Castiglione del Lago, Montepulciano & Assisi

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Castiglione del Lago:  Pablo’s Place, Montepulciano, and Assisi

When we started planning our time in Tuscany we had intended to stay in Montepulciano.   After booking.com showed a few locations, Hotel Boutique Castiglione seemed the most appealing, so we reserved it, and soon after booking.com charged our card.  Later, when planning out travel days, I realized this hotel was not actually in Montepulciano, but 20 miles to the east.  When I messaged the property to inquire about  parking, I received directions and also a sweet request: “ Please bring us something from Oregon.”   Finding something uniquely Oregon isn’t too difficult, but finding something that will hold up for 8 weeks of travel and not take up much room in our carry-on-only bags was more onerous.  We ended up deciding on an Oregon Pine scented travel candle and a tin of Jacobson’s sea salt.  And we’ve carried these gifts through Greece, Croatia, Bosnia, and parts of Italy and now we’re heading to Castiglione del Lago in the Italian countryside, on the border of Umbria and Tuscany.

Anyway, back to the present.  From the center of Florence, we take a tram to the airport, then a bus to the rental car.   We chose to rent the car at the airport location to avoid negotiating city traffic in Florence.  We begin by driving to Castiglione del Lago and are instantly charmed by this adorable lakeside village.  Even more charming is our host Paolo at Hotel Boutique Castiglione.  We are welcomed with “Hello” and “Beautiful” and feel like honored guests, or maybe family depending on how you feel about your family.  

Walking about town this first week of December, we see all the Christmas decorations ready to go, including a slightly creepy life sized Nativity seen with mannequins.  The old town is only 200 meters long and two streets wide, so our walk doesn’t take too long.  Next to the lake is an old fortress that looks to host outdoor cinema, but is obviously closed for the off season.  

When we reenter the hotel lobby, Paolo is waiting with a warm and boisterous welcome “Is  beautiful?”  Then he insists on making our dinner reservations at the local cantina and we are happy with his recommendation.  We learn that Paolo has lived in Castiglione del Lago his entire life and pretty much knows everyone, certainly everyone in the Old Town area.  At breakfast he proudly shows us photographs of when he met Pope Francis.  Paolo had his arm around the pope and was beaming.  He was also happy to show us the official “blessing” received for his family by the pope.  It comes as no surprise that Paolo is also a mayor or running for mayor, we aren’t entirely sure which.  But everyone seems to know and like him, that is completely understandable.

We drive to Montepulciano, the original Tuscan village we wanted to visit.  Navigation is simple, however some of the roads are a tad neglected, but nothing Tom can’t handle.  We get lucky and find free parking on one end of town.  I find a cute blue beret without spending too much time or money.  There are more shops and shoppers here than in Castiglione del Lago, but it’s still not very crowded.  At moments, we find ourselves alone in a street which emboldens our curiosity, and we open doors and peek in a church or two.  Walking uphill into town, we find the restaurant/winery Paolo recommended and enjoy a delicious lunch, then a walk through their ancient wine cellar.

Back in Castiglione del Lago, much to our delight the town has decided to turn on the Christmas lighting.  The restaurant next door has no availability except outside, so we huddle up next to an outdoor heater and enjoy a dinner of fondue.

Side Note:  At home, we normally eat dinner between 6 and 7.  In Italy, most restaurants don’t even open until 7:30, so we’ve had to adjust.  Often we see diners coming in at 9:30 or later!

The next day we venture further into Umbria to the medieval mountain town of Rasiglia, known for its meandering streams and waterways.  Winding through mountainous roads with stunning vistas, the drive is well worth the time, even though Rasiglia is very small.  During the 16th century, the streams and waterfalls powered the woolen mills, dyeing factory, and wash-houses.  Walking through the ancient village is a meditation on time.  Peering into centuries old shops, with looms holding abandoned works, frozen in time, all while the water rushes around and through, creating a contradictory experience of stillness and movement.

On to Assisi, where we enjoy a brief but meaningful visit to Saint Francis’ tomb and (so called) Inferior & Superior Basilica.  The Saint Francis prayer has always been particularly meaningful to me (and many others, no doubt).  I leave a prayer for a dear friend.  There is no photography allowed in the inferior basilica nor in the crypt, but I was able to take a picture in the superior basilica.  The workmanship is awe inspiring, which, I suppose, was the intent.  The exit was into a gift shop, ala Disney, then onto a trinket store lined street.  Seems like nothing Saint Francis would have endorsed.

Our last dinner is back at the Cantina again and our only regret is not ordering the affogatto the first time we ate here!

Next up:  a drive across Tuscany

5 thoughts on “Castiglione del Lago, Montepulciano & Assisi”

  1. Your well thought out appreciations of where you are and enjoyment of what you see makes me feel happy you are my friend to share. I enjoy every moment you show ♥️. Thank you!

  2. Kathleen Moneymaker

    Photos and commentary are so rich! I just want to know if you bought the snow being sweater (first photos) for Tom for Christmas? I so appreciate your writing and descriptions of where you are, what you are up to…and what’s going on around you. Thank you SOOOOO much for sharing your wonderful adventures with us❣️
    😘💚🙏🎄🧑🏼‍🎄🎁☃️🎉🧡🕯️

    1. Hah! Tom is not interested in adding to his luggage (yet). I however have added much. My suitcase is now a magician’s hat. We did send home a few things, but I’ve added more still: two pair of socks, a pair of fleece pants, a dress, two hats, a scarf, a puffer jacket & a pair of Chelsea boots! Compression bags and packing cubes for the win!

      Thanks for the kind words, Kath. Hope to see you when we return.

  3. Your perceptions of what you’re experiencing and seeing open a visual for me that I’m loving – I really can imagine what it must be like in that all-but-deserted village of Rasiglia. Into this journey 3 1/2 months and you’re still as intrigued and awed by what surrounds you. It’s beautiful! Thank you for sharing so honestly.
    xxooMargie

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