Tuscany: How to Step into a Postcard, Leave the Crowds Behind, and Gorge on Award-Winning Fragola Gelato

Two years ago, we tacked on a few days in Italy after a vacation in the South of France. Like a great appetizer, it made us hungry for more. We spent two days in Florence, two days in Sestri Levante, and one day in Milan. We left dazed from our five day tease and have dreamed of returning to Italy ever since.

Italian Summer Memories

For our return trip, we didn’t want another whirlwind tour. We wanted a deep dive, all in one place, to truly get a taste of La Dolce Vita. I researched so many destinations. Lake Como. Sicily. Capri. Venice. But Tuscany was the real dream.

Tuscan HillsAfter reading Marlena de Blasi’s the Lady in the Palazzo, I wanted the rolling hills, the markets, the wine, the food. Tuscany was calling my soul.

Druckman Family Cypress SunsetI found a gorgeous villa on Home and Away near a small spa town called Casciana Terme. The villa was located on an olive grove, with a pool that overlooked rolling fields of grapes. A small wooden playground and an in-ground trampoline was tucked in the back of the property. Once I found it, I didn’t sleep until I had confirmation that the villa was ours.

Tuscan Villa ChairThe villa was even more amazing that we could have hoped. So remote that it defeated all GPS devices, the directions involved turning onto a dirt road after a yellow hut. But inside was pure luxury. The owner, Claudia, is a lawyer in Florence with impeccable taste. Everything, from the exposed beams to the Villeroy and Boch china was gorgeous, but not so fragile that having kids there was stressful.

My sister Charlotte at Spritz O'Clock
My sister Charlotte at Spritz O’Clock

After taking a day to recover from our travels, easing into vacation thanks to a delicious meal cooked by the housekeeper, we ventured off on a series of day trips.


We biked the ramparts of Lucca, endured an epic tantrum from Sophie who was still wondering how we got so far from home, and closed with a raucous meal at Trattoria da Leo. When your meal begins with the waitress plopping down 1.5 liters of Chianti, saying, “I bring you little more than you asked for. If you drink it, you pay for it. Bon appetito,” you end up having a very, very good time. The restaurant was loud and not fussy, and the line of locals stretched around the block. Simple but delicious food. Golden tortelli lucchese, rich egg yolk pasta stuffed with meat, topped with a rich meat ragu. Pairs great with overflowing chianti!

Jack and Bella LuccaWalking through Lucca felt like getting a taste of Italian life. There were few tourists, and just before dinner, we mixed with Italian families doing what they have been doing for centuries, strolling the ramparts of this fortress town to work up an appetite.


Florence was a little over an hour away from our villa. We began our day there by catching the Mercato Centrale just before it closed. The food stalls on the ground floor of this indoor food market are studded with treasures like black truffles for 12 euros. Once the stalls closed, we headed upstairs to the newly renovated food court where every member of our 9 person party found their dream come true.

Amidst all these great foods to choose, a piano stood in the corner with a little sign, asking people to play it. Bella, made adventurous by all the tastes and smells, sat down and treated diners to an Adele song.

Florence CollageOnce again, we steered clear of Florence’s museums, still feeling like it would be more painful than inspiring to hope that any of our four kids could appreciate the beauty of Michelangelo’s David. Bella wanted to shop for purses. Jack wanted to take selfies. Juju wanted more gelato and Sophie just wanted to be carried. Next time, we promised. Next time.

So we strolled the streets, shopping and bargaining, letting Florence wash over us. We finished the day at our favorite restaurant in Florence, Trattoria Dei 13 Gobbi. Two years ago, we had our favorite Florentine steak there and our favorite Pasta al Pomodori. This return visit didn’t disappoint. I strongly recommend this delicious family-friendly trattoria to anyone who visits Florence.

Cinque Terre

Cinque TerreInstead of doing Cinque Terre by train and hiking down to the villages, we hired Diego of Fish ‘N Chill to help us discover these five gorgeous towns by sea. His boat seated 7, so he brought a smaller boat that Steve and Jack drove. The drive to Monterosso, where the boat was anchored, was long and treacherous. The last half hour was hair pin turn after hair pin turn. Steve went from road to sea effortlessly, driving around a pretty little motor boat in the Adriatic like he had lived there all his life. It was one of those “my hero” moments that you don’t often have after 15 years of marriage.

Jack Cinque TerreThe day on the water with Diego is a relaxing and stunning way to experience the Cinque Terre. Diego feeds you a delicious lunch made by his mother of foccaccia, baked vegetable studded pastries, and little spreads. He serves wine made by his parents, and at sunset, a gorgeous platter of fruit with his family’s limoncello. You’ll alternate between walking the towns and swimming in private nooks. We felt like royalty all day.

Vanessa Cinque Terre


Our villa was just 20 minutes from Pisa, and there was no way the kids were going to miss taking a selfie of themselves pretending to hold up the leaning tower. Learning the history of how the tower came to lean was a cautious tale of architectural woes. Climbing the tower was dizzying and fun.

Tower of Pisa Cherub StatueThe town of Pisa was overrun with tourists and hordes of men selling selfie sticks. After our climb up the tower and a session of selfies, we hightailed it out of Pisa and returned to the calm of our villa in the hills.


Volterra ArchVolterra and San Gimignano are two fortress hill cities 30 minutes away from each other in Northern Tuscany. Volterra happens to feature on less bus tours and has a more authentic feel. We loved Volterra so much that we returned for a second day, to wander its cobblestone streets and watch the alabaster artists as they carve sculptures. The kids were blown away by the Roman Theater ruins that were buried by garbage for centuries, and unearthed by mental hospital patients. We walked by the Palazzo dei Medici, now a high security prison, but did not score reservations to eat at the secret restaurant inside.

VolterraWe had our most memorable meal of our two week vacation in Volterra, at the Ristorante Enoteca del Duca. If I say Spaghetti Carbonara with Truffles, do I really need to say anything more? Ask to sit in the romantic back garden if you eat there. It will be a meal you will remember forever.

Casciana Terme

I list the sleepy little spa town here not as a major destination in Tuscany, but as a placeholder for an award winning gelateria and a romantic restaurant. The town was a 10 minute walk from our villa, a beautiful stroll through vineyards and olive groves. At night, in the dark with only our iPhones to light our way, it was delightfully scary for the kids.

Tuscany Walk
La Carabaccia had a gorgeous garden with tables tented in white tulle. Their menu was studded with seafood, and we returned a second night there to enjoy the heaping bowls of steaming muscles we saw every table around us enjoying. Their gnocchi was Juju’s favorite Italian dish of our vacation. And the steak topped with truffles and ribbons of lardo is something I will be dreaming of for the rest of my life.

Sophie GelatoGelateria Il Cigno sits at the edge of a small piazza, and welcomes huge crowds every night. Their strawberry gelato (FRAGOLA!) has won awards in Italy. Jack and I gave it our own award, and made it our destination for afternoon walks. Starting at 9PM, this is the place to be, as entire families congregate, everyone enjoying heaping beautiful cones of gelato.

Cooking Class in Tuscany

My brother in law, the mezza luna ninja.
My brother in law, the mezza luna ninja.

I’ll be doing an in-depth, dedicated review of Arianna and Friend’s Tuscan kitchen cooking classes, but let me add it to this long monster post, just so that you don’t miss their great services in Tuscany. Arianna is lovely, and no trip to Tuscany would be complete without doing SOMETHING with her. In addition to the cooking classes that she offers both at your villa or in cooks’ kitchens, she also offers market tours, olive oil tastings, truffle hunting, pasta factory tours, and so much more.

Jack Mezza LunaThey came to the villa, cooked with us all afternoon, showed us how to make pizza and pasta, and then served us a feast that went on late into the night. Bottom line, don’t plan a trip to Tuscany without reaching out to Arianna.



4 Responses to Tuscany: How to Step into a Postcard, Leave the Crowds Behind, and Gorge on Award-Winning Fragola Gelato

  1. That’s it. I’m done for the day. All I want to do is plan my own trip to mimic yours. What a wonderful vacation with memories to last a lifetime. Thank you for sharing all the amazing detail!

  2. Thanks for letting me step out of my office and into your vacation for a moment. What a nice getaway for me and what an amazing vacation experience for your family!

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