Working Remotely in Montepulciano, Italy
This is part of my remote work travel series where I review places I visit as a digital nomad. Check out the rest of my posts and follow me on Instagram, YouTube, Substack, or on TikTok for more travel content!
Imagine this: you stroll across a cobblestone street, and beyond is a view of rolling hills, vineyards, and lakes. You go to a local shop and get fresh local produce, and since it’s October, you pick up some chestnuts to roast over the stove in your farmhouse-modern Airbnb that’s on a winding street right off the main plaza. For dinner, you can watch the sunset at a winery, or enjoy a meal in a Michelin-star restaurant with brick arches and cozy interiors.
Welcome to Tuscany.
Why You Should Work Remotely in the Tuscan Countryside
Most of my time working remotely in Europe has been centered around cities. Prague, Budapest, Rome, Milan — the list goes on. However, Florence and Montepulciano have had a unique impact on me: I feel a sense of slowness I didn’t get before.
When we were driving around the U.S., some of my favorite places to work remotely were the small towns. I approach my work with a certain intensity, so having walkable small towns helps me to get out of my head and into my body and surroundings in a way that feels healthy and holistic.
However, when the noise inside my head is matched by the noise of the city, I can get overwhelmed. That’s why I prefer LA to NYC — Los Angeles feels like interconnected suburbs, and you’re never too far from a hike or beach boardwalk. New York is all noise and traffic and hustle: it’s never quiet. In LA, you can find quiet in a number of places, and you can get to nature or a yoga studio in record time.
My time in the Tuscan countryside felt like a welcome reset, and if you’re planning to work remotely in Italy, it has to be on your list.
What to Eat in Montepulciano, Italy
Podre Il Casale
The #1 rule of eating out anywhere that’s not a major city in Italy? Get a reservation in advance. Tables fill up quick, and restaurants expect that each table will be occupied the whole night, so they only plan for a certain number of guests. COVID has also made restaurants be more reservation-forward, so do your research in advance.
All of the food we had was good, but nothing really stellar jumps out at me other than the gelato place Sgarbi that has the best fresh juice in town, and the incredible sandwich shop La Schiaccia dell’Opio. (Italy’s sandwiches are next level.)
So, I’d recommend you pick a few places, get reservations in advance, and go from there. Just keep in mind there are no good breakfast spots here, other than some good espresso and crepe places, so what we did is bought some fruit and snacked on those and espresso in the mornings.
What to Do in Montepulciano, Italy + the Tuscan Countryside
The best thing to do in Montepulciano? Relax. Take in the views. Eat a sandwich. Stroll around the quaint streets. People watch. Go into the cathedrals. Look at art. Visit local shops. Travel to wineries. Go to local towns like Piensa. Drive around without an agenda.
If you’re going to be an aimless explorer anywhere, this is the place.
Here’s what our itinerary was when we were exploring Tuscany on my day off:
Podre Il Casale for Lunch. What a stunning restaurant. Highly recommend this place!
Visit Pienza. An adorable town with gorgeous views.
Visit the Chapel Vitaleta. A chapel on a hill that’s a decent walk away on a dirt path away from the parking lot.
Visit San Quirico d’Orcia. Another neat little town and a good spot for a snack.
Dinner in Bagno Vignoni. Home to a natural hot spring, cool cliff views, and some neat dinner and drink options.
Where to Stay in Montepulciano, Italy
We stayed at this place in Montepulciano and it was one of my favorite stays so far, and I can’t recommend it highly enough. You’re at the top of the hill and in the center of town, so everything you’re looking for is a short walk away. Because there are a lot of events in town on weekends and parking can be tough, it’s best to stay in town and then drive to neighboring areas for day trips.
You could also stay in a neighboring town, but from my research I’d recommend you stay in Montepulciano! The best Airbnb’s were also here, as well.
RELATED: The Best Travel Cards for Digital Nomads
Remote Work Tips for Digital Nomads in Montepulciano and Tuscany
As a digital nomad, you’ll need to pick an Airbnb as your home base in Tuscany. I recommend Montepulciano because it’s large enough to have lots of shops and restaurants, and located next to a lot of quaint towns. It’s also close to the train station and easy to get to. (We took a local train from Chiusi to Montepulciano, and then took a cab recommended by our Airbnb host up to our Airbnb. Always see if you can pay ahead for taxis!)
When you’re in the Tuscan countryside, you need to take advantage of slow living and breathtaking views. Try and lighten your workload and take day trips. I spent an entire day at wineries and exploring tiny towns, and then snoozed through the weekend in-between wanderings around Montepulciano. I felt more inspired for the work I had to do, and clustered all my Zoom meetings into two days so I could take advantage of such a perfect place to rest and reset.
Our Airbnb had good WiFi but the cell service is spotty up here, so I had a few calls that kept dropping. It never hurts to ask your Airbnb host to send you a screenshot of their WiFi speed test before you book! Especially in more remote areas, you’ll need to make sure you can stay connected if your work depends on having Zoom-friendly WiFi speeds.
Last Two Cities on My Remote Year
When I embarked on a trip to Winter Park, CO a year ago, I had no idea I was going to be traveling for almost twelve months straight. Since then, I’ve lived out of a suitcase while growing my businesses and sharpening my craft, and it’s been a helluva ride.
We’re headed to Venice, Italy and then London, England — and then back home to Los Angeles!
I see my return to LA as a cozy conclusion to 2021. I’m going to be nesting in my home, doing some design projects, and wrapping up my workload for the year. Then, we’ll be planning for 2022, which will be a much more travel-lite year, but we’re still planning on doing another Europe trip as well as a smattering of weekend trips and getaways. Travel has forever changed my perspective on the world, and I’m looking forward to continuing to learn more about our world when I can, while finding a bit more groundedness in my home city next year.
I’m grateful that my career as a freelance writer has allowed me to travel, and if you’d like to become a digital nomad as well, check out my course on how I made $100,000+ on Upwork as a freelance writer!
No matter where your journey takes you in the new year, I wish you well!
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