Italy Part 1: Fun Edition (Florence) – Oct 2021

Itinerary:

Milan

Unless you are heading up to the Dolomites, Milan doesn’t really fit in too neatly with a typical Italy itinerary. It does have just as much history as any of the other major Italian cities, the incredible Duomo, and The Last Supper (located in an incredibly unique environment). Only 2 hours away from Florence on the impressive, clean, and comfortable rail system, Milan was our first stop when we got in.
With our efforts to plan out the “big details” of our trip, we had neglected to book the required entrance to the Convent of Santa Maria della Grazie, which is needed in order to view The Last Supper. Luckily, Athea was able to check just a couple days before, and there was availability for a walking tour that included entrance to the convent!
The tour of the convent was pretty fascinating – especially the efforts that the church has taken to maintain the painting over the years, and to avoid damage to this precious piece during the bombing of WW2. Unlike most pieces of that era where the paint was applied to a wet fresco surface, this paint was applied to a dry surface, which caused it to begin to fade/flake off relatively shortly after the painting was completed. The painting is still faded, but viewing it from the opposite end of the chapel, it almost feels like you are looking at a 3D room carved out of the wall – an incredible effect for the era it was painted in. I am sure it was much more impressive in the early years of the painting, when the colors were in full force.

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After visiting this convent we continued the walking tour across the city, past the sites typical of a well-preserved medieval city – Sforza Castle (with massive moat), Parco Sempione, and Basicila of Sant’Ambrogio. Then we were transported 300 years in the future to the bustling Galleria Vittoro Emanuele II, which felt like being dropped into the middle of the Gilded Age, complete with iron roofs and mercantilist energy.

After stepping out of the Galleria, we immediately arrived at the Piazzo del Duomo, framed by the massive Milan Cathedral. The only thing more impressive than the sheer size is the attention to detail throughout – every spire is topped with a life size sculpture, with the top spire crested by a 13-foot tall, gold-plated Madonna statue.

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Orvieto

Also a convenient train ride away from Florence, Orvieto is an impressive Tuscan hill town with Etruscan roots. The town is beautifully perched up on cliffs, with access conveniently addressed by the funicular that starts at the train station. On a late October morning, it seemed like we had most of the place to ourselves, although the tourists started funneling in after noon.

With wide streets, towers and walls to be scaled, and impressively ornate architecture for such a small area, I would call walking through Orvieto on a nice day the perfect “easy day” adventure. We still put in about 8 miles of walking in addition to the elevation gains (Torre del Moro) and descents (Jacob’s Well).

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Fiesole

By Monday Athea was off at work, so I had to fend for myself. I was getting itchy not biking, so I took a tram in the morning to the local bike rental shop (Florence By Bike) to look for a mountain bike to take on the hill trails north of Florence. I ended up with an aluminum rigid cruiser bike (I’d guess it was >35 pounds?), but with road tires, it wasn’t really built for the mountain biking trails I was looking at. Intrigued by this post, however, I was excited to bike, even if I had to stick to the pavement.

The first 4 miles or so, the bike didn’t really matter – the limiting factor was the bike lanes (lack thereof), unpredictable traffic, and construction scaffolding scattered about the city. Once I got out of the congested city streets, however, the route immediately began a steep uphill ascent. Unbeknownst to me (until I started seeing the many signs), I was riding the route of the 2013 World Cycling Championships – and apparently a still popular route for cyclists, as I was passed regularly by spandex-wearing Italians of all ages on shiny road bikes. Still, on a clear day, it didn’t take much climbing for the views to be tremendous, and the entire route twisted up the hills with beautiful hillside villas framing the sides of the narrow road.
Fiesole itself was a beautiful hillside town, reminiscent to me of any Tuscan hill town, just with the sprawling city of Florence visible from the valley below. Fiesole had some intriguing ancient Roman/Estruscan ruins, and information signs showing they were proud to assert their unique history apart from Florence (at least up until 1125, when Florence conquered it and began using the area as their hillside retreat for the wealthy).

The great thing about road cycling in a place like this is that with most of the uphill conquered on the way to Fiesole, I was able to just continue up on additional roads to explore the rolling hills beyond. All in all a pleasant 20-mile ride that I regret not spending a little more time on.

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Poggibonsi / San Gimignano

Biking to the town of San Gimignano from Poggibonsi is the perfect example of an accessible, easy day trip from Florence using the excellent high-speed rail system. At 9am I caught a 14€, one-hour train ride from Florence to Poggibonsi, where I was able to walk to the local bike shop (Bike Room Poggibonsi) and ask for a walk-in rental bike. Unfortunately the bike owner spoke zero English, but with the help of another one of the customers, I was able to get the details: only bike available was an e-mountain bike, but it would only be 30€ for the day.

With the e-bike, the 12 km climb from Poggibonsi to San Gimignano passed by quickly. I locked up the bike outside the city and walked inside, needing to take care of the issue that seemed to come up every day in Italy – finding a place to pee! After a morning coffee, I headed into the middle of the city to climb the Torre Grossa, the tallest tower in the town and conveniently the only one open for climbing. The history behind the towers is fascinating – essentially a mix between ensuring security in the event of inter-rival battles, and a Medieval **** measuring contest to showcase personal wealth and power. In many cases, the towers appear to just have been built out of the middle of existing houses, leading to a unique design.

After leaving San Gimignano, I decided to head to the roads on the north of town, to Certaldo, lured by the vast fields of vineyards painting the surrounding hills. The ebike made these “cheat miles” go by quickly, with the speeds on the uphill sections not much slower than those on the downhills. The most surprising thing to me about this 15-mile loop was that it seemed that every single space along the highway, as far as the eye could see, was covered in either villas or short vineyards – making for expansive views in every direction.

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After finishing the loop back, I took a short detour to Santa Lucia, which provided great panoramic views of the San Gimignano skyline. The final descent back to Poggibonsi cranked up the adrenaline, speeding past terrain that slowly shifted from country villas, to suburban houses and shops, to the city of Poggibonsi. Returning the bike and walking the 5 minutes back to the train station, I was able to make it back to Florence by 6 PM – just in time for dinner!

Bologna

I have to give an honorable mention to Bologna. It’s not really marketed as a major tourist destination in the states – in fact, the Rick Steves Italy book only grants it a paragraph to say “it’s crowded, and not special, but here’s a couple restaurants near the train station”. But since it was on the way home on our afternoon train from Milan, and heralded as a foodie destination, we figured we should give it a chance.
We verified that the city was crowded – so much more so since we ran into an Anti-Vax passport, Antifa rally in the city center (politics is a fascinating thing). The interior of the city is remarkably quirky, from the half-finished facade San Petronio Basicila (they ran out of money midway through and never ended up finishing it) to the two leaning towers (that actually have a greater “lean” than the Leaning Tower of Pisa). These two towers are the only remaining artifact of a great medieval skyline that is covered in a fascinating article here.
And the food? The food was great. All in all, I’d say that visiting Bologna for dinner isn’t a bad idea for a quick train stop.

And why are there only four days of activities on this trip? Unfortunately, that’s a story for Part 2…