Nearly 15 years ago, we had our first real international travel experience together while studying abroad in Florence, Italy. Since then, Tuscany has always held a nostalgic place for us. For our first big trip of spring, we decided to do a roadtrip in Tuscany, to check out hill towns and some of the secondary cities in the region.
Top Attractions and Things to Do
Day 1: Pisa and San Gimignano
We started the trip with a quick, smooth, 2 hour flight from Frankfurt Hahn airport, and landed in Pisa in the early afternoon. Since we were in the area, we started the trip with a quick stop at the famed leaning tower, which was leaning much more than expected, but was also surrounded by pushy tourists trying to get the perfect shot of holding up the iconic structure. We took a quick walk around the grounds, admiring the ornate architecture of the Piazza del Duomo, including the cupcake-like baptistery, before high-tailing it away from the tour buses and heading out into the countryside.
We drove about 90 minutes to San Gimignano, and by this time, we were hungry, sweaty and tired. For each of our destinations on this trip, we would have to park our car outside the old towns (which are for the most part pedestrians and local traffic only) and walk in to our accommodations in the center. This time, we had the unseasonably warm afternoon sun on our backs as we lugged our bags uphill into the walled medieval city center. Dave kept chanting "pizza" in desperation, and to his delight we passed a shop selling slices and cold beers. As Erin checked in to the hotel, Dave downed his slice and sipped his beer while overlooking the main square of town.
San Gimignano is famous for its preserved medieval tower houses that dot the skyline, and for its Romanesque and Gothic architecture, which caused the entire center to be named a UNESCO World Heritage Site. After getting changed in our hotel room, which looked out over the edge of town into the surrounding hills, we climbed the Torre Grossa bell tower, which gave us views across the entire city and the rolling hills surrounding town. We climbed up a somewhat sketchy interior staircase, which caused Erin to sweat profusely and swear under her breath as she made her way to the stop. Luckily, we made it up on the hour and watched and listened as the bell towers across the city rang out in unison. The views stretched for miles, and we spent time taking in the sunset from the highest point in the city.
We headed back down to ground level and picked up a couple of slices of pizza, which came with little hand holds to keep the slices stable and the hands clean. We enjoyed our pizza and drinks on the church steps in the main square. After our meal, we explored the city on foot from end to end, walking through empty stone walkways, crowded squares, rows of souvenir shops, and wine and meat shops selling the famous local wine and prosciutto. After dark, the day-trippers mostly disappeared, and the town quieted significantly. We walked along the empty streets before turning in for the night.
Day 2: Monteriggioni and Siena
We awoke to a neon sunrise over the hills out our window, and headed out early to our next stop, a medieval walled down that was mentioned in Dante's Divine Comedy. We chose this down due to its dramatic and intact stone walls and its place among the vineyards in the Chianti region.
We parked at the base of the valley and hiked through the vineyards toward the town, the entire time with views of the fortress walled city. We stopped for Dave to get some drone shots, and continued on up into the town, sliding on the time-worn smooth uphill stones guiding our way.
We started our visit with a quick climb to take in the views from atop the walls, to get our bearings. Since it was early, we were among only a handful of other visitors wandering the streets of the sleepy little town of less than 10,000 people. Since the city was historically of strategic importance due to its location between Florence and Siena, the people of the town had to always be prepared to lock up the walls and be on the defensive. For this reason, they planted massive gardens that they used to sustain themselves when they couldn't access the farmland outside. The large urban gardens live on, and gave the whole city a refreshing, spacious feeling.
After having a light breakfast and exploring the streets, we hopped back in the car and drove to the outskirts of Siena, where we parked and marveled at the views of the famous striped Siena Cathedral, which sat atop a heap of orange and white buildings tracing up and own a hillside and valley. We made our way into the city, and were amazed by its beauty but also by the hoards of locals and tourists clogging the streets.
Siena is famous for its food, architecture and art, but also for Palio, the horse race that takes place in the Piazza del Campo, the shell-shaped town square. We learned that each of the districts within the town compete for spots in the race and hold parades leading up to the race, which takes place in late summer. We would learn more about the parade the following morning, when we were woken up by a line of drummer boys dressed in Peter Pan-style costumes.
After dropping our bags and cooling off in our B&B, we headed to a nearby gourmet grocery store, which makes its own trays of foccacia-style pizzas. We picked up a few slices and some Pellegrino, and ate at standing tables, Italian-style. Next, we made our way through the crowds to the Piazza del Campo and then on to the Cathedral. Despite the hordes of people, we pushed through into the chruch, dating from 1380, and were blown away by the unique and ornate style of the structure. Originally, this cathedral was planned to be the largest then in the world. However, the Sienese ran out of money due to war and the plague and made a simpler construction plan. The original wall of the planned but unfinished part of the structure remains, and through an internal staircase, visitors can climb for a grand view of the city , which we would do later in the day.
After checking out the church and baptistry, we took an afternoon rest to escape the crowds, hoping the day visitors from Florence would clear out in the early evening. We stepped out to cooler weather, and fewer people, but we still had to weave our way through tour groups to make it to the line to visit abandoned church wall view point - since the view point is just a small section on top of a wall, it only fits 28 people at a time, so we knew we would have to wait a bit to get the perfect sunset views over the city.
We waited outside of the museum through which you access the view for about 30 minutes, and were entertained by Italian tourists yelling at the museum employee managing the line. One particular woman really chewed the guy out when he let her know the visiting hours had ended, and she deliberately disobeyed him by joining the line anyway. Once we made it inside the building, we had to wait on each level before we could join the final line on the top floor. By this point, we were tired of waiting and tired of people, but Erin was determined that if the mean woman would get to see the view, she would as well. We held out, and were glad we did, because we hit the wall just as the magic hour started, when the dipping sun illuminated the medieval structures and surrounding hillsides. On our way out, we saw the lady be allowed to enter the last viewing from the top for the day - karma didn't get her this time.
We decided to head to the edge of town to get a different view of the city. We grabbed some prosecco and watch the sun dip over the edge of the city from a public bench on the edge of town, cool and away from the crowded center. A few nuns passed by and Dave hid our drink to be polite, and then we headed to dinner at a local osteria recommended by our hotel proprietor. Although we always try to eat local while we travel, we find it difficult (but delicious) in Italy because most of the time we don't eat dairy. We compromised our position and feasted on fresh pasta with local Parmesan and Pecorino cheeses, a truffle tagliatelle, crispy zuchinni blossoms, tomato salad and bruschetta, all washed down with local wine. We floated home after the 2 hour feast, stopping for gelato on the way back. Even though it was delicious and totally worth it, we both paid for it by being kept awake half the night with stomach aches.
Day 3: Thermal Bath Fails, Pitigliano and Montepulciano
We started the following morning groggy, having slept little due to our off-diet feast the night before. Our morning started with a low rumble that turned into an unavoidable pounding from the drum line outside our window, where a local district paraded through the streets in costume. Although we felt a little off of our game, we packed up, hiked out of town and hit the road in search of smaller towns with hopefully fewer people and a few crazy looking hot springs that Erin spotted online.
Our first planned stop was at the Terme de Saturnia, a group of hot springs and cascading waterfalls in the countryside about 90 minutes south of Siena. We tried to arrive early, to avoid what we thought might be a crowded spring Sunday, but apparently we didn't arrive early enough. Once we were about 2 miles out, we started to see RVs, campers and all forms of transportation lining the streets, and people carrying beach bags and heading toward the springs. We pulled up across the valley from the supposedly tranquil swim spot, and were suprised to see what looked like a packed concert full of people enjoying the baths. We didn't anticipate having to be up close and personal with a thousand people as part of our zen hot springs experience, so we took a few pictures and hit the road.
We had more luck at our next stop, the hill town of Pitigliano, known as the Little Jerusalem of Italy. We drove along winding roads in lush greenery, and were shocked when we followed a curve in the road and just around the bend, hundreds of tannish-grey buildings clung together atop a steep hill. We immediately pulled the car over to take in the view. After photographing and filming the city from every angle possible, we headed into town, hoping to find some takeaway lunch we could eat in a shady square.
The town dates from 1061 and some of the original Etruscan structures remain, so we took our time exploring the buildings and viewpoints out to the valley below. We also explored near the synagogue (which are somewhat rare in Italy) and a local kosher grocery store, deli and bakery. Apparently, many Jewish people fled Rome during a time of persecution by the Catholic state and took refuge in the cave houses of Pitigliano. After the promulgation of anti-semetic laws under Nazi influence, all of the Jewish people in town reportedly escaped capture with the help of their Christian neighbors. We loved learning the history of the little unknown town and appreciated its combination of historical significance, natural beauty and few crowds - this was one of our favorite stops on the trip. We couldn't find anything but sit-down restaurants though, so we continued our trip with empty stomachs.
After Pitigliano, we gave the thermal bath option a second shot, and headed out in search of the San Filippo baths, which were allegedly less crowded as they required a hike through the woods to access. After driving for about 30 minutes, we once again came upon a caravan of bathers heading into the woods in search of hot springs, so we gave up on the idea of soaking the day away in turquoise natural hot springs with views of the rolling hills of Tuscany.
Instead, we drove through the famed Val D'Orica, with its sloping wildflower covered peaks and valleys, and curvy streets lined with cypress trees, on our way to Montepulciano. We learned that cypress trees were often planted to commemorate soldiers lost in battle, so although they are identified with Tuscany and are famously beautiful, for locals, they are apparently a sign of pain and sadness. On our way, we drove down dusty one lane roads and through miles of vineyards and neon yellow fields of flowers. Outside of the cities, the driving in Tuscany is some of the best in Europe - low on traffic and big on views.
In the late afternoon, we made it to Montepulciano, a medieval and Renaissance hill town known for its Vino Nobile (widely considered one of the best wines in Italy), honey, lentils, ham, pasta and cheese. We checked in to our hotel, only to learn that what we thought was a hotel was really a homestay in a family house - and our room felt like a basement apartment where the grandma of the family used to live. While we try as much as possible to keep it simple while traveling, we didn't expect a basement apartment filled with old couches, dusty vases of fake flowers and creepy paintings on the wall. Dave even had to take a painting down because he thought it would give him nightmares. We came to refer to our place as "Grandma's basement" throughout the rest of the trip.
Since we were still a little leery of heavy Italian food from our meal in Siena, we kept it simple and enjoyed a light meal of roasted veggies, bruschetta and local wine. We wandered the streets and Dave found a secret lookout to watch the sun set over the hills in the distance - the spot also featured a friendly but seemingly ill cat who was happy to have our attention for a while. After dinner and the sunset, we explored the streets a bit more before returning to grandma's basement for a creepy night in the homestay.
Day 4: Luxury Outlets and Lucca
We woke up early with a desire to get out of our weird accommodation as quickly as possible. We were in such a rush to check out that Dave accidentally stole the key to grandma's basement, which we had to mail back to Montepulciano from our next destination. We headed out of town quickly and headed north toward Leccio. When we first visited Florence, we heard about some elusive designer outlets (think Prada, Gucci and Fendi) that were only reachable by car or a combination of a train and taxi. Nearly 15 years ago, we made the trek to these country outlets, had the first true luxury shopping experience of our lives (with Erin getting Fendi and Prada shoes, and Dave picking up a Prada shirt) and almost got lost in the country for a night, sprinting for the last train back to Florence.
This time, we heard that the outlets had gone a bit more mainstream, but we were still stunned to pull up to see a complex of a giant outdoor mall, featuring not only Italian but luxury design stores from around the world - surrounded by too many tour buses to count. Realizing we may have made a mistake, we made stops in a few stores before retiring to the Gucci cafe for a surprisingly delicious breakfast. The waitress asked Erin "would you like me to put some truffle oil on your eggs?" - so we knew we were in for a good meal.
After fueling up, we made a second attempt at shopping, waiting in line with at least 100 Chinese tourists to visit the Gucci store. Dave talked Erin out of buying some ridiculous but cool slides and we gave up and hit the road. Maybe it is the style of the times, or maybe we are just older, but the thrill of finding the luxury item at a steep discount just didn't work this time.
We continued the drive north and arrived at our final stop, the town of Lucca, known for its in-tact Renaissance era city walls, which are now lined with jogging and bike paths. We checked in to our B&B and were delighted to see that our room looked out onto Roman ruins and featured a secret door and narrow passage connecting us with the kitchen and dining area. We spent an hour or so working, and then hit the streets to check out the town.
Lucca was of significant importance in Roman times. At the Lucca Conference, in 56 BC, Julius Caesar, Pompey, and Crassus cemented their political alliance known as the First Triumvirate. Keeping this ancient history in mind, we slowly toured the lively piazzas before grabbing some foccacia, pizza and sparking waters and eating a chill lunch on the steps of the main cathedral. The sun was shining, the crowds were sparse, and we were eating some warm-from-the-oven pizza - we were happy to be in Lucca.
After an afternoon rest and work session, we headed back to the streets of town and tried to get lost until our dinner reservation at a local spot. This dinner went the same as the one in Siena - we ate local, it was delicious, and we ended up feeling not so great afterwards. Sometimes you just have to make the sacrifice - the food was spectacular - we devoured lentil soup, seafood pasta and even a local beef dish and then rolled ourselves home for the evening.
In Italy, and in all of Europe, we try to always remember the history and age of the places we visit. As Americans, we grow up in surroundings where everything is new, historically speaking, and on of our favorite parts of Europe is to be surrounded by Roman ruins, medieval castles and Renaissance artwork everywhere we go, but particularly in Italy. This one of the reasons why we keep coming back.
Day 5: Lucca to Pisa to Germany to Luxembourg
We woke up in Lucca to the smells of local apple cake baking in the kitchen on the floor below. We headed down our secret passage and feasted on an expansive breakfast spread including Italian meats and cheeses, fresh-squeezed juice, homemade bread and the aforementioned cake before hitting the road for our drive back to Pisa.
We dropped our rental car, and headed into the tiny airport, only to be greeted by one of the longest security lines we'd ever seen, stretching nearly the entire length of the airport structure. We waited in line, grumbled about the slow people around us, and wished we could just fast forward time for the next couple hours. Once we finally made it through the line, we entered the terminal, which looked like a campsite, we people spread out all over the floors and on any open surface. This was undoubtedly the time we were most grateful for our Priority Passes - we escaped the humid, overcrowded mess and chilled for the next hour, watching YouTube videos and snacking until it was time to head out. We boarded our RyanAir flight and were back in Lux by early evening.
Although the fame of Tuscany is widespread and we found it hard to escape the crowds at times throughout our trip, we still managed to find country roads and city streets where we were completely alone and able to take in the beauty of the region. Although the major cities in Italy are must-sees, checking out the smaller towns is worth the time. Next up, spring sun and doing our own version of House Hunters International in the Costa del Sol, Spain.
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