Are you planning your dream trip to Italy? Well, no trip to Italy would be complete without exploring the Tuscan countryside. You need to add these must-see, best towns in Tuscany, Italy, to your itinerary!
This past fall, we went on a week-long road trip around the Tuscan countryside, visiting all the best towns and destinations. We explored the stunning landscapes, historic architecture, and experienced authentic Italian culture. While we loved visiting the larger cities in Italy, like Florence and Rome, it was so refreshing to get outside the city and explore the charming towns and beautiful countryside.
In this blog post about the best towns in Tuscany, you’ll not only learn about Tuscany’s must-visit destinations but the best time to visit and other must-know visiting tips. So keep reading to help you plan your bucket list trip to Italy!
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Best Towns in Tuscany Table of Contents:
When to Visit the Best Towns in Tuscany
The best time to visit Tuscany is either in the spring (April to June) or early fall (September and October). The weather tends to be moderate – dry and warm, but not the hot summer heat! The fall is the harvesting season for the grapes. Keep in mind, this is also the peak tourist season and the busiest time of year.
We visited in early November, which is the off-season for Tuscany. Many of the wineries were closed or at a limited capacity since the grapes have already been harvested. While some wineries stay open into November to expand the season, many are closed. So be sure to check all wineries and book any tours before your trip so you are not disappointed upon arrival!
Unlike many people who visit Tuscany, tasting the delicious Italian wine was not our ONLY purpose for visiting. So we actually loved visiting during the off-season because it was so peaceful and quiet!
Best Towns in Tuscany, Italy
Before we dive into the details of each town individually, we wanted to share that there are a lot of similarities between towns (while remaining to have their own unique charm). Many of the towns are not filled with endless activities “to-do” but rather meant to be enjoyed at a slower pace with lots of wandering and stopping to take photos.
That being said, almost all the towns have a church to visit, a tower to climb, a Piazza to gather, wine shop that offers tastings, and, oddly enough, a torture museum. Depending on how many towns you visit, you may not want to partake in all those activities at each one (because they do start to blend together honestly). During our visit, I (Sydney) was actually 5 months pregnant, so we sadly did not get to climb any of the towers. As they do not recommend climbing towers for pregnant ladies, even if you are in good physical shape.
Unless you have lots of time to explore Italy, specifically the Tuscan region, we recommend you choose 2 to 3 of these towns to incorporate into your itinerary. As mentioned above, we spent a month in Italy with an entire week just in the Tuscan countryside, so we had plenty of time to explore!
Montepulciano
We are starting with our favorite town in Tuscany – Montepulciano! It was made up of incredibly charming cobblestone streets and Renaissance architecture. Not only that but there were many viewpoints throughout the town with breathtaking views of the Val d’Orcia and Val di Chiana. It’s a decent-sized town, so there are plenty of streets to wander through and restaurants to enjoy a meal at.
A few sites we’d recommend seeing during your visit to Montepulciano:
- Walk Il Corso & explore the side streets
- Stop by Piazza Grande
- Climb the Torre di Pulcinella (clock tower at Palazzo Comunale)
- Soak in the views at Vaduta Panoramica Viewpoint (43°05’40.0″N 11°46’51.0″E)
- Eat pasta at Porta di Bacco (we saw them making it by hand through a kitchen window & it was delicious!)
This is a Tuscan town you CANNOT miss! If you only have time for one town during your visit, make it this one.
Pienza
Pienza was a very close 2nd on our personal rankings list for best towns in Tuscany! It’s on the smaller side but incredibly charming, with stunning views along the city walls over the Tuscan countryside. If you don’t plan to grab an espresso at a local cafe or enjoy pasta at one of the restaurants, you could probably spend about an hour here and see it all. This town definitely felt like a hidden gem of Tuscany!
A few sites we’d recommend seeing during your visit to Pienza:
- Walk along the city walls, specifically Via del Casello & Via Gozzante
- Enjoy the view of Piazza Pio II & the Pienza Cathedral from Palazzo Comunale
- Walk on Corso il Rossellino
- Watch the sunset while eating dinner or sipping on a glass of wine at Idyllium*
*We didn’t eat here because they were closed during our visit, but the views from the tables were incredible! We wished we’d been able to enjoy a sunset from this spot.
San Gimignano
San Gimignano is often called the “Town of Fine Towers” because it’s known for its striking skyline of 14 well-preserved medieval tower houses. Wealthy families in the 12th and 13th centuries originally built these towers as symbols of power and wealth. It’s incredible that many years later, there’s still a few standing, making San Gimignano so iconic!
A few sites we’d recommend seeing during your visit to San Gimignano:
- Walk along Rocca di Montestaffoli & Parco della Rocca for beautiful views
- Climb Torre Grossa
- Visit the Santa Maria Assunta Cathedral
- Taste the unique flavors & award-winning gelato at Sergio’s Gelateria Dondoli*
- Stop by the Palazzo del Popolo & Palazzo Comunale
*Honestly, we didn’t think the gelato was THAT good. We’ve had worse, but we have also had a lot better! For tips on finding the best and most authentic gelato in Italy, watch our gelato Instagram Reel!
Pisa
Pisa is home to the world-famous, Leaning Tower of Pisa! It’s definitely one of the most touristy things to do in Tuscany and maybe all of Italy. But when in Italy, you should see it at least once!
If you do want to climb the Tower of Pisa, we HIGHLY recommend getting your tickets in advance as they do sell out. The ticket office does offer combo tickets to see all the sites surrounding the tower (Cathedral, Baptistry, Camposanto, & Museum). During the time of our visit in 2024, a “Complete Visit & Tower” ticket was 27€ per person, and a “Complete Visit” ticket (no tower climb) was 11€ per person. You can always check their website for the most up-to-date pricing and ticket information.
But after visiting the Leaning Tower of Pisa and surrounding buildings, explore the town of Pisa! Once you get off those first few streets surrounding the touristy area, it gets even more charming.
A few sites we’d recommend seeing during your visit to Pisa:
- Climb the Tower of Pisa
- Walk around the Piazza del Duomo
- Visit the Cattedrale di Pisa (one of our favorite churches we went inside in all of Italy!)
- Wander Borgo Stretto & go shopping
- Stop by the Piazza dei Cavalieri
Photo Tip: Walk to the other side of the Piazza del Duomo (near the ticket office) to take photos, as there’s hardly anyone over there. Everyone is mostly lined up along the walkway (opposite side of the Piazza) right when you walk in!
Siena
Siena is a medieval hilltop city in Tuscany. Yes, we know it’s not technically a town, it’s a small city, we still wanted to include it on the list!
What sets Siena apart is its beautifully preserved historic center, which is actually a UNESCO World Heritage Site, where narrow cobblestone streets lead to the Piazza del Campo. It’s also home to the Palio di Siena, a world-famous and deeply traditional horse race that takes place twice a year (in July & August). The race dates back to medieval times, where Siena’s contrade (districts) compete.
A few sites we’d recommend seeing during your visit to Siena:
- Climb Torre del Mangia
- Explore Piazza del Campo
- Visit the Duomo di Siena (Cathedral of Santa Maria Assunta)
- Wander the streets of Via di Città, Via di Diacceto, Via Camporegio, & Via Vallepiatta
Of all the towns we visited, this was by far the most busy! That being said, we did visit on a Sunday afternoon. We visited all the other towns in the mornings/afternoons on weekdays.
Lucca
Lucca is a charming town recognized for its remarkably preserved Renaissance-era city walls that encircle the historic center. Unlike most defensive walls, Lucca’s are fully intact, and you can actually walk up on them! It’s also known for its unique oval-shaped Piazza dell’Anfiteatro, built atop the ruins of an ancient Roman amphitheater.
A few sites we’d recommend seeing during your visit to Lucca:
- Walk up along the city walls
- Climb up the Torre Guinigi
- Visit the Duomo di San Martino
- Stop by Piazza di Anfiteatro
During our visit, they were actually breaking down from Europe’s largest comic convention. So the charming vibes were a little…less charming, we’ll say. Sadly for us, many of the popular sites and areas were covered with half-set-up white canvas tents and workers actively breaking down the convention infrastructure.
Tips for Visiting the Best Towns in Tuscany
#1. Arrive early
This is especially important during peak season! If you want a more peaceful experience, wandering the charming streets and taking in the views without crowds of people, then arrive mid-morning. In almost all the towns, we arrived mid-morning and stayed until mid-afternoon. That way we could enjoy a peaceful morning but stayed until it got a little more active, which was fun for eating and shopping!
Another way to help avoid crowds is by visiting on weekdays! Weekends are naturally busier as locals will also be out exploring. But after spending a month exploring all over Italy, we learned there isn’t a true *off season* in Italy. It’s always busy, and there are always tourists! There are just *less* busy times and *more* busy times. Check out some of the crowds we experienced in larger cities (like Rome & Florence) in this video!
If you want to see more about our experience visiting these charming towns in Tuscany, check out our Tuscany Instagram highlight! Don’t forget to give us a “follow” for even more Italian content. And feel free to send us a DM on Instagram with any questions you have to help plan your trip to Italy – we’d love to help!
#2. Parking Outside the City Walls
Since these towns are charming small towns in the Tuscan countryside, you won’t be able to drive or park directly inside any of these towns. All the car parks (or parking lots, as we say in the U.S.) are located just outside the city walls. Some are a short walk, like Pienza, while others, like Siena or San Gimignano, are quite a hike to get into the hilltop towns!
There are a few parking areas you can choose from but we wanted to share where we parked for each town:
#3. Have your Camera ready!
If you’ve made it this far, you’ve gotten a glimpse at just how picturesque these towns in Tuscany are. You will want to have your camera ready to take all the photos!
While iPhones these days have pretty awesome cameras, we always recommend a “real” camera over just a phone camera. The difference in quality is incredible! For reference, all the photos you see in this blog were taken on our Canon R Mirrorless camera with the Canon RF 24-105mm Zoom Lens. It’s our go-to travel camera and worth the investment!
But, if you’re not ready for that level of camera, we’d recommend this Fujifilm X100VI point-and-shoot digital camera. We’ve recommended it to a few of our family and friends who wanted a higher quality photo than a phone but aren’t ready for a bulky, manual camera. They have all LOVED it!
Here’s a link to all our favorite travel camera gear that we use to capture our adventures all over the world!
Save this blog post about the Best Towns in Tuscany to plan your bucket list trip to Italy!
If you love visiting small towns, check out our blog post about the 8 Must-See Villages in Switzerland!
Another fantastic blog with phenomenal travel tips – gorgeous photos – and an absolutely pleasure to read!! I want to book a trip to Italy now😂😂🤍