Italy | Florence, Montalcino & Montepulciano, Venice

Phew! 16 countries in 6 months is amazing, intense, and far too much as we have said in our 6 month check in post. We found ourselves running out of steam, but we still had about 30 days left in our Schengen Visa (EU body that regulates visitors and immigration) so we agreed that we would spend it in one place. Knowing this, around the end of summer we started talking about whether there was someplace we had been to that we would want to go back and spend that amount of time. While there were some contenders, there was another place that we had been to years and years ago, and we have not been back since (including during this sabbatical). We loved it, but our overall exposure to everything this country has to offer was limited. The choice quickly became very apparent and very easy…

We were going to spend a month in Italy! We looked specifically at options that were central, had a lot to do, had a decent sized airport, and it was relatively convenient to get to other cities around Italy. There were a couple of options, but the one we have heard the most consistently amazing things about was Florence.

Benvenuti a Firenze!

Jeremy and Valerie the day they arrived in Florence, with Ponte Vecchio in the distance.

We found an Airbnb in the center of the city, not far from the central train station about a 5 minute walk to the Duomo. We knew we needed in-unit laundry and a kitchen to minimize eating out. We also realized that the one we chose was going to be in a big touristy area, but since we had never been there before we wanted convenient walking distance to most things. Further, we assumed that by November the tourist season was over, kids were back in school, etc., so it would at least be quieter than normal. While it did get cold (there were days in the 40s Farenheit), the timing did end up being important because despite the season and the weather it was still quite busy. We commented several times how we couldn’t imagine what it would be like in the dead heat of summer with perhaps 2, 3 or 4 times as many people.

We won’t recount every day we spent in Florence, and quite frankly we could not do it even if we tried! As you can imagine, living there is different than vacationing there. A lot of days were just spent in the apartment staying warm and watching movies. That said, here are some highlights of our time in Florence including a few adventures we took to other parts of Italy.

The greatest luxury of spending a month in one place is the shift in perspective. You transition from a tourist—ticking off a checklist—to a temporary resident soaking in the rhythm of daily life. Our apartment’s proximity to the Duomo meant that our days were punctuated by the sight of the truly magnificent dome. It became our North Star. No matter how lost we got in the winding medieval streets, we could always look up and find our way. We chose not to climb it, having heard tales of the claustrophobic climb, but have heard that the views are stunning.

Michaelangelo’s David in the Galleria dell’Accademia di Firenze

Of course, you can’t be in Florence without paying homage to its most famous resident: Michelangelo's David. We booked tickets for the Galleria dell'Accademia (a must, even in November) and walked into the main hall to see him standing there, illuminated under a skylight. No picture can prepare you for the reality of it. The scale, the perfection of the human form, the intense gaze. It's an overwhelming and surprisingly moving experience. We spent nearly an hour just sitting on a bench, marveling at this singular masterpiece. We were also really mesmerized by Michaelangelo’s “The Prisoners” (also known as “The Slaves”). We learned that he used a technique called “non finito” (meaning unfinished), where parts of the sculpture are left rough and seemingly incomplete, creating the dramatic impression that the figure is fighting to break free from the raw marble. Art historians debate whether this was an  intentional philosophical statement about the human soul struggling to escape its mortal, earthly form, or simply because the massive project they were intended for was repeatedly downsized and ultimately left incomplete. Either way, the effect is breathtaking.

Palazzo Vecchio, the Uffizi Gallery, Piti Palace and Boboli Gardens

A day spent wandering the vast halls of the Uffizi Gallery brought us face-to-face with Botticelli's The Birth of Venus and Primavera, but the sheer scale of the Uffizi is staggering. Room after room is filled with masterpieces by Giotto, Leonardo da Vinci, and Caravaggio. After a few hours, we found ourselves experiencing a weird kind of sensory overload. Needing to clear our heads and breathe some fresh air, we sought a different kind of Renaissance artistry. We crossed the Arno River across Ponte Vecchio and made our way to the Pitti Palace, the former home of the powerful Medici family, to explore the palace and its famous Boboli Gardens.

Path toward the Fontana dell’Oceano in Boboli Gardens

Walking into the gardens in late November was a unique experience. The lushness of summer was gone, but we still got the remnants of fall with beautiful orange, yell and red leaves adding to the already beautiful and serene setting. The air was crisp and clean, and with far fewer people than in peak season, it felt less like a tourist attraction. We were so lucky to just have this quiet stroll in this grand, open-air museum.

We wandered without a map, exploring the various paths, running into amazing fountains and sculptures at every turn. We walked through the main amphitheater that rises up behind the palace, climbed the long, sloping path flanked by cypress trees, up to Neptune’s Fountain. From the highest point, there is yet another stunning panoramic view of the city, this time looking back towards the Duomo from the south. We then made our way down the long path toward the Fontana dell’Oceano, the crunch of our footsteps on the gravel was often the only sound as the sun set in the distance.

Montalcino, Montepulciano and Surrounding Tuscan Villages:

With Florence as our base, the iconic wines of Tuscany were just a short drive away. We couldn’t be this close and not spend some time wine tasting! For Valerie’s birthday, we rented a car and set out for the Val d'Orcia, a region south of Siena so picturesque it's a UNESCO World Heritage site. This is the Tuscany of postcards with rolling hills bathed in a soft, golden light, cypress trees standing like sentinels along winding roads, and farmhouses dotting the landscape.

Jeremy in his happy place.

Our first stop was Montalcino, a fortified hill town famous for producing one of Italy's most prestigious red wines, Brunello di Montalcino. The town itself is a charming maze of stone streets, culminating in an imposing 14th-century fortress. From our room in the hotel, we looked out over the sprawling vineyards that give the world its Brunello. We hired a guide for two days to take us out to several of the wineries. Some big and some small, but all were absolutely delicious. At one of them, we were treated to a lovely lunch of fresh pasta and bolognaise paired with a wine tasting.

Day two of our tasting was to the nearby town of Montepulciano, perched dramatically on a limestone ridge. If Montalcino felt rustic and robust, Montepulciano felt grand and elegant. We were lucky to have our driver because it is quite the steep hike up its steep main street to the stunning Piazza Grande at the town's summit. We only had to walk down it! The square of the town is flanked by the beautiful town hall and cathedral. We were there just barely too early in the season because they were putting up all the stands for the Christmas Markets, literally kicking off a week later. Montepulciano is renowned for its Vino Nobile, another superb red wine. We explored one of the historic cellars that run deep beneath the city's palaces, a cool, cavernous world of giant oak barrels and aging wine. We met back up with our guide, who took us up to another small town, Pienza, famous for Pecorino cheese. We picked up some cheese and salami, and walked the edges of the town watching the sunset over the Tuscan hills. 

One our drive back to Florence, we made a detour to the town of Panzano in Chianti. The purpose of this stop was for a very specific and fun experience. In this town is a butcher who we have seen on tv a number of times, Dario Cecchini. The video below is him welcoming everyone to the restaurant.

On tv he comes across as this larger than life character with a contagious zeal for what he does and a love for making people happy with food. Across the little street from the Maccelleria (butcher shop), he also runs a restaurant. It is only open on the weekends, and it is a truly unique experience. It is a set menu and everything is served family style at these long tables. You are sitting next to a random group of people (shockingly we were sat next to a young guy from Riverside, CA!) all there for the same thing, a smorgasbord of beef! The meal is an exploration of using the whole animal, as Dario is a huge advocate for respecting the animal and not wasting a thing. It was so much food, all delicious, and Jeremy got out of his comfort zone, trying some things that neither of us would normally choose off a normal menu.

This part of the world is truly magical. Seeing it in pictures or movies/tv does not do it justice. Highly recommend anyone spend some time here if you can!

What a view of Tuscany!

Venice

Being just a short 2 hour train ride to Venice, we knew we had to make our way there for a couple of days. The high-speed train from Florence whisked us there and the experience of stepping out of the Santa Lucia train station is truly unforgettable. We feel like we are repeating ourselves here, but seeing the Grand Canal, bustling with water taxis, vaporettos (water buses), and the occasional sleek, black gondola is like stepping into a movie set. We commented how it was almost like walking into an amusement park, which, ironically is unfortunately the way this city is going with so many of the locals moving away and using their homes as vacation rentals, so it really is almost entirely tourists.

We were expecting Venice to be crowded, and while it was, but being there in an “off” season made it more manageable. Like Florence, we couldn’t imagine how absolutely crushing it would be in the middle of summer. Our hotel room looked right out to The Rialto Bridge, and waking up to the sounds of boats and the bustle of people was exciting.

One of the many canal photos from Venice.

We made our way to the Piazza San Marco, where we sat and had a glass of wine, people watching with the shimmering mosaics of St. Mark's Basilica and ornate Doge's Palace as the backdrop. The true magic of Venice revealed itself when we deliberately got lost. We would pick a direction and just walk, leaving the main thoroughfares behind. Within minutes, the noise of the crowds would fade, replaced by the lapping of water against stone and our own footsteps echoing in narrow alleyways. We discovered quiet canals, tiny arched bridges leading to private courtyards, and charming little squares where we would stop for a coffee or light meals. We skipped the expensive gondola rides as it was quite cold and often rainy, and we much preferred either walking or taking the water bus. Our time in Venice was short, but quite frankly 2-3 days is really all you need to take in its beauty.

Looking back at our time in Italy and Florence specifically…

Our month in Italy was the perfect antidote to our travel burnout. Slowing down allowed us to do more than just see Italy; it allowed us to settle in and feel at home amongst the generous and welcoming Italian people. We learned the simple pleasure of the evening stroll, the ritual of the morning latte at a local bar (never after 11 AM!), and the joy of finding our "favorite" everything.

Florence was the perfect anchor, a city of immense history and art that still felt vibrant and youthful. The trips to the Tuscan countryside and the dream-like city of Venice were perfect complements, showcasing the incredible diversity packed into one country. As our 30 days came to a close, we felt rested, inspired, and completely captivated. We came to Italy to run out the clock on our visa, but we left with a renewed and enhanced love for the country.

Make sure you read the blog post on our time in Dubai in which we recount our “Escape from Florence.” Italy just did not want to let us go!

Un saluto all’Italia! Where To Next?