Monday, the last day of August, found us hoisting our bicycles onto the train in Arezzo. It would have been relatively easy ride down the fertile Valley to Cortona, but time was short, so we opted to use the train for detours like this. Cheryl had been south of Cortona to the town of Castiglione del Lago on Lake Trasimeno, and had always wanted to visit the mysterious medieval town-fortress that dominated the plain. It is a beautiful part of Tuscany, rich with vineyards and farms. The train ride itself was quite scenic, with the mountains on the left and the valley to the right. We got off in Camucia, which is the town on the rail line at the foot of the mountain. The train station had both towns’ names on it, but Cortona was not nearby. Instead, it sat about 5 km away, at the end of a two-lane road that climbed straight up out of Camucia. In less than 3 km, we climbed 670 meters above the valley, arguably the most challenging climb all summer.

It was worth it. Even as we parked our bicycles at the San Luca Hotel at Piazza Garibaldi, we were treated with the most incredible view. Far beyond Lake Trasimeno, the valley stretched out to the hills around Orvieto. To the west, I could see the Torrita di Siena and Montalcino blocking the view of Grosseto and the coast. The hotel spilled down the cliff from the edge of town. We entered reception at the top floor, and our rooms were on the “fourth floor” — four stories below.

Unlike many other medieval towns, Cortona does not have modern buildings surrounding a historic center. Once you reach the city itself at the top of the hill, it is like stepping back in time. It was even difficult to find such simple things as a supermarket or the post office, because the 14^th century buildings all looked alike. We climbed to the very top to visit the Sanctuary of St. Margaret, following a torturous stone road aptly named the Via Crucis (The Way of the Cross). The 12 Stations of the Cross mounted in the wall by the road indicated that the local faithful probably used this outdoor route during Holy Week. We came back down by the normal main “road,” which took us past sections of city wall that had been built by the Etruscans.

The next day, we rolled back down the hill, but this time we took a provincial road, which was longer, but not so steep. It still took next to no time to get back to the train station. An hour later, the train was zipping past Arezzo. We alighted at the main Santa Maria Novella Station in Florence. Cheryl had found us a place at the Machiavelli Palace Hotel near the station, which was also near everything else downtown.

What can I say about Florence, that has not already been written, said, and filmed? Cheryl had been there more than once, and I had lived there, so we went to things that were not in the Michelin Guide. She took pictures of the central market, which has become a large gastronomic exhibit hall. We browsed the markets, and took a taxi to the Piazzale Michelangelo, which has arguably the best view of the city. Along the way, I made the taxi driver stop at Via Niccolò Macchiavelli No. 1, so that I could show Cheryl where I lived when I first moved to Italy. It seemed absolutely unchanged from when I was nine years old. After getting something to drink and taking pictures at the top of the hill, we walked back down to the city using the combination of stairs and small streets favored by pedestrians. The Borgo Santo Spirito had some wonderful shopping. We spent some time sniffing tea in a tea shop, and Cheryl bought some to send home. We looked at fabrics and admired other merchandise on display.

The Campanile of the Duomo was covered with scrim, hiding the massive restoration work going on. I would have to come back for that. The Duomo was impressive inside and out. You can read about the details in any guidebook or online.

Cheryl likes art, and the painters setting up in the various large piazzas downtown offered so many different styles and subjects that it felt like an outdoor art gallery. She almost bought a picture from one artist outside the Basilica of San Lorenzo, then arranged to come back. It rained, and we figured that he would not be there, but we found him the next day. She had to settle for a different picture, but I was glad that we found him again.

Thursday morning (3 September), we set out for Bologna, planning to take the train to Prato first, to skip the suburban rush hour. Cheryl got ahead of me as I settled the bill at the hotel, and I missed the train to Prato. That I was an hour behind her starting out did not pose a problem. We were both headed for downtown Bologna, and we both were used to riding alone. When I got to Prato, I raced downtown to take a picture of the Duomo with the Pulpit of the Sacred Girdle by Donatello. On my way through town, I saw Cheryl riding in the other direction, but I could not turn around. She would have left me behind on the 850-meter climb out of Vaiano north of Prato anyway.

State Highway 325 follows the Bisenzio River valley north, climbing over the ridge line near where the Apuan Alps become the Apennines between Tuscany and Emilia Romagna. The train plows under the mountains in a straight line, and after Vaiano, there is no room by the river for a road. The scenery compensated for the endless kilometers of switchbacks, but I needed a rest break and a snack at Sasseta, halfway up.

Just over the ridge, I did not need a road sign to tell me that I had left Tuscany. The road surface deteriorated immediately. The ride remained scenic until I reached the Po River plain and the SS 325 began running near the Autostrada A1. Soon I was in the industrial suburb of Sasso Marconi, and riding on the SS64 into Bologna. Just as the SS 64 turned into a multi-lane expressway, I found a bike path through a large park, which took me downtown. Cheryl was not so lucky, and had to share the road with heavy, high-speed traffic. She arrived shortly before I called to make contact, in time to be waiting when I arrived.

She had found us quarters a few blocks from the train station at the north end of the historic downtown: I Portici Hotel. After 100 km and the challenges of the day, settling into luxury felt very good. I could not afford to make a habit of it, but she had done so well with the other places, that an occasional four-star hotel with a first-class restaurant did not break the budget.

We spent two days in Bologna, walking through downtown, visiting the churches and museums. Cheryl had been there before, but I had not. I particularly enjoyed Museum at the Academy of Fine Arts. Bologna means good food, and we ate well, including dinner in the hotel one night, and in the shopping district during the day. One thing we did not eat was spaghetti alla Bolognese, because there were too many other offerings on the menus. I definitely plan to return to Bologna.

Saturday morning, it was time to move on. Two major must-see events of Europe 2015 still lay ahead: the Biennale in Venice, and Expo 2015 in Milano.

Until next week,

Smooth roads and tailwinds,

Jonathan.