Plan Not to Plan (a Perfect Stay in Tuscany)

I wish I could say, “I’m writing this from the tower of a castle in Tuscany,” but instead I’m back in Los Angeles dreaming about the tower at Castello delle Serre, where my 13-year-old daughter, Olivia, and I just spent one magical week.

“Plan not to plan,” is what Kaci Matthews told me she would advise visitors staying at Castello delle Serre, the beautiful Tuscan castle that's turned luxury bed and breakfast that she and her husband, Antonio Gangale, own and run along with Antonio’s father, Salvatore.

The castle sits atop the medieval village Serre di Rapolano, close to Siena and a short distance from Montalcino, Montepulciano, and Pienza. Originally built in the 9th century, its most recent update (before Salvatore purchased it in 1994 and, along with Antonio, made it what it is today) was done in the 1800s.

It's a stunning property – with 20 guest rooms that benefit from the addition of electricity and running water – but the true beauty of the place is that Kaci and Antonio help you plan the perfect Tuscan vacation once you arrive. That was something I gleaned from glowing Trip Advisor reviews, and it was one of main reasons I booked it, the others being the availability of a pool and A/C (it was August!) and its central location that would make all of Tuscany accessible by rental car.

My plan (that I did plan) was our week prior in London and Venice, so by the time we reached Tuscany, I wasn’t sure how much or little we would feel like doing (especially with each other).

But despite Olivia being the fun, witty travel companion this divorced mother of an only child feels lucky to have raised, I still found myself cancelling something I’d booked in advance almost every day in London and Venice. Granted, a five-hour walking tour past “30 of London’s Top Sights” did not take into consideration how jetlagged we’d be, nor that a 13-year-old might have zero interest in a five-hour walking tour even if “it would provide a great overview of this great city!” (That was my final unsuccessful pitch to a girl with a pillow over her head.) But I also found myself cancelling dinner reservations I’d made just days prior at Someplace Someone Said We Must Try Their Something, because a walk around Covent Garden led to last-minute theater plans, or a perfect prosciutto, arugula, and parmesan pizza left us needing nothing more than gelato to top off the night.

So what Kaci and Antonio offer is exactly what a planner like me forgets to make room for: spontaneity and flexibility.

According to Kaci, many people make the mistake (although she doesn’t like to use the word “mistake”) of hopping from place to place in Tuscany, which means you are always packing and unpacking and losing days between check-in and check-out. That was one mistake I did not make (and I’m happy to call that a “mistake” because it’s one that I’ve made plenty of times). Instead, as the end of our end-of-the-summer adventure, I booked six nights at Castello delle Serre.

I was worried that might seem too long. Spoiler: It was not. I could have stayed there forever. I mean, how important is eighth grade really?

Antonio greeted us in the majestic foyer when we first arrived. He also checked us in, brought our bags to our room, parked our rental car in their private lot, and helped us find the perfect spot for dinner. To say that he and Kaci are “hands-on” would be an understatement, but the part of their job they love most is helping guests plan days according to their interests (or mood) and directing them to little-known spots they’ve discovered across Tuscany.

The restaurant we went to our first night, San Rocco Ristorante Pizzeria, was a family-run place a five-minute walk from the castle. Perhaps more importantly, it was where Olivia and I first tried pici. Our new favorite pasta is like spaghetti but thicker, and frankly, we don’t understand why it’s not an option in Italian restaurants across America. This is yet another reason why everyone must, at some point in their lifetime, go to Italy.

I booked a deluxe double room with a beautiful ceiling fresco — every room here is unique and beautiful — but once we arrived, I couldn’t resist upgrading to the upper tower suite. I should add that because Castello delle Serre is a luxury bed and breakfast (as opposed to the five-star hotel it could be if they had more staff, a spa, and a restaurant for lunch and dinner service), even the most expensive rooms seem downright reasonable, especially when compared to the sky-high cost of hotels during Italy’s high season.

On top of feeling like a bargain, the upper tower suite might be the most beautiful room I’ve ever stayed in. Now, I’ve stayed in some beautiful rooms. But the views. The views!

The tower is separate from the main part of the castle and literally towers over the sparkling blue pool. The first floor is the entrance, the second has a marble bathroom and a sitting area with a pull-out sofa, and the third floor has a bedroom and many arched windows that provide the kind of 360-degree Tuscan views that dreams are made of.

We could see and hear the bell tower of a nearby ancient church, and from our private roof terrace (our private roof terrace!) we watched every sunset try to outshine yesterday’s.

Although we never wanted to leave our tower – some days we only did so only for breakfast or a dip in the pool – armed with Antonio and Kaci’s detailed directions (including where to park and where to find the best gelato), we day-tripped to Sienna, Cortona, San Gimignano, and Florence. Florence, of course, can’t be seen in a day, but it was a nice taste for Olivia, and, after a few hours amid tourist crowds, we were happy to return to our medieval village.

Antonio and Kaci arranged the perfect cooking class at La Pietre Vive. We made a four-course dinner of panzanella salad, homemade fettucini with fresh tomato sauce, chicken with sweet wine, and apricot panna cotta.

Every night they sent us to restaurants we would never have found, including Hostaria del Benandante, just around the corner, where it’s hard to get a table not because it’s trendy, but because there are only six tables. The owner/chef explains the evening’s menu (which she handwrote on a blackboard) before taking your order and cooking your delicious dinner.

On our final night at the restaurant at Agriturismo Podere Casato, a beautifully restored Tuscan farmhouse overlooking the Chianti countryside, we enjoyed the best sunset and the best truffle pasta of our trip.

Before we left, Kaci shared that she grew up in Houston and met Antonio on a dating app when she was working for Deloitte & Touche in Rome. Not ready to tell her he owned a castle, he said he “worked in a hotel.” As he described Castello delle Serre, she realized she had stayed there ten years earlier with her mother in the upper tower suite and had even taken a cooking class with Salvatore in the castle’s kitchen. When she told Antonio she knew the place and the owner, Salvatore, he admitted that Salvatore was in fact his father, and that they owned and managed the castle together.

Now Kaci lives full-time at Castello delle Serre with Antonio and their two young children while her father-in-law scours Italy for other castles to restore. Although it seems like a dream existence (not to mention a perfect rom-com), living in a castle is also a lot of work. She or Antonio are at the front desk from sunrise to (beautiful) sunset, and in their brief off-season Antonio works to upgrade the property and they scout for new places to send guests. This year, her goal is to find a new local farm for a cheese tasting and picnic. The one they used to recommend got too popular.

So maybe the dream existence is doing exactly what we did: spend a magical week feeling like royalty in a castle tower, reap the benefits of the owners’ local knowledge, make lasting memories, then go home and plan (that is, to not plan) your next adventure.

Ready to go to Tuscany?

While we agree it's a good idea not to overplan any trip, you'll need some guidance. Start with our downloadable three-day guide to Florence. It's like having a concierge in your pocket.