As a traveler, I notice new things every time I return to a place.
So when members of the Pioneer Press travel club began advocating for us to return to Tuscany, the destination of our first trip to Europe in 2021, I was happy to oblige.
And I can unequivocally say that Tuscany is as beautiful as I remembered. The medieval walled cities, the wine, the food and the sunshine (oh, the bright, warming Tuscan sunshine!) brought back all the memories.
During those seven gorgeous days in October, I also learned a lot of new things about this region, all while hanging out with the best readers out there, all of whom I’m happy to call friends.
Here’s a rundown of what we did on the tour, which was conducted by Collette Travel.
Lucca
After a late-afternoon arrival and a fabulous welcome dinner at our historic hotel, Grand Hotel Francia and Quirinale in the famous spa town of Montecatini Terme, we all got a solid night of sleep before setting off for this medieval walled city.
Our local guide, a loud and proud Lucca resident, regaled us with the city’s history during a leisurely walk. Lucca began as an Etruscan settlement (nearly 200 years before Christ), was a Roman colony, an independent republic known for its silk trade (a few people on our tour bought beautiful, hand-woven scarves here) and eventually, part of Italy.
The city inside the walls is remarkably well-preserved, and the fully intact wall itself has been ingeniously turned into a 4.2-kilometer walking trail and park system. Doctors of Lucca residents charmingly prescribe wall walks for their patients who might need to lose weight or improve their cardiovascular health, so it’s full of residents and tourists of all ages.
We wandered through the Piazza dell’Anfiteatro, a public square shaped like an oval that was once a Roman amphitheater and marveled at the marble-clad church San Michele in Foro, which was commissioned in 1070. Inside, there are massive works of religious art and also the body of San Divino Armeno, one of Italy’s oldest mummified saints, displayed in a glass coffin on the altar.
After we broke with the group for some free time, my husband and I tackled about a third of the wall walk, then traversed back through the city and stopped at the sidewalk patio of Des Arts wine bar, where we ordered pasta and risotto, both studded with fresh porcini mushrooms, as it was the season for them.
On the way back, we stopped at Fattoria Carmignani, a woman-owned winery, where we took a peek at the vineyards and sampled some of their wines, paired with fun bites like crostini and pumpkin soup with spicy croutons.
Florence
The first time I visited this culturally rich city, it was just after Italy’s doors opened after the pandemic, and it was busy, but nothing too crazy.
Now, it seems, every baby boomer with means from all areas of the world has put Florence (Firenze in Italian) at the top of their to-do list. Locals are fed up, rightfully so, with the hordes of tourists, so much so that Collette no longer takes groups to see David, Michelangelo’s marble masterpiece, as sometimes people waiting in line get spit on or yelled at. I skipped it this time, too, even though some in our group made reservations to go in their free time. As marvelous as he is, if you’ve seen David once, well, you’ve seen him.
Our local guide instead focused on the Duomo, or the Cathedral of Florence, and its massive, ornate green- and pink-marble facade and dome. We craned our necks to see all the marble statues, columns, inlays and mosaics, and wondered at the massive dome. Completed in 1436, it’s still the largest masonry dome in the world.
Funnily enough, our tour did not go inside the cathedral, which is reportedly sparse compared with the outside, which was made as ostentatious as possible to impress foreign investors, most of whom had no interest in actually entering the structure.
Florence is famous for its leather, and four years ago, I bought a purse that I had been using ever since. I treated myself to a new one, knowing it will last me at least another four years, and probably more. Gold is also a huge deal in this city, and a few travelers purchased some quality pieces.
Ed Fleming receives the wine he purchased through a wine window in Florence, Italy. (Jess Fleming / Pioneer Press)
During our free time, my husband and I wandered across the Ponte Vecchio, a stone bridge lined with jewelry stores. As fun as it was to window shop, the walk was worth it if only for the view from the middle, with the reflections of buildings lining the Arno River creating a painting-like photograph and an epic selfie.
The other side of the river from the cathedral and the Uffizi Gallery (the massive art museum in downtown Florence) proved to be much quieter. I wished we had more time to explore, but we did have enough time hit one of the wine windows in the city — tiny portals into a restaurant that are just big enough for, well, a glass of wine. The windows were used during the plague for medieval contactless transactions, which felt a little too close to home just a few years after the COVID pandemic. Still, sipping a crisp white on a quiet street of Florence felt cosmopolitan and cool.
We tried to stop at All’Antico Vinaio for its social-media-famous mortadella sandwich, but the line was way down the block, and we had to meet our group soon. So we wandered a block down and found a slip of a deli that served one of the best sandwiches I’ve ever eaten: mortadella, burrata cheese and a pistachio pesto on spongy focaccia. I have fewer than zero regrets.
As busy as Florence was, this second exploration leads me to believe that I could return on my own and find the quieter parts of the city just as charming as the ones that attract the big crowds.
Montecatini Terme/Montecatini Alto
On my previous visit to Tuscany, we stayed in Montecatini, but I opted to go to Siena instead of taking a tour of this city. This time around, it was on the official agenda rather than an option, and I’m so glad!
Montecatini Terme is a spa town, but not in the way Americans think of a spa — for centuries, people seeking a cure for various ailments have drunk the saline, mineral-rich water, which comes out of the Earth at around 90 degrees Fahrenheit.
The first written record of the spa dates to 1201, but the city wasn’t really established until the end of the 18th century.
In the city’s heyday, celebrities as well as regular people from all over the world came to relax and rejuvenate. There’s even a red brick sidewalk that winds through the city and is inlaid with bronze medallions honoring famous people who have visited. The sidewalk leads to the biggest remaining spa, Terme Tettuccio, so it is an easy way to find your way there.
After a spa treatment, a walk is recommended, so the city is built around a sprawling park with walking trails and benches offering plenty of space for reflection and relaxation.
After the state stopped sponsoring spa treatments — yes, you could even get your hotel stay covered — Montecatini Terme lost some of its luster. Its gorgeous town hall, built in 1914, has a leaky roof that the city can’t pay to fix. There are plenty of empty storefronts and structures, including one of the former spas and its most historic hotel.
But there’s still plenty to love about the city of about 20,000 people. There are excellent restaurants, plenty of shopping and a beautiful town square. These days, tour groups are the lifeblood of the city, many of whom choose Montecatini for its abundance of hotel space and central location within Tuscany.
That night, we took the funicular up to Montacatini Alto, the medieval hilltop city above Montecatini Terme. The view from the top is incredible and worth the nominal fee to get up there. There’s a little square with a handful of shops and restaurants, and if you climb a little further, you can see part of the ancient fortress. We ate at Ristorante La Torre, where my husband and I shared a Bistecca alla Fiorentina, or Florentine steak. It’s a bone-in loin steak from a young heifer, and its beefy flavor is unmatched. Because it’s a very lean cut, it needs to be served fairly rare, so those who don’t like red-inside steak should steer clear.
Pisa
The view from the top of the Leaning Tower of Pisa in Tuscany. (Courtesy of Ed Fleming)
Lots of Tuscan residents like to hate on Pisa and its leaning tower, mostly because of the massive amounts of tourists who come for that one picture. You know the one, where they pretend to be pushing the tower into an upright position?
But I do think the heavy marble tower, which was already leaning when it was completed in the 14th century, is striking enough that it’s worth a bucket-list visit. The entire square in which the tower is located is beautiful, too. If you have time, swing into the adjacent cemetery, called Camposanto Monumentale. The sprawling Gothic structure contains medieval frescoes, some of which have been partially washed away by flooding, and others of which have been restored to their original splendor.
Bodies of important townspeople and religious figures are buried below your feet, entombed in the marble that’s so abundant in the area. Roman sarcophagi, which have been emptied of bodies, line the sides of the cemetery, too.
On this trip, my husband and I decided to climb the tower, which is a vertigo-inducing endeavor. The stairways are narrow, and foot traffic flows both ways. The number of tourists going up and down is capped to ensure stability, although modern fortifications should preserve the tower (and its lean) for centuries to come.
For lunch, we followed our tour manager Kim Bizzarri into town to find cecina, a chickpea pancake of sorts, stuffed into a slice of focaccia. It’s hard to believe that the simple, tasty sandwich is actually vegan! And cheap — house-made bread stuffed with fresh, wood-fired cecina at Pizzeria Il Montino was about $3.
Afterward, we headed to a local agritourismo farm for a cooking class. Agritourismo is a program in which people rent out rooms in their farm estates to people looking for a relaxing, pastoral vacation. There were several guests at the farm, lounging in the common areas while we chopped, kneaded and whipped our meal into shape. Many travelers made homemade pasta for the first time! I am an old pro, but was definitely missing my trusty KitchenAid, which makes rolling the dense dough a breeze.
The sunset from an agritourismo in Tuscany, Italy. (Jess Fleming / Pioneer Press)
Nevertheless, we enjoyed an excellent meal with a fiery Tuscan sunset over picturesque vineyards as our backdrop.
Siena
This charming, medieval hilltop city is my favorite of those I’ve visited in Tuscany.
Siena is known for its annual Palio horse race, which has been taking place in the (not as big as you might think) Piazza del Campo town square since the 1600s.
Different contradas, or neighborhoods, sponsor each horse in the race. And each neighborhood is represented by a different animal. Statues, door knockers, baptismal fountains and flags around each contrada let you know where you are.
Each neighborhood also has a museum dedicated to its participation in the race. We toured the museum for the Selva (forest) neighborhood, which is represented by the rhinoceros. (The museums are private, and tours are available by appointment only.)
Race winners get a silk banner, bragging rights, and not much else, but the ornate banners are displayed in the museums, as are the medieval costumes still worn by neighborhood representatives in the ceremonies and parades that happen before the race.
After our tour, we ate at a restaurant on the square, where we watched residents and tourists soak up the sunshine and shared small portions of pici (thick spaghetti) two ways — in a simple garlic-tomato sauce (all’Aglione) that the city is known for and cacio e pepe (cheese and pepper sauce). They were both utterly delicious.
And since we still had a little time, we paid a few Euro to tour the inside of the breathtakingly ornate Siena Cathedral. Its black-and-white striped columns, plaster busts of popes from the 15th and 16th century, mosaic-tiled flooring and intricate marble pulpit are worth every penny. I didn’t get to see the interior last time I visited, and I highly recommend doing so if you have the opportunity.
San Gimignano
Our last day in Tuscany came way too fast.
Luckily, we got to visit a lovely cheese cooperative, where workers and happy cows and other animals live in harmony, and the cheese they make is a fantastic product of both species’ labor.
Our group in San Gimignano, Italy. (Courtesy of Kim Bizzarri)
After our tour, we were treated to a cheese board containing many of the products produced at the farm, from honey to jelly to popped farro and yogurt.
Afterward, we wandered through the quaint, walled fortress city of San Gimignano, which is known for its 14 remaining medieval towers, built in the 12th century by competing families to show off their wealth.
If you climb up to the top of the fortress ruins, you can capture many of the towers in a single photograph, but better yet, you can marvel in a 360-degree view of the stunning Tuscan countryside. After we did so, we descended to a little restaurant next to the town church where we indulged in a carafe of Vernaccia, a crisp white wine grown nearby, and some enchantingly floral saffron risotto topped with crispy, smoky speck ham, two ingredients that are produced nearby.
San Gimignano is known for its art community, and we bought a lovely painting of the city streets from an artist who had set up shop across the street from the restaurant.
Our farewell dinner was at Antica Osteria Toscana in Montecatini Terme, where we were delighted by the house red wine, ribollita (bread soup) and the most melt-in-your-mouth pork chop any of us had ever tasted.
My conclusion? I can’t wait to return to Tuscany for a third time, with or without readers. The food, the wine and the scenery are just that special. If you haven’t been, put it on your bucket list.
Most of our Pioneer Press group at an agritourismo where we took a cooking class. (Courtesy of Dave Olson)
Want to travel with Jess?
We have just a handful of spots left in our tour of Scotland, which runs May 10-19, 2027.
On this 10-day tour, our stops include Edinburgh, Inverness, the Isle of Skye, Glasgow and more. We’ll visit a family-run Highlands farm and check out the sheepdogs at work, marvel at Neolithic ruins on the Orkney Islands, tour a few castles, hear a bagpipe demonstration and, of course, taste that famous Scotch whisky at a local distillery.
For more information, or to book the tour, go to groups.gocollette.com/en-US/link/1371575.
If you have any questions, email me at eat@pioneerpress.com.
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