Beyond the Day Trip: Cortona Tuscany Travel Guide

Move over Montepulcino, we have a new favorite town to use as our home base in Tuscany!  I’ll admit it, I was skeptical of Cortona Tuscany because of all the hype around Under the Tuscan Sun.  (I really need to write the post I’ve been thinking about how the beaten path is beaten for a reason.)    

This summer, we spent three weeks in Italy.  One of the things we challenged ourselves to do was to add in some new places on our itinerary.  I headed to my Tuscany hotel bucket list, did some research, and off we went. After our first apertivo in the Piazza Grande in Cortona, I knew we had found somewhere special.  We had some of the consistently best meals in Tuscany and left with a list of more restaurants we wanted to try.  The people were incredibly warm and welcoming.  

We enjoyed Cortona so much that we returned for a long weekend in October after finding cheap flights to Rome.  It was just as magical.  I can say, without any qualms, that we will be back to Cortona.  Tom says we need to go back during Christmas.  He thinks it will be just as magical as Montepulciano at Christmas.  

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Where to Stay in Tuscany

Monastero di Monastero and Spa

Looking for another Tuscany home base? Check out Palazzo Carletti in Montepulciano!

The Monastaro Spa

In light of safety measures, you will need to make a reservation for the vitality pools, sauna and spa. (Make sure to do that!)  You’ll be given a two-hour block and there is a maximum of six people allowed at this time. From there, they will provide you a time slot for the sauna and you are free to use the vitality pool and the ambiance is magical.

On both trips, I booked the Mediterranean massage and it’s the perfect way to relax after a long day.

The property also offers an outdoor plunge pool, which was refreshing in the summer.  We skipped it in October because it was a little too windy and chilly for that, but it is still a lovely time to visit.   

Where to Eat in Cortona

When I was planning my second trip to Cortona, I reached out to Sara, former student-turned writer-and-Italian-trained-chef, and asked her what she does in Cortona.  She said, “Eat.  Walk around.  Eat some more.”

Sara isn’t wrong.  There aren’t enough meals in Cortona.  And, since we practice intermittent fasting, there really aren’t enough meals in Cortona.  There are so many amazing restaurants and not enough time.  

If you’re looking for a relaxing culinary adventure in Tuscany, head to Cortona.  Don’t let Cortona’s small size or day trip destination fool you.  You’ll want to get reservations, especially if you are traveling during busy seasons.  When we visited in October, we found ourselves going from restaurant to restaurant to find a table for two, only to be disappointed.  In some cases, there may be as few as 5 tables in a restaurant.  

If this is your first trip to Italy, it’s important to know that the goal of most restaurants is not to turn the tables as frequently as possible.  When you reserve a table, it’s yours… which means walk-ins are not easily accommodated.  Also, as far as availability, Cortona restaurants operate on more limited hours, rather than providing continuous service.  You’ll see a seating for lunch and maybe one or two dinner seatings at 7:30 and 9:00.  If you’re not used to eating that late, consider taking advantage of apertivo.  Cortona’s apertivo scene makes for great people watching!

Make sure to check out my tips for eating in Italy.           

La Bucaccia Cortona

After our first Michelin dinner in Dubrovnik, we were less intimidated by these restaurants.  I know that sounds silly, but we figured that most Michelin starred restaurants would have an exotic menu, be very expensive, and likely over hyped compared to our taste.  

La Bucaccia is none of those things.  The best way to describe the menu is creative.  It takes a number of Tuscan specialties and makes them into one-of-kind delights that you won’t find on other menus.  Just thinking about the Chianina beef and truffle ravioli makes my mouth water.  It’s easily why we booked the restaurant on our second trip.  Also memorable was the table-side cantucci and vin santo.  They literally take the cantucci from the oven, slice it at your table, and serve it warm.  What could possible be better than that??  

The reviews on the service at La Bucaccia are interesting.  Personally, I find the service at La Bucaccia to be a bit of dinner theater.  The owner, Romano, peacocks throughout the restaurant, alternating between seeming harassed by the business of operating the restaurant and his genuine delight to share food and wine recommendations.  (He has never steered us wrong whether recommending wine or dessert.)  He can be sarcastic, kind, and absolutely hilarious.  I think you have to take it for what it is and just enjoy the moment.  

We’ve only eaten in the small dining room, though I think the outside tables would be very enjoyable, particularly at sunset or blue hour.  I find the stone walls of the cellar to be cozy and quite charming.  It’s perfect for a romantic meal, anniversary dinner, or if you’re in the mood for a bit of a splurge.  Everything we’ve ordered at La Bucaccia has been delicious.  I don’t think you’ll be disappointed.           

Trattoria La Grotta in Cortona

If you’re looking for a more low-key experience (or have a bigger group), consider booking at table at La Grotta.  Despite its location, tucked away off one of the main squares in Cortona, Trattoria La Grotta offers an incredibly delicious and memorable meal.  While I loved their pastas (we ordered three!), the tagliata di manzo with olive oil, green pepper, and rosemary stole the show.  I don’t know if I’ve ever had a piece of meat that was that tender.  I ordered the Tuscany cake for dessert, though admittedly I was torn between that and the pear and chocolate cake.  Next time, I’ll be saving room for that.  

The service is classic Italian: quietly attentive and unassuming.  As we finished each course, the plates were cleared and the next course was shortly on the table, warm and fresh.  We found them to be very accommodating, especially when we wanted to try multiple pastas.  I was especially impressed when the waiter remembered that we had come looking for a table the night before, only to be turned away from the delicious scents wafting from the restaurant.

Similar to La Bucaccia, La Grotta is built into the stone walls of Cortona.  With arched entryways and stonewalls, it’s easy to see why it is called the cave.  Each entry way leads to another dining room.  We enjoyed table in the corner where it was easy to talk and enjoyable to people (and plate!) watch.  The decor is classic Tuscany.  

I definitely recommend booking a table at La Grotta for lunch or dinner.  It fills up quickly.           

Trattoria Dardano

With multiple large dining rooms, if all else fails, maybe you can get a table at Dardano.  Dardano isn’t a last-case-scenario restaurant though.  It’s a great restaurant if you’re on a budget, want to beat jet lag, or looking for a casual meal.

We go to Dardano for their pastas.  The first time we visited, I asked the waiter what he recommended.  He hesitated a bit, then leaned in to quietly say that he loves the tortellini alla Norcina since it’s something you can’t find anywhere else in Cortona.  He’s absolutely right.  It’s delicious and we definitely went back for that.  However, Dardano is also where I discovered a love of pici al fumo.  This smoky tomato pasta with bacon is delicious.  If you can’t travel to Tuscany any time soon, Sara teaches virtual cooking classes and I’ve seen pici al fumo on her menu!  (I need to take that class and learn how to make this Cortonese specialty.)  Once Dardano understood that we wanted to try multiple pastas, they plated them separately for us, which ensured that we were both able to try a little bit of everything!  Also, don’t miss their house-made sausage!  It’s delicious!  

Dardano is a casual restaurant with very friendly service.  It’s a classic Italian trattoria, in my mind.  It’s great for groups because of its size, but it also has several intimate tables as well.  They have a smaller overflow dining room if you’re looking for somewhere a little quieter.          

Trattoria Etrusca

Trattoria Etrusca is a tiny dining room near one of the main gates of Cortona.  We dropped in for a late lunch hoping to secure a table and found the dining room full.  Thankfully, an Italian couple that was finishing up their coffee took pity on us and insisted that we take their table.  There are maybe 5 tables in the place, so this was very kind.  

The menu is small and heavily dependent on what they are cooking that day.  There’s  handwritten menu on the door.  This is incredible because it means everything is fresh – from the pasta to the sauces.  We opted for some Tuscan meats and pappa al pomodoro as starters.  From there, we moved onto the pastas.  The ravioli al fumo was incredible.  Tom really enjoyed the pici all’aglione.  Everything was served piping hot, which was much appreciated on such a windy day.  

If you’re unsure what to order, ask Mario what he recommends.  As with most restauranteurs in Italy, they will be happy to make recommendations.  Similarly, they are quick to let you know if you’re making a mistake in ordering.  Don’t be offended – be glad that they are willing to speak up and help you enjoy a great meal.  

We were one of the last tables to finish our lunch.  We didn’t feel rushed or pushed out.  They offered coffee and dessert, but we opted out of that in favor of some spa time and a nap.  

Read More: Italian Hill Towns in Tuscany & Umbria

Don’t Miss in Cortona Tuscany:

Santa Margherita

While many of our adventures in Cortona have been limited to walking, eating, and spa-ing, I would be remiss if I didn’t tell you how incredible the Basilica of Santa Margherita is.  It’s quite a hike, but it’s worth it.  There are a few churches that have taken my breath away, and Santa Margherita is one of them.  (I also love the Siena Duomo and the Piccolomini Library.)   

There also a number of church that you can visit on the way up, so make sure you take advantage of them!  It’s a good way to break up the hills.  

Take a Bike Tour of Cortona

We visited Cortona four times before we booked an organized tour of Cortona.  This e-bike tour is the best way to get off the beaten path and see so much more of Cortona.  (It’s also the best way to skip all the day trip crowds!)  Our guide, Valentin, provided a robust tour of the sites around Cortona and allowed us to really go beyond the guidebooks and the surface of Cortona.

We particularly enjoyed seeing the sights that are difficult to reach on foot and impossible to appreciate in a car.  Having  an e-bike made it very easy to get around, and Valentin and his staff took the time to allow for some sightseeing, along with provide information about the area history.  There are numerous stops for photos of the countryside and the major sites, abut Valentin is happy to answer questions and make recommendations if there is something in the area you really want to see.  I was impressed with how proactive his team was in getting things scheduled for other people on our tour so that they could make the most of their time in Tuscany!  We ended our tour with my favorite gelato in Cortona, which Valentin agrees is the best!  

This was only the second bike tour that we had done, but I found the e-bikes very easy to use.  Valentin and his team are committed to keeping everyone safe and making sure the group stays together.  While this isn’t an easy ride, the e-bikes do make navigating the hills much easier!  I would not hesitate to book another bike tour of Tuscany with Valentin.  

Art Gallery Hopping

Cortona’s city center is small and there are some incredible galleries to check out.  There’s an outdoor loggia that often houses special exhibitions.  When we were there in October 2021, they were showcasing Vicenzo Martini, an artist who creates fantastical paintings with vibrant colors, recognizable cityscapes, and a little bit of fun, too.  I regret not buying one of his Christmas ornaments for our travel Christmas tree!  They were quite fun.

I also love Galleria Nazionale.  Some of the paintings showcased are so gorgeous that they look like photographs.  People are truly so talented.  It showcases Italian artists and offers everything from original Tuscany paintings to still lifes.  

On a small side street off Via Nazionale lies Galleria Il Pozzo, which has a variety of print types, mediums, artists, and styles.  If you’re looking for a small art souvenir, this is probably the best place to find it.  They had a beautiful sketch of Venice that I was really wanted to bring home, but alas the size was too small for my purposes.  They have an extensive selection, so be prepared to take your time!  

These are not mass produced souvenirs or pieces of art, so they might be a little more expensive than your typical souvenir.  The quality, however, is outstanding and will make a great souvenir to enjoy for years to come.  

Oh, and last but not least, don’t forget to stop by Gelateria Snoopy for some of the best gelato in Cortona.  Further, you can bookmark all of my Tuscany recommendations on Trip Advisor.        

Read more for help creating an itinerary for one week in Italy.