Tuscany with Kids (San Gimignano, Pisa, Lucca)

Romantic hilltop towns. Medieval town squares. Vineyards as far as the eye can see. Farm-to-table restaurants. Italian wine. Pecorino cheese. Olive groves. Ahh, Tuscany. 

We just returned from a wonderful week in this paradise. We explored seven towns in seven days, ate fabulous food, and ran free in the most beautiful town squares. We visited family farms, saw saffron-picking and cheese-making in progress. We explored old fortresses and cycled along ancient city walls. We ate gelato every.single.day. The kids filled their pockets with olives, wine corks, acorns, and fall leaves. After all, it's the simple memories that are sometimes the most treasured ones.

 Enjoying the side streets of San Gimignano

Enjoying the side streets of San Gimignano

Some people shy away from bringing kids to Tuscany because they are worried there is not enough to do. To be honest, I think that is the reason we enjoyed it so much. Tuscany brings everything back to the basics. It allows you to appreciate life, food, countryside, architecture, and, most importantly, the company you keep. In Tuscany, there are no time commitments. No one is in a rush. There are no lines to wait in (except, maybe for gelato . . . and those go quickly)! There is no traffic. It was exactly what we needed, particularly after the whirlwind start to the school year. We had fabulous weather (October in Italy is gorgeous . . . and just the right temperature) and a great central location in a very small village called Ortimino. 

If I tried to fit everything we did during the week into one post, it would be far too long, so for the sake of your sanity and mine, I'm breaking down our trip into two parts. Here is how we spent our first three days (Ortimino, San Gimignano, Pisa, and Lucca): 

Day 1 - Ortimino

We chose Ortimino because of its proximity to so many great Tuscan towns (30 minutes to San Gimignano, 40 minutes to Florence, less than an hour to Siena and Pisa), but also because the home we found in Ortimino fit our family perfectly. We wanted to be in the Tuscan countryside, and this location was as picturesque as all of the images you have in your head. 

 Under the Tuscan Sun at Casa Alina in Ortimino

Under the Tuscan Sun at Casa Alina in Ortimino

We spent day one exploring our local digs and getting to know our countryside home. We paid a visit to the local bakery (the first of many), had dinner at the local pizzeria, and went on walks from our home through the forest and into the vineyards. We met our neighbors and played ladder toss in our backyard. We ventured to the local deli and picked out fine Italian meats, cheeses, pastas, pesto, olives, and wine to prepare for the week.

While Ortimino probably wouldn't make any must-visit lists, it was important for us to explore our home base for the week and get to know our surroundings.

Day 2 - San Gimignano

How do you put this place into words? 

 The drive to San Gimignano

The drive to San Gimignano

From afar, this place  is like something you've never seen before - tall stone towers rising in the distance on the top of a hill surrounded by rolling vineyards of green, yellow, and orange on every side. As you walk into the old city walls of San Gimignano, it is like walking into the set of a movie. It is almost unbelievable to imagine that San Gimignano is real. That people actually lived here hundreds of years ago. With stone towers, archways, a medieval fort, a central gathering spot around the town well (now, conveniently, a wishing well), San Gimignano is romantic, magical, and unbelievable all at once. I read something that said that in the evenings, when most of the tourists have left and the street lamps give off an amber glow, San Gimignano is even more magical. I believe it.

 The beauty of San Gimignano is all around

The beauty of San Gimignano is all around

What we did in San Gimignano

1. Had lunch at a trattoria on a quiet side street (Trattoria Chiribiri)

2. Explored Rocca di Montestaffoli (the medieval fort)

 Beautiful views and a great spot for exploring - Rocca de Montestaffoli, San Gimignano

Beautiful views and a great spot for exploring - Rocca de Montestaffoli, San Gimignano

3. Indulged in some amazing gelato (Gelateria Dondoli), and frolicked in the town square

 The first of many gelatos in Tuscany, compliments of Gelateria Dondoli

The first of many gelatos in Tuscany, compliments of Gelateria Dondoli

4. Ambled through the town to take it all in

 Ballet in the town square of San Gimignano post-gelato

Ballet in the town square of San Gimignano post-gelato

Tips for visiting San Gimignano

  • Parking just outside the city walls of San Gimignano is easy. There are at least 3 designated parking areas, so choose one and you are only a very short walk from the city walls
  • The town is small and easily walk-able. If you have a young child, a baby carrier is better than a stroller (this holds for most towns in Tuscany).
  • There are some very cool boutiques and toy stores in San Gimignano. If you have time, and the kids have patience, it is worth window-shopping. My kids discovered some very cool wooden crossbows and arrows (with suction cups at the end), which we then went back to get on our last day in Tuscany. This was their one take-home item from our trip, and it was a good one!
  • Some people climb Torre Grossa, the tallest tower in the town, for beautiful views of the countryside. Depending on the ages of your brood, it might be a better idea to head over to Rocca di Montestaffoli (the fort), which is far less touristy and also provides a lovely (and free) view from one of its towers. The climb is merely a set of 12 stone steps that my 3-year old had no trouble conquering.
 The view from Rocca de Montestaffoli - uncrowded, easy, and no cost to climb up here . . 

The view from Rocca de Montestaffoli - uncrowded, easy, and no cost to climb up here . . 

Day 3 - PISA

Our only goal in Pisa was to show the kids the Leaning Tower, and because Pisa is so close to Lucca (15 minutes by car), we paired the two for a day trip.

 Finding some great green space to play in Pisa

Finding some great green space to play in Pisa

Pisa actually surprised us, as the kids had a fabulous time running free on the lawn in front of the Piazza dei Miracoli. Remember when I mentioned that Tuscany is not about time commitments? This is what the trip was about. Finding the best places to run, play, and take it all in, with no set schedule.

What we did in Pisa

1. Took silly photos in front of the Leaning Tower of Pisa (this is required, really).

2. Sat at a cafe in front of Leaning Tower for cups of hot cocoa (and a chance to use the bathrooms).

3. Played with other kids on the lawn in front of the Piazza dei Miracoli. This would also be a great place for a picnic!

Tips for visiting Pisa

  • Parking was quite easy. We paid to park in a designated lot very close to the Leaning Tower and other sights.
  • Because Pisa has so many tourists, it also has vendors trying to sell you different types of items. This is annoying. Prepare the kids, keep them close by, and just roll with it. This is part of visiting Pia.

Day 3 - Lucca

After an hour and a half in Pisa, we were in the car bound for Lucca. We only went to Lucca because a friend of a friend had recommended that we visit it. Thank God for that friend of a friend. San Gimignano might have been our favorite town, but we had the most fun in Lucca. Why? Because this place is dynamite for an active family.

 On a bike made for 5 in Lucca

On a bike made for 5 in Lucca

I read some helpful tips on cycling the old city walls from Thrifty Travel Mama. This is the thing to do in Lucca, and the town is set up for it. As soon as we entered the old walls of the city, we found Cicli Bizzarri, rented a super-awesome 5-person bike (only mom and dad pedaled) and made our way leisurely around the defensive city walls, which were designed by Leonardo da Vinci. Lucca's walls are significant because they were never breached, unlike most cities in Tuscany. Lucca is in such a scenic location, with the mountains as a backdrop, and the whole place feels relaxed and low-key (a huge contrast from its well-known neighbor, Florence).

 A true explosion of fall in Lucca in October

A true explosion of fall in Lucca in October

The old city walls are perfect for biking, jogging, or just strolling. Because we visited in the fall, the trees were just plain showing off. There were explosions of gold and orange along the entire bike route. As we were just enjoying one another, the bike, and the passers-by (trust me, they were enjoying us, too), we stopped for lunch at San Colombano, which was just along the bike route. It offers such a great place for the kids to run, play hide and seek, and explore the defensive city walls. It also was one of the best meals we had in Italy, so "don't pass go" - head directly for this perfect lunch spot.

After a fabulous lunch, we hopped right back in the bike and came across a playground. We stopped for some playground time, finally finished our 4km loop around the city walls, returned the bike, and settled in for gelato, of course. As the day was getting late and my crew was tired, we did not explore the city of Lucca itself. So much to do, so little time!

What we did in Lucca

1. Rented a five-person mega-bike from Cicli Bizzarri, and cycled the city wall route (4km)

 Happy biker in Lucca

Happy biker in Lucca

2. Stopped for lunch at San Colombano

3. Discovered a playground just past San Colombano (inside the city walls) 

4. Indulged in gelato after returning our rental bike

Tips for visiting Lucca

  • This is the only town where we did not have to pay for parking. We found a lot about less than 1km from the city walls.
  • There are two bike rental shops right next to each other. If you are not satisfied with the options at Cicli Bizarri, check out the second one.
  • Ask for a lock for your bike if you plan to stop for lunch with the bike in tow.
  • Stay longer than we did so that you can explore inside the city walls! Here is some great advice on what to do in Lucca from Thrifty Travel Mama.

In the next post, I'll share our adventures in Siena, Florence, Pienza, and at a few farm-to-table restaurants in the countryside. Stay tuned!