May 2022 – Feb 2023

It’s been a while since we had a good adventure, so I told my bud we needed more bear and bud adventure time.

Off to camping we go – we’re headed to the valley of fire to do some solo camping. Annoyingly, my bud seems to have misplaced the poles for my Sumi tent. Fine, I’ll share his. The red rocks look pretty nice, I’ll accept the shared accommodations compromise.

Suddenly I hear - “Clomp, clomp clomp”. What is that? I look out from our tent to find wild big horn sheep trotting around my camp like they own it.

I guess they were kind of cool. They climbed up the rocky mountains super quick. Time to tuck in for the night since we have plans in the morning.

We wake up early and drive to the nearest little airport. Nicholas has decided to finally learn to fly like I do, and there’s no better way to learn than trial by fire. Time to jump out of a plane! That’s right - Nicholas couldn’t find anybody that wanted to go skydiving with him, so it’s just me and him. The instructor wouldn’t let me go in the plane for some reason. I told him that I was a pro and I should be the one teaching people to fly, but he ignored me. Jerk. I guess I’ll just see Nicholas in the air.

Really I’m the real pro and they should have brought me.

It’s been a while since I last visited the Grand Canyon, and one thing I was upset about last time was that I didn’t get to go down. Sure, it’s pretty up top, but who wants to see the canyons without actually going into them. This time would be different. Although Pokin is still recovering and can’t hike, I’m forcing my bud to gear up and go all the way down. PoOn had the idea of doing this hike called Bright Angel Trail, which involves hiking 9.9 miles and  descending 4380 feet. Sounds good.

Eric and Po On joined him, and we all had lemonaide at Phantom Ranch at the bottom of the canyon. Nice work. Now it’s time to haul it back up.

Overall I like the Grand Canyon, it’s nice, but definitely better when you do the whole trip. It did take a long time though, next time I’ll make my bud run it. Pokin met us up for part of it, thinking it would be a shorter trek. Little did she know she was just making herself suffer by going down the steep switchbacks to immediately come back up. Sucker!

We arrived in Rome at night, which is the correct way to arrive in Rome. You stumble off the highway, navigate increasingly chaotic streets, and then suddenly the Trevi Fountain is just there, lit up like a movie set someone forgot to take down.

The hotel was old in the way that Rome hotels are old — stone stairs, questionable plumbing, and an elevator that was essentially a wrought-iron cage with a brass call button and a prayer.

Day 1: The Colosseum and the Vatican

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We hired a guide. Not just any guide. An actual archaeologist. The kind of person who gets excited about mortar composition and can tell you which emperor ruined what by looking at a brick. This turned out to be the best decision of the entire Italy trip.

The Colosseum is one of those places where the scale doesn’t make sense until you’re standing inside it. You know it’s big from photos. You don’t know it held 50,000 people, had a retractable awning system, and could flood the arena floor for naval battles. The Romans were insane in the most impressive possible way.

Our archaeologist guide didn’t just tell us facts. He showed us a display case containing a piece of pottery that he personally dug up. His own artifact, excavated from a site in Rome, now sitting behind glass in a museum. He pointed at it the way a parent points at a kid’s school photo. “That one. I found that one.” I’ve never seen someone so proud of a piece of broken clay.

From the Colosseum we walked to the Roman Forum, which is what happens when you leave an entire civilization’s downtown abandoned for a thousand years.

The Forum is a strange place. It’s simultaneously the most historically significant few acres in Western civilization and also just… a field of broken columns with cats sleeping on them. Temples, courthouses, marketplaces, everything that made Rome Rome was here, and now it’s a park with informational signs.

Up on Palatine Hill, the view opens up and you can see the whole thing laid out — the Forum below, the Colosseum in the distance, the city spreading in every direction.

After the ancient half of Rome, we did the Vatican half. It was hot. It was humid. Pokin was cranky because it was hot and humid. We went anyway.

The Vatican Museums are overwhelming in the way that only a 2,000-year-old institution with unlimited acquisition budget can be. Every hallway has more art than most countries’ national museums. You walk past things that would be the centerpiece of any gallery on earth and they’re just… on a wall. In a corridor. Next to a fire extinguisher.

From the Museums we went straight to St. Peter’s Basilica. If the Vatican Museums are “a lot,” St. Peter’s is “too much, deliberately.”

After all that history and religion, we needed drinks.

Jane and Pokin had discovered Aperol spritz somewhere around day three of Italy and hadn’t stopped ordering them since. The blue one was somebody’s idea of adventure. The limoncello was mine by default because it was the closest thing to a dessert drink available.

Day 2: The Rest of Rome

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The next morning we did what you do on your second day in Rome. You walk.

The Pantheon makes you feel small in a way that’s different from the Colosseum or St. Peter’s. Those places are big because they wanted to impress you. The Pantheon is big because someone solved a structural engineering problem that wouldn’t be solved again for over a thousand years, and they did it with concrete.

We ended Rome the way we ended every Italian city.

Rome is exhausting, overstimulating, too hot, too crowded, and completely worth it. Two days is not enough. Two weeks probably isn’t either. But we had pizza, we saw an archaeologist point at his own pottery, and Pokin got her spritzes. Not bad at all.

On the way from Tuscany to Rome, Pokin found us somewhere to stay that was exactly Bob’s speed.

La Badia di Orvieto. A 12th-century Benedictine abbey, converted into a hotel. One of the oldest hotels in Italy. Bob used to work as a chaplain, so staying in an actual abbey was basically a professional field trip for him.

The abbey was founded around 1100 by Benedictine monks and has been through the usual Italian gauntlet of centuries — built, abandoned, fought over, rebuilt, abandoned again, eventually converted into a hotel by someone who understood that tourists will pay good money to sleep where monks used to pray.

The inside is all rough stone walls, antique furniture, and the kind of coffered ceilings that make you wonder how many people it took to carve all that by hand. The rooms used to be monks’ cells, which sounds grim until you see the view from the window.

The tower is a twelve-sided Romanesque structure with a crenellated top. Twelve sides. Not eight, not ten. Twelve. Someone in the 12th century decided a round tower wasn’t complicated enough and a square tower was too boring. I respect the commitment to geometry.

But the real draw was the ruins.

Part of the original abbey church is still standing — roofless, open to the sky, with Gothic arches framing views of Orvieto on its cliff in the distance. It’s the kind of place where you walk through a pointed stone archway and suddenly feel like you’ve wandered into a video game cutscene.

The abbey was actually for sale around this time. Someone with deep pockets and a love for medieval restoration could have bought the whole thing. I looked into it. Briefly. But I’m not sure the credit card I took from Nicholas’s wallet would cover it.

After exploring the abbey, we headed up to Orvieto itself. The town sits on top of a massive tufa cliff, and unless you feel like driving up a series of increasingly questionable switchbacks, you have two options: a funicular (a cable railway up the cliff face) or the Percorso Meccanizzato — a system of escalators and moving walkways carved directly through the rock.

We took the funicular up and the escalators down. Because why use one ridiculous cliff transport when you can use both.

Yes. Escalators. Through a cliff. Most towns build stairs. Orvieto said no, we’re going to carve a mechanized pathway through solid tufa and install moving walkways inside it. The funicular gets all the fame, but the escalator tunnel is the real flex.

Once you’re up, Orvieto is classic Italian hilltop town — cobblestone streets, stone buildings, and views that drop off into the Umbrian countryside like someone forgot to build a railing.

And then you turn a corner and see the Duomo.

Orvieto’s Duomo is absurd. Gold mosaics, Gothic spires, a rose window the size of a small apartment, carved portals, striped marble — it looks like someone took a normal cathedral and then let a very enthusiastic committee add things for 300 years. Construction started in 1290 and the facade wasn’t finished until the 17th century. That’s the kind of timeline that produces this level of excess.

The interior is all alternating dark and light striped columns — a style that makes the whole nave feel like it’s vibrating. Frescoes, stained glass, and the kind of silence that only exists in buildings where people have been whispering for seven centuries.

I tried to get everyone to visit the weapons museum. There is, apparently, somewhere in Orvieto where you can see medieval arms and armor. But nobody wanted to go. “We’ve been walking all day” and “my feet hurt” and other excuses. An actual weapons museum. In a medieval town. On top of a cliff. And we skipped it. I’m still upset.

We ended the day the way we ended most Italian days.

Dinner on a terrace as the sun went down over the Umbrian hills. Pizza, because sometimes after a day of 12th-century abbeys and Gothic cathedrals and escalators through cliffs, you just want pizza.

Tomorrow: Rome.

Our last morning at Villa Cicolina and there was only one thing on the agenda.

That pool.

We had spent two days running around Tuscany — olive oil tastings, dairy farms, wine, Montepulciano, photography tours — and hadn’t properly used the pool yet. Criminal.

Now, to be clear, I do not approve of pools. Pools are just organized water, and water is my enemy. Pokin has threatened me with baths enough times that I have a healthy distrust of any body of liquid larger than a cocoa mug. But I will admit — from a safe distance, on a dry lounger, under an olive tree — this pool looked very good.

Nicholas was in his SpaceX shirt, lounging under the olive trees, scrolling his phone. Pokin was somewhere being productive. I supervised from the lounger. Dry.

This is what the villa was for. Not racing to appointments. Not navigating bollards. Just sitting by a pool that drops off into a valley and pretending the rest of the world doesn’t exist. Preferably without getting wet.

We could have stayed all day.

We did not stay all day.

On the way out of Montepulciano, we stopped at a vineyard. Not for a tasting this time — just for the views. At this point we’d had enough wine education to last a lifetime. But the landscape around these estates is something else entirely.

The vineyard had a little garden, neat rows of vines running down toward the valley, and that view of Montepulciano up on its ridge that makes you understand why people have been making wine in this exact spot for centuries.

Before getting on the road to Rome, we stopped for lunch at a little deli in town. The kind of place with a glass counter full of cured meats and a guy behind it who just starts putting things on a board without asking too many questions.

Salami, prosciutto, cheese, bread, pickled vegetables. Simple. Perfect. The kind of lunch that doesn’t need a menu or a reservation, just a counter and someone who knows what they’re doing.

Then we got in the car and pointed it south. Rome was waiting. But Tuscany had been good to us.

Today was tour day. But first, Montepulciano itself.

Montepulciano can be a little bit confusing because it’s the name of a medieval hilltop town in the province of Sienna in Tuscany, and it’s also the name of a wine that is not produced in Tuscany.

We had a photography tour booked for the evening with Alfredo, so we spent the day exploring the town. The real Montepulciano. The one on the hill.

The thing about Montepulciano is that it’s built on a ridge, so every street either goes steeply up or steeply down, and the alleys between them are narrow enough that you can touch both walls.

Every few turns you pop out to a viewpoint where the rooftops give way to the Tuscan countryside below. Terracotta tiles stepping down the hillside, cypress trees in the distance, the whole postcard.

We found a quiet garden terrace tucked behind the town walls, rested on the steps of an old church, and eventually did what you do in any Italian hilltop town at lunchtime.

Come photography tour time we got into the car and it became a game of racing for light.

We started at the Windows 95 wallpaper spot.

This involved pulling onto the side of a highway, scrambling down the embankment of an overpass and wading waist deep into grass for the perfect angle.

Then we moved to the Gladiator ending scene. To get here, we wound our way up and down various semi-steep roads, down the back driveway of a school before wading through more grass.

From this angle, outside of the wheel marks of mowed lawn, it would be difficult to discern what era we were in. We rested here for a good long while, crouched on the hillside, watching rippling waves of grass fields and feeling the breeze, waiting for Alfredo to take a smoke as we heard his tales as a reportage photographer. And tales Alfredo had, from stories of how he gained the trust of DRC Congo generals to facing down guns on the inner streets of LA in his search for the story.

The sun was starting to set, so we set out towards another set of hilltops, turning up and down more roads, questionable roads, then finally definitely not roads. Alfredo didn’t care. The man was chasing light.

We hiked up through fields of golden wheat to catch the ridgeline, our little group trudging uphill with tripods and camera gear like the world’s most over-equipped sunset pilgrimage.

Alfredo continued to tell us tales of his time as a reportage photographer as we watched the light change and the sun set –

– before we finally raced back to catch Montepulciano at night.

So here’s what happened.

Pokin had booked a wine tasting at a place called Podere Le Berne, a family-run estate in the hills outside Montepulciano. It was supposed to be for all four of them — Nicholas, Pokin, Bob, and Jane — plus me. A nice afternoon out in the vineyards, learning about Vino Nobile di Montepulciano from the Natalini family, who have been growing grapes here since the 1960s.

Bob and Jane weren’t feeling up to it. Too tired from the previous day’s adventures.

So it was two humans and a bear.

Two humans who don’t particularly care about wine.

And a bear who definitely does not care about wine.

But we had a guide, we had an appointment, and Pokin does not cancel things. So off we went.

Podere Le Berne sits on a hillside about fifteen minutes from the villa. The kind of place where the vineyard rows run right up to the front door and the views go on forever.

The tasting was conducted by the family — not a hired guide, the actual people who make the wine. They walked us through the vineyard, showed us the cellar with its big oak casks and aging barrels, and explained far more about soil composition and fermentation than two reluctant attendees and a stuffed bear needed to know.

Nicholas bought some obligatory wine. As one does when you’ve just been given a private tour by the family who made it and they’re standing right there watching you.

The real highlight of the day was getting back to Villa Cicolina and actually enjoying the place. The morning had been a rush — arrive early, drop bags, run off to tours. We hadn’t actually settled in.

Now we did.

The room had terracotta floors, exposed beam ceilings, an iron-frame canopy bed with white linens, and an antique wardrobe that looked like it had been there since someone important lived in this place. Which, given that it’s a Tuscan villa, was probably several centuries of important someones.

The villa had that specific quality where every room felt like it had been decorated by accumulation rather than intention. A fireplace here, a china cabinet there, a rug that predates everyone staying in it. Nothing matched and everything worked.

The next morning, with no tours booked and nowhere to be, I finally got to see the grounds in proper daylight. And this is where Villa Cicolina really earns its reputation.

An infinity pool that drops off into a valley of vineyards and olive groves. Sun loungers under ancient olive trees. The kind of view that makes you briefly consider abandoning your entire life and becoming a person who just lives in Tuscany and reads books by a pool.

Briefly.

There are games to be made.

But I’ll admit — Tuscany does something to you. The light, the rolling hills, the cypress trees. It looks exactly like you think it will, and then it looks a little better than that.

Not bad at all, Villa Cicolina. Not bad at all.

Tuscany day! Of course Pokin booked us another full day tour, so I was forced up at 7am along with everyone else for breakfast and to get on the road.

Turns out our car was stored halfway across the city, so they needed time to fetch the car for us. I could have slept more had I known this! Someone failed at planning.

Some time that felt like 30 minutes later, the car pulled up in front of the hotel, and it was time to navigate out of Firenze. A little less stressful out than getting in. The bollards were down, so a few left turns and we were out of town (though it still gave us a scare to see the poliza with their lights on behind us.)

I was excited about Tuscany. I enjoyed my France trip to Provence 10 years ago and it felt like Tuscany would be similar.

We were staying in a place called Villa Cicolina, and after a couple of hours on to the autostrada, we pulled up.

And we were all promptly glad we got the full deal on car insurance. The place was very lush, but they also left branches draped over the driveway. In fact, the bushes were so dense we weren’t sure at first if we had gone up the right street, and Nicholas had to very grumpily back down the driveway while the car proximity sensors beeped madly at us because the bushes were so close.

Eventually we arrived at the right front entrance, to the surprise of the owners.

“You’re here very early,” she remarked.

I agree, I thought. No one should be forced to travel this early.

“Oh it’s because we have a tour booked,” answered Pokin.

Our rooms weren’t ready, but we were able to leave our bags while I scouted the property. Definitely reminds me of our trip to France. Lots of flowers. Looks good.

Nicholas parked the car in the parking lot down the street away from the bushy roads. I made sure to greet him on his return. He looked a bit grumpy.

Then it was time for our tour. Pokin booked a tour with a guide named Chiara from Montalchino Wine Tours. The itinerary was an olive oil tasting, a visit to a dairy farm, and a wine tasting. I wasn’t interested in any of those so I mostly planned to nap in the bag at first.

The olive oil place they stopped at was named Frantoio Fregoli. It was definitely not olive oil season so most of the machinery was disassembled, but the owner Francesco came by to give us an explanation of everything. He also showed us how the machinery worked. That got my curiousity piqued. I got out to take a look.

We learned that the highest quality olives are harvested around October when they are still green, and at time, only 10% yield is possible. But olive oil harvested then has the highest percentage of polyphenols. If you harvest closer to December, you can have a higher oil percentage but there is major flavour and polyphenols loss. Temperature too, affects the percentage and the ideal temperatures are between 10oC-27oC. Francesco walked us through their machinery designed to cool the production so that the temperatures never exceed 27oC.

We also learned that good quality olive oil starts to lose its number of polyphenols once opened. Try to use up your olive oil within weeks! Organic olive oil at the property had close to 800 polyphenols, whereas their regular olive oil had around 400. Every year, olive oil loses around 100 polyphenols. Finicky stuff!

Francesco demonstrated how to do a proper olive oil tasting (you want to draw air in through your teeth), and we learned that Tuscan Olive oil has a peppery bitter taste. We tried to buy some olive oil (still waiting to pay), and then we were on our way.

We had time to kill before lunch, so Chiara took us to Pienza. Unlike many of the other towns in the region, Pienza was built during peaceful times, so it didn’t have the typical fortifications common in the area.

Pienza as it looks now came to be thanks to Pope Pius II. Story has it that Pope Pius II was born in the region back when Pienza was known as a small village named Corsignano. He felt like as pope, he should come from a more beautiful and representative town for a pope, so he had Pienza rebuilt for use as his summer residence. Pienza, “city of Pius,” is known as an ideal Renaissance town, and was one of the first towns to apply urbanist planning concepts that were later applied to other cities across Europe. It also seemed to be the centre point for many spots around Tuscany. It was super hot and sunny so I wasn’t that up to explore, but we snapped a few photos before heading on to lunch.

Our next stop was to Il Casale, a Dairy Farm that produced a variety of pecorino cheeses. This was when Pokin learned that Pecorino cheeses described any kind of sheep’s milk cheese.

Apparently cheeses were brought in by the Sardinians. Tuscany used to be a really cheap region, and so many Sardinians immigrated to the area, bringing along their cheese technique.

Il Casale was perched up on the top of a hill, with beautiful views of the surrounding countryside.

I was impressed. I got a few pics. Everyone sat to eat lunch. The food was good. For them. They liked some sort of salad leaf named mizuna (portaluca in english). I didn’t. I’m not a goat.

Then it rained. On all of us. I was less happy about that. This giant raindrop landed perfectly into Pokin’s espresso cup which splashed coffee all over her. That was a little amusing.

Let me tell you about ZTLs.

If you ever drive in Italy, you will encounter something called a Zona a Traffico Limitato. Traffic-restricted zone. Basically, the historic city centers are off-limits to cars unless you have a special permit. They enforce this with cameras and, in some cases, retractable metal bollards that rise out of the ground like tiny angry sentinels.

Keep that in mind.

So we’re driving into Florence. The hotel has given us these elaborate instructions involving pulling up to a specific spot and calling the front desk. It’s in a ZTL. We navigate to where we think we’re supposed to be, and drive through what we think is the entrance.

And then, behind us, the bollards go up.

We are now trapped inside the locals-only streets of historic Florence with no way out. The bollards require some kind of resident access to lower. We do not have resident access. We are tourists in a rental car who just accidentally infiltrated a pedestrian zone.

We call the hotel. The man on the phone is genuinely confused by how we got inside. Apparently an emergency vehicle had just driven through seconds before us, and the bollards hadn’t risen back up yet. We slipped in behind it like the world’s most accidental car thief.

The hotel sent someone to collect the car and spirit it away to wherever it was supposed to be. Which, honestly, was probably where we were anyway. The whole thing took about fifteen minutes and felt like a heist movie where we were the incompetent criminals.

Welcome to Firenze.

The hotel itself was one of those places that’s been decorated by someone who believes “too much” is a starting point. An art hotel. Every surface had something going on.

The bathroom in Nicholas and Pokin’s room looked like someone had a tile budget they needed to burn through by Friday. Floor tiles. Wall tiles. Ceiling tiles, probably. I half expected the towels to be tiles.

It was a lot.

For our day in Florence, Nicholas had done something unusually civilized. He’d hired an actual art historian to give us a private guided tour. This was going to be the “art and culture” day. Which, for a bear who mostly cares about gaming and cocoa, sounded like a lot of standing around looking at paintings.

It was actually pretty good.

The Duomo is one of those buildings where you turn a corner and it just fills your entire field of vision. You can’t take it all in. It’s too much marble, too many colors, too much detail. It’s like someone rendered a cathedral at maximum settings and forgot to optimize.

Brunelleschi’s dome. Built in 1436. Still the largest masonry dome ever constructed. The man figured out how to build it without scaffolding, which is the kind of flex that doesn’t get old even after six centuries.

Our guide walked us through the piazzas explaining things I would absolutely forget by dinner. But in the moment, it was genuinely interesting. He knew the stories behind the statues, which families hated each other, who commissioned what to spite whom. Italian history is basically centuries of rich people being petty with marble. I respect that.

The Loggia dei Lanzi is basically a free outdoor museum in the middle of Piazza della Signoria. Just world-class Renaissance sculptures sitting out in the open air, free to look at. No ticket, no queue. This is the kind of energy all museums should have.

Then we went to see David.

Not a David. THE David. Michelangelo’s. The one.

I will say this: photos don’t prepare you. You walk into the Galleria dell’Accademia, you go down a hallway, and then there he is at the end of it, seventeen feet tall, lit from above, standing in his own domed alcove like he owns the building. Which, let’s be fair, he does.

The detail is absurd. The veins in his hands. The tension in the pose. Michelangelo was 26 when he finished this thing, carved from a block of marble that two other sculptors had already given up on. My only critique is that it isn’t a sculpture of a bear.

After the morning of culture, we stopped for a proper Florentine lunch. A rustic trattoria, long table, the works.

The guide marched us to Lo Scudo on Via dell’Oriuolo, near the Duomo, and informed us that we would be ordering the pappa al pomodoro. Not suggested. Informed. It’s a traditional Florentine bread soup and apparently the only acceptable lunch for someone visiting Florence under the supervision of an art historian. He also insisted on the bistecca alla fiorentina — a massive T-bone from Chianina cattle, grilled rare, sliced on a board, and shared at the table. It’s the signature dish of the entire city. The steak is so important to Florence that they sell it by weight and will look at you funny if you ask for it well done. Our guide said something to the effect of “you do not cook a Chianina past pink, it is disrespectful.” Fair enough.

The Uffizi was next. One of the most famous art museums in the world. Home to Botticelli’s Birth of Venus, works by Raphael, Caravaggio, Titian. The kind of place where you walk past a painting worth millions and barely notice because there are forty more behind you.

The Uffizi has this corridor with windows overlooking the Arno and the Ponte Vecchio, which means you’re trying to appreciate priceless art while also wanting to stare out the window like a kid in school. I stared out the window.

The Ponte Vecchio. Bridge full of jewelry shops. Been there since 1345. It’s the only bridge in Florence that the Germans didn’t blow up in World War II because apparently even Nazis had aesthetic limits.

After the museum tour, Bob and Jane split off to do their own thing, and Nicholas and Pokin went to find dinner. They found it in a tiny alley.

The wine was local. The truffle was fresh. The alley had exactly three tables. This is how you eat in Italy. You don’t go to the place with the biggest sign. You go to the place where the peacock feather murals are and the burrata arrives with truffle shaved tableside.

After dinner, we walked. Florence at golden hour is doing that thing cities do when the light gets low and everything turns the same warm color, like someone put an Instagram filter on reality except it’s been doing this for centuries before Instagram existed.

We walked along the Arno as the sun dropped. Past the Ponte Vecchio, past the old grotto walls with ferns growing out of Renaissance stonework, past the point where the city starts to feel less like a museum and more like a place people actually live.

Then Nicholas decided we were walking up a hill. Because of course he did.

Piazzale Michelangelo. The famous viewpoint above the city. You walk up a winding road through cypress trees and then Florence just… opens up below you. The Duomo, the Palazzo Vecchio, the Arno, all the terracotta rooftops. The whole city laid out like a painting of itself.

We stayed until the streetlights came on and the sky went from gold to purple. I’ll give Florence this: it knows how to end a day.

We closed the night the only way you close a night in Italy.

Nicholas said this was some of the best gelato they’d had on the entire trip. I looked at the flavor selection and saw mostly fruit and nut situations. Not nearly enough chocolate. If your gelato counter doesn’t have at least four chocolate variants, I’m not interested. Nicholas needs better priorities.

Firenze. Trapped by bollards, educated by an art historian, humbled by David, fed truffle in an alley, and rewarded with a sunset. Could have been worse.