Europe 2025: Siena


Retiring to Sienna

For the final destination in our trip, we decided to take a car. In part this was to be able to enjoy the Italian countryside, but also so we could maintain control of our own schedule when it came to the return trip. It would have been a couple hours by train, and the prospect of doing that with a flight schedule to keep made both of us nervous.

With our additional luggage, the tiny car that we’d originally slated to rent just wasn’t going to cut it. Even with an upgrade we had to keep one of the bags in the back seat. They bumped us up, though, to a nice BMW. It had lots of fancy lighting and unlike our rental on Crete the navigation system synced up properly which was a blessing.

BMW

BMW

It was a nice drive from Bologna to Siena, with all the hills, small towns, church spires and vineyards you’d expect. There were also a surprising number of long tunnels cutting through the hills.

🎶 Secret tunnel 🎶

🎶 Secret tunnel 🎶

Our place in Siena was called Siena Hills Apartments. Even with a stop at a full-sized Decathlon on the outskirts of Bologna, we were early for check-in. The folks at the desk encouraged us to just wait downstairs at the restaurant and bar.

Siena skyline

Siena skyline

We took the elevator down and followed the signs to more of a dining room than a restaurant. The “bar” was just a counter along the room with three bottles of liquor on a shelf. Even stranger, everyone sitting at the tables in the early afternoon looked to be at least thirty years older than we were… and they were staring at us. It honestly felt like we’d wandered into an old folks home and were the most interesting thing that’d happened there in an age.

Amber noticed as we’d descended some other branding on the signs in addition to the Siena Hills Apartments. A quick web search explained all – apparently the facility was a retirement community, but since it wasn’t entirely full they rented out the remaining rooms for travelers.

Cycling the Hills of Tuscany

The entire reason for us going to Siena, though, apart from the good things we’d heard from my brother and sister-in-law, was a special treat for me. We’d originally been talking about going to the Dolomites which get rave reviews online, but the mountains are really about hiking which is neither of our jam. Then Amber had the brainwave – what if I wanted to bike in Italy. A little searching and emailing turned up a private guide for the one full day we had to be in Siena, perfecto!

The meeting point was a bike shop called Siena Velo. We arrived a little bit early, and Amber dropped me off, parking in the neighborhood being a hassle. I wandered into the shop where it was very evident that the guy running the shop spoke as much English as I did Italian. He managed to convey that my guide would be along, though.

Siena Velo

Siena Velo

Smile, you're biking!

Smile, you’re biking!

My guide showed up soon after. Francesco was one of those people you just know is a cyclist. He had that triangular frame, wide shoulders, wiry strong legs. At some point early on I asked how much biking he did. It turned out he was semi-professional rider.

“What’s that mean specifically, semi-professional?” I asked.

“You train like the professionals, you just don’t get paid yet.”

I, as the kids say these days, was cooked.

We started in the city and had about five kilometers to ride until we hit the real countryside. It started off fine, with me keeping a reasonable pace even with a fair amount of hills.

Tuscan castles in the distance

Tuscan castles in the distance

The smiles are fake but the fun is real

The smiles are fake but the fun is real

The Chianti region was so gorgeous to ride through. Vineyards and farms were everywhere, down little winding roads, behind hedges. Often the farmhouses were built up right to the edge of the roads, as if they’d been constructed before there had been much motor traffic. About 30% of the time we were on gravel, which I’d always wanted to try. (Truth be told, I prefer standard road biking.)

The vineyards

The vineyards

Me and the vineyards

Me and the vineyards

We took a break at a spot and had some local cola and cold water. Not pedaling, it was easier to have some good discussion. We talked about school – Francesco is going to college in economics – and many other topics.

Breaking for local cola

Breaking for local cola

Past the halfway point, I’ll be honest, I was struggling. In the initial messages I’d confidently said I could comfortably ride up to 60 kilometers (about 40 miles) and that was true. But the description of Chianti as “rolling hills” was not what I thought of as rollers. These climbs were intense and long. The roads were winding, so most of the time you couldn’t see to the top. It would seem like the segment you were on would top out when you just reached the turn, only to be cruelly betrayed as the climb continued.

But those downhills were exhilarating. Zooming down as fast as I was willing to go, the wind cooling me off from the growing intensity of the sun, the scenery flying by. It was awesome and made the pain worth it.

Lunch was at Agricola Fabbrini, basically a small farm that served lunch. The meal was pitch perfect for that point in the ride, with nothing too heavy but lots of flavor (and water). There was a panzanella very like what we make at home, cured meats, and a light frittata. Wine they made on site was available, though I only had a little bit given the remainder of the ride still before me.

Agricola Fabbrini

Agricola Fabbrini

Homemade after meal wine

Homemade after meal wine

They toured us around the farm after we had eaten. We got to see their cattle – much fewer than they used to have apparently. The dining room had pictures of their prize winning bulls from years past. It was so fun to see, and you could hear their pride in the heritage of the farm as they showed us the various fields they owned and how far they ran.

A young calf

A young calf

Prize winning cattle

Prize winning cattle

There were also chickens, lovely little flower gardens, and as we mounted up to ride off ripe fig trees.

Figs warmed by the sun

Figs warmed by the sun

The last stretch of the ride was the shortest, but my legs were really hurting by then. In the earlier parts I could slow down a little or take a brief pause and then bounce back. By this stage, the pain in my quads was making it hard to just keep moving at all.

My guide would zip out ahead, often out of sight, then turn back to encourage me when I’d lagged long enough. “Let’s go, let’s go!” I can still hear him chanting as he pulled away from me as if we were on flat ground.

Thinking of the ride even now brings a warm smile to my face. Truly a highlight of the trip, and such a caring and thoughtful gift of Amber to come up with it!

'You want the bike? Now pedal!'

‘You want the bike? Now pedal!’

I wonder what Amber got up to while I was riding?

What Amber did instead

What Amber did instead

Refreshing Sienna

The retirement home apartments did have a pool, and we got some good time lounging over the couple of days we were in Siena. At one point I decided I should take advantage of the “bar” such as it was. They had a brief drink list so I picked a negroni. It was brought out by a nervous looking young staffer.

“It’s the first one I’ve ever made. Tell me if I did it right?”

Thankfully for both him and me, his instructions must have been good because it was a nice mix of bitter and sweet, icy cold and perfect for the poolside.

Our nicest meal was at Al Tocco where we ordered Florentine steak, a massive thick cut served upright. For pasta along with we had the pico pecorino, which was done just right.

Hilariously, an American couple at the next table over from us was ordering after dinner coffee and asked for a cappuccino. The waitress’ dismay was visible to us, and we chuckled, being in on the “secret” knowledge that Italians will normally make no secret at all. Cappuccino is only for the morning! You cannot have it after lunch, let alone after dinner!

About Sienna

Okay, so I do actually know what Amber did while I was biking. She parked the car carefully, and walked into Siena to see the place before we did our big visit the next day. The care in parking was called for because of what’s known as the ZTLs – Zona a Traffico Limitato – where driving is prohibited in certain areas. Siena was known to have these, and they are not well marked much of the time. Amber was nervous the whole time driving in Italy because of the horror stories she’d heard of folks getting 300 euro tickets in the mail months after a trip because a camera caught them.

Steep streets in Siena

Steep streets in Siena

It turned out that we had timed our visit for some sort of city-wide festival. Amber found them setting up for the evening activities, with long tables running down the streets where folks would be dining later. Even by the time she left later in the afternoon, though, parking was a nightmare so between that and my exhausted frame we didn’t venture back.

Tables ready to party

Tables ready to party

Different neighborhoods of Siena all have their own flag and symbolic animal. This was on full display, including costumes.

Neighborhood flags

Neighborhood flags

More flags

More flags

Yet more flags

Yet more flags

The next day when we did come back for our entry to Il Duomo, things were still happening. We managed to catch a small parade, complete with song which echoed down the narrow stony streets.

Festival parade in Sienna

Singing in the square

Il Duomo

A long walk uphill from the nearest parking was the big sight to see in Siena – a medieval cathedral called Il Duomo.

Il Duomo

Il Duomo

Images in the entryway

Images in the entryway

Big old doors

Big old doors

Like many of the grand places in Europe, it was timed entry. We lined up in the already streaming sunshine with all the other tourists and waited our turn. I was slightly nervous that my shorts would be a problem – we’d heard of such requirements before but forgot the day of – but thankfully I wasn’t given a bag to cover my shameful knees.

Il Duomo stripes

Il Duomo stripes

Stripes and ceiling

Stripes and ceiling

The interior had a really interesting striped pattern, with dark black lines running horizontal everywhere. The effect was very bold, making the space far more dynamic than many churches I’ve seen.

Looking up

Looking up

More choir books

More choir books

The choir library

The choir library

It’s hard to really describe in detail how intricate and beautiful such spaces are. So much goes into them over so many centuries, it’s hard to do it justice.

Paintings in Il Duomo

Paintings in Il Duomo

The pulpit

The pulpit

Statues in the museum

Statues in the museum

Heads of saints (?) watching

Heads of saints (?) watching

It's us

It’s us

Across the court was a museum which had many additional objects and rooms. Amber didn’t follow up the stairs more than a level or two, already hurting from her tromping around the day before.

Books in the museum

Books in the museum

Among the features of the museum, though, was that from the top floor you could get out onto a narrow walkway and see amazing views across Siena.

View from the top

View from the top

Il Duomo in panorama

Il Duomo in panorama

The rest of Siena

The rest of Siena

The climb back down from the panorama

The climb back down from the panorama

Backtracking

After our tour of Il Duomo, it was time for us to head back to Bologna and begin the return trip home.

Bags packed to go

Bags packed to go

Along the highway, we stopped at a roadside spot for some food, except it wasn’t on the side – it spanned the whole highway! This seemed novel, but it was absolutely packed with angry fussy travelers (ourselves soon contributing to that number) so we grabbed our food and split as fast as we could.

Our return flight to the US was from Athens, so we took another bus in the sky “courtesy” of Ryanair from Bologna back to Athens. Amber had picked out a little bed and breakfast calls the St Thomas B&B. We arrived late, but one of the draws of the place was that it was very close to the airport but also walking distance from a taverna.

The host had been told we needed an early departure, and ordered us a taxi and had breakfast already prepared and in our room fridge since we would be gone before the normal meal began. He had sad news, though, when we made to head out to the taverna. Apparently it was closed because it was August. We ended up picking at some of the breakfast items a little early and just going to bed.

Getting the extra bag added turned out to be a hassle because our tickets were with Air Canada, but the first leg was Swiss Air instead. Sharing no systems, we had to walk to a separate desk where someone called up Air Canada to get things settled. Thankfully for once lines weren’t enormous, so our problem didn’t slow anyone else down and we were there in plenty of time.

There was, though, one leg of the journey we were concerned with. In Zurich, we had only 55 minutes from landing until the flight to Vancouver departed. We talked to the staff and there wasn’t much to be done. “If it let you book it, it should be possible.”

We got off the plane as promptly as we could in Zurich and literally ran through the airport. With great relief, when we turned the corner to where the gate was, we found enormous lines still waiting. We joined a first line that was doing passport checking, and by the time we got through that the boarding line hadn’t even drained entirely.

The rest of the trip went smoothly, and Cora picked us up at the airport. Such an amazing time, and a fun look forward to what life might be like for us when the kids have moved out.