Confessions of a Middle Aged Man in Lycra – Tuscany Trail Part 2 Episode 1

by | Jun 30, 2026 | Travel | 59 comments

The big day finally arrived, my start of the Tuscany Trail.  The check-in and packet pickup was staggered over 3 days so as to not overwhelm the towns and base camps with 5000 people at once.  I got the second to last time slot for pickup, Friday morning, and in order to collect my bottle of wine at the finish, I needed to complete the 450 kilometers by Tuesday evening.

After breakfast we checked out of our hotel and drove the 10 miles to the start at Venturina Therme.  While parked in an illegal spot I assembled my bike in the hot sun.  By 10:30 I was packed up and ready to roll.  Today was going to be the longest day, 123 km to reach the first base camp where I planned to sleep.

And I’m off. In more ways than one.

The ride started out with a 200m climb up to the town of Campiglia Marittima. The road was steeper than I expected with gradients of 17%, and it felt like my heart was racing, hitting a peak of 170 bpm, likely just adrenaline and the excitement of finally being under way.  Nevertheless about halfway up I stopped at a farmhouse offering free olive oil tastings.  I’m not here to race.  I’m here to enjoy myself, so calm down and take it easy, buddy.

Reaching the top of the climb and rolling into the town square of Campiglia Marittima it felt like the ride had really begun.  As soon as I parked my bike in front of a shop to buy a Fanta, a bird crapped on my head.  I don’t know if that’s a sign of good luck in Italy like it is in some other countries, but I wasn’t pleased.

Beware of birds.

On the descent out of town I had to pay close attention to the map to make sure I didn’t take a wrong turn, which would result in a steep climb to get back on track.  After the descent it was a mostly flat 15km run to the coast emerging at Nano Verde, the kind of beachfront snack shack I’d expect in Mexico.  Some people went for a swim, but the thought of riding another 100km with a crotch full of abrasive salt crystals and sand didn’t appeal to me.  Instead I got an espresso, filled up my water bottles and used the restroom before hitting the road.

The trail was sandy as one would expect by the beach.  I started to worry that the next 12km along the beach were going to be a slog pedalling through sand, but soon we were on a bike path with a more compacted surface.  Before long the coast transitioned from beach to headlands and the road became bumpy and rutted as we climbed up to a nice sea view.

At about kilometer 60 we turned inland to head north into the wind.  The route guide said there were no services for the next 60km with the possible exception of a small bar that may or may not be open, so I filled my bottles and grabbed a sandwich before heading off.  The good news is that the bar was indeed open so I stopped in to get a gelato and filled up my bottles at the fountain across the road.  The bad news is I still had about 35km to go over a rocky, rutted and steep climb before reaching the day’s destination.  

I was worried about there being enough room at the base camp.  It was the first one along the route, so I figured it would be crowded.  About this time my front brake started acting as if there was debris in the brake lever preventing it from operating smoothly.  Not wanting to delay, I pushed on and figured I’d look at the brake later.  It was still working, sort of, and how important is the front brake anyway?

Home stretch.

The going was slow over the hills and through the woods, but I made it with a couple hours of daylight to spare.  After pitching my tent I took a cold shower in the communal showers made from shipping pallets and garden hoses.  German dudes were showering naked while the women waited patiently on the sidelines not wanting to get in the showers with a bunch of naked men.  I assume they were German (and men, not women with penises).  Who else would do that?  Maybe the Dutch.

Home for the night.

All cleaned up and looking semi-respectable I wandered into town for a cheap bowl of pasta and a very large beer before heading back to camp to peruse the Morning Links from the comfort of my tent.  I could hear riders rolling in even after dark, but that didn’t stop me from falling sound asleep. With all the middle aged guys in tents, I expected to be kept awake by a constant stream of people making their way to the bathroom, but it didn’t happen.  Maybe they were all dehydrated, or maybe I was too tired to notice.

At dawn of day 2 riders started getting up at dawn.  I decided to lounge around for a while.  Why rush?  I’m on vacation.  There’s dew on the tent and I want to let it dry before packing it away.  Eventually I got up and made my way to the bathroom where there was a long line for the crapper.  Note to self, get up early to beat the rush, especially when there’s only one john for a couple hundred people and the toilet paper supply is iffy.

After packing up I tried diagnosing the problem with my front brake but couldn’t figure it out, so I cycled to the town square for cappuccino and some pastries before setting off.  Today was going to be less distance than yesterday, about 100km, but a lot more climbing, about 2000 meters.  A lot more climbing also means a lot more downhill, so a fully functional front brake would be nice to have, but whatever.

Looks like California but with old stuff.

About 40km into the ride we started the longest climb of the day and one of the longest of the whole ride, about 400 meters over 7km.  I filled my bottles at a fountain at the bottom of the climb before heading up.  The first half was on pavement and not too steep.  I passed a guy on the side of the road who was bleeding from his elbows.  He said he was hit by a motorcycle, but it was a mere flesh wound not requiring assistance.  The Carabinieri had just left him, so I assume he was OK.

Soon we turned onto a dirt road and from here things got tough.  The gradients kept getting steeper.  10%, 15%, 20%.  I started putting on my pain face, and after seeing others push their bikes, I decided to get off and walk too.  I just didn’t want to be the first.

Textbook pain face.

At the top we rode along the ridge for a while before a nice long descent to the river Orcia and then we began a slow climb on dirt roads to Pienza.  I had intended to make a short detour to see where part of the movie Gladiator was filmed, but it would have required more climbing, it was hot, and I was out of water.  Instead I headed to town and was glad to find the fountain where I guzzled about 3 bottles of water.  Bikes are not allowed in the center of town, so I locked up my bike and wandered into town for a panino and a sugary drink.  I sat in the shade watching the well dressed tourists pass by.

Approaching Pienza.

Out of Pienza we began a nice paved descent until suddenly the course took a shortcut down what was probably the original road from hundreds of years ago.  Many of these old paths have paving stones down the middle which can make for a ride that will shake your kidneys out your ass.  It’s probably here that I lost my lock from the side pocket of my pannier.  Hikers likely were able to make a nice collection of fruits, sandwiches and water bottles from the passing riders.

Are you not entertained?

Safely back on pavement with kidneys still intact we started climbing again to the town of San Quirico d’Orcia where it was time for another gelato break.  The road out of San Quirico did a full 360 loop before heading down another 8km to Torrenieri, which was home to a base camp.  I considered stopping here, but it looked empty so I pushed on to the next camp.  I later regretted my decision when I saw on Instagram that they had steak and sausages on the menu in Torrenieri.

More old stuff.

I pushed on to the next base camp at Buonconvento about 15km down the road.  Leaving Torrenieri the trail met up with Via Francegina which is a pilgrimage route from Rome to Canterbury much like El Camino de Santiago.  The ride would share much of the route for the next 100km or so.  The trail also met up with many of the roads used in the Strade Bianche bike race, which is what initially drew my attention to riding in this area.  It was a blast to be zooming up and down these gravel roads, though they are not nearly as smooth as they appear on TV.  Luckily this late in the day I had the road mostly to myself so I could go at my own pace and pick my own line.  I can’t imagine riding these roads in a peloton.  The trust those guys have in their skills and the skills of the other riders is insane.

Sometimes that trust is misplaced.

Finally around 6 PM I pulled into Buonconvento, but nobody seemed to know where the base camp was.  I lurked around the water fountain asking for direction until finally I decided to read the route guide.  When in doubt, RTFM.  As it turned out the camp was only about 100 yards away hidden in the middle of a city block connected only by a narrow passage.  Of course there was no signage as this was Italy, and they don’t really do organization, not since Mussolini anyway.  I paid my 10 Euros, pitched my tent, took a warm shower, and grabbed some dinner.  I had the choice of pasta or a meat dish for about 5 Euros.  I should have taken one of each, as I was burning about 5500 calories a day, but I didn’t want to be greedy.

I used the remaining daylight to take a closer look at the front brake.  It had not engaged properly on a fast downhill curve which could have sent me into oncoming traffic, so I figured I better do something.  I discovered that the brake pistons weren’t retracting fast enough when I released the brake lever, so there was slack in the brake cable and the ball at the end of the cable was getting caught.  The root cause was either that the brake pistons were dirty or there was increased drag in the brake cable.  Either way, I couldn’t properly fix it now, but at least I had a workaround.  Just release the brake lever slowly to prevent slack.

My recovery drink.

This was the halfway point in the ride in terms of both distance and climbing, or so I thought.  As this article is getting long and Glibs is always in need of content, I’m going to split this into two parts.  So stay tuned for more Confessions of a Middle Aged Man in Lycra as we make our way through Siena, Monteriggioni, San Gimignano, Montalpacino, San Bonjovi, Nina, Pinta, Santa Maria, and much, much more.

About The Author

JaimeRoberto feckful & gruntled

JaimeRoberto feckful & gruntled

Am I being detained?

59 Comments

  1. Sensei

    After pitching my tent I took a cold shower

    Phrasing?

    • Aloysious

      Mr. Roboto left that softball hanging.

      I giggled.

  2. Threedoor

    17%.

    That’s no joke.

  3. Fourscore

    I ask myself, “Why does a middle aged man in Lycra does this?”

    I know, I know, there are things we have to prove to ourselves but why?

    • JaimeRoberto feckful & gruntled

      Because it’s there. But also because it’s a good way to see the scenery at a different pace than you would otherwise.

      • Fourscore

        I’m glad you took us along, vicariously.

        I had a few work days in Italy, many, many years ago, about 60 or so. Looks like some places haven’t changed a lot since then.

      • DEG

        I’m glad you took us along, vicariously.

        #metoo

  4. Michael Malaise

    This is amazing. Sounds like an epic way to spend a vacation to be honest. I have a crazy idea that my son and I will spend a couple weeks in rural England hiking village to village but I am not sure that will ever happen. Maybe.

    • dbleagle

      Try the path along the Hadrian Wall. Coast to coast, history by the kilometer and reasonable length. It is also hilly, but not too hilly.

  5. Evan from Evansville

    Agreed, this is the perfect bike ride vacation. That part of the world properly is fucking beautiful. I’m surprised and glad they’ve got a pretty well working system of places to pitch your tents and shower. That’s a proper adventure, right there.

    I do love how Euro towns still have medieval arches in use throughout their streets.

  6. DEG

    OT: Condom maker wants to make Lynn, MA the condom capital of the world

    A historic creamery in Lynn has become the new home of one of the country’s largest condom distributors.

    Global Protection Corp, a sexual health and wellness company, recently relocated its headquarters from Boston’s Seaport to the renovated building at 630 Lynnway, saying the move makes Lynn the nation’s busiest hub for condom shipments, with about 250 million condoms passing through the facility annually.

    Once known as the “Shoe Capital of the World,” Davin Wedel, founder and CEO of the company, said they are now calling Lynn the “Condom Capital of the U.S.”

    • Evan from Evansville

      “Oh, honey baby, I’ll make your creamery even more historic with my own creamery goodness. Rub ya right in the hub…”

    • Sensei

      Global Protection Corp, a sexual health and wellness company, recently relocated its headquarters from Boston’s Seaport

      More dicks from MA coming to NH!

      • DEG

        Commuting to Lynn from NH is probably just as painful as commuting to the Seaport District from NH. Lynn is northeast of Boston, but I-93 goes straight south from NH into Boston going near the Seaport District whereas there is no equivalent road from NH into Lynn.

        Actually, maybe if you want to live on the NH Seacoast the commute to Lynn might be easier. Though good luck finding a decent place there cheaper than you would in MA.

      • DEG

        oh wait a minute…. there was a joke in there that I missed?

        I guess it is time to call it a night.

      • Sensei

        lol!

    • Fourscore

      250 M, that’s it? Some guys aren’t doing their share. Too much pulling their load, so to speak.

      • Threedoor

        88M

        We pull out.

  7. Evan from Evansville

    I kinda enjoy how Justice Action Jackson is pulling shit that makes the others cringe. I don’t analyze the SCOTUS beat, but directly calling out another Justice is, IIRC, incredibly rare and a very tsk-tsking thing to do. With the birthright citizenship decision, “Justice Ketanji Brown Jackson agreed with the opinion in full, but wrote to respond to Clarence Thomas’ dissent, arguing that Thomas fundamentally misunderstands what the Reconstruction Amendments — the Thirteenth, Fourteenth, and Fifteenth Amendments — are trying to accomplish.

    “Despite his longstanding endorsement of a ‘colorblind’ Constitution, Justice Thomas, now surprisingly suggests that the Citizenship Clause was a race-conscious remedial measure, relating only to ‘freed slaves such as Dred Scott’ — but that narrow vision of the Fourteenth Amendment bears little relationship to the history of its ratification.”’

    I’m quite sure Thomas is fuming. ‘THAT bitch is telling ME that *I* misunderstand?! Justice, please.’

    • rhywun

      I mean, it’s blindingly obvious that the writers of the Fourteenth Amendment had anchor babies and bankrupting the natives in mind… right?

      Yeah… she is a dependably stupid activist, which is exactly why Joe nominated her, but Roberts… JFC what a squish. You can often count on him to chicken shit out of controversial but correct conclusion.

    • creech

      Perhaps the drafters of the 14th should have been more precise with the language of the amendment if they wanted even more constraints on birthright citizenship.

      • slumbrew

        “Shall not be infringed” is apparently up for debate. There’s nothing the drafters of the 14th could have changed that would move it beyond debate.

      • rhywun

        IIRC the disputed phrase is “subject to the jurisdiction thereof” which at the time it was written was obviously understood to exclude the children of illegal aliens until the left got around to twisting it to their advantage and here we are.

    • slumbrew

      Jesus, that midwit calling out Thomas publicly has to be rage inducing. Which may, in fact, be the point, come to think of it.

  8. DEG

    OT: Unpossible. MA has strict gun laws

    Though, I did see a report claiming the pick up truck had NH plates.

    I-Team sources said that Massachusetts State Police stopped a pick-up truck allegedly involved in a shooting at Highland Common in Berlin and that one person in the car may be armed.

    The alleged shooting in Berlin took place at 3:30 p.m. in the parking lot, according to Berlin Police. They said that officers had originally responded to a report of an assault, but were informed about possible gunshots on the way there. Around an hour later, I-495 in Lowell was closed by the Massachusetts Department of Transportation.

    • cyto

      They closed an interstate?

      • cyto

        Oh, FFS.

        We used our robot dog to break the window, but unfortunately the window tint we couldn’t get past it. We had to use non-lethal rounds to break the rest of the window. We used a drone to identify that the suspect was deceased,” Massachusetts State Police Deputy Superintendent Dan Tucker said.

        They had a standoff with a corpse.

        And their super-cool robot dog couldnt break a window and couldnt help.

      • Chafed

        It’s good he was dead because otherwise every commuter would have killed him.

  9. Evan from Evansville

    Happy birthday, Thomas Sowell! 96!

    I can do that, and it’s not that I don’t wanna! I just haven’t had time yet!

      • Fourscore

        Count me out! No way, Man!

  10. kinnath

    I have returned. Call off the dogs.

    • Fourscore

      Grass is cut? Relax, cool down with some of your favorite beverage.

      • kinnath

        Yes, the grass is done

      • Aloysious

        I read beverage as cleavage.

        Still works.

  11. kinnath

    If I ever go to Tuscany, it will be for the sole purpose of drinking wine.

    • DrOtto

      It’s about the same price as the water, so it just makes sense.

      • slumbrew

        No kidding.

        Alla Vecchia Bettola, Florence – they bring out the gallon bottle of house wine, 5€, all you can drink. It was excellent.

  12. The Bearded Hobbit

    Hey all,

    After 7 days and 6 nights we are back home, safe and sound. The firefighters did a terrific job and were able to treat this fire more or less as a controlled burn. We won’t have to worry about a fire from the west anymore, all of the fuel has been consumed and most of the trees are going to survive.

    Thanks for your concern over the last week.

  13. cyto

    This afternoon we had one of our silly side discussions about air conditioning adding heat to the outside, warming up cities.

    Just to point out how silly that idea is, a small city lot of 0.2 acres will absorb about 4,000 Kilowatt-hours of solar energy over the course of a day. A 2 ton AC unit for the house on that lot would produce maybe 70 Kilowatt-hours of waste heat. During that day.

    Now, the entire earth is getting hit with that kind of radiation all day, every day. And it radiates that heat back out into space. We know that because we do not melt into a giant ball of lava. The earth is in balance for heat coming and going.

    That is why it is hot over the AC condenser when it is running, but in general the AC waste heat is negligible.

    That energy is a drop in the bucket of all the energy that is being dissapated every day.

    / nerd alert

    • Threedoor

      Urban heat islands are a thing but I think it has more to do with concrete and asphalt than forest heat sources.

    • UnCivilServant

      It’s that stage of internet arguing where straws are grasped where the “It’s technically correct” is the gound upon which they stand.

    • rhywun

      I made fun of it too and I am by no means an expert in any of this stuff but it has always been my suspicion that puny humans are not having the colossal impact on Gaia that lefties think they are. Rather they pretend we are so they can control us. They don’t believe it, either.

      • Evan from Evansville

        “They don’t believe it, either.”

        The Useful Idiots do. With religious zeal. They were told the end was nigh, they bought it and did what they were told to make the world ‘a better place.’ They changed their habits to accommodate recycling, low-flo and ECO-everything. Like many/most ‘standard’ religions, I imagine the followers don’t ‘follow’ much after they perform their rituals. (Particularly when others can see.)

        The religious vacuum must be filled. Angry Climate Daddy perfectly fits what a wrathful god from yore would bring.

      • rhywun

        The Useful Idiots do

        Yeah, I mean the pols.

  14. slumbrew

    San Gimignano

    I am incapable of saying that name without doing so in the style of the Commendatore singing Don Giovanni…

  15. Evan from Evansville

    “Florida woman claims cocaine found in her butt after arrest must’ve been from ‘intimate encounter’
    A Florida woman picked up an extra felony charge when she wildly tried to smuggle nearly 4 grams of cocaine into a county jail through her “jail purse.”

    Front purse, back purse, jail purse, bonus purse. I tells ya, I purse my lips at all these purses. Her lips pursed ’round that fat 8-ball, comin’ to the clink ta party. (Her not in a jail and in a good mood? Bit of a cutie. Would party with. I’ll have her lined ’round the block.)

    • Threedoor

      Prison purse. Female
      Prison wallet. Both sexes.

      • Brochettaward

        Oh, but do you know what a prison First is?

      • Threedoor

        My dad said when he did time someone would fart in the cell block at night and the response from somewhere in the dark would be “ah, a virgin!”

  16. Brochettaward

    The kiddie diddlers in the house passed the KIDS Act. So now the kiddie diddlers in the Senate get to weigh in on it, too.

    Then the kiddie diddler in the White House gets to decline to veto it.

    When they’re done diddling the kids they just want to be able to didlde you, too.

Submit a Comment