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2 Week European Itinerary #2: Italy's Tuscan Countryside

I’ve traveled through a lot of Europe’s most popular cities, but I haven’t made it to nearly as many as I’d like. For the next few weeks, I’d like to explore some of my future wish list itineraries to some of the continent’s (ever so slightly) less popular destinations and the many reasons I feel them calling my name now that I’ve visited some of the biggest tourist draws.

Itinerary #2: Italy’s Tuscan Countryside – 2 Weeks in a Central Location like Siena Day 1: Arrival, Explore Siena Day 2: Relax Day (ex. Golf & Wine Tastings) Day 3: Assisi & Perugia Day 4: Montalcino & Montepulciano Day 5: Volterra & San Gimignano Day 6: Relax Day (Siena) Day 7: Orvieto & Civita di Bagnoregio Day 8: Cortona Day 9: Bologna Day 10: Relax Day (Siena) Day 11: Florence (pass Monteriggioni) Day 12: Cinque Terre or Pisa & Lucca* Day 13: Relax Day (Siena) Day 14: Departure

*Note: If you haven’t been to either of these options already and want to fit in everything, I recommend removing the Relax Day on Day 2 and replacing it with Pisa and Lucca. Also, you could obviously rearrange any of these days to split up your travel and relax days how you best see fit—or not relax so much and explore Rome for a day or even overnight—about a 2.5 hr drive away. The weather report is also a big factor in potentially rearranging your itinerary during your trip since you probably don’t want to explore certain sites—like the Cinque Terre—in the rain.

The Why: Who doesn’t dream of drinking wine and eating a gourmet Italian lunch under the Tuscan sun, wandering quiet cobbled lanes while taking in gorgeous medieval architecture, and driving through rolling hills of olive groves and vineyards? I’ve been to Italy—twice, in fact—but I’ve never gotten a chance to truly appreciate Tuscany. We hit the bigger sites in the area—Florence, Pisa, Lucca, and even the gorgeous Cinque Terre, but I have never visited the hill towns and small cities that make up so much of the countryside. Spending 2 weeks in a central location—I always dreamed it would be a little villa outside of Siena—would allow so much time to explore. The great thing about this trip is that it’s so flexible because you’re staying in one central location for the entire time. You will need a car, but this enables you to change your plans at a moment’s notice. I couldn’t help but add in a few of the area’s bigger draws for those who haven’t been fortunate enough to yet get to visit them: Florence, Bologna, even potentially Rome… but there is so much flexibility in this trip that they could either be removed and replaced with a small, local village or given even more time depending on your preferences.

Siena Stock Photo

Siena: The small city is filled with picturesque courtyards, colorful churches, quaint streets, several good museums, and lots of pedestrian (the city center has been traffic free since 1966). It is a perfect home base for wandering, enjoying evening strolls, restaurants, and gelato. Everything in Siena seems to focus around Il Campo, its central piazza. From there, you can walk to pretty much all of the city’s top sites or just take a seat and enjoy the atmosphere.

Assisi: The big draw in Assisi is the Basilica of Saint Francis, but the old town definitely deserves a stroll, as well. Wander the back streets, explore around the city walls, and visit the Roman Forum. The Basilica, site of Saint Francis’ remains, is covered in frescoes and worth arriving at opening to try to avoid some of the crowds. (1:30 from Siena) Perugia: Only about a 30 minute drive from Assisi, Perugia has plenty to offer with less of the tourist crush. It is much bigger than Assisi but has a historic core that is easy to explore. With galleries, historic architecture, picturesque squares, and some breathtaking churches, it’s definitely worthy of the rest of your day! (1:15 back to Siena)

Montalcino: The views from Montalcino are phenomenal; staring down at the vineyards and olive groves surrounding the city you understand why the city is so well known for its Brunello di Montalcino wine and olive oil. The city is surrounded by massive walls and contains a well-preserved castle fortress. After wandering the city, you can crisscross the countryside doing wine tastings and have lunch at one of the many vineyard enroute toward Montepulciano. (45 mins from Siena) Montepulciano: 45 mins from Montalcino, Montepulciano is famous for its Vino Nobile wine. So they’re the perfect cities to tie together in a day (as long as you drive carefully and monitor your alcohol intake!). As with most of the hill towns, you’ll encounter great views, a beautiful piazza (Piazza Grande), and some fine historic sites. (1 hour back to Siena)

View from San Gimignano, Photo Credit: Jaclyn Scotto

San Gimignano: San Gimignano is famous for its 14 towers—they can’t be missed from the surrounding countryside. It has Italy’s best preserved medieval skyline, but in its heyday, the city actually had as many as 72 towers. Be sure to get a view of this spectacular sight from a distance before entering the city. This one has been on my bucket list for a while now. While it may be extremely touristy nowadays, I still find it to be a must-see Tuscan site. (45 mins from Siena) Volterra: Volterra is a natural pairing with San Gimignano for a day trip. Only about a 40 minute drive apart, it offers some of the best views of Tuscany with less of the San Gimignano crowds and tourist feel. It oozes authenticity. Plus, it’s home to a phenomenal Etruscan museum (Museo Guarnacci) and an attractive central plaza (Piazza dei Priori). (1 hour from Siena)

Orvieto: Orvieto is known for its colorful cathedral, ceramics, and Classico wine. Unlike many of the other hill towns, it sits on a flat piece of land—a volcanic butte jutting above the landscape. Traffic free and well preserved, it’s one town in particular that I wouldn’t want to miss. Plus it has several medieval palaces—and caves! The caves can even be toured to get a glimpse of how the Etruscans once lived. Outside the city, some of the area’s famous vineyards can be visited en route to Civita di Bagnoregio. (1:30 from Siena) Civita di Bagnoregio: Only 30 minutes from Orvieto, this may be the hill town I want to visit the most out of all of them. Sitting atop a pinnacle, it is entirely surrounded by a canyon, making its skyline all the more prominent. There is only one way in and out—by footbridge—so the city is traffic free and has the feel of stepping back in time. It is extremely well preserved, not highly populated, and not overly touristy. The highlight here is simply wandering the back streets and alleyways and taking in the scene. (1:40 from Siena)

Tuscany, Photo Credit: Jaclyn Scotto

Cortona: Sometimes you just need to have a day to relax in a spot that isn’t where you’ve set up shop for your trip. Cortona seems to offer that option quite nicely. Only an hour’s drive from Siena, it just gives off that stop-and-stay-awhile vibe. Known as the location where they filmed the movie “Under the Tuscan Sun,” it is the epitome of what a hill town should be. There are walls around the entire city, and the top is capped off with the Fortezza del Girifalco. If you take the exhausting hike, you will be rewarded with some phenomenal views of the surrounding countryside. Cortona invites you to relax—take a cooking class, have a gelato in the piazza, or people watch. Also, if you have time, take a 10 minute detour to the Eremo Le Celle convent just outside the city—home to Saint Francis for several years. Peaceful and secluded, it will give you a break from the tourist crush and maybe even the chance to attend a one of a kind mass.

Bologna: Bologna has one of the largest and most well preserved historic old towns in Europe. Famous for its long porticoes and city towers, it’s worth the drive to spend a day exploring. While considered a ‘university town,’ it’s also a ‘food town,’ so bring your appetite. Be sure to spend some time on the famous—and huge—Piazza Maggiore, full of shopping, cafes, and gelato! Climb one of the towers to be rewarded with a postcard view of the city. And don’t forget to get an up-close look at some of the famous porticoes during your city wanderings. (2:15 from Siena)

View of Florence, Photo Credit: Jaclyn Scotto

Florence: Florence can be a busy, congested city full of tourists, but there is a reason it draws so many each day—it has tons of world-class sites all crammed into one compact old town. Having already been there for several days, I would still go back and could find plenty more to do. My favorite place in all of Florence wasn’t the Duomo or Michelangelo’s David in the midst of the hustle and bustle of this city but in the peaceful corners of the Boboli Gardens. It feels less like being a in a city and more like being in the middle of the Tuscan countryside. There are sculptures interspersed throughout the garden, and the views over the city are beautiful, as well. Hiking up to the top of the garden for the view is very, very worth it. However, since by now you’ve probably taken in plenty of Tuscan landscapes, there are several other awe-inspiring sites the first time visitor will not want to miss. The top site is the city’s Duomo. The colorful façade, gorgeous interior, and famous dome are the first stop on most tourist’s itineraries. Then there’s the Pitti Palace—once the home of the king of Italy—which adjoins Boboli Gardens; the often photographed Ponte Vecchio (bridge); the world-famous Ufizzi Museum; the Accademia Museum, home of Michelangelo’s David; the Bargello Museum, a fascinating old prison housing several works by Donatello and Michelangelo; and the Church of Santa Croce, the resting place of Michelangelo, Galileo, Machiavelli, and several other famous Italians. You couldn’t hope to cover half of the city’s most famous sites in a day, but any one of them are worth your time. (1:15 from Siena and right past Monteriggioni) Monteriggioni: Along your route to Florence, it is worth looking out for the small village of Monteriggioni. With perfectly preserved walls, and bastions with 14 towers, it is worth a quick stop-off to at least to catch a glimpse of its walls and skyline from afar.

Cinque Terre: The Cinque Terre is a bit harder to access than your average Italian tourist destination, but it’s worth it. I’ve been fortunate enough to visit here, and I would still go back again (and again and again). It is a place like no other. The pastel Cinque Terre (‘Five Lands’) is made up of five distinct villages: Riomaggiore, Manarola, Corniglia, Vernazza, and Monterrosso al Mare—four of which are situated on the Ligurian Sea. Cars are not permitted inside of the towns’ limits, so the best way to get in is to park above the first village (Riomaggiore) and walk the trails, take the train, and/or ride the boat connecting the villages. These colorful, terraced villages feature harbors, vineyards, beaches, plenty of seafood, and stunning views. Not to be missed: A stroll on the Via dell’Amore (the scenic path connecting Riomaggiore to Manarola), a boat ride down the coast to see the villages from the water, a hike to the famous viewpoint over Vernazza, and relaxing on the beaches of Monterrosso al Mare. (2:45 from Siena)

Pisa: The Leaning Tower of Pisa is probably one of the most recognizable sights in the world. Basically famous for leaning, it had to be partially corrected to keep it from falling over altogether, but no one has ever attempted to fully correct it; “The Tower of Pisa”–its true name–just doesn’t have the same ring to it. You’ll find the majority of tourists posing in a dramatic fashion with the tower or simply wandering around the grounds taking in the site from all angles. The complex actually consists of several buildings—a Cathedral, Baptistery, Monumental Cemetery, Opera Museum, Sinopie Museum, and of course, the Leaning Tower. Quite frankly, I wasn’t overly impressed with the tower, but it seems to be one of those sites everyone needs to see for themselves once in their lives. (1:40 from Siena) Lucca: 20 minutes from Pisa, Lucca is a small but very unique walled city. It is a pleasant place to spend an afternoon wandering, particularly along the walls which are fully intact and function more as a park than a fortification. You will find less English, i.e. less tourists, and more ‘real Italian’ here than in a lot of the rest of Tuscany. I found it to be significantly more enjoyable than overrun Pisa. (1:40 from Siena)

Relaxing: One of the things I love about this trip is its flexibility and the ability to relax as you choose. You could change up the itinerary any way you want. Whenever you feel the need to just kick back and enjoy a day staring out at the beautiful Tuscan countryside, drinking a glass of wine, or playing a round of golf, you can. If you want to linger somewhere and save a paired city for another day, you can. I don’t think I’ve ever gone on a relaxing vacation like this without some sort of a set itinerary, but I’d like to try one!

City Connections: Connecting all of these locations can be done in many different ways (there are trains and buses and tours if you plan it out right), but I recommend simply renting a car for this particular trip. It may be a little pricier, but it allows you maximum flexibility and minimum stress—not rushing to catch your connections or being on someone else’s timetable. You can stop off at a roadside vineyard or pull into a country restaurant at a moment’s notice. It’s vacationing as it should be.

This vacation sounds like the perfect opportunity to relax and enjoy plenty of Italian culture, food, wine, and architecture at your own pace. If you try a variation of this itinerary, please update me on how it goes!

A Note on Vacation Rentals: There are plenty of ways to go about finding a vacation rental that will fit your needs and budget. From HomeAway to Airbnb to FlipKey, the internet has opened an entire world of possibilities. You can find everything from a huge villa with a pool to a small studio in a city center. Just be sure to plan ahead since the best places are usually taken first during peak travel seasons.

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