We spent five days in Tuscany, staying in the town of Siena. We picked Siena as our home base because it is well connected by bus to the other hill towns in Tuscany and easy to get to from Florence. It was a good pick because we loved it here. We stayed in an apartment in the heart of Siena, so seeing the main piazza, Il Campo, or getting to the train and bus stations, were just a short walk away.
Note: This article was written in 2014 during our trip around the world. It is a recap of our experiences during this time in Tuscany. In September 2022, Tim and I returned to Tuscany, spending about 10 days here. We plan to write a lot more about Tuscany and the towns listed in this article.
Siena is considered a hill town in Tuscany, although it really feels like a small city. We loved walking through the narrow cobblestoned streets, which we did most nights to go to Il Campo. Tyler and Kara liked bringing their soccer ball to see if there were any kids interested in playing pick up soccer. They got lucky one night, playing with a family from Poland.
It was much less crowded here than in Florence, so it was a nice break from the hoards of tourists in Italy in July. We had great weather, with temperatures in the very low 80’s during the day. Almost every day, around 3 pm, no matter where we were in Tuscany, there would be a thunderstorm that would pass by. It happened so regularly that you could almost set your watch by it. Once the storm passed, the skies would be clear again and we were rain free until the next afternoon.
LEARN MORE: One Perfect Day in Siena
One afternoon we climbed the tower overlooking Il Campo and Siena. The views of Siena and the surrounding countryside are amazing.
We also visited the Duomo in Siena. This place looked wild on the inside. Tyler and Kara called it the zebra church.
We spent one afternoon visiting Arnie and Linda, friends of mine from Maryland, at the Tuscan villa they were renting. Tyler and Kara were thrilled to go swimming in their pool, and Tim and I loved talking with other adults and enjoying some great Tuscan wine.
We spent a day touring the hill town of San Gimignano. San Gimignano is one of the most popular hill towns to visit in Tuscany, partly because it is so easily connected to Florence and Siena with the public bus system.
During our final day in Tuscany, we spent a little more money, renting a car for the day. It was wonderful to have the freedom of a car, to go where we wanted to, no longer at the mercy of the unreliable SITA buses. Unfortunately, we learned that Kara gets carsick, throwing up in the parking lot just outside of Montalcino.
Montalcino is a small hill town. This town is packed with shops trying to lure people in to buy their Brunello di Montalcino wine. It was still too early for lunch (restaurants did not open until noon) but shops were open for wine tastings. My favorite part of the day was tasting various wines from the region. We bought one bottle of Montalcino wine to drink once we got to Germany.
A half an hour drive later, and with no tummy troubles from Kara, we made it to the beautiful town of Pienza. This town, which is very small, is a medieval town with all of the buildings built from stone. We walked the pedestrian streets, enjoyed the magnificent views over Tuscany, and did a little window shopping. We visited on a Monday, apparently the day of the week this little town closes up shop, so all restaurants were closed for the day.
We ended our Tuscan tour at Montepulciano. This town was the biggest of the three we visited today. It sits high on a hilltop, overlooking some of the best scenery of Tuscany. Storm clouds were rolling in and it was getting close to 3 pm, so we only had a little time before rain would be falling.
By now we were starving, so we ate lunch at a great little restaurant, with views out of town and over the countryside. We ate pizza and pasta for lunch, Tim and I had a little wine, and I will never get tired of the food in Italy.
Just as we were about to leave the restaurant, the skies opened up. Instantly the temperature dropped twenty degrees and we were stuck in a downpour. Determined not to let rain ruin our fun, we walked through Montepulciano in a torrential downpour. We took shelter once the thunder and lightning really got going, and waited out the passing storm. These afternoon rainstorms are crazy!!
This ended our day touring Tuscany by rental car. The other days we had left in Siena we spent on homeschooling, much to the delight of Tyler and Kara.
Tips on Touring the Hill Towns
Tuscany is amazing. It’s worth at least a few days on any itinerary to Italy. The hill towns are all linked by the SITA bus system, but in order to see Tuscany this way you have to have a lot of patience. On more than one occasion, the buses would show up 45 minutes late, or fail to show up at all. It was incredibly frustrating. I would recommend either renting a car or hiring a driver.
There are many other hill towns to visit and you would need at least a week in Tuscany to try to see all of them. Honestly, by the time we reached Montepulciano, they were all beginning to look the same.
My favorite part of Tuscany was driving through the countryside, past fields of sunflowers, vineyards, and farmland. Tuscany is beautiful, the wine is delicious, and this is a place we would like to return to again someday.
Update from 2022: Without a doubt, renting a car is the best way to tour Tuscany. If you don’t feel comfortable renting a car, then consider hiring a driver or taking a tour, since this will include your transportation and an experienced guide.
Tours of Tuscany
Make your travel planning easy and join one of these tours of Tuscany.
More Information for Your Trip to Italy
TUSCAN HILL TOWNS: Check out our detailed guides to Montepulciano, Pienza, Montalcino, San Gimignano, Lucca, Volterra, Arezzo, and Cortona. We also have a One Day Siena Itinerary.
FLORENCE: If you are planning your first visit to Florence, don’t miss our guide to the 10 Best Things to Do in Florence. We also have a guide about how to visit the Florence Cathedral and related sites, the best rooftop bars in Florence and the best viewpoints in Florence.
ITALY ITINERARIES: If you are just beginning to plan your Italy itinerary, take a look at our 10 Days in Italy Itinerary for four different ways to spend 10 days in Italy. We also have a detailed 10 day itinerary that includes Rome, Florence, the Cinque Terre, and Venice. For those with more time, check out our 14 day Italy itinerary, which covers the highlights of Italy.
BEST OF ITALY: In our guide to the Best Places to Visit in Italy, we list 20 beautiful destinations to consider for your next trip to Italy.
ROME: For a list of the top experiences in Rome, read our article Best Things to Do in Rome. Learn how to put these together in our 2 Day Rome Itinerary, where to eat in our Rome Restaurant Guide, how to visit the Colosseum, and where to stay in our Rome Hotel Guide. And don’t miss our guide to the Best Rooftop Bars in Rome.
We have TONS more information about Italy in our Italy Travel Guide, including Rome, Florence, Venice, Tuscany, the Dolomites, the Amalfi Coast, the Cinque Terre, and Puglia.
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Not sure if it’s because I’m on my phone but I don’t see any links to book a tour? Also, I see you recommend driving. Is that easy to drive in Italy?
There are 3 tours listed at the end of the post. It should also appear on your phone. We used the bus to get around several times in Italy and had nightmare experiences. So, we recommend driving or hiring a private driver. Driving in Italy is easy, just like driving in Europe or the USA. Cheers, Julie
Your website has been so helpful! I am wondering a few things. Currently have a plan for almost 3 full weeks in italy in may/June. Currently have siena on here for a few days because of what you have written. I love quiet towns and traveling to the ones around them. But wondering if I should cut two days to go to cinque Terre? Also where did you book/rent the car in siena? Thank you!
We loved the Cinque Terre. But it can be a hard decision, if you have to choose between Tuscan hill towns and the Cinque Terre. It depends on the experience you want…beautiful, small towns in Tuscany or the busier, colorful coastal towns of the 5Terre. We rented our car from a company that was within walking distance of the Siena train station. It was one of the major companies, like Avis or Hertz, but it’s been awhile and I can’t recall exactly which one it was. It may have been this Hertz. Cheers, Julie
First of all, your blog is so helpful and interesting! Second, I think you mentioned renting a car one day in Siena. Did you book in advance? Also, were you able to rent an automatic car?
Yes, we booked our car in advance. Most international carriers (Hertz, Avis, Budget) will let you know what type of car you are renting (manual vs automatic). But yes, you can usually rent an automatic car. Have fun! Cheers, Julie
Your pictures look amazing! I have never considered Siena as a base to explore Tuscany, so thank you for the tip. When do you think is the best time to visit it?
We had a great experience in the summer (mid-July) but it was crowded. I think the best time to visit Tuscany is May to June and September to October. If I went back to Tuscany, I would pick the fall harvest season. I think that would be an awesome experience. Cheers, Julie
I have spent 1 1/2 years in Europe, most of it in Italy. 30 years later I am about to spend 2 weeks there with the love of my life that enjoys adventure and hiking like I have never known. I stumbled across your pages. We plan to do soo many places that your family has done and it is sooo inspiring to me to read all of your incredible reviews. Your detail is wonderful and reassures me that from Rome to Capri to Sienna and finishing in Cinque Terre will not disappoint. I know neither of you at all but after reading and seeing soooooooooooo many of your families photos I feel emotionally connected. The smiles on your children’s faces tell amazing stories. Thank You for all of your passion in your postings and God Bless.
Erik & Kim, Seattle WA.
Thank you so much for the wonderful comment! I am glad we could inspire you. It sounds like you have an amazing trip ahead of you. Everywhere you are going is just so wonderful. I miss Siena the most…not the most popular destination for many people but it is a place that I just fell in love with. Have a great time in Italy and thanks again! Cheers, Julie
Wow, Tuscany is a very special place! All of Italy looks like just the place to anyone looking for spectacular scenery, at any given time. Even the pictures of the clouds rolling in were amazing! I cannot wait to visit one day. Stay safe & keep the posts coming, Leslie
I am loving the pictures and keeping up with your travels! Thank you for sharing this amazing experience!
My wife and I, a few years ago, rented an apartment in Siena right off the Campo. It was just behind the University of Seina. We had visited Siena a few times before and had rented a small villa outside of town before then. We had a car and used it to go to many of the same towns you visited. One of the best travel times we had every had. Hope to go back some day. Your blog with the pictures brought many wonderful memories. Viaggiare in sicurezza!
Looks like a a great time for all of you. Just be safe , the world is a crazy place right now… I am loving your pictures!!