We’re finally posting on the locations from our first, epic, post-retirement trip, which entailed, as noted above, a prolonged foray to Europe that ultimately spanned more than 2 months. As noted in the trip overview, this trip entailed multiple segments – in the Italian peninsula, Sardinia, Sicily, Malta, Normandy, and Portugal. Pretty great experience that commenced shortly after the second WolfeStreetTraveler retired, where we bought one-way tickets and could explore locations without having to solve crises at work or worrying about getting home in time for an important meeting. Very liberating change of pace.
Sunrise over Italy’s west coast as we head into Rome.
Tuscany served as our kickoff location for the trip. This would be our third time in the region, which really is quite awesome. The first took place in 2004, when we biked through the area. We then returned in 2021 for a road trip through Cinque Terre and Tuscany. And now, just 2 years later, we found ourselves here again. Although we knew we wanted to start our inaugural, post-retirement trip in Italy, we could have launched our journey anywhere on the peninsula.
But the Brandts (and KJQ) coincidentally were heading to Tuscany at the same time we were heading to Italy, so the timing was perfect to hang with them as the start of our trip. We would spend the first 5 days here, before heading north (and then immediately south, but that’s the story of the next post).
Another sunrise the first day in Italy from the terrace at our guest house on the estate of Castello Brandt.
First stop: Pienza. “It is first mentioned in documents from the 9th century. Around 1300 parts of the village became property of the Piccolomini family after Enghelberto d’Ugo Piccolomini had received the fief of Montertari in Val d’Orcia from the emperor Frederick II in 1220.“
We were delighted to visit, inasmuch this was a well-regarded Tuscan hill town that we had yet to experience during or previous two Tuscan tours.
The remarkably monochromatic and stately Duomo di Santa Maria Assunta (Pienza’s cathedral):
The cathedral was commissioned by Pope Pius II (a member of the Piccolomini family who was born in Pienza) and consecrated in 1642; the piazzetta in front is named for the pope.
“Pienza Cathedral prominently features the Piccolomini coat of arms (a crescent moon with stars, representing Pope Pius II’s family) on its facade and a gothic window behind the altar, often combined with the Vatican keys and tiara, symbolizing papal authority and the Pope’s power over heaven and earth, linking the church to the Holy See. These symbols, especially the crossed keys (gold for heaven, silver for earth), are central to the cathedral’s design, reflecting Pius II’s vision for his ideal Renaissance city.
Key Elements:
- Piccolomini Arms: The distinctive crescent moon and stars are the family emblem of Pope Pius II (Enea Silvio Piccolomini), who commissioned the cathedral.
- Keys of St. Peter: Two crossed keys, one gold (heaven) and one silver (earth), signify the Pope’s spiritual authority, as seen on the well in Palazzo Piccolomini and potentially in the cathedral’s decoration.
- Papal Tiara: The three-tiered crown (tiara) often accompanies the keys, representing the Pope’s threefold power (teacher, judge, ruler).”
Pienza certainly ranks up there in charm, but it’s super tiny. Based on the strong recommendation we received from our safari travel friends that this was their favorite Tuscan town, we thought it would be just as charming as it turned out to be, but more substantial.
KJQ selfie hijinks:
Pienza’s bell tower, which was silenced the year we visited due to complaints by tourists in nearby hotels. Which pissed off the locals who consider the bells to be part of the town’s character (kind of like us when Appomattox was removed from the intersection of Washington and Prince in 2020. . .). Smithsonian magazine featured an article on the row titled, “This Italian Town Silenced a Historic Bell That Kept Tourists Awake. Now, Locals Can’t Sleep.” Indeed.
Dunno – some cloister somewhere? This was 2.5 years ago, so we don’t remember everything. But it was picturesque and atmospheric nonetheless.
Pretty cool portal from Pienza to the Val d’Orcia below:
Another pathway to the Val d’Orcia:
And there it is:
Pretty quintessentially Tuscan, as it happens:
Pretty awesome lunch at Ristorante la Terrazza della Val d’Orcia:
Heading out of Pienza, through its city walls:
Next field trip: Tenuta Valdipiatta for some fine brunellos (albeit in the rain – but this gets way worse):
A brief respite on a belvedere over the vineyards:
The wine tasting clearly elicited different emotions from the tasters:
Next day: a decent hike near Gaiole in Chianti.
Starting with a stroll around the 1000-year-old Badia Coltibuono Abbey:
Including the gardens that we were not supposed to be in, and from which we were brusquely ushered out (still worth it!):
The hike continues through countryside. . .
And the village of Montegrossi, founded in 500 – 600:
Small but mighty (and mighty old):
And a cool winery that we stalked through, seeking KJQ’s gate to salvation to cut a leg off the hike and get to town to grab a well-deserved lunch:
The gate!
Key component of a post-hike lunch:
And the first of two nights of epic Trivial Pursuit competitions at Castello Brandt:
The winners of the first night:
Here’s the much worse rain – torrents during our visit to Montepulciano, which we had visited back in 2005 during our bike trip in Tuscany:
Wet but happy(ish):
On the way back, a quick stop (for a few of us) at the monastery Badia a Monastero, founded in 867 (beating the longevity of the monastery visited during our hike):
A final hike starting at Borgo Castelvecci (similar in structure to the borgo we stayed at during our last visit to Tuscany in 2021 – an ancient village converted into a hotel campus):
And then a stroll around the nearby hamlet of Valpaia, followed by a final Tuscan lunch before heading out the next morning.
The Brandt villa:
Pretty good digs:
And the cocktail that would dominate all of our European travels henceforth, but that one of the WolfeStreetTravelers would not imbibe, initially decreeing it too girly, and sticking to red wine. That point of view would change rather dramatically as the trip progressed. . .
Final evening in Tuscany:
And a final game of Trivial pursuit, where Team MadiGrace won once again:
Morning of departure at the guest house:
You can take the herpetologist out of the country but not the herp out of the herpetologist.
Gracie would be moving on, too – first to Venice, then to Valencia to stay with her cousin Quinn, who was in his second Spanish semester of mechanical engineering.
The Cyprus-tree lined lane departing the villa’s area on our departure:
On to Portofino!
WolfeStreetTravel 