Birthday Wishes Come True at Tuscany’s Castello di Casole, A Belmond Hotel

Birthdays are a big deal in the Cooke family, and Rachel Cooke, along with husband Brian, made a pact with their two daughters, Ayla and Revely: On each of their 16th birthdays, they get to choose the destination for their annual family vacation. Ayla, who turned 16 in February, picked Italy (good choice, Ayla!). But according to Rachel, her eldest initially wanted to go to the Amalfi Coast. “Like many teens, our girls are really into Instagram and so they see a ton of beautiful pictures. That was definitely part of her decision,” says Rachel.

Ayla’s choice was understandable. Just hearing the region’s name conjures images of coastal roads and craggy cliffs, alfresco meals in the lemon-scented air, bougainvillea-covered villas and sunbathing next to a cerulean sea under orange-and-white-striped umbrellas. But once Rachel got down to the brass tacks of planning a trip for their active family of four with her Ciao Bambino Family Travel Advisor, Kiki, things took a turn toward Tuscany.

Tuscan Paradise Found at Castello di Casole, A Belmond Hotel

It turns out that Castello di Casole, A Belmond Hotel, delivered all the Instagram-worthy birthday beauty the Cookes wanted and more, thanks to its gorgeous hilltop location in the heart of scenic Tuscany and spectacular nightly sunsets. A restored castle and a steady sprinkling of that Belmond hospitality pixie dust added to the magical moments created and photographed this summer.

“Of course, we looked at the website and every picture is breathtaking so we kind of knew what to expect, but still, we were blown away,” Rachel says.

Rolling yellow and green hills capped with medieval villages, and undulating valleys dotted with grapevines and olive groves, shape a landscape that fills a traveler’s imagination with wonder. Even driving up the cypress-lined road into the 4,600-acre resort is a picturesque pinch-me moment.

“We spent the first part of the vacation touring Rome and Florence,” says Rachel. “But arriving in June, Italy’s big cities were beautiful and inspiring, but also hot and crowded. So by the time we got to Castello di Casole, we needed it. It was paradise.”

Refined Amenities and Relaxed Service

In line with a traditional Tuscan estate, Castello di Casole, A Belmond Hotel, consists of a medieval castle and hamlet engulfed by idyllic vineyards, hills and wooded views. The castle itself dates to the 10th century but has been modernized and refined with all the detail and indulgences discerning travelers expect from a 5-star stay. Throughout the years, Hollywood and real-life royalty have visited, as have other VIPs and families like the Cookes.

The castle and adjacent buildings house 39 rooms and suites, while 28 restored farmhouses in the surrounding countryside can be rented as private villas. All blend Italian charm and modern touches, from antique headboards and custom-made linens to upholstered velvet sofas, alabaster soap dishes and more.

But what really nurtured the Cookes’ dolce vita dreams was the chilled-out staff. “We love nice hotels, but sometimes they can feel claustrophobic if we have to feel buttoned up all the time,” said Rachel. “I loved that our girls could just be teenagers. Someone was there when we needed them, but we never felt like we had to straighten up or act a certain way.”

Ciao Bambino is a member of Belmond’s Bellini Club, a select coterie of hand-chosen luxury travel advisors who can pass on exclusive perks to their clients. Rachel took advantage of a resort credit at the spa, located in the castle’s old wine vault, complete with barrel ceilings, restored stone walls and lush valley views.

Rachel also found Champagne waiting in her room upon arrival, as well as a welcome gift with laptop stickers and postcards — a big hit with her girls, who took them home as souvenirs. Staff also left necessities like lip balm and sunscreen for excursions or sitting by the pool in the Tuscan sunshine.

The Cookes took advantage of the onsite fitness center as well. As an early riser, Rachel was thrilled to find a coffee maker in the room, and Ayla and Revely loved hanging out by the pool as well as testing out the Dyson hairdryers.

“Every little thing Castello di Casole did felt like there was thought behind it. We were pampered and taken care of, and nothing was missed,” says Rachel.

Location, Location, Location

Considering the size of the Castello di Casole estate, it would be easy to skip sightseeing altogether and spend days exploring the massive property and nearby villages. Although the resort has delicious dining options, including oven-fired pizzas, Rachel says her family appreciated the access to surrounding villages too.

They visited Mensano, just a mile from Castello di Casole, and Radicondoli, 5 miles away. Both quaint Tuscan hamlets are made for meandering and casual dining on Tuscan steaks and anything made with truffles, two items Rachel says they enjoyed often. “And of course, we ate tons of gelato too,” she adds.

For those who do want to wander farther afield, Castello de Casole is a perfect springboard for visiting other desirable Tuscan destinations. The wineries of the Chianti can be reached in a half hour. Siena is just 45 minutes east, and Florence is an hour and 15 minutes north.

The Italian coast is one hour away by car, while the popular towns of Volterra, Montalcino and San Gimignano are easily reached for morning espresso or an afternoon Aperol spritz. The small medieval village of Casole d’Elsa, the resort’s namesake, is less than 15 minutes away.

“I am really grateful that Kiki was honest with us and redirected us to Tuscany and to Castello di Casole,” says Rachel. “She really understands the rhythm of our family and found us the right balance of exploration and relaxation.”

And even though Ayla’s birthday was in February, the Cookes celebrated their newly minted 16-year-old in Italian style. “We let her have a small glass of Chianti and then roasted her,” Rachel says with a laugh.

Relevant Links:

Browse all family-friendly destinations and accommodations in Italy on Ciao Bambino

52 things to know before traveling to Italy with kids

1 to 2 weeks in Italy: How to create a family-friendly itinerary

Essential tips for a Tuscany farm stay with kids

The secret to a toddler-friendly Tuscan holiday? Ciao Bambino!

5 tips for planning a family-friendly wine tour in Italy

What to do in Florence with kids

Editor’s note: Photos courtesy of Castello di Casole, A Belmond Hotel, except where noted.