I didn’t know what dating in midlife would be like—I had met late husband in college when I was only 18—but I swallowed my fear and took the plunge in the summer of 2019, two years after losing my husband. David and I “matched” through an online dating app about four weeks later. I was terrified to start dating again after spending forty years with one man, but I was lonely. I had begun to realize that, at least for me, life was meant to be shared. I was starting to think less about my loss and more about the new chapter in my life. Before we ever spoke on the phone, David and I spent a lot of time texting.
“I’m not sure about dating a widow,” David texted during one of those early exchanges.
“Well, I’m not sure about dating a man who’s been divorced twice,” I responded, a little offended.
We both laughed about this later and spent time discussing which was harder—trying to compete with the memory of a loved one who had died, what I called the sainthood of the departed, or trying to deal with an ex who was still very much alive and who we would be forced to interact with at family functions. The reality was that both situations could be challenging, and we committed to each other to be sensitive about our pasts.
When I was planning our adventure in Italy, while I did consider David, the reality was that Italy was my second home—I’d been to Rome over 25 times already and brought over a hundred guests to Italy over the past fifteen year. I was the one seeking citizenship, and it felt natural that I should be the one planning the trip.
I had been the travel planner in my family and circle of friends for as long as I could remember, and I knew I was good at it. I loved the process of researching places and coming up with a plan, but everyone who knew me also knew I had a supreme need to be in control. David knew this too and respected me enough to abdicate most of the planning for the trip.
“I’m just excited that we have the opportunity to do this,” he said when I asked him if he had any requests for our time abroad. “I trust you to come up with a great itinerary.”
And so I had plotted out everything ahead of time. After our first two weeks getting settled in, we would take a long driving trip north to Bologna and back. A couple weeks later we would fly to Sicilia and spend time in Palermo and the northwest side of the island. At the end of our time, once spring arrived, I planned for a trip to the southern end of the Amalfi Coast, first looping through Caiazzo and Caserta north of Napoli before spending a few days in Salerno.
I was very purposeful in selecting these itineraries. They were places that were almost entirely new to me—even though I’d been to Italy so many times, there was still so much to discover, and I wanted to take advantage of our extended time here to do that. But also, if I returned to the places Greg and I had travelled to together, I worried that it would stir up too many memories for me and that David would be haunted by Greg’s and my past. That just didn’t feel fair to him.
There was one place, however, that I did want to return to, Montalcino, in the heart of the Brunello wine region of Toscana. David had been learning about red wines from Italy and I wanted him to experience these world class wines in the region where they were produced. I knew we’d be passing near this area anyway after leaving Bologna. The last time I had been to Montalcino was after Greg’s death, when I went with a friend for a gastronomic tour of Toscana that included truffle hunting, visits to farms and olive oil producers, and wine tastings. We had visited a family-run winery just five minutes outside of Montalcino that offered agriturismo stays, and I remembered thinking at the time how cool it would be to come back and stay someday. Plus, I’d always wanted to visit in the winter when I knew every menu would offer the classic pappardelle al ragù di cinghiale, one of my favorite pasta dishes of Italy, featuring wide fresh pasta noodles with chunks of tender wild boar braised in a rich tomato sauce. This trip, I rationalized, would be different than what Greg and I had done, so I floated the idea to David, and we agreed to add two extra nights to our itinerary after leaving Bologna.
When we got to Montalcino, it looked deserted, and I quickly realized that Toscana in winter was going to be very different from how I remembered it from my previous trips. We drove straight through the small town and down the hill on the other side to reach Agriturismo Piombaia where we would be staying for two nights. Our room was one of a few offered for guests in a charming stone house with wooden beams and shuttered windows. Despite the low cloud cover and drizzle of winter, the view across the vineyards from our room was breathtaking.
Very few places in Montalcino, we found out, were open for dinner offseason, but Sosta, right next to the fortress, had a table free. Even though I’d been here before, I wanted to try something new, so we ordered two classic antipasti from the region that I’d never tried on my prior visits. 
Tonno del Chianti was originally created by Chef Dario Cecchini from Panzano in the Chianti region. Pork shoulder was cooked very slowly in olive oil and garlic until tender and resembling the texture of tuna, then served with pickled red onions. We both thought it tasted like any other braised pork and wasn’t even that tender. We also ordered the beef tartare which, typical of Italy, was a massive portion of chopped beef mixed with an egg and spices.
While the tartare was really enough for a meal, we ordered more. David had the winter beef stew, and we could tell by the sauce the meat had been braising in Brunello wine. The richly colored almost purple beef was served with white beans and was perfect winter food. Without hesitation I had ordered the pappardelle al ragù di cinghiale which was as good as I remembered it.
The next morning while we waited for the clerk from the front desk to bring our breakfast—a massive basket of meat, cheese, breads, sweets, yogurt, milk, and homemade peach preserves that would easily last for days—we discussed where we should head to explore the area. I wasn’t sure because everything looked closed for the winter, and I wondered if I had made a mistake suggesting we come here offseason.
David was still waiting for me to lead the way as I’d done so far on our trip, so I suggested that we drive back towards a large cantina we had noticed driving into Montalcino to see if they offered a wine tasting. They were open, but we were disappointed to learn that the old family run winery that used to be here had been bought out by a French conglomerate. 
We shared a tasting—a Rosso di Montalcino and a Brunello di Montalcino—but found them lacking in character.
“Remember that road that went up behind Piombaia? Why don’t we see what’s up there?” David asked, for the first time taking the lead on what we’d do next. I remembered the road he was talking about, so drove back in that direction. As soon as we saw the sign for a winery, Tenuta Crocce di Mezzo, with cars in the parking lot, I pulled over and parked the car. The place was tiny, but the door was open, so we walked in.
“E’ possible di fare una degustazione?” I tentatively asked the men inside, hoping it wasn’t too early in the day for a wine tasting. They all looked at each other, and then one guy asked when.
“Addesso?” Again they looked at each other but then he shrugged his shoulders as if to say, why not?
Paolo was kind, generous with the pours, and eager to share the history of the region and their small operation. He spent time taking us into to the cellar and explained that they only make about 35,000 bottles a year. “It’s very small, and it’s hard to compete with 250 Brunello producers in such a tiny region,” he explained. We bought two bottles, and he refused to accept a fee for the tasting. Maybe it hadn’t been a mistake to visit Montalcino in the winter after all, we thought as we stashed our wine in the car.
We spent the rest of the morning exploring, with David taking the lead. “Let’s go see the abbey,” he suggested, referring to a shuttered abbey a couple of miles from Piombaia. As we left the abbey, he noticed a sign for a frantoio. “Want to try to find that?” he asked. “I know you like to taste olive oil.” Although we never found the frantoio, it didn’t matter to either of us, because the landscape was so indescribably beautiful that we just kept driving around and stopping to take pictures of the view.
“This is why Americans love to come to Tuscany,” I said.
“What’s not to love about this place? These views are amazing,” David said.
We were both hungry at this point, so I drove into Montalcino and parked by the fortress. “There’s really not much to see at the fortress,” I said. “Let’s just peek inside and then get lunch.” I knew I sounded like a know it all, which I regretted as soon as I spoke, but I’d been to the fortress many times and didn’t want to waste time there. I knew that wasn’t fair to David, who was so enamored with the castle that he was taking pictures from every angle inside the small courtyard, so I followed him into the open space.
After a couple minutes he disappeared around a corner in the back of the courtyard. I went to find where he had gone and was surprised to find a sign for an enoteca. I had never seen the enoteca on any of my prior visits to the fortress so assumed it must be new. But when I went inside and asked the man behind the counter when they had added the enoteca, he assured me it had always been here. David was excited he had been the one who discovered it and asked if I had been upstairs before. Of course I hadn’t since I hadn’t even known the place existed.
Suddenly David became the tour leader. He paid the one-euro fee, and we climbed up the stairs for the advertised panoramic view. I was stunned by the nonstop views of the Tuscan landscape and couldn’t believe I’d missed this opportunity before. We walked the sentry walls on top of the fortress for a full thirty minutes, gazing at the rolling valleys dotted with fog, the symmetrical lines of the vineyards, and the beauty of the town of Montalcino itself. I could tell David was tickled that he had made this discovery, which made me happy for him. Although I had been worried that coming here would stir up memories of being in Montalcino with Greg, instead I was thinking how great it was to be here with David. He and I both loved to explore, which was of course why we were on this adventure in Italy together.
After exploring after the fortress, we found a pretty restaurant open for lunch and the only other guests inside were two young families with four kids between them. We were hoping to share a platter of antipasti meats and cheeses with a flight of Brunello tasting, and the waiter was very accommodating. I had originally been disappointed that the old wine bar near the fortress where Greg and I had done a tasting was closed, but now I was happy we had found something new and different.
We had scheduled a tour and tasting at Piombaia while we were in Montalcino, and we got back from lunch just in time for our 4:00 degustazione appointment. We made our way to the cantina out in the vineyards, where we found them in full swing bottling rosato, a new pink wine in their lineup. We had been told the tasting would last an hour, but Maurizio was generous with his time, with sharing his knowledge around biodynamic farming, and with his pours of wine. We stayed with Maurizio, talking, and drinking more wine than I’m sure was planned for a tasting, for over two hours. We didn’t want the evening to end.
Before arriving in Montalcino, I had expected David to experience a new place, but I ended up experiencing an old place in a new way. David wasn’t Greg, and traveling with him would always be different than my travels with Greg. Despite how many times I had been to Italy and how many things I could show David, there would always be times that he would be able to show me something I hadn’t noticed. The fortress experience helped me relax
my need to control every piece of our itinerary for this special adventure in Italy and set the tone for the rest of our trip.
During the remainder of our time abroad, David and I took turns. Whenever I suggested something to do for the day, he’d figure out something new to add in. We were perfect travel partners, and I was reminded almost every day while we were exploring Italy together how lucky I was that I had found someone with whom to share this new chapter in my life.