You’ve possibly pictured the scene a hundred times… sipping an espresso by the pool as the sun rises over a rural landscape, and all your favourite people slowly surfacing as the smell of coffee and freshly baked pastries creeps into the air. Checking into a luxury group villa for a week or two of sunshine, relaxation, and simply being together is what memories are made of. But a large group holiday takes careful planning, even when it doesn’t involve a special occasion or anniversary. Whether that group is made up of friends or family, what’s important is that your luxury villa satisfies everyone’s needs, from the number of bedrooms and bathrooms to proximity to an airport and how independent everyone wants to be.

Sicily’s extraordinary landscapes and history, delicious food and wine, and fabulous beaches make the island an ideal choice for a special occasion or group getaway. Warm sunshine from April to October is a bonus, and with Wish Sicily, you’ll find villas to suit all opinions, with a whole range of indulgent add-on experiences and activities.

Style, charm and tradition in southeast Sicily

Rocca di Pietra is a 6-bedroom property combining 5-star comfort with traditional Sicilian charm. The lovingly restored rural home in southeast Sicily features family heirlooms, rustic stone walls and Caltagirone ceramics, while outside, Hered terraces and a canopied lounge look out over a stunning infinity pool and the countryside beyond. Independent access to each of the six bedrooms allows that extra touch of privacy; step inside, and you’ll find loZy beamed ceilings, contemporary art and modern bathrooms. At the end of the day, dine out at a selection of local restaurants or book a private chef to whip up a Sicilian feast for you to see.

Five-star comfort on your own rural estate

When it comes to dream locations, the cluster of converted farmhouses on the Le Case di Tindari estate (sleeps 21) in northeast Sicily is hard to beat. Heart-stopping views, vast enjoyment al fresco, with views across the patchwork of olive groves and green fields towards the amounts of space, and an extraordinary attention to detail inside and out make this a very special place.

Comprising a stylish main villa and six cottages, all beautifully furnished with exquisite ceramics and antique furniture and set amongst 30 hectares of olive and oak trees, the accommodation is perfect for groups seeking a countryside luxury villa rental with individual properties. At the heart of the complex is a superb 18m shared infinity pool with striking views over the coast and the Sanctuary of Tindari.

The long sandy beaches of the Tyrrhenian coast are close by, with the raw beauty of the Nebrodi mountains forming a backdrop to the luxury holiday villas. As a result, there’s spectacular hiking at your fingertips, but the Nebrodi Nature Reserve’s small hilltop villages are also part of the experience, providing an insight into the rich gastronomy characterising Sicily’s interior.

For a memorable group outing, charter your own private boat trip around the Aeolian Islands and enjoy exploring the islands at your own pace, cooling down with dips in inky hideaway bays.

Space for all on a multi-generational holiday near Modica

Multi-generational holidays can be really special, but accommodation the needs of different generations is never simple. Couples without children and grandparents may want Hme out to relax, and some families simply need some downtime. At Villa Ciaceri (sleeps 16), the accommodation allows you to do just this. Alongside the main villa, two independent self-contained annexes provide the perfect space for a quiet morning coffee or to snatch an hour to yourself to read and snooze.

PrioriHse Hme for a quiet early morning swim in the pool or a soak in the magnificent jacuzzi before the more boisterous younger members of the party appear: the garden has been cleverly designed with the pool area set slightly apart from the main house, separated by a traditional local stone courtyard, lawns and tranquil greenery filled with exotic palms and mature olive trees.

There’s certainly space at Ciaceri to simply immerse yourself in the gentle pace of the Sicilian countryside. But when you do want to step up a gear, there’s no shortage of things to do. Sandy local beaches include Marina di Ragusa, Donnalucata and Calamosche beach on the edge of the Vendicari nature reserve, while anyone in the group seeking culture and history should head straight for the real stars of the Val di Noto: Modica, with its theatrical, sculpted Duomo di San Giorgio, Ragusa, Scicli and Noto.

Pool fun and glorious gardens

Sicily’s enviable climate means that between May and September, the chances are you’ll be spending most of your time outdoors. Which perhaps explains the popularity of Villa Cecilia Trabia. This fabulous holiday home on Sicily’s north coast is just an hour from Palermo, overlooking the sea and with a RIB and rowing boat available for hire.

The accommodation (sleeps 22) is split over a main villa and three separate cottages. But it’s the lush Mediterranean garden, awash with exotic palms, ancient loquat trees and tropical flowers, that makes Villa Cecilia Trabia so special. Endless hours are spent outdoors, immersed in the fragrant scent of the garden, either in the shade of the vast furnished gazebo, or on covered terraces, patios and in the garden’s shady nooks and crannies. And when you need to cool down, there’s the remarkable pool complex: how often do you get a 20m pool, a children’s pool and a huge jacuzzi all to yourself?

But you can’t come to this part of Sicily without exploring. Pop into Trabia for local shopping and restaurants, or splash out on Michelin star dining at Mec Restaurant in Palermo and at I Pupi in Bagheria.

Booking your large group villa

So, when should you book your luxury group holiday villa? Booking the perfect villa for a large group is never simple, and if you’re restricted by specific dates or criteria, the advice is always to book as early as possible. If you’ve set your heart on staying near the coast, it’s even more important to get ahead of the crowd and snap up your dates without delay.

For more information on any of these villas, or for further inspiration, visit here.

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