Day trip to Cortona with Together in Tuscany and Umbria

Day trip to Cortona with Together in Tuscany and Umbria

As someone who constantly talks about her love for Umbria and Le Marche, Tuscany comes in further down my list. Sure, it’s one of the most popular regions for people visiting Italy, with the stunning art in Florence and famous vineyards producing Chianti, but how could it compare to the family run vineyard in Le Marche that survived an earthquake, or the freshest seafood in Puglia with people who will give you liters of olive oil from their family grove. I’ve learned though, that with people who know Tuscany well and have relationships with small businesses in the towns and across the countryside, there’s more to this region than meets the eye. 


On a day trip with Together in Tuscany and Umbria, Edoardo and I got up bright and early to explore Cortona and its surrounding area, complete with stops by local monasteries, the copper and flower market in the center of Cortona, a fantastic lunch full of authentic Tuscan food, and a wine tasting at a family-run small vineyard. 


The best part of this trip was I had to do absolutely no work ahead of time. While usually I’m frantically researching the best train deals, local festivals going on, where to eat based on reviews and compiling lists of what to do, Denyse took care of every aspect of this trip. This women-owned and operated business makes their guests’ experiences the priority and even on a holiday like May 1, were willing to dedicate their time to show Edoardo and I around.  


Guests using their services have the option of a private driver picking them up from the train station and taking them to the stops on their itinerary, something that becomes even more valuable when you consider how spotty the public transport and even taxi coverage is of this area in Italy. If you’re renting one of their local apartments or villas, a member of the team will meet you and bring you directly to your accommodation, no need to figure out how to get their yourself the first time. 

After taking the 2 hour train from Termini Station in Rome to the Terontola Cortona station, Denyse picked us up and we went by car to the other stops on our itinerary for the day. After everything, we were brought right back to the station and took our train back home in a food and wine-induced coma. 


While the type of experiences that Together in Tuscany and Umbria offers cover a variety of activities, we did a mix of cultural/historic and food/wine-related stops. To start, we went to the remote Eremo Le Celle where we saw St. Francis’ cell in the monastery. It was only a short drive away from St. Margaret’s sanctuary which offered a stunning view of the Tuscan countryside. From there, we walked down through the historic center of Cortona, a super charming medieval town that’s the perfect central spot to stay if you’re looking to explore more of this area in Tuscany and into Umbria (Perugia, Lake Trasimeno, Orvieto and Montepulciano are all short drives away). 


While walking through Cortona, we saw a few of the charming apartments that guests can rent for their stay and a few of the many churches and convents that are located in the center. As it was a holiday, there was an open market full of flowers and antiques going on, with both locals and tourists walking around. Before heading to lunch, we grabbed spritzes at an outdoor table and enjoyed the break from the rain. 


Lunch at a Tuscan Trattoria

Lunch was everything I could’ve asked for, from the abundant tagliere of meats and cheeses for antipasto, to the bottle of San Giovesese we split. Everyone ordered the Tuscan specialty of pici, a thick homemade pasta that goes perfectly with cinghiale (wild boar) or the wild asparagus that’s currently in season.

Trattoria Toscana was perfectly rustic, with decent prices and ample plates of pasta. Even if you’re only passing by Cortona, I think it’s worth a stop in for lunch!


Tasting of 3 local wines at Cantina Canaio

Possibly my favorite part of the day was the wine tasting we did at this small local vineyard just outside Cortona. This area is central to so many famous wine-producing estates, like Montepulciano, Syrah and many others, so I knew we were in for a treat. 

At Cantina Canaio, we enjoyed the a tasting of 3 wines and tour of the facilities by Simone. While I don’t know a lot about wine, Simone made understanding the production process and difference between all three kinds we tried very accessible. Their merlot (cAlice) is named after the owners’ granddaughter and was delicious, while I enjoyed the Syrah so much I came home with a bottle.

Rather than going for the easier option of a vineyard with tastings already set up, I loved how Denyse has relationships with so many small businesses in the region. It truly made the experience more unique and rewarding hearing the story from the owners themselves.  

What does Together in Tuscany and Umbria offer

Other than the Cortona tour, they also have villas and apartments for rent and experiences like chocolate making tours, wine tastings and bespoke cooking classes. Beyond this, Denyse and her team are so helpful about figuring out the logistics of your trip, including details that make it feel super special. 

Book your longterm stay or day trip with a discount

If you’re interested in any of their services, Denyse is offering my readers 10% off any longterm stay, day trip or experience with this link. This isn’t an affiliate link, but I think it’s a great opportunity to add something really unique to your trip if you’re staying anywhere in central Italy.