Exploring Tuscany: Side Trips from Florence


Last Updated on February 24, 2024 by Grant

Florence is definitely a must-see city. In fact, of the big cities in Italy, it is our favorite. But if you really want to enjoy Italy, you must explore the smaller towns too.  Some of our favorite small towns can be found in Tuscany, not far from Florence.

Several of these towns can be enjoyed in a few hours, as a day trip from Florence. Others can easily provide several days worth of exploration and relaxation.

However you decide to plan your Italy vacation, we hope that at least one day will be spent enjoying the relaxed easiness of a small town.

(Disclaimer: When we link to places where you can buy our stuff or places we stayed, we are using special codes that earn us commissions on the sales at no additional cost to you. Please see our Review Policy  for more information.)


Perhaps the best-known small town in Tuscany is Pisa. Everyone has heard of the Leaning Tower of Pisa, right?

There is more to the Piazza dei Miracoli in Pisa than just the Leaning Tower.
There is more to the Piazza dei Miracoli in Pisa than just the Leaning Tower. Be sure to see the Duomo and the Baptistry.

What everyone may not know is that the tower is just one of several buildings in Piazza dei Miracoli. Of course, the focus for most visitors is the tower, but the cathedral and baptistry are worth a visit as well.

The plaza is almost always filled with tons of tourists, 90% of whom will be trying to do a “hold the tower up” pose, or some other variation of it. We skipped that idea and just tried to get some interesting pictures (most, unfortunately, with a few tourists in the foreground).

Holding up the Leaning Tower of Pisa
As you can see, the standard pose of trying to hold up the tower is pretty popular.

If you really want to, you can pay to take a few hundred stairs up to the top of the tower. Supposedly the tower is perfectly stable and has been reinforced so that it will not lean any further. But, I am already a bit terrified of heights, so there is no part of me that wanted to climb to the top!

On our second trip, in 2017, we had a guided tour through the piazza, including the baptistry and cathedral. We were on a group trip, so we can’t recommend a specific tour, but get one if you can. The tour guide provided a lot of additional information that we missed on our first trip.


There is not much of interest in Pisa other than the tower, but it was certainly worth the visit. In 2013, we spent a couple of hours in Pisa on the way from Riomaggiore to Florence. In 2017, we visited as a half-day trip from Florence.

The train from Florence will probably take about an hour each way. A bus will likely take a little longer (1.5 – 2 hours). Once in Pisa, allow a couple of hours to get to the plaza and explore.

One of the cool features of the baptistery in Pisa is the acoustics and every hour or so, someone comes in to sing a few notes to demonstrate what it sounds like inside. When you go, be sure to time your visit to the baptistery to hear the demonstration.
One of the cool features of the baptistery in Pisa is the acoustics and every hour or so, someone comes in to sing a few notes to demonstrate what it sounds like inside. When you go, be sure to time your visit to the baptistery to hear the demonstration.

In 2013, we walked from the train station to the plaza. In 2017, we walked from the bus station. Both will take about 20 minutes of easy walking. I am sure there are local buses or taxis if you have limited mobility.

If you have luggage with you, there is a storage room at the train station. We stored our backpacks here and it was easy to use and reasonably priced.

Pisa is definitely worth a visit, but I don’t think it needs more than about half a day, at the most.


You may or may not have heard of Cortona. You probably have heard of the book and movie, Under the Tuscan Sun. Yep, that’s Cortona.

Throughout our month in Italy, we said “This is our favorite place so far” MANY times. Our trip just kept getting better and better. Ultimately, Cortona landed at the top of our favorite cities, especially among the small towns.

The hills of Tuscany surround Cortona.
The Tuscan Hills surround Cortona.

Cortona is very small. It is upon a hilltop in southern Tuscany. It is everything you’ve ever imagined Tuscany would be.

Things to Do

There really isn’t much “to do” here. There are a few small churches and a monastery just outside of town. I think there are a couple of museums about the history of the town.

Walking the streets of Cortona.
We loved walking the narrow streets of Cortona.

We spent most of our time just wandering around. There is literally a wall around the city, so you can’t get lost here. Cortona is big enough that a map is helpful at times but small enough that it is not essential.

What is most amazing about Cortona is that you have to search to find a place that does not have an amazing view! Seriously, every corner, every peek between the buildings, offers another “oh wow” view of the countryside.

There are other towns in the distance, farmland, and towards the edge of the horizon, a lake. I can certainly understand the appeal of renting a house in Tuscany for the summer after about four seconds here!

The Bell Tower in Cortona.
The Bell Tower in Cortona.

We had dinner at Trattoria Dardano, which was delicious and reasonably priced. We absolutely loved the food in Tuscany; definitely the best we had throughout Italy.


The train from Florence will probably take about an hour and 30 minutes. It is important to note, however, that the closest train station is 3 km (nearly two miles) outside of town.

Grape vines line the hill sides of Cortona.
The Italians will truly plant grapes anywhere they can.

We did get a taxi from the train station to the hotel, one of only a handful of times we did not walk or use public transportation. A two-mile walk on winding hillside roads just did not seem like a great idea, especially since it was raining.

You could enjoy Cortona as a day trip from Florence, but spending at least one night would be much more enjoyable. Our stop here provided a great opportunity for us to slow down, relax and recharge.

We stayed at the Hotel San Luca, right at the entrance to the town with great views and a good restaurant.

Read Trip Advisor Reviews and book the hotel.


After enjoying a relaxing morning wandering the streets of Cortona, it was time to move on to Siena. Siena is one of the “bigger” small towns of Tuscany. While it certainly is not as big as Florence, it is much bigger than Cortona.

The Siena skyline

While I’m sure there are lots of other reasons to spend time in Siena, in early July, the draw is the Palio. In fact, we planned our entire month-long itinerary around being in Siena for the Palio.

The Palio

The Palio is a bareback horse race around the main piazza, Il Campo. It is run twice a year, on July 2 and August 16. If you have seen the James Bond movie Quantam of Solace, then you have seen at least a glimpse of the Palio.

A trial run for The Palio.
Riders of the Palio running a trial on the long stretch of the course.

Before the “main event,” there are six trials and many other events over several days. We arrived in town just before the first trial and stayed through the final race, a total of four nights. Without the Palio, I think that Siena would be worth a day or two, at the most.

The main square, Il Campo, where the Palio is held, is considered by some to be the best square in Italy. You should certainly spend some time in the square, Palio or not. Actually, relaxing in city squares (and people watching) is one of our favorite ways to enjoy a European town.

The bell tower in the Campo, or main square, of Siena.
The bell tower in the Campo, or main square, of Siena.

Other Things to Do

Additional must-see sights in Siena include the Duomo and Baptistry, both of which are very ornate. At some point, Siena and Florence were in a “battle” to be the “better” city. Thus, there are some fairly impressive and ornate sites that you would not generally find in a small town.

The Santa Maria della Scalla Museum had a Steve McCurry photography exhibit while we were there. He is a National Geographic photographer, so we got to see some amazing photos. You may not recognize the name, but you probably know his photo “The Afghan Girl.”

The Duomo of Siena.
The Duomo of Siena.

This exhibit was definitely an unexpected treat! Even if you can’t catch a Steve McCurry exhibit, this museum is worth a visit.


Siena is a little over an hour from Florence via direct bus or car. The train may take a little longer, as it will likely have other stops. There really is no reason to have a car in Siena, so train or bus is our suggestion.

The views of Siena from the walls of the Fortezza Medicea.
One of the best views of Siena is found by walking the walls of the Fortezza Medicea.

While the bus maybe a little faster, the train will likely be more comfortable and more scenic, especially through Tuscany. Note that the Siena train station is at the bottom of a hill, so you may want to take a local bus to the city center. It is certainly walkable, though, if you prefer to get some exercise.

While you can see the highlights of Siena as a day trip from Florence, it is a big enough city to justify spending a night or two. If you really like some of the “comforts” of a big city, but want to experience the charm of a small town, Siena is a good mid-size city.

And, if you can manage to be in town for the Palio, it will be that much better.

We stayed at the Hotel Albergo Chiusarelli, which was amazing! Great location, great food, and managed to accommodate us when we decided to add an extra night at the last-minute… Not easy to do on the day of The Palio!

Read TripAdvisor reviews and book the hotel.


Ok, so we are cheating a little here, as Assisi is not actually in Tuscany. Assisi is a neat little town in Umbria, which is just south of Tuscany. You probably already know that it was home to Saint Francis, who is most often remembered as the patron saint of animals.

The Basilica of San Francesco d’Assisi.
The Basilica of San Francesco d’Assisi was built to honor St. Francis immediately following his canonization.

The Basilica of San Francesco d’Assisi is another very pretty church. That said, it really was not super-special for us. While we certainly appreciate the beauty of the church and the life and work of St. Francis, we saw a lot of amazing churches throughout Italy, and this one was no different.

Unfortunately, we saw so many gorgeous churches and awesome views, it started losing some of the “wow factor.” I feel bad even thinking that much less writing it, but it’s true.

The Umbrian Hills from Assisi.
The Umbrian Hills from Assisi.

The city itself is very clean, the streets are easy to navigate and overall, the town is very peaceful.  Like Cortona, Assisi is situated on a hilltop with fabulous views of the Italian countryside below.

While we enjoyed Assisi, we probably would have gotten a lot more excited about the church and the city if we had visited two or three weeks earlier in our trip.


It took us about four hours and four different trains to get from Siena to Assisi. As mentioned before, train travel is not always the most efficient, but it is generally more comfortable and more scenic.

Assisi with the Umbrian hills in the distance.
Assisi with the Umbrian hills in the distance.

A direct train from Florence will likely take about 2.5 hours; add another 30 minutes, or so, if you have to change trains. From the train station, you will need to take a bus into town.

There are a few buses from Florence to Assisi, but it probably will not save you a lot of time or money. Definitely do your research, though, because transportation options can change at any time.

Bonnie waiting for the bus in Assisi.
Bonnie waiting for the bus in Assisi, ready to start the trip home.

Again, Assisi could be seen as a day trip from Florence, but an overnight stay might make it more relaxing. I certainly think seeing Assisi on the way to or from Florence is a good option. A few hours, or maybe half a day, should be ample to see the sites. Add on a bit longer if this is your one and only small town.

The Hotel Sorella Luna was very comfortable and conveniently located.

Read TripAdvisor reviews and book the hotel.

Small Town Tips

Visiting a small town is a wonderful experience, but it does take a bit more advance planning and research. Train stations are not always convenient, especially in the hill towns of Tuscany. Even the regional bus station may not be right in town.

Trenitalia automated ticket kiosk.
Grant using the train ticket kiosk. These automated kiosks are very easy to use and make train travel a breeze!

A car could be useful if you want to do a “tour” of several small towns. That said, you will likely only use it to get from one town to another, as you can typically walk everywhere once you arrive.

You likely will not find any chain hotels, such as Hilton or Marriott, in the small towns. Check out TripAdvisor for the best hotels in town and links to get the best price.

Choosing the Right Town

These are just four of the MANY amazing small towns in Tuscany.  There are plenty of other towns that we would love to visit and that would make a fabulous side trip from Florence.

There are also tons of amazing small towns in other regions of Italy, such as Varenna, Amalfi or any of the towns of the Cinque Terre. We just happen to think that Tuscany has some of the best. There is just something about the views from a hilltop, especially when combined with the amazing Tuscan wines!

An evening stroll through Cortona.
Going for an evening stroll after the rain subsided in Cortona.

So, how do you choose where to go? Honestly, just do some research and go with what feels right. Cortona was our favorite small town and would be our recommendation, hands down. That said, we have found that one person’s favorite is not always another’s.

Go with what interests you…wine-making, cheese-making, beach or lakeside, or maybe you want to do some hiking. There are tons of great options for just about any interest.

If you are in Italy for the Palio (July 2 and August 16 of each year), then we highly suggest you go to Siena for at least a couple of days. The experience of the Palio is unlike anything else. Seriously, do anything you can to be in Siena for the Palio if it is at all a possibility. Be sure to read our article on the Palio here.

Regardless of where you end up, our goal is to get you out of the big city, into a smaller town. For that is where you will find the true beauty, charm and authenticity of Italy.

Travel Resources
What do you use to find a flight?

We use Skyscanner to find deals on flights. Skyscanner has a great interface and compares tons of airlines for the best pricing and routing. That said, it does not always have every airline and some airlines will have better deals on their website. Still, Skyscanner is a great place to start.
Click here to search for a flight.

What do you use to find a hotel?

We typically stay at Hilton properties, so we use the Hilton website. You can find good Hilton Honors discounts or AAA discounts for a hotel there. We make great use of our free night certificates from our Hilton Honors American Express.
Click here to book a Hilton property.

If there are no Hilton properties available, we use TripAdvisor to read reviews and book the hotel. We find we can get the best price that way.
Click here to search for a hotel.

We recently partnered with Stay22 to add interactive maps to each of our destination posts. This will allow you to see a plethora of hotels and vacation rentals all in one responsive map of the area.

What if I need more space than I can get at a hotel?

We use Vrbo for the times when we have rented a cabin for a weekend getaway, like this cabin in Townsend, TN, or needed to rent a house for a large family vacation. We had a great experience with them in terms of refunding deposits when COVID hit and will continue to use them.
Click here to search for a vacation rental.

Who do you use for rental cars?

As a general rule, we book with Hertz for rental cars. We have had nothing but good experiences with them. Plus, we really like unlimited mileage and not worrying about crossing state lines. We have even rented from Hertz overseas in both Slovenia and Croatia.
Click here to book a rental car.

How about booking a cruise?

We have found some amazing prices for booking a cruise through Cruise Direct. We have saved a lot of money on our cruises compared to what we found elsewhere, making a last-minute Bahamas cruise even cheaper.
Click here to book a cruise.

What if I want to rent an RV?

We highly recommend Outdoorsy for RV rentals. We rented a camper van for a week to visit Rocky Mountain National Park for the elk rut and Custer State Park for the Buffalo Round-Up and had a blast. The program was easy to use and we really enjoyed the freedom of having a camper van for that trip.
Click here to rent an RV.

What do you use for booking tours?

We don’t often book tours. Typically, we like to do stuff on our own. That said, there are some experiences you can’t have any other way. So, when we do want to book a tour, we always check Viator first.
Click here to book a tour.

Do you use anything to get discounts on the road?

We make extensive use of both Good Sam and AAA on the road. Good Sam is normally regarded as a discount card for RVers at campgrounds and Camping World but anyone can use the 5 cents off a gallon at the pump at both Pilot and Flying J.
Click here to get a Good Sam membership.
We have had AAA as long as we have been married and it has more than paid for itself in discounts at hotels, aside from the peace of mind of having roadside assistance. Add in paper maps and the ability to get an international driver’s license and it is more than worth it for any traveler out there.
Click here to get a AAA membership.

Some of the best sites in Italy may be in the big cities, but the charm is often found in the small towns. Here, we explore several small towns in Tuscany. Each of these towns can be visited as a day trip or a one- or two-night stay on your way to or from Florence.
Enjoy this story? Be sure to pin it on Pinterest and share it to Facebook and Twitter!

Leave a Comment

I accept the Privacy Policy