Not New Anymore, Not Quite Routine – Week 4

By Esterina & Daren Anderson

Another week under our belt. This was another week about settling into a routine. We had some online work to do. We had a few calls. We did some shopping. Our house is now fully set up, and we can find our way around town pretty well. Nothing especially blog-worthy.

We did take time to adopt one of the rituals of Italian life: Market Day. Most towns in Italy have one, and Italian markets are much more than the typical “farmers market” we see in the U.S. To visualize an Italian market day, picture a good-sized farmers market combined with some food trucks and Walmart spreading all its goods out on tables and trucks in the town square. Market day is as much about shopping for cheap clothes, linens, and kitchenware as it is about artisanal cheese and organic broccoli rabe. You can even buy dog beds. Our town’s market day is Tuesday from 8:30 to 1:00. We took Koji, who now loves markets, and did a good amount of shopping for things we needed around the house. But we made the mistake of then heading to the main grocery store in town, Coop, and doing our weekly shop. This was simply too much shopping and stimulation for one of us (EA). We came home tired and a bit cranky—but well stocked for the week.

This was also a week for exploring our immediate surroundings. We live on a hill, surrounded by more hills. There are farms all around. A flock of sheep grazes in the valley below. There are horses, donkeys, and chickens nearby, as well as the ever-present olive groves and vineyards. Every road is either straight up or straight down. The road leading up to our house is so steep that cars, bikes, and even walking dogs all struggle to make it up. But despite the hills, exploring the area on foot has been fun. There are multiple little streets—paved and dirt—leading to hilltop clusters of farms and houses in all directions.

Esterina explored the area by taking really long runs—one was 90 minutes this week. While she doesn’t intend to be out so long, once she gets out there she keeps seeing roads—either on the map or en route—she wants to explore. She’s always beat when she gets back home, but always has new vistas to describe and a rich collection of sights and sounds to process.

New running shoes help. Somehow, she left her running shoes at home and had to buy multiple pairs—cost escalating with each new purchase—before landing on one that felt cushioned and supportive. Sometimes you do get what you pay for. Daren started exploring the surroundings more seriously on his bike. The hills and narrow roads pose a challenge, but it’s also a great way to explore the immediate area more closely.

We had our first major storm this week: two days of heavy, cold wind and rain. The house shook. The doors and windows were drafty. It was so loud that Koji—previously unwilling to hike up the stairs to the second floor—ended up at our bedside in the middle of the night. He was so scared by the noise that he decided to relocate to our bedroom for safety and security.

We’ve decided to work in a mix of day trips, long weekends, and more substantial trips over the next year, with a goal of exploring every corner of Italy. This week we took a day trip on Saturday. Val d’Orcia is in the southern part of Tuscany, and it is home to some of the most iconic scenery in the region. If you’ve seen movies or photos featuring stately rows of cypress trees, hilltop walled cities, rolling hills, fields of green, and ancient stone farmhouses, they were probably filmed in Val d’Orcia.

This region is about 90 minutes from our home, so we headed out on a road trip with a rough route mapped out to take us through the most beautiful scenery and to some of the most picturesque towns. Our first stop was San Quirico d’Orcia, a small town with ancient walls, a beautiful piazza, and a church built in the 11th century. We spent an hour sitting outside at a café, having a light lunch, chatting, and drinking coffee in the main square. Next stop was Bagno Vignoni, an ancient hot springs/thermal bath used since Etruscan times for soaking and healing. Last stop was Pienza, described as the “Jewel of the Val d’Orcia.” It was indeed a jewel.

It’s always a worry that overblown descriptions of beautiful places will leave us disappointed, but that wasn’t the case with Pienza. The beauty exceeded our expectations. Perched high on a hilltop overlooking green fields and rolling hills that extended to the horizon, Pienza was stunning: ancient stone walls and buildings, a Renaissance cathedral, lovely shops and cafés, and some outstanding local products like Pecorino di Val d’Orcia (cheese). We spent several hours strolling the walls, exploring the shops, and taking in the breathtaking views over the valley below. It helped that the weather was perfect—about 60 degrees and bright blue skies.

We’d like to say that the day ended on a high note with a great meal and a relaxing evening. But reality needed to reassert itself after a magical day. This isn’t a storybook—it’s real life. Things can’t be too perfect. After taking in all the sights in Pienza, we decided to head home, order takeout, and watch a movie. This had been a standard ritual back home, usually on Friday or Saturday night. And takeout meant Indian food.

We were very excited to find that Italy has its own version of Uber Eats (called Deliveroo), and on Deliveroo there was Indian food: Tandoori and Curry House in nearby San Giovanni. We placed our standard order: samosas, garlic naan, chicken tikka masala, and saag paneer, with kheer (rice pudding) for dessert. We laid out a tablecloth on our coffee table for some meal-in-front-of-the-TV dining and waited. And waited. And waited. It took well over an hour for the order to arrive. By then it was nearly 8:30 p.m. “Hangry” summarizes the mood.

When it finally arrived, we discovered that Indian food—at least in Italy—doesn’t come with rice unless you order it (we didn’t). So add 20 minutes to whip up some rice. Finally, time to eat… the most disgusting food we’ve ever tasted. It looked vaguely like Indian food, but there the similarities ended. Imagine chicken cubes with some onions and a bottle of Ragu tomato sauce. And a handful of frozen spinach thawed in the microwave and mixed with cubes of paneer cheese.

Esterina bailed and had popcorn. Daren suffered through the horror. And then the movie was terrible. We chose Mary Supreme, and after a dog burst into flame halfway through, we looked at each other and said, “Why are we watching this?”

How silly. None of this matters in the least, but when you change up your life and make a big move, there is a learning curve. Some things don’t translate well. And if you expect to replicate routines and comforts of home, you may be disappointed. But who could complain even slightly after a day exploring one of the most beautiful places on earth? Even we couldn’t really manage it—other than to laugh and go to bed with a smirk and a reminder that nothing is perfect.

Update from Esterina this week: https://esterinaanderson.com/2026/03/29/beef-stew/

Update on musings from Daren this week: https://esterinaanderson.com/2026/03/29/learning-the-rhythm-of-italy/

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

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

Learning the Rhythm of Italy

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!

On the Perfectly Curated Scene

This morning I sit in a beam of sun with a light breeze and the sound of water lazily lapping against the boat. Blue water and gentle waves surround me everywhere, rocking the boat to & fro. The slightest poofs of wind pop against the dark navy blue Bimini every so often, adding a different sound to the nautical melody that plays upon my ears.

Finally, I am relaxed for a few minutes and enjoying a cup of freshly pressed coffee while it’s still warm enough to enjoy—but not so warm that it is creating more heat than I want so early in the morning.

It’s not too cold or too hot today, but the constant rocking in Vineyard Haven harbor woke me up at 6am. It is actually dry this morning, so I didn’t mind coming up top into the cockpit with some blankets to temper my body just right. It’s already 7am, which means I have an hour before we dash off to the next place, in which I will sleep about 90% of the trip—and my life away.

It’s already 7am, which means I should start to hurry. Start putting away things that will move during the passage, and take a truly nasty, rocking and slamming dinghy ride to some of the sketchiest streets Martha’s Vineyard has to offer—just to walk the dog.

What at home takes less than a minute to get the dog outside for a walk (or even faster when we open the back door) turns into a 3x-a-day, at least 10 minutes each way (60 minutes total) event involving a dinghy that I still can’t figure out how to use. Add walking past dozens of warning signs about not allowing a dog in the made-up looking “pristine” spots amongst ship garages, the smell of diesel on a hot summer day, and tools strewn about. Dog pee on that small grass bed would of course ruin the whole scene.

So it is at least another 10 minutes per trip—or longer, since I actually like moving my body more than a few steps at a time. This makes walking the dog eat, at the bare minimum, 2 hours a day.

When I crash (and I mean crash) into bed every night, I wonder what the heck I did all day. I brought pastels to do art with. Yarn to knit with. A yoga mat. Books to read. But somehow day after day passes, and I’m happy if I just walked on land for more than a few minutes.

Yes, I am happy. It really is nice to appreciate small things like stretching your limbs by taking full steps on solid land. Or the feeling of a cool breeze (or any breeze really) when you are hot.

Or the art of doing nothing.

No—I lied there.

There is no doing nothing. Just living is all we do. Preparing something to eat, washing the dishes from it, cleaning up, changing my clothes. Even washing my face and brushing my teeth seems like a lot of work—and a lot of time. So much time that these things kind of take the whole day.

Some people refuse to boat with dogs—too much hair, too much pressure to get them on a walk. And they are absolutely right that it does consume your time. But I love my dog that much. His excitement makes bringing him so much more worth it. But he is a time suck.

Yesterday is what Daren called maintenance day. We got fuel and water. We did laundry and grocery shopped. It was Saturday. Seems like a good day to do those things. But other than sailing from Cuttyhunk to Martha’s Vineyard (which, for someone who doesn’t know how or like to sail, is sort of like throwing hours of your life into the sea) and having dinner with our friends (and dog walking, which I slept through the first iteration of), we did nothing else.

What would take maybe an hour or two for chores at home consisted of at least 6 hours of what shouldn’t be (especially on a “vacation”) labor-intensive work. The level of exertion in doing the smallest of things, combined with the lack of exercise, leaves my body feeling like a total pile of mush.

No lounging, no reading, no art, no exercise, no catching up on shows, no knitting—just keeping ourselves and the dog alive and fed.

We have and will see some absolutely stunning places. I’ve been vlogging the trip. These do not take a lot of work. I take short clips all day, and in my years of work experience with technology and multitasking, I can whip these together throughout the day rather efficiently.

Look at this perfect photo! These are not hard to capture—they are everywhere. I picked those flowers from wild areas by the fire tower while on a run in Cuttyhunk. Cool, huh?

But the vlogs and photos only show the beautiful stuff. I crop—or if I can, never capture—the many unsightly things right out of the crafted, curated scene. You don’t see the dumpsters everywhere. Us taking out our stinky trash or figuring out how to get pumped out. Recycling is an issue that we are temporarily choosing to ignore.

The surroundings of boating areas are often filled with broken lines and lobster traps, utterly despicable bathrooms, sparse maritime stores that look like a sad mini version of Home Depot, and slimy barnacles growing on everything you might need to touch during the day.

I like this, but I also dislike it. I miss being able to freely use water or taking a real shower. I miss not worrying about how and when to charge my devices. This is all very nice, even without modern conveniences—but not for a “vacation.” I don’t want to work so hard during my time off.

If we were retired and this was our life, I would be all in for a month or two a year.

Being on a slip vs. a mooring or anchor is better in that at the very least I could go for a run without being charioted to land on a dinghy. I ran a total of one time. I had 45 minutes before I had to meet Daren and ran with the flowers that are in that great picture most of the way.

At a slip on the dock, we can use water and electricity without conservation. But it’s still cramped and hard to cook and shower. It’s still a hike past the “no dogs” signs. The marinas and boatyards are often still very sparse, smelly, and ugly places. Not to mention the heart-stopping average rate of $8–10/ft per night during the summer.

I do love seeing places by boat. I truly do. I love Koji’s excitement when we get in the dinghy and he has no idea where we are going, but he is excitedly up for anything because he is with his owners. I love being with my dog and husband, and when we get to—friends—doing a little of nothing but existing.

However, it’s not just the curated shots and video clips it looks to be.

I have worries too aside from this pretty great trip. I feel guilt sharing them because my problems seem small in a world where stable food, shelter, and clothing are not a given. But I refuse to be another number out there using social media to only highlight the good stuff in my life too, adding to the fluff of it all.

I don’t want to feel guilty for telling the world it’s not all perfect here either. I am real, and I do not have a great day every day. More than that, I don’t want to be a part of the social media problem. I don’t mind sharing the not-so-great parts of my life because I’m a real person with real feelings, and most of my life is not the perfect pictures posted.

This is the first time in 9 days I’ve had 45 minutes to just sit and think and write. It was quite lovely. The scene was perfect. But my coffee is now cold, and it’s time to get up and do all those ugly things. Time to charge my phone again, which mysteriously uses battery power 4x faster about 10 feet from the shore.

Maybe I’ll have time like this again before I go back to work in 8 days. Or maybe I won’t. What I do know is that while I do enjoy this and I am having a lot of fun—this really is, for me personally, a far cry from a vacation.

It’s a beautiful, perfectly curated scene in which you can choose to ignore the ugly, focus only on the ugly, or find a medium in between.

I’m toeing the in-between line—but I haven’t been swayed to ignore it.

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.