This summer, my family took our very first trip together to Europe — and we did the flights from the U.S. to Dublin and most of the intra-Europe flights on miles!

We saw some amazing things, ate some of the most fantastic food imaginable and dipped our toes in speaking other languages. It was priceless.

You can read how we booked a trip for four to Europe on miles in this post.

Tuscan countryside view San Gimignano
Tuscany is everything we’d always dreamed … and more

So far I’ve told you about our experiences in Dublin, Paris and Bologna, Italy. Next up is beautiful Tuscany.

Note: This post contains affiliate links for which I may earn a small commission if you make a purchase after clicking through.

Since reading “Under the Tuscan Sun” by Frances Mayes many years ago, I’ve always wanted to see Tuscany and I’m sure I’m not alone. It was everything I dreamed — and more.

[convertkit form=5025289]

Driving to Tuscany

In Bologna, we rented a car through Hertz Europe at the Bologna Airport and then parked it outside the city in a paid parking lot. In many old Italian cities, there are restricted zones within the city where you cannot drive. The streets are old and narrow and generally only utility vehicles and sometimes scooters are allowed. If you drive in one of these zones you will be fined, so make sure you look into that before driving into town.

Because our vacation rentals from Vrbo in both Bologna and Tuscany were within the old town section of the cities, we opted to park outside in a parking lot (which ranged from 15 to 25 Euros a day).

The team at Hertz Europe was fantastic in getting us set up with a car with as many American comforts as possible. We are Hertz Gold, courtesy of being a Marriott Rewards member (it’s an added free perk), which affords you speedier service and upgrades.

After our time in Bologna, we headed to our homebase in Tuscany, San Gimignano, a medieval Tuscan walled hill town popular with tourists but utterly charming. It was about a two-hour drive on the Autostrada.

San Gimignano

San Gimignano Cafe View
Piazza de la Cisterna in San Gimignano

San Gimignano is in the northern section of Tuscany not far from Florence or Siena, another bigger popular medieval Tuscan town. It is a UNESCO World Heritage Site, as it’s so well preserved.

La Via Francigena, San Gimignano
La Via Francigena is an ancient pilgrimage route walked by Christians headed to Rome. It helped raise of the prominence of San Gimignano, which was right on the route.

The town itself is said to have been founded in 63 B.C. though it had inhabitants long before during the time of the mysterious Etruscans. The first historical document mentioning the town name dates to 929 A.D., and during the Middle Ages, the town came to prominence because of its position along La Via Francigena, a pilgrimage route for Christians from Canterbury to Rome.

If you’re interested in learning more about the route, I wrote in an-depth article about walking La Via Francigena as a modern traveler. I also just finished a wonderful memoir by Chandi Wyant called “Return to Glow” of her journey along the gorgeous route.

San Gimignano Church
One of the ancient towers in San Gimignano along with one of their main churches in the town

San Gimignano features 13 of the original 72 towers built by families in the Middle Ages to display their power. It truly is like walking through time to a period 1,000 years ago!

The city is enclosed in walls, but with tantalizing views of the Tuscan countryside as you wander toward the outskirts. Quaint boutiques, trattorias (casual Italian restaurants), bars (unlike American bars, Italian bars serve coffee, wine and light snacks and pastries) and churches line the streets of this easily walkable town, beckoning you in.

San Gimignano Restaurant
Possibly the most romantic restaurant in the world?

We found the most romantic restaurant in the world just outside the walls with dining in a lovely garden overlooking the countryside. We had a fantastic dinner as the sun set over Tuscany. One of my top travel moments ever!

Tourists are bused over to the town during the day, so it can get quite busy, but as soon as 5 p.m. hits, most of the tourists leave and you have a magical town in twilight to yourself and with the lively locals, many of whom sit outside on their stoops reading the paper or a book or chatting with one another.

That makes it a great reason to stay there, so you can enjoy the town by night. Of all the Tuscan towns we visited, San Gimignano was hands down my favorite, just the right size and so utterly full of charm.

Our Amazing 12th Century Vrbo Accommodations

We truly had some fantastic rentals through Vrbo on this trip. This was our first time booking vacation rentals through Vrbo (formerly HomeAway), and especially with traveling in different countries, we were nervous about what to expect. They blew us away — in a good way!

San Gimignano Vacation Rental Front View
View onto the piazza out of the front of the San Gimignano vacation rental; Credit: Vrbo

In San Gimignano, we stayed in a 12th century building right on one of the main piazzas, which is probably the most famous because it features a medieval cistern. Here is the link to the exact apartment if you want to book it yourself!

One side of the apartment looked out on the square with large shuttered windows opening right out onto all the action and the other side of the apartment looked out onto the Tuscan countryside with some of the most beautiful views you can imagine.

The apartment was HUGE by any standard and was only $260 per night. It had two bedrooms plus a loft area with two beds that the kids LOVED and with the most awesome wooden spiral stairs leading up.

There was a full eat-in kitchen with stove and refrigerator, a full dining room where we ate our share of wood-fired pizzas, a sitting room and two bathrooms.

San Gimignano Vacation Rental Loft
Our boys loved sleeping in this amazing loft area of the apartment; Credit: Vrbo

The only downside was no air conditioning, but you’d be surprised how cool Tuscany can be even when it’s 90 degrees! We closed everything up during the day to keep in the cool night air and not allow the sun to heat everything up (plus, we were out and about most of the day), and then opened everything up at night for cross-breezes and used a fan to help with air circulation as well.

There is also a washer for catching up on some laundry.

San Gimignano Vacation Rental Dining
The full dining area and charming wooden stairs going up to the loft; Credit: HomeAway

Here is the apartment on

[Want to learn Italian? Here’s how to do it quickly in 5 steps]

Other Tuscan Hill Towns

We used San Gimignano as a base to explore other Tuscan hill towns. First we drove south about two hours to Pienza and Montepulciano and spent the day exploring those two cities.

Beware when driving through Tuscany, because three out of the four of us got carsick (and we never do) driving the twisty winding roads. Plus, I think even though we had an automatic car, you can still feel every gear shift in a European car. So it’s not a terribly smooth ride. My youngest even got physically ill upon arriving in Pienza.

Here are some tips to help kids avoid car sickness.

Pienza Tuscany

Pienza is also a UNESCO World Heritage Site and has a different feel than Siena or San Gimignano. For a hill town, it’s small and relatively flat. Pope Pius II turned his hometown into the “ideal city of the Renaissance,” his version of Utopia. As a result, it has more of a Renaissance feel like Florence than the other hill towns.

Be sure to check out the Piccolomini Palace (through which are gorgeous Tuscan countryside views), the Cathedral and the lovely town square.

Pienza Tuscany
The view of the Tuscan countryside from Pienza aside an ancient cistern

Pienza is incredibly quaint with flower boxes dotting the windows and small winding streets and is also known for its Pecorino cheese. It seems the mobs of tourists have not discovered this one yet, so we found it to be relatively uncrowded.

Montepulciano Tuscany
An unfinished church in Montepulciano

We also headed to Montepulciano, which is just a few minutes away, and lovely to behold in the distance. This town is much larger than San Gimignano and VERY hilly, so be prepared to get a calf workout. Montepulciano is also apparently where the films “Twilight” and the sequel “New Moon” were filmed!

Finally, we spent a day in Siena, probably one of the more famous Tuscan towns and an ancient rival to Florence. It is large and lovely with a grand square and perhaps my favorite church of the trip, the Duomo of Santa Maria Assunta, which is shockingly different than the other Medieval and Gothic churches we came across.

It holds a number of important relics and is grand and ornate in the Romanesque style with black and white striped columns throughout the interior.

Siena Tower View Go to Travel Gal
At the top of Torre de Mangia, Siena

The Piazza del Campo is huge and fabulous though hot on a summer’s day with the sun beating down. We also enjoyed climbing the Torre de Mangia for panoramic city and countryside views.

Piazza del Campo Siena
The sprawling, beautiful, but hot, Piazza del Campo. The Torre de Mangia is behind us.

As Catholics, we also stopped by the Basilica of San Domenico to see quite an unusual relic of a very important individual in Church history, declared to be a saint: St. Catherine of Siena.

The church actually has what is said to be her head on display. Catholics believe the bodies of holy individuals to themselves be holy and worthy of reverence (not worship).

The Basilica of San Domenico in Siena, where you can see what is said to be the head of St. Catherine of Siena

The story goes that Catherine died in Rome where she was buried, but was from Siena. Siena felt she should be buried in her hometown and stealthily stole the part of her body that would be least noticed under cover of night from the Rome church. A lot of this went on in Medieval times, as important relics drew many visitors to your city.

Tuscany was absolutely delightful, and I hope to go back and explore more of the lovely towns. We did not make it to Cortona, the subject of “Under the Tuscan Sun.” Maybe next time!


Read More:


  • Lyn Mettler

    Lyn Mettler is a longtime travel writer for US News & World Report, USA Today 10Best and The TODAY Show who created Families Fly Free, a program which teaches families her simple system to use travel rewards to fly for free.

    View all posts