, establishing residency, and, perhaps most importantly, finding a local gelato spot.

Some of you may be wondering how we were able to pick up our lives in the U.S. and move to Italy. Were there major bureaucratic hurdles? Was the Italian system difficult to navigate? As of today, Koji and Daren are officially residents of our comune here in Italy (similar to a township or municipality), and Esterina is well on her way to becoming an Italian citizen.

So how did we do it?

As Americans, we can enter countries in the European Union without a visa and stay for up to 90 days within a 180-day period. After that, you must leave what’s known as the Schengen Area—a group of European countries with largely open borders. Staying beyond 90 days without a visa is not permitted. Based on this, we would normally not have been able to contemplate a year or more in Italy without going through the lengthy process of getting a visa before coming here.

Our situation, however, is a bit different. Daren’s brother, Keegan, successfully applied for Irish citizenship several years ago by documenting his Irish ancestry through their grandfather. That eligibility extended to Daren, who followed the same process and obtained an Irish passport. When he left the U.S., he exited using his American passport but entered Europe (via Frankfurt) using his Irish one. As an EU citizen, he now has the right to live and work anywhere in the European Union indefinitely including Italy.

This week, we visited the local comune office in Figline to formally declare residency. Armed with an Irish passport, proof of income, an Italian tax ID (secured before arrival), and a signed lease, we entered the building, took a number and prepared for what we expected would be a long wait. Based on the stories we had heard about Italian bureaucracy, we braced for the worst. Instead, our number was called within five minutes.

The language barrier proved to be the biggest challenge. English is not widely spoken here. But after some effort, an English-speaking clerk stepped in and helped complete the process. The final step was what they call a “police check,” where a local officer visits your home unannounced to confirm that you actually live there. We stayed close to home for several days, not sure what to expect. to our surprise, the officer showed up just three days later, on Friday morning. After confirming our residency, he simply said, “Congratulations, you are Figlinese.”

Esterina’s path is a bit more complex but also progressed this week. She is applying for citizenship under jure sanguinis—“right of blood.” Because her father remained an Italian citizen, she is eligible to be recognized as one as well. With the help of a lawyer, she has gathered extensive documentation—birth certificates, marriage records, and more—to prove her lineage and her father’s uninterrupted citizenship. Her application process is now underway. Once formally submitted, she will be allowed to remain in Italy while it is processed, even if it exceeds the 90-day limit. The timeline is unpredictable, anywhere from a few months to much longer, but we’ve cleared an important hurdle and the police check confirmed her presence at the registered address, so we are now free to travel and are happy to have overcome this important hurdle.

Koji, too, needed to become a resident of Figline. Fortunately, his process was straightforward. Before leaving the U.S., we obtained a required USDA health certificate with help from our local vet, ensured his microchip was in place, and confirmed his rabies vaccination. With these documents, along with our tax IDs and passports, we emailed the regional public health veterinary department and were offered an appointment within two days. At the visit, his chip was scanned, paperwork reviewed, and within ten minutes he was officially registered. He now even has a pet passport, allowing him to travel throughout the EU.

We spent a great deal of time preparing for these processes and expected significant obstacles. So far, however, everything has been surprisingly efficient and manageable.

A wooden window with a curtain, featuring a colorful sign inside that reads 'Benvenuti a casa nostra, Anderson' against a backdrop of a stone wall and outdoor terrace. — Clearly Marking our door – advice we got for the Police check

A house number sign featuring a painted jalapeño pepper above the number 5, next to a vintage intercom mounted on a stone wall. — Clearly Marking our door – advice we got for the Police check

There were, of course, other administrative tasks, particularly around taxes, that proved far more complicated. Establishing ourselves in the Italian tax system as self-employed “digital nomads” required the help of both an Italian/U.S. accounting firm and an Italian tax lawyer. The short version: all our 2026 income, even what was earned before we moved, is taxable in Italy. While a U.S.-Italy tax treaty prevents double taxation, Italian rates are higher, making our eventual tax bill somewhat uncertain. We won’t have clarity until we file in Italy in September 2027. For now, we are legally set up to live, work, and pay taxes here. Fun indeed.

Amid all this, we’ve also spent more time exploring our new home base of Figline. At first glance, it felt a bit gritty—not exactly Siena or San Gimignano. But it has everything we need: grocery stores, a weekly market, pharmacies, restaurants, and easy access from our apartment just a few miles away.

And over time, it has grown on us.

The “grittiness” seems to be part of the Italian landscape. Public spaces can feel a bit worn, but Figline has a beautiful central piazza, complete with church bells and outdoor cafés, all surrounded by ancient walls. It’s a real Italian town, with very few tourists. We’ve started to settle into daily life here—haircuts, pharmacy runs, casual meals—and it’s beginning to feel familiar.

Last night, the piazza came alive with a Latin Festival—music, food, and drinks from Spain, Mexico, Argentina, Venezuela, and a host of other Latin countries. This was even more exciting than it might sound because in Italy, finding non-Italian food is a bit of a challenge. In many towns, including Figline, it hardly exists at all. Finally, a burrito and a taco! We can’t say that the food was great, but it was something different for a change. And the scene in town was lively and fun. Children were playing in the square. A DJ played Latin music. Italian women spontaneously broke into dance, and it seemed as if the entire town was in the square strolling, dancing, laughing, and enjoying the evening.

And then, to our delight, we discovered an exceptional gelateria right in the piazza—one that had been closed during our previous daytime visits. On a Friday night, it was buzzing, with over 40 flavors on display. There’s even a “doggie cup” for Koji. To our surprise, some of the best gelato we’ve had in Italy is right here in our own town. Chocolate fondant, hazelnut cream, and cream pistachio are our top 3 favorites so far. We’ve already gone twice and fully intend to work our way through the entire menu.

Promotional poster for the 'Sabor Latino' event featuring a couple dancing, vibrant colors, and details about the event in Figline Valdarno, Italy, including dates and location.

A cup of dog ice cream topped with two dog-shaped biscuit treats, one brown and one yellow, placed on a glass table.

Another truly amazing thing is how amazingly beautiful the spring is here in Tuscany. There are wisteria and wildflowers all over the place. We wish we could share the smell of the Wisteria through this blog. These are some photos from a walk just this afternoon and outside of the piazza last night.

Narrow pathway flanked by walls covered in greenery and purple flowers, leading towards a rustic house with a chimney and satellite dish under a clear blue sky.

A grassy field filled with small flowers, including white and yellow blooms, with trees in the background. A person and a dog are walking in the distance.

Our apartment has also proven to be a great choice, though finding it was not easy. We spent weeks researching and traveling, deciding between urban vs. rural, north vs. south, coast vs. hills, before settling on Tuscany. It felt like the safe, perhaps even cliché, choice. But the infrastructure is excellent, the location is central, and the presence of both tourists and expats adds a layer of comfort.

Our place is part of a converted stone farmhouse, now divided into about a dozen apartments. Ours spans two floors, with two bedrooms and two bathrooms. It sits on a hilltop with sweeping views of the surrounding countryside. We have a small porch where we can eat outside, a pool with lounge chairs, and beautiful gardens to walk through. With sunny days and temperatures in the high 60s this week, we’ve already spent time reading by the pool and enjoyed our first dinner outdoors.

That said, adjusting to a much smaller kitchen and refrigerator has been a challenge. As two people who enjoy cooking at home, we’re learning to adapt to limited space and fewer appliances, but not without some grumbling.

These are the kinds of details you don’t think about when imagining a move like this. Our trips around Tuscany have been picture-book worthy. But the rolling hills, historic towns, and unforgettable meals are only part of the story. The real experience is built from the everyday: haircuts, paperwork, grocery runs, and evening gelato in the piazza. These are equal parts of the tapestry we are weaving as we build this new life here in Italy.

Some more photos of our place that we are falling in love with more and more each day.

A cozy kitchen featuring a wooden table and chairs, a tall storage unit with bottles, a refrigerator, and warm-colored walls. Natural light illuminates the rustic decor, including a rug and wall art.

A cozy kitchen featuring wooden cabinets, a dining table, and a tiled floor, with a staircase leading to another room in the background.

Thanks for taking the time to read. We’d love to hear your thoughts!

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Beauty in the Large and the Small

Posted on 04/06/202604/06/2026 by Esterina Anderson

This past week we spent three days in Florence. It is a gorgeous city steeped in art and history. The Medici, who ruled the city for 300 years, placed enormous value on art—particularly painting, architecture, and sculpture. They used their vast wealth to bring the greatest artists from around Italy to Florence, where they could create masterpieces and experiment with new techniques. It’s not an overstatement to say that the Medici were the founders—or perhaps the midwives—of the Renaissance.

Everything about Florence is big. The statue of David is 17 feet tall and weighs 12,000 pounds. The Duomo, Florence’s famed cathedral, can hold 30,000 people and is one of the largest in the world. Its dome, designed and built by Brunelleschi, remains the largest masonry dome ever constructed. And the crowds in Florence are enormous as well. We were there during the first week in April—not even high season—but the crowds were impressive.

I’d call this phenomenon “big crowds to see big things.” Everyone has heard about the great sights in Florence, and they come in droves to experience them. The line to get into the Duomo stretched halfway around the building (we took a pass). Crowds on the Ponte Vecchio were so dense it was hard to get across. We waited in line for 20–30 minutes to enter the Boboli Gardens. Despite the crowds, we thoroughly enjoyed and appreciated the beauty of this magnificent city—great works, great sights, great food, great city.

I’ve been reading about the life and teachings of St. Francis. Although I’m only at the beginning of what I hope will be an ongoing exploration, I’ve learned enough to know that he would not have thought much of these big, beautiful things. St. Francis found beauty in the small things and preached the importance of simplicity, nature, and faith through action. He didn’t like big churches, big titles, or showy deeds. He cautioned against the dangers of pursuing the “three P’s”: power, prestige, and persona.

I was thinking about him a few days ago while walking Koji first thing in the morning. In the past, I would have been in a bit of a rush. I always walked Koji early, right after getting up, which meant his walk was a chore to complete before breakfast, coffee, and getting to work. While I tried to use these walks to clear my mind and appreciate my surroundings, my thoughts were often elsewhere—focused on “big things” like an upcoming presentation, a meeting, or a deadline.

Big Sights & Scenes from Florence

My walks here in Italy have been different. There is no rush. There are few big things to worry about.

On this particular morning, Koji was very into sniffing. In the past this would have annoyed me. This time, I let him sniff to his heart’s content, which gave me time to appreciate the beautiful views from our hilltop property. This time of year there are wildflowers everywhere—yellow, orange, purple, and white. Whole fields are dotted with them, but they’re so small you miss them unless you stop and look closely.

Then, in the distance, I heard the faint tinkling of what sounded like cowbells. I would not have noticed them had I not paused in silence while Koji sniffed. As I searched for the source, I saw a flock of sheep grazing in the valley below. The bells were sheep bells, not cowbells. Mountains in the distance were snowcapped, and a layer of fog covered the valleys below. In the past, I would have missed this entire scene.

It was as much a masterpiece as any painting in a Florentine gallery. But unlike those in Florence, this one was mine to enjoy without the crowds. Its components were small, everyday things: flowers, fog, and sheep.

Scenes from Morning Walks with Koji

I loved Florence and will absolutely go back to see more. But there are two messages for me in these contrasting experiences. The first is that if we spend our time only seeking out the “big things”—great domes, statues, and famous paintings—we will miss the great works of art that exist everywhere in nature. They are not celebrated or recorded, but they are there for the taking if we only stop and look.

And therein lies the second message: these natural masterpieces are easily missed. We likely overlook hundreds of them every day when we are preoccupied with other things. Slowing down, even for a few moments, opens us up to appreciating the masterworks in our own backyard.

Learning the Rhythm of Italy

Posted on 03/29/202603/29/2026 by Esterina Anderson

By Daren Anderson:

This week was about settling in. We’ve now been in Italy for four weeks, and it feels like we are starting to get the hang of things. We bought the Italian version of an EZ Pass and felt very proud breezing through the tolls without stopping, just like back home. We shopped at a local market for housewares and some food. We took Koji to establish care with a new veterinarian, and we got a membership card at our favorite grocery store.

Mastering some of these day-to-day basics has been rewarding and has helped us start to feel settled, but it’s also given me a chance to think about how different it can be to be “settled” in a new country. Italy is a modern, Western country with a language and culture that overlap with ours in so many ways. There are many similarities to life back home. But when you step back and look at the mechanics of daily life—the minute components that make up our activities and routines—differences emerge that require some adjustment.

A big contributor to these differences is history and the varied ways our societies have developed. I would describe Italy as a thoroughly modern country, as advanced in consumer technology and infrastructure as the US, but superimposed on a physical environment that was built, in some cases, over a thousand years ago. Yesterday we looked upon a beautiful church in the small town of San Quirico d’Orcia that was built in the 1100s. Buildings are old. Roads are old.

Even the location of towns is different. Have you ever seen a town in the US built on top of a hill? Or encircled with large stone walls? Likely not. In the US, most towns and cities are in valleys or along major rivers. That’s probably because American towns were not built with the need to defend against raiding barbarians in the 500s. However, Italy is filled with walled-in, hilltop towns. When you gaze out over the Tuscan countryside, you see hills everywhere capped with beautiful towns. Hilltop towns are one of the best things about Italy. Today they are beautiful and historic. In ages past they were ideal for hurling rocks, arrows, and spears down upon invading hordes and keeping them at bay. Such a need simply didn’t exist when Albany or Peoria were founded.

This geography and history drive some of the most obvious differences between living in Italy and living in the US. You drive up incredibly steep hills to reach many towns and cities. Roads are very narrow. Navigating through cities—a topic I explored in more detail in a previous blog—is fraught with challenges: squeezing through tight passages and bumping over cobblestones. It simply can’t be done with a large vehicle. Cities were designed and laid out in the Middle Ages or earlier. They certainly were not built with SUVs and 4x4s in mind. An 18-wheeler will never deliver supplies to a business in an Italian town.

Which is why Italians, almost without exception, drive very small cars. There are models that simply don’t exist in the US, like Opel, Citroën, the Mercedes A-Class, or the BMW 1 Series. Fiat 500s and Pandas are among the most common vehicles, and they are rarely seen in the US except as novelties for a few Italophiles. There are no Chevy Tahoes. There are virtually no pickup trucks.

Parking is very different too. It is rare to drive up to a store, pull into a well-apportioned parking lot, and walk in to buy your shampoo. While some stores have parking lots, most are on city streets requiring parallel parking, or parking in a parcheggio (parking lot) outside of town. Our favorite very large, very well-stocked grocery store does have a nice parking lot—but the spaces are really tight and narrow. Our car, with its range of cameras and sensors, sounds like a horror movie as beeps, tones, and progressively dire chimes ring out just to pull into a space at the Coop.

In addition to the physical differences, there are others that have taken more time to recognize. There is a cadence and schedule in Italy to which we are still adapting. Much of it centers around eating. We are breakfast eaters and always start the day with a decent, healthy meal. That hasn’t been an issue since we tend to eat at home or, when traveling, at a hotel with a breakfast buffet catering to tourists. We’ve been able to find our favorites—oatmeal, cereal, eggs, cottage cheese, and yogurt—without difficulty.

For Italians, breakfast is espresso or cappuccino and a pastry. A breakfast like this would leave us both cranky and barely functional. The first real meal in Italy is pranzo (lunch). Lunch starts at 1 p.m. and can run from 1–3. It is considered the main meal of the day. Interestingly, outside tourist towns, everything closes at 1 p.m. until as late as 4 p.m. to allow time for pranzo. This means that if you have shopping or errands—or even just want to window shop in a new town—you need to get it done in the morning. By 1 p.m., you should be seated in a restaurant or, if you are like us and prefer a sandwich at noon, find a way to occupy yourself from 1–4.

Dinner is where we’ve struggled the most. Stores and businesses reopen, and whole towns seem to awaken around 4 p.m. But if you are looking for dinner at six, you’d best cook it at home. Most restaurants won’t even offer seating until seven. And you’ll often be the only one there until 8 p.m. If you are like us and prefer to be heading toward reading and bed around 9:30, you’ll be doing so with a full stomach—which is a prescription for heartburn and a bad night’s sleep.

We haven’t sorted out how to adapt to this new cadence yet. When we are home, it’s easy. We make our own food and eat when we prefer. If we have errands to run, we do them in the morning or after four. It’s more of a challenge when we are traveling and sightseeing. Then you are more at the mercy of the Italian schedule.

One thing we’ve discovered that offers a potential solution is the café. Every town has at least one, usually in the piazza, with a mix of indoor and outdoor seating, a display case of sandwiches and pastries, a commercial espresso machine, and a full bar. Most have decent non-alcoholic options as well. These places serve as a bridge between the main meals. Italians seem to use them for coffee and pastries in the morning, and for drinks and light snacks in the late afternoon. Aperitivo hour, which picks up around 5 p.m., finds people sipping Aperol spritzes or glasses of wine. For us, these are great places to get a bite at noon, or—if we’ve had a full pranzo—a lighter dinner at 6 or 7. We’re still working it out. I’ve been surprised at how out of sync we feel based on these differences in schedules.

Other notable differences: dogs are everywhere. It’s quite a shock initially to walk into a restaurant and see dogs at their owners’ feet under the table. You’ll see them in grocery stores, clothing stores, or pretty much anywhere else. Dogs are extremely popular in Italy and accepted nearly everywhere. We read that dogs—even large ones like Koji—can accompany you on trains. The Italian airline ITA just adopted a policy allowing you to purchase a “seat” for your large dog on domestic flights. It’s been nice for us in that we can bring Koji on most outings and he gets to explore parts of the world his dog mind could previously not have imagined—like a grocery store, a cheese shop, or, yesterday, a china shop (a bit dicey). It does lead to more barking.

Which brings me to another subtle difference: the ambient background noise of daily life in Italian towns. Barking dogs are everywhere. It’s rare to take a walk without hearing them. Chimes are a constant presence. These are brass bells, not electronic imitations. Every town has bell towers atop its churches and municipal buildings. They ring the hours and sometimes the half and quarter hour. At Mass time the bells ring out all over town. More subtly—perhaps unique to our location on a hill in Tuscany—on my morning walks I can hear the distant tinkling of bells around the necks of the sheep in the valley below. These sounds may not even register at first, but they form part of the rich tapestry of life in Italy.

I could write about many other large and small differences—like the confusing electrical outlets (10A, 16A, two-prong, three-prong, large prong, small prong—I bought three different extension cords before getting the right one), or the challenge of finding over-the-counter meds (you buy them in surprisingly small quantities at a pharmacy). I could write a whole blog about traffic circles, which are a huge improvement over traffic lights and stop signs.

But the more important point is that daily life is shaped by history in ways we rarely notice when we’re at home. The routines, the infrastructure, the timing of meals, even the size of our cars—all of it reflects decisions made long before we arrived. Living somewhere new makes those invisible assumptions visible.

And that, I think, is what it really means to begin settling in. Not just learning where to shop or how to pay tolls, but slowly recalibrating your expectations of how a day unfolds. You stop measuring everything against home. You start noticing the logic in the differences. And eventually, without quite realizing when it happened, the unfamiliar rhythms begin to feel less like disruptions — and more like another perfectly reasonable way to live.

Thanks for taking the time to read. I’d love to hear your thoughts!

Please feel free to leave a comment or subscribe for future updates.

A black dog on a leash walking through a colorful shop filled with decorative pottery and glassware. — Koji in a China shop!

Narrow cobblestone alleyway with colorful buildings, featuring green shutters and a shop window displaying swimwear. — You would not drive an SUV up this street!

Back to Work on Our Terms

Posted on 03/21/202603/23/2026 by Esterina Anderson

By Daren Anderson

The main event this week was both of us going back to work. Well, sort of. But what a different feel this new “work” had for both of us. Both Esterina and I worked for decades in large organizations and held various positions, I at Community Health Center, Inc., and she at the VA. Over the years we worked in different places, had a variety of different roles, and for a long time we both worked from home. But we always worked for someone, had a boss, and had a schedule that generally featured Monday to Friday hours.

This type of work has a cadence that is familiar to many people and generally includes an early morning alarm, a hectic lunch packing, a commute, squeezing in exercise, a rush to prepare dinner, and a “living for the weekend” type of feel. This cadence leads one to think about Wednesday as “hump day” and to celebrate Fridays with “TGIF.” It can feel as if you are wishing your life away. We both enjoyed our jobs, but this daily schedule, at this phase of life, was feeling increasingly constraining. We wanted more independence.

Quitting our jobs and leaving the country was what some might consider an extreme way to find that independence. Last June Esterina retired and, not far behind, on March 1, I followed suit. However, I don’t think either of us considers this true “retirement.” We’ve both spent decades refining our skills and developing our expertise in our fields, and we are not ready to stop using them altogether. We are lucky enough to have complementary skills that are in demand and can be utilized digitally and remotely. The big change from our past work, one that we are adjusting to officially this week, is that we are now working for ourselves.

Prior to leaving, we created and registered a new company, Anderson Healthcare Advisors, LLC. Officially it is a partnership, co-owned and administered by Esterina and me, that provides consulting services to selected clients. With this structure we are free to pursue opportunities that interest us and remain engaged to the extent that we’d like. Prior to leaving work I had put out a variety of feelers to companies and people that I had worked with over the years. Several expressed interest in our new venture, and as of this writing, we have contracts with four of them.

This week, we began working in earnest. We were not sure how it would feel to start working again after only two weeks of being retired in Italy. The truth is, it felt great. For me, it was energizing to dive back into topics like telehealth and rural healthcare improvement, to write memos and white papers, and to conduct some online research. What was most liberating was knowing that I could start work when I chose and stop when I wanted. This allowed us both to get up without an alarm, have a leisurely breakfast together, exercise when we wanted, and sit down at two different desks and work when and as long as we chose.

It’s only been a week, but so far we’ve both really appreciated being engaged on a limited basis and bringing a bit of structure into our as-yet unstructured lives. We know that we are incredibly lucky to have the freedom to do this — our work translates well to remote consulting, and we are at a stage of life where we have both the experience and flexibility to try it. Still, I suspect that some version of this approach might resonate with others who feel weighed down by the weekly grind. We worked in that rhythm for many years, preparing—perhaps unknowingly—for the option to step away. When the opportunity presented itself, we took it.

We also chose to define “work” more broadly than just the consulting engagements and as such to build in structured “work time” each day that we are not traveling. Both Esterina and I have a long list of things we would like to do that can be classified as “productive”. From writing blogs to creating art, to learning Italian, and perhaps even to writing a book, we both tried this week to create a structure of daily work that enables us to do so. While much of this week focused on the new consulting work, we both also used the structured work time to start pursuing our other goals as well.

I’ve been surprised at how many people, when contemplating the concept of retirement, worry about not having anything to do and being bored. Neither of us could imagine how this could be. But I will say that re-engaging in “work” demonstrated the importance of being productive. There are so many ways to be productive. But I can definitely see that getting up each day without some form of productive engagement could get old really fast.

So we’ve mapped out a new cadence for our new life. The schedule is loose and flexible. Perhaps you could call this semi-retirement. The good thing is that we can ramp up or ramp down the amount of work, and we have the freedom to deviate from the plan at any time. The main thing that we both craved at this phase of our lives was more freedom. And that is what our new lives now provide.

It’s only been a week, so we’ll call this a pilot. But already it feels like we’ve found something we were both craving — not retirement, exactly, and not work as we knew it, but something in between. A rhythm with purpose, structure without rigidity, and days that feel intentionally shaped rather than scheduled. At this point, I think this next chapter may be less about stepping away from work, and more about defining what work means for us.

Views from my new “desks”.

Daren’s Perspective: Manifesting a Dream

Posted on 03/17/202603/23/2026 by Esterina Anderson

Our Life in Italy

A shared dream, lived through two perspectives

I’ve had a lot of time recently to reflect on dreams. Not the kind you have while sleeping, but the things we wish for, hope for, and sometimes, if we are lucky, plan for. I’ve been struck by how many people, when they hear about our plans to move to Italy, say that we’re living their dream. It seems that lots of people—including us—have imagined living abroad, and particularly in Italy. And with good reason.

Italy is the land of La Dolce Vita. It’s a place of great food, famous landmarks, incomparable art, and fascinating history. Everyone has seen images of its stunning hillside towns and seaside villages perched on cliffs overlooking the Mediterranean. These images seem to live in our collective consciousness.

Over the past two weeks our own dream became manifest as Esterina and I packed up our home, our dog, my bicycle, five boxes, and six suitcases and moved to Tuscany. We were excited to the point of giddiness as our plane lifted off. But as we arrived and drove into town toward our new home, I have to confess that I felt more than a little trepidation.

As I thought about where this feeling was coming from, I realized that when you act to realize a dream you are taking a big chance and putting yourself at risk. Now the dream has to deliver. What if it doesn’t? What if it’s not everything you imagined? Honestly, how could it be?

In the contemplative stage of creating and sustaining a dream, we build images in our mind’s eye of what that dream will be like. Often those images come from photographs, movies, and social media. Dreams contain the best vision of what we expect to see and experience, but they leave out the more mundane aspects of daily life.

So as we drove up the steep cobblestone street, turned into the driveway and began unpacking boxes, I experienced an odd blending of dream and reality. There was a gorgeous Tuscan vista from our pool, looking out over the hills. From our window we could see small hilltop towns and farms. Roosters crowed, sheep bleated, and everything was in bloom.

Superimposed on this, however, were the practical realities of daily life: learning about recycling and garbage collection; navigating a somewhat gritty town to find the grocery store; figuring out cell phone plans; and simply establishing a routine of sleeping, eating, and dog walking in a new—and very hilly—place.

None of this is to say that dreams don’t live up to their promise. They certainly can. So far, this one is doing pretty well.

A few days ago we took a day trip to San Gimignano, a truly spectacular medieval hilltop walled city. As we walked up the main street toward the piazza, I felt as if I were experiencing exactly the visions I’d imagined from my armchair back in Branford—almost to the point of déjà vu. The city was storybook beautiful and gave the strong impression of transporting us back in time.

This morning we took Koji for a walk down a hill and along a babbling stream in the woods. The air was fresh and the early morning was filled with birdsong.

But I do think that when we dream about something, we exclude the mundane in favor of the sublime. Part of making a dream real involves blending the best of what we’d hoped for with the humdrum elements of everyday life. So far, it’s a heady mix.

So what have we seen and done that has matched—or even exceeded—expectations?

First, Tuscany is truly spectacular in a way that photographs simply can’t capture. The hills are dotted with towns and farms and covered with olive groves and vineyards. The sun and clouds of early spring create an ever-changing play of light and color that transforms the landscape from moment to moment.

Tuscan buildings are colorful—hues of yellow, orange, and brown—highlighted by dark green or brown shutters and brick arches.

The towns themselves are gorgeous. Perched on hilltops and often enclosed by ancient stone walls, each one centers around a piazza with a church and a bell tower that rings out the hours. Everything feels ancient, but beautiful. There is even a slight shabbiness that adds character to the scene. Laundry hanging from windows reminds you that these are not tourist theme parks but real towns where real people live their lives.

And the food really is better.

Whether from the local farmers’ market or the grocery store, everything tastes fresher. I had assumed this might prove to be a cliché, but it’s absolutely true. Yesterday we shopped at a local market and bought fresh onions, artichokes, and tomatoes, along with cheese from a small cheese shop. Even the meat and produce from the grocery store are noticeably more flavorful than what we typically find back in the United States.

We’ve done a lot in two weeks. We are approaching each new day with excitement, grateful for the chance to watch this chapter unfold. We’ll walk the dog, exercise, and cook oatmeal. And we’ll take in the vistas, admire Renaissance art, and enjoy fresh pasta. Perhaps that’s what it really means to live a dream—not escaping ordinary life but discovering that even the ordinary moments are part of it.