Tuscan Hill Towns, April 10 – 18, 2019

Three sixty-something guys went cycling for eight days through Italy, more or less Florence to Rome. The trip turned out to be much more of an athletic event than expected, with some of the steepest hills I have ever cycled.   Also, I had heard that Tuscany was over-touristed.  Could we, on bicycles, discover the real Tuscany?

This trip began as a vague idea.   Lyman and I had been searching for the next big bike ride in Europe, preferably Italy, Spain, or southern France.   Lyman’s friend (now also my friend) Randy Greenberg, a computer professional, taught Lyman some tricks when searching online for air fares.   We needed a low price to anywhere.

I live in Chapel Hill NC. The closest airport is Raleigh/Durham.   Lyman and Randy live in Austin TX.   Using Randy’s suggested apps we found round trip on American Airlines RDU airport to Rome airport in early April for only $ 533.00!!     Short flight to Charlotte NC, then nonstop to Rome!!     Only $633.00 round trip Austin TX to Charlotte to Rome!!   Lyman and I could go most of the way on the same airplane!!

These deals were too good to pass up.  As it turned out, these prices were only available for a few days.   Lyman and I agreed to fly to Rome in early April.    A few days later Randy agreed to join us.    We hurriedly bought the tickets while the price was still low.   We could work later on the details.

The flights going over had issues.  There were thunderstorms in Charlotte that delayed me twenty-four hours.   Due to that same weather Lyman and Randy were transferred by American Airlines to British Airways who subsequently lost Lyman’s luggage (i.e. bicycle) for an even longer amount of time.    We were two days behind schedule when at 12:45 PM on a Thursday we stepped off the high speed rail line at Santa Maria Novella station in central Firenze (Florence).   It had taken us from central Rome to Florence in under two hours.  Disclaimer: I have great friends Mandy and Iano who live in Florence.  With all the hassles we had been through we wanted to start bicycle riding immediately.  My apologies to Mandy and Iano for not calling you up while in town.

In the Florence train station we put together our folding bicycles, all Bike Friday brand.  We would make a good commercial for them.




Randy Greenberg



Lyman Labry


photo by Randy Greenberg



Over the next eight days we would cycle most of the way back to Rome, taking a circuitous route.


Otherwise from random we picked the town of Empoli for the first night because it was about twenty-five miles from central Florence.  We knew nothing about this town.

Finding a bicycle route out of Florence was challenging.   Larger Italian cities have confusing layouts.  Streets change names.  Roads change one-way directional status seemingly every block.

Finally we did break out of Florence.  Heading towards Empoli that first afternoon we were being chased by rain storms.  There was a gravel bike path along the Arno River some of the way.


Randy is very outgoing.    Despite the language differences he managed to start a conversation with this couple and convince them to pose for a picture   They were out picking rapa, a type of edible greens.    You can see the dark rain clouds in the background.


photo by Randy Greenberg


Eventually the bike path ended and we cycling on conventional roads with the traffic, threading along the Arno River.  As it was getting dark and as rain started we luckily made it into central Empoli and under the shelter of an awning.

Empoli does not seem at all touristy but very Italian.

We got drinks and snacks at a table on the street and watched the locals go by, or stand around our bicycles.


The rain eventually slowed down and I called a hotel just a couple of blocks away.   Asking in broken Italian, I was able to secure a room with three beds for eighty-five Euro, breakfast included.   What’s not to like?

After checking in and showering we looked for somewhere to eat that evening.   The only real restaurant open in Empoli was the fanciest looking restaurant we ate at our entire trip.     The food was delicious and really not all that expensive.

First course was one portion each of tagliatelle with artichokes.   I believe artichokes are in season in April.

For the main course I got tuna, seared rare.   The vegetables in the center were as delicious as the fish.


Randy got mixed fried seafood.


Lyman got another fish entree whose name I cannot recall.



The service was friendly and helpful.   At the end this guy poured us glasses of some kind of dessert wine, on the house.


The next morning I was impressed by the minimalist decor at the hotel breakfast.

We picked as our bicycle destination this second day somewhere we had indeed heard of, the hill town of San Gimignano.   We would once again have to dodge the rain.

Leaving Empoli we cycled through the streets of town.



Eventually we transitioned to pleasant country roads.

The bike riding this day varied between steep rural roads with little traffic, and relatively flat roads along the valley floor that teemed with large trucks.  After a few hours we parked our bicycles in front of this place for lunch in the town of Certaldo.

In this working class town we talked to two guys about our age on on the street before entering the restaurant.  They told us what to order: they said to get pasta meccanica followed by codfish cakes.    Following a practice of old Roman families I read about somewhere years ago we all got the same thing, which was what those guys suggested.



We had coffee but skipped dessert.  Just we were leaving it started to rain.   We ducked over to a covered outdoor cafe to wait out the rain with post-lunch beers.      We sat in this cafe for over an hour until Randy’s very handy use of cell phone weather maps indicated (correctly it turned out) that the storm was going to pass just to the south of us in our ride to San Gimignano.   As soon as the rain let up we biked off with still threatening clouds in the distance.



San Gimignano is a true hill town, visible from miles away.  This day it was surrounded by storms, sitting at the top in a defensible position with its distinctive medieval towers, threatening those who would attempt to bicycle up that steep hill.    The roads got steeper as we got closer.




We had taken a back road to avoid traffic.   The scenery was lovely and the pavement smooth. However, in all my bicycling I had never seen a grade so steep.    I have always prided myself on not walking my bicycle.   I did make it up this hill, but I cannot remember being so winded.   My sixty-three year old lungs were burning bright.    Lyman, Randy, and I were all windedly making jokes about having heart attacks.

Lyman approached the entrance to the walled city of San Gimignano.


The center of town is, or course, at the very top of the hill.   We found a nice hotel on the main square.  This was the view out the hotel window.


That night at the hotel we had ribollata, the Tuscan vegetable soup.    We walked around the town after supper.



According to Wikipedia tourists have been coming to San Gimignano since the late nineteenth century.     We walked around after breakfast the next morning.   Our fellow tourists were out in force.  Many had just arrived by tour bus.  Sure, there were some Americans here.  There were also Asians; Chinese.   There were French, Germans, British, and Italians from other parts of Italy.   Many came with with Selfie sticks.



In our modern world we all stare at our phones, or take pictures of everything.


On this Saturday morning there was a small farmer’s market.   Artichokes indeed are in season.   I bought Tootie a jar of honey.



photo by Randy Greenberg

From the back side of town you could just enjoy the view.


Our bicycle destination this third day would be the larger city of Siena.   We wanted to make our bicycle route as scenic as possible, on roads with the fewest cars.

Google Maps has a defect that has plagued me here in the USA, it does not differentiate between paved and non-paved roads.   At one point this day we found ourselves pushing our bicycles through the mud.




photo by Randy Greenberg

Stuck in the mud I advocated turning around.    I was outvoted.   The road luckily did improve dramatically just over the ridge.

By the time we had found a larger main road it was already past time for lunch.    We were on the outskirts of a town called Colle di Val D’Elsa, which sat, of course, up on a hill.   On the outskirts, down on the principal two line highway was Pizzeria Osteria 900.   A sign out front advertised two course pranzo (lunch) twelve Euro, wine and coffee included.

We were the only customers.   It turned out to be one of the best meals of the trip and certainly the best value.    The apparent owner was a thirty-something looking woman who later told us she had moved to Italy twenty years ago from Albania.   The waiter, her son,  looked about twelve years old.

Once again we all got the same thing.   First course was pasta with what she described as homemade ragu.  Delicious.


photo by Randy Greenberg

While we were eating the pasta we could hear in the kitchen the woman pounding to flatten chicken breasts.     Second course was lemon chicken and we each got a contorno (side dish) of carrots.   Italians do NOT like to mix different kinds of food on a plate.


It was all wonderful and we pressed her to accept more money for additional wine as we each had quickly downed the included one glass.    She charged us six Euros for an additional half liter.

Woozily back on the bikes still had another fifteen or twenty miles to Siena.    On the way we chose a short but steep climb to get a coffee at the medieval walled town of Monteriggioni.


There were a lot of tourists in this small town.  More local was a was a Catholic procession on this day before Palm Sunday, accompanied by strumming guitars.


Shops sold leather goods, a product of this region.   I pondered whether I could show my face in Chapel Hill wearing shoes like this.


Back on the road we cycled further on towards Siena, mostly uphill.

Compared to the hill towns Siena (population 54,000) felt like a real city.     It is about the same population now that it was in the year 1350.   I am sure there are a lot of tourists but they did not seem to overwhelm the place.



We biked into the central city and stopped for a beer, to ponder our next move.

photo by Randy Greenberg

We found a somewhat shabby but low cost hotel room with three beds.  After supper that night we walked around the city in the dark.   Just a couple of blocks from the hotel is the Piazza del Campo where they have been staging the annual Palio horse race for almost four hundred years.


The next morning this was the view out of our hotel window.   The second photo is Randy’s bicycle on that same street.


photo by Randy Greenberg


We biked out of Siena on this Palm Sunday morning.



For quite a distance we shared our route with a footrace, likely at 10-k.


Our destination this day would be the hill town of Montalcino.     From more than ten miles away you could see Montalcino looming in the distance at the top of a hill/mountain.    The hill appeared larger and steeper the closer we got.






We fought our way up this mammoth hill, arriving central Montalcino just as it was begining to rain.   To celebrate our ascent we bought a bottle of relatively high-end wine, a Brunello di Montalcino.

Because of the rain we ended up spending that night in Montalcino at this hotel, Albergo il Giglio.   It was all quite nice.


The next day was another beast of a climb, first riding east to the hilltop town of Pienza, then turning south to the hilltop town of Montepulciano.

This is the three of us after admiring the view from Pienza.

Halfway up some hill, Lyman and Randy paused to scope out the situation.


Some workers were thinning the olive trees, then burning the branches.


Yes, there are a lot of towns around here whose name starts with Monte.    Montepulciano was another great hill town, requiring another huge sweaty climb.

The hotel we found here was run by a woman about our age who clearly had artsy tendencies;  I wish I had taken her picture.  That evening we wanted a lighter evening meal.    We first sat down at an informal pizza joint but loud Lynyrd Skynyrd music convinced us to leave before ordering.  At a restaurant down the street a woman indicated they were open.    When we entered, she walked into their dining room and turned on the lights.   Obviously we were the only customers.

Pici is a form of homemade pasta frequently seen in Tuscany.   We had it several times.


Each strand is made by hand.  Traditionally this was peasant food, and the noodles contain only flour and water, no eggs.  Dough is rolled thin on a flat surface, then cut into strips.   Each strip is then rolled by hand into a tubular shaped.    They are then boiled and combined with sauce.  This younger woman and who I assumed was her mother were the only ones there.  They invited us into the kitchen after the meal and showed where they were making pici.

On the way out the older woman wanted to pour us a complimentary sweet liquore but for some reason we declined.   I am still not sure why.

The next day we bicycled about fifty miles, including some major hill climbs.  In mid-morning we stopped for a cappuccino at a gas station bar.    European gas stations frequently have nice bars.   No paper cups here, unless you ask.  That is Randy’s hand and water bottle on the right side of the picture.


After a serious climb we ate a sandwich for lunch al fresco in a small hill town, San Casciano Dei Bagni.   We chatted with two twenty or thirty-something Australian guys who were quite nice but ultimately seemed like clueless idle rich.   They had flown over in Business Class to be in Europe for several months but did not really have a plan.

Although that town had been seemed to be on a hilltop, after lunch we climbed even higher.   I looked back at the town.


The afternoon cycling was delightful along roads with no cars and surrounded by silence.    Sure, the hills were steep but at least the road was paved.    Until it wasn’t.   Cycling on gravel roads is trickier.    We pressed on.



We finally cycled into a river valley and along smoother, flatter roads with more traffic.    We had now left Tuscany for Umbria.  Our destination that evening was to be the town of Orvieto.  We really had no idea what to expect, and could not believe what we saw ahead of us.  Orvieto is built on almost vertical cliffs.   It was astonishingly formidable, especially after having cycled all day long.    Fourteenth century invading armies would certainly have been intimidated.

We somehow got up that hill and collapsed into a cafe to order a bottle of wine!   The bartender provided some nice free appetizers.


Dinner that night was at Trattoria La Palomba.    I had called an hour or two earlier for a reservation.  Italian restaurants like to be called, even on short notice.   It was packed but they had a table waiting for us.    This place is a little higher end than most other restaurants we ate at on this trip.

There was strangozzi (shoelace) pasta with shaved truffles.



It was followed by delicious meat main courses.  I got palomba, a type of dove.   The excess sauce was spread on toast.


Lyman ate roast lamb.

Randy got cinghiale, stew of wild boar.


And my favorite, a contorno of chicory greens.



We also split a dessert.

It was all wonderful, really.  Eating at places like this is what I like to do.


The next morning we walked around the vibrant city of Orvieto.



This included the cathedral with its distinctive multicolored marble.



photo by Randy Greenberg

Lyman, who is an architect, has a good eye for details, like noticing this door hinge.


This was to be our final day of bicycle riding.   Our flights home departed the next day from Rome airport.    Our biking destination this final day was to be the small city of Orte.

Of course this bike ride began with a steep downhill from hilltop Orvieto.   First we had to bicycle through the city gates.


We cycled along a river valley.

About 11:45 AM we were passing by a small town and Randy announced that he was running out of gas, he really needed to eat something.   We were not ready for lunch yet, so he went into a cafe by himself to refuel while Lyman and I waited outside.   In America this would have been done at a Mini-Mart.   Here in Italy they have much more style.


photo by Randy Greenberg


The downhill “road” from that small town was so steep that we had to walk the bicycles.


An hour or two later in a dingy, flat, and drab looking town we had lunch at a motel/cafe/pizza place.   I am always on the lookout for great vegetable dishes.   Here to accompany the pasta was vignarola, the Roman stew of braised spring vegetables, especially artichokes and fava beans.


photo by Randy Greenberg

After lunch we still had about fifteen or twenty miles to Orte, our train station.   The cycling turned out to be much more challenging than expected.   Along the Tiber River the narrow flat valley was consumed by a rail line, an autostrada (freeway), and an older highway packed with trucks.   Google Maps also showed a network of smaller roads more amenable to bicycling.   Some of these roads were flat and well paved.

Sometimes the roads were much worse.   To our dismay these smaller roads frequently zigged at steep angles up the cliffs lining the river.    Sometimes the pavement just stopped and the roads became rutted gravel.   These were some of the steepest grades I have ever experienced.




Sometimes when things go bad they actually get better.  The roads improved.   Our destination town of Orte, we discovered, sits on a cliff overlooking the Tiber River.

The rail line does not actually go to Orte, it goes to something called Orte Scalo, at the bottom of the hill by the river.    We thought this meant we would not have to climb that hill, but got so lost in finding Orte Scalo that we ended up at the top of the hill anyway!  We arrived at Orte Scalo train station about five in the afternoon.   Orte Scalo is the end of the line for an hourly Rome area commuter train that, with seventeen stops, goes all the way through Rome then beyond to terminate at Rome Fiumicino Airport.  We took our bicycles apart and carried them onto the train for the two hour ride.  From there we took an Uber to an Airbnb near the airport.

Fiumicino is a beach town and has at least one really good seafood restaurant, Ristorante Sfizi di Mare.   If you ask they will serve, for a flat charge, a meal of seafood appetizers, dozens of dishes brought one after the other.    Sicilian seafood salad was just one of many.


It made a pleasant final Italian meal before our outgoing flights the next morning.



3 responses to “Tuscan Hill Towns, April 10 – 18, 2019”

  1. Wonderful! Really enjoyed viewing the pics of all the scenes, plated dishes, and the iron hinge of a hand grabbing another.

  2. Excellent report. This is trip I’d love to do!

  3. Excellent account. I’d love to do that trip someday.

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