Birthdays are a big deal in the Cook family, and Rachel Cook, along with her husband, Brian, made a deal with their daughters, Ayla and Revlee: For each of their 16th birthdays, they could choose the destination for their annual family vacation. She chose Ayla, who turned 16 last February Italy (Good choice, Ayla!). But according to Rachel, her eldest son first wanted to go to the Amalfi Coast. “Like many teenagers, our girls are really into Instagram so they see a ton of beautiful pictures. This was definitely part of her decision,” says Rachel.
Ayla’s choice was understandable. Just hearing the name of the region conjures up images of coastal roads and rocky cliffs, al fresco meals in lemon-scented air, villas covered in bougainvillea and sunbathing next to the azure sea under orange-and-white-striped umbrellas. But once Rachel started planning a trip for her active family of four with Ciao Bambino family travel advisor, Kiki, things took a turn for the better. Tuscany.

Tuscan paradise is found at Castello di Casole, a Belmond hotel
It turns out that Kasauli Castle, Belmond Hotel, delivered all the Instagram-worthy Christmas beauty the Cookes wanted and more, thanks to its stunning hilltop location in the heart of scenic Tuscany and stunning nighttime sunsets. The restored castle and constant sprinkling of Belmond hospitality dust added to the magical moments created and photographed this summer.
“Of course, we looked at the website and every photo was breathtaking, so we kind of knew what to expect, but still, we were blown away,” Rachel says.
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Yellow-green hills covered with medieval villages and undulating valleys dotted with vineyards and olive groves. A landscape that fills the traveler’s imagination with wonder. Even driving down the cypress-lined road to the 4,600-acre resort is a great moment.
“We spent the first part of the vacation on tour Rome And Florence“But when we arrived in June, Italy’s big cities were beautiful and inspiring, but also hot and crowded,” says Rachel. So, by the time we got to Castello di Casoli, we needed it. “It was heaven.”

Upscale amenities and comfortable service
In keeping with a traditional Tuscan estate, Castello di Casole, A Belmond consists of a medieval castle and small village surrounded by idyllic vineyards, hills and wooded views. The castle itself dates back to the 10th century, but has been modernized and refined with all the details and amenities discerning travelers would expect from a 5-star stay. Over the years, Hollywood and real-life royalty have visited, as well as other dignitaries and families such as the Cooks.
The castle and surrounding buildings have 39 rooms and suites, while 28 renovated cottages in the surrounding countryside can be rented as private villas. They all blend Italian charm with modern touches, from antique headboards and custom-made linens to velvet upholstered sofas, alabaster soap dishes, and more.

But what really fueled Cookes’s dolce vita dreams was the laid-back staff. “We love nice hotels, but sometimes we can get claustrophobic if we have to be cramped all the time,” Rachel said. “I loved that our girls were just teenagers. There was someone there when we needed them, but we never felt like we had to straighten out or act a certain way.”
Ciao Bambino is a member of Belmond’s Bellini Club, a select group of carefully selected luxury travel advisors who can pass on exclusive privileges to their clients. Rachel took advantage of the spa credit at the spa, which is located in the castle’s old wine cellar and features barrel ceilings, restored stone walls and views of the lush valley.

Rachel also found champagne waiting for her in her room upon her arrival, as well as a welcome gift with laptop stickers and postcards – a big hit with her girls, who took them home as souvenirs. The staff also left out essentials like lip balm and sunscreen for excursions or sitting poolside in the Tuscan sun.
The Cookes took advantage of the on-site fitness center as well. Being an early riser, Rachel was thrilled to find a coffee machine in the room, and Ayla and Revelli loved spending time by the pool as well as testing out Dyson hairdryers.
“Every little thing Castello di Casoli did seemed like it had an idea behind it. We were pampered and taken care of, and we didn’t miss anything,” Rachel says.

Location, location, location
Given the size of the Castello di Casoli property, it would be easy to skip the sightseeing altogether and spend days exploring the massive property and surrounding villages. Although the resort has delicious dining options, including oven-baked pizza, Rachel says her family appreciates the access to the surrounding villages, too.
They visited Minsano, just 1 mile from Castello di Casoli, and Radicondoli, 5 miles away. Both quaint Tuscan villages are designed for casual, casual dining on Tuscan steaks and anything made with truffles, two items Rachel says they enjoyed very much. “And of course, we ate a lot of gelato, too,” she adds.

For those who want to wander further afield, Castello di Casoli is an ideal starting point for visiting other sought-after Tuscan destinations. Chianti’s wineries can be reached within half an hour. Siena is just 45 minutes east, and Florence is 1 hour and 15 minutes north.
The Italian coast is a 1-hour drive away, while the popular towns of Volterra, Montalcino and San Gimignano are easily accessible for a morning espresso or afternoon Aperol. The small medieval village of Casole d’Elsa, the resort’s namesake, is less than 15 minutes away.

“I’m really grateful that Kiki was honest with us and redirected us to Tuscany and to Castello di Casoli,” Rachel says. “She really understands our family rhythm and found the right balance for us between exploration and relaxation.”
Although Ayla’s birthday was in February, the Cooks celebrated their 16-year-old the Italian way. “We let her have a small cup of chianti and then we roasted her,” Rachel says with a laugh.
Related Links:
Browse all the family-friendly destinations and accommodations in Italy on Ciao Bambino
52 things to know before traveling to Italy with kids
1-2 weeks in Italy: How to create a family-friendly itinerary
Essential tips for a farm stay in Tuscany with kids
The secret to a kid-friendly Tuscan holiday? Ciao bambino!
5 Tips for Planning a Family-Friendly Wine Tour in Italy
What to do in Florence with children
Editor’s note: Photos courtesy of Castello di Casole, a Belmond hotel, except where noted.