I never intended to visit Italy, but our spontaneous trip inspired me more than I imagined it could. Nick and I escaped for 6 weeks to the Italian countryside, where we cat-sat (via Trusted Housesitters) in the picturesque town of Citta Della Pieve. Our visit coincided with the olive harvest, which was a welcome surprise. We only spent half a day picking olives on a neighbor’s farm, but I will never forget climbing into the trees to reach the olives or meeting the neighbor’s donkey, Nuvola.

Other than harvesting olives, our days were spent hiking, biking, and exploring the neighboring towns. It sounds like we were pretty active, but we did do a lot of resting too – which we really needed after another season of guiding in Alaska. Below, I’ll share a few of my favorite adventures so that if you end up in Tuscany or Umbria down the line, you can enjoy them too.

Prior to our visit to Tuscany and Umbria, we spent 2 weeks exploring the Dolomites (which were absolutely mind-blowing). If you’d like to read about our time in the Italian Dolomites, click here.

What are Tuscany and Umbria Like?: Tuscany and Umbria are a tapestry of churches, markets, farmland, and artwork - a place where people live in harmony with the land and welcome visitors with open arms. From your first bite of pepper-dipped pecorino cheese to landscapes that seem hand-painted by Michelangelo’s brush, this country delights all who visit. It’s impossible not to fall in love with the UNSECO-protected cities, the weekend markets, the colorful ceramic studios, the wine, the sun-ripened olives, and the museums.

First, here are my top tips for visiting Tuscany and Umbria:

Download the following Apps: If you’re planning on going on airplane mode while you are traveling, it helps to download Google Translate (Italian), WhatsApp, TrenItalia, The Fork, and Google Offline Maps for the regions you are visiting.
Carry Cash: Although you can use a card almost everywhere you go, Italians prefer to be paid in cash. It helps to have a few Euros on hand at all times. In urban locations you actually have to PAY a euro (in cash) to use the bathroom, which definitely inconvenienced me during a high stakes moment in between trains at the Florence Train Station.
Rent a Car: Renting a car is the easiest way to travel around in Tuscany and Umbria. We found the bus system to be less than reliable (at least in the off-season), and ended up renting a car for a few days at a time from a small place in Chiusi called Noleggiare. It cost us about $25/day for an automatic car. Request an automatic car unless you are a stick shift pro. And as a reminder, you will need to get an international driver’s license prior to arriving in Italy, otherwise you could face a hefty fine (we got ours from AAA). The trains are also very good (we used them for travel between the major cities Milan/Florence/Rome), but it’s important to check for union strikes (which are announced ahead of time) as our travel was delayed twice by these.
Try to Speak Italian if you can: Whenever possible, try speaking Italian. Italians appreciate you trying and won’t make fun of you if you get it wrong. Simple phrases that gave us more confidence included: "Buongiorno (sometimes shortened to just ‘giorno,’”) “Buonasera (sometimes shortened to just ‘sera’” “Bona Note,”) “Vorrei due cappucini per favore,” “prego,” and “È possibile?” We practiced on Duo-lingo a little before coming.
Don’t visit towns or plan to do anything between 1-4PM: Most shops and restaurants close down for Riposo from 1-4PM (a time to rest and spend with family).
Make Dinner Reservations, and don’t plan to eat until after 7:30PM: Restaurants don’t open up until at least 7PM, and it’s dorky to show up at 7. The Italians will let you know that. Restaurants prefer that you make advanced reservations via WhatsApp or The Fork. The Fork is a European dinner reservation app.
Learn from the Locals: The people and the land in Tuscany and Umbria are intertwined. Everything feels slower, and no one seems stressed (although that is a very easy assumption for a tourist to make). Forget to-go cups, to-go-meals, etc. Slow the heck down, talk to the people sitting at the table next to you, pet their dog, eat some good food, and when you are done with your meal, order a cappuccino and continue slowing down. The best advice given to us by our kind hosts Raymond and Leonardo for exploring Italy was: “if a door is cracked, open it. It is an invitation to enter.”
Prepare for Italian Cafe/Coffee Culture: Italians have different eating habits - Breakfast isn’t heavy and typically includes a croissant and a cappuccino. That’s hard to get used to when you are a mountain-gorlie used to fueling with a giant breakfast burrito and slamming 3 black coffees before 10AM. Try not to order a cappuccino after 10AM — this will queue locals into the fact that you are a tourist. If it’s after 10AM, order an espresso. If you are enjoying a meal, don’t order coffee with it. Save your coffee order for after the meal. You’ll get nods of approval. And for god’s sake, don’t take your drink “to go.” Food and drinks are meant to be savored. The only thing you are allowed to walk and eat is gelato (and maybeeee a sandwich). SLOW down, you silly American.
Shoes & Fashion Things : Italians LOVE fashion, designer clothing, and nice shoes. Nick and I got away with jeans, flannel shirts, and sweaters most places, but it was clear to us that it is a culture that prides themselves on lookin’ nice.
The food in Italy is just better: Get pumped. The food in Italy is truly exceptional. Mainly because it is made with simple ingredients. Pasta is made with flour and eggs (that’s it). There aren’t added ingredients, sugars, salts, or preservatives in any of the food. Prepare to have the best pasta and pizza of your life. That being said, aside from the big cities, there really isn’t any diversity in the food in Italy — it’s pretty much all Italian or nothing :)
What to Bring Home as Gifts from Italy: There are a hundred and one amazing gifts to bring home from Italy. We sent wine home from Montepulciano (in Tuscany), purchased art in Cortona, carted home hand-painted ceramics in Derruta, and shipped freshly-pressed olive oil home from the local farms.

Visiting in October & November: October and November are the off-season. Expect crisp days (temperatures in the 40s-60s) and some rain. We were told it was the rainy season but only experienced about 4 days of rain in the 6 weeks we were there. Be fore-warned, Gelato shops close down in the winter (except for in the warmer tourist destinations like Rome).

WHAT DO TO AND WHERE TO VISIT IN UMBRia and Tuscany, ITALY:

For our itinerary, we were based in Citta Della Pieve: Citta della Pieve is a small town perched on a hill on the border of Tuscany and Umbria. It was our basecamp for 6 weeks. Nestled perfectly off the beaten tourist circuit, this true Italian town abounds in culture and beauty. There is very little English spoken. I wouldn’t necessarily recommend driving here just to visit for the day because it is so quiet, but it was the perfect place for us to post up and live for 6 weeks. Everyone was so kind, we got to harvest olives in the fields, and it was truly glamorous Italian countryside living. We tried just about every restaurant in town. Our favorites were Trattoria Bruno Coppetta, Locanda Della Picca, and Taverna Del Perugino (for thin-rolled pizzas). For lunch, Il Pizzicagnolo makes sandwiches that were to die for. For cappuccinos or aperitivos, Matucci is the social hub of the town.

Visit Deruta for Hand-Painted Pottery that will Blow your Mind: I still have to pinch myself when I think about Deruta. I LOVE pottery and ceramics. I could’ve spent a million dollars and hours here, strolling the streets, watching artists hunched over half-painted bowls. I’m glad my friend Alison recommended that we visit. Once we entered the walls, we were treated to open doors overflowing with colorful ceramics, kind artists who wanted to tell us about their processes, and the evolution of colors in the region. I bought a few gifts here to bring home, but chatting with the artists was one of the best parts. Give yourself at least a few hours here, and don’t forget to stop by the ceramics museum in town. I get bored easily in museums and left feeling inspired by the fact that humans have been creating pottery for a LONG, LONG time.

Bike around Lago Trasimeno and have Lunch in Castiglione del Lago : Lake Trasimeno is the largest lake in Italy, and there is a beautiful biking path that circumnavigates the lake (60km in total). You can rent bikes in Castiglione del Lago for the day. The lake felt like home, and the city felt decided more casual than other Italian cities. As you peddle around the lake, watch sailboats breeze by the olive-tree dotted shoreline. After your ride, treat yourself to a meal in Castiglione del Lago. The best Foccaccia sandwich we had in Italy was at the unassuming La Schiaccia dell'Opio, and the best cappuccino we had was at Pescatore Cafe (right on the waterfront). We are told that Darsena (on the water) is the place to go for live music on the weekends, although we never made it to the 9PM start time.

Fisherman casting off the shore of Lake Trasimeno

Visit Montepulciano for Wine: Montepulciano is a medieval town known for its Vino Nobile, a red wine produced in the region. We spent about 3 hours here and enjoyed strolling through the streets, popping our heads in the churches, eating canolis, and taking the underground wine tour. Many of the shops offer tastings and wine shipping deals to the US. We ended up sending 6 bottles home to each of our families from this shop. A visit to Montepulciano can easily be combined with a trip to the neighboring town of Pienza or even Bagno Vignoni and the thermal springs (see below).

Underground Wine Cellars in Montepulciano.

Sample Pecorino Cheese in Pienza: Let me say that I wasn’t a cheese snob until I was. Pienza wrecked me in that department. Pecorino cheese is one of the oldest cheeses in the world. It is made from sheep’s milk. If I’m honest, I was expecting to try it once and move on (I was expecting it to be a soft cheese, but its texture reminds me of a hard Parmesan). There are only a handful of artisan cheese makers and Shepards left in the region. Pecorino’s flavor is refined by the flavors of the meadows that the sheep graze on, and Pienza is one place you can safely pick up an original pecorino. The town itself is also worth exploring, offering a UNESCO-protected vision of piazzas, churches, and corridors tucked above the Val d’Orcia.

A little charcuterie board we put together with our friend Matt when he visited. Pecorino Pepper Cheese from Pienza on the right.

Take a Dip in the Thermal Pools near Bagno Vignoni: Despite its small size, you’ll find a generous splash of Italian flair in this small town. Since the 9th Century, pilgrims have stopped here to bath in the natural hot springs on their journey to Rome. Today, the main square is filled with a pool of naturally-fed thermal water and the town abounds in various upscale wellness spas. If you’d like to take the casual approach (like we did), you can dip your feet in the water near the center of the town. The waters are said to have healing properties. You can also drive down below the town and swim in the natural pools for free (although it was too cold to do this when we visited). Many people prefer the springs at Bagni San Filippo in the lower Val d'Orcia. Or, if you are open to spending a bit more (and want to get the warmest waters), Hotel Posta Marcucci was a beautiful hotel that I wandered into which looked like it had a cool pool and spa experience for about $37euro/pp.

Shop for Art in Cortona: Although Cortona boasts a rich Etruscan history, today, this historical hamlet draws thousands of tourists who flock to see the Under the Tuscan Sun filming location. The town itself is small and quaint. It is surrounded by a patchwork of scenic valleys and Cyprus trees and protected by stone walls. Behind its walls, you’ll find some of the best small-town shopping in Umbria. We enjoyed visiting, having lunch, and shopping for gifts for our families. Nick and I found that many of the other small Italian towns didn’t have an approachable “print/painting gallery.” But we found one in Cortona that we really liked. Shop at Galleria Il Pozzo for watercolor prints, oil paintings, and photography. While in town, you can also look for designer scarves, ceramics, and pasteries. Pay a detour to Eremo Francescano “Le Celle,” a sacred monastery founded by St. Francis of Assisi in the 13th century. The grounds of the monastery are very peaceful and make for an excellent photograph. You should also stop in to see the ceiling of Basilica di Santa Margherita.

Our favorite art gallery in Tuscany and Umbria in Cortona.

Eremo Francescano “Le Celle,” a sacred monastery in Cortona, Italy.

Ride the Cable Car in the Medieval town of Gubbio: I liked Gubbio. It felt different than the other towns we visited in Tuscany and Umbria. Maybe I liked it because it was a Medieval town. Or maybe I enjoyed it so much because (like Deruta), they also had beautiful ceramics shops. While there, I recommend wandering into the artisan shops (see photo below). I also recommend taking the weird cable car to the top of Basilica di Sant’Ubaldo. The Colle Elleto cable car (or Funiva as it’s called) costs a few euros to ride. The cars are shaped like weird, basket-like bird cages and you have to sort of stand vertically on them as they whisk you 6-minutes up to the top of the mountain. It’s definitely an experience. At the top of the mountain, you can pay a visit to Basilica di Sant’Ubaldo, have a cappuccino in the cafe, and marvel at the views of the Italian countryside. We didn’t visit the ceramics museum here, but it is also supposed to be wonderful.

View from Funiva Colle Eletto in Gubbio - and the weird birdcage baskets.

Hike to the top of Mt. Amiata: As a traveler who prefers nature experiences to bustling cities, one of my favorite adventures in Tuscany was hiking Mt. Amiata. This 7+ mile, 2000ft round trip hike takes you through Europe’s largest Beachwood Tree Forest to the top of Mt. Amiata, the highest point in Italy’s Sienna range. The navigation on the route is a little tricky (especially when the path is covered by leaves), but if you follow the AllTrails map you can’t get too lost. The hike isn’t hard or super steep, but offers a steady uphill through the sunspeckled Beechwood trees. At the top, you can eat at one of the restaurants and savor views of the surrounding valleys. You can also drive to the top, if you prefer to skip the hike (but where’s the fun in that!).

I hope that these suggestions and photos inspire you!

Italy certainly inspired me, and I’ve been busy cooking up some new designs. In November, I released a new alpine pattern, a new alpine trail running pattern, three olive branch color-ways, and a biking design. You can purchase these all in my Spoonflower Shop (as fabric, wallpaper, tea-towels, etc.) or show your support on Instagram (with a like, a comment, a referral or a follow).

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WHAT DO TO AND WHERE TO VISIT IN UMBRia and Tuscany, ITALY: