Tuscany: Where Our Digital Editor Will Return Once Her Travels Resume

Eleven family members. Three generations. One idyllic Tuscan holiday.

A small hilltop town in Tuscany, Italy
Tuscan countryside at sunset
A small hilltop town.
A view of the countryside from our villa.

With our 2020 travel plans temporarily on hold, we find ourselves returning to memories of past adventures, finding joy in journeys that resonated, inspired, elevated — and that taught us something meaningful about ourselves and the wider world we share. In this new series, we revisit our best–ever trips with you, and hope you’ll do the same for us. This week, senior digital editor Kate Wells travels back to Tuscany, where she visited with three generations of family members in the summer of 2018.

enRoute Tell us why this trip in particular keeps coming back to you now — what made it so memorable?

Kate Wells My mind keeps wandering back to the landscape: gentle hills and rows of grapevines; olive trees and regal cypresses; a mix of dusty country roads and wide–open spaces. But it’s also the people I was with: My mom and stepdad, my brother and his wife, my stepsister and her husband, my stepbrother and my husband and our two young daughters. We’re self–isolating with my mom and stepdad, but we’re daydreaming of being with the whole gang, sipping Aperol spritzes by the pool at the villa or eating dinner in the streets of Mensano late into the night. We were supposed to return in August but had to cancel the trip – it will be extra meaningful when we do get to go back.

April 8, 2020
Rooftops in Florence
Rooftops in Florence.

ER How did travelling with three generations strengthen your relationships with your family?

KW Spending a week together in a rented villa meant we had a lot of opportunity for connection, those spontaneous conversations that happen over espresso in the morning or driving to the local deli on a Porchetta sandwich run – not to mention the bonding that can occur while trying to navigate the parking situation in a medieval hilltop town. Our daughters also loved getting 24/7 attention from their grandparents and aunts and uncles.

ER How did you keep 11 people happy (and not wanting to strangle each other by the end)?

KW The whole point of family travel is to create shared memories, but it’s also important to be flexible and let people do their own thing, especially when you’re dealing with different generations. We researched attractions ahead of time and talked about what activities the group wanted to do together, then we blocked off those times in the itinerary so that couples, families or smaller groups could plan around them. We also bookended the trip with group dinners – it was nice to kick off and wrap up the trip together. My husband and I really appreciated that my mom and stepdad babysat our girls so that we could spend a day in Florence, just the two of us. It felt like a mini getaway within the trip.

Tourists on the dome of Florence Cathedral
The Medici Fortress in the medieval town of Volterra
Tourists on the dome of Florence Cathedral.
The Medici Fortress in the medieval town of Volterra.

ER If you could return to Tuscany tomorrow, what’s the first thing you’d do?

KW I would spend an afternoon at Boboli Gardens, a sprawling garden behind Pitti Palace in Florence. The 16th century garden features ancient Roman sculptures (and some works from the 16th and 17th century), along with elements of traditional Italian garden design, including an amphitheatre, fountains, grottoes, citrus trees and gravel pathways flanked with cypresses. It’s all so gorgeous. You can climb the stone steps up the hill and be rewarded with a stunning view of Florence.

ER Describe your travelling style in 30 words or less.

KW Loosely scheduled. I might make a few dinner reservations, block off an afternoon to visit a gallery, but I also leave room for spontaneity – those unplanned discoveries often become the most memorable.

Grapevines at Querciabello, a biodynamic winery in Chianti
Grapevines at Querciabello, a biodynamic winery in Chianti.
Vineyards in the Chianti region, as seen from Castello di Ama
Vineyards in the Chianti region, as seen from Castello di Ama.

ER What was your favourite souvenir from this trip?

KW A bottle of 2014 Chianti Classico Riserva from Querciabella, a vegan, biodynamic winery surrounded by oak forests high in the Chianti hills. The road to get there is winding and not for the weak of stomach – but the award–winning wines and view of the surrounding valleys are worth it. My souvenir is long gone, but one sip transported me back to sunny Tuscany when we opened it back home in Toronto.

Florence and the surrounding hills
Florence and the surrounding hills.

We’d love to hear about your favourite travel memory. Just send us a photo and 50–100 words about why this trip in particular had such an impact on you — and why you can’t wait to go back.