Multi-Destination Stays: Your Guide to Multi-Week Holidays in Europe

Have you ever found yourself halfway through your holiday wishing you’d booked more time away? In our annual client survey, we found more than 80% of our guests experienced this ‘mid-stay melancholy’. To banish this, why not extend your trip by adding on an extra destination? Below we share the perfect destination and villa combinations for a longer stay, you don’t have to confine your trip to just one place.

Italian charm - from Sicily to Puglia

Tenuta Falconeri to Masseria Belvedere

Stylish and luxurious, drawing on the Arabic influence that can still be felt in parts of the island today, Tenuta Falconeri is a dreamy southeast property from our luxury villas in Sicily - and the perfect start to a twin-destination holiday in Italy.

From the sleek lines and classical arches of Tenuta Falconeri, the rustic beauty of Puglia’s Masseria Belvedere makes a fine contrast. The product of a painstaking and loving restoration, this masseria welcomes you with the warmth of old stone, and offers easy access to both the Torre Guaceto Nature Reserve and the stunning sight of the ‘white city’ of Ostuni.

Double trouble - from Puglia to Corfu

Palombara Piccola to Olika

If you like to experience a true mix of diverse landscapes and cultures, a multi-destination holiday between Italy and Greece could be just what you’re looking for.

Begin in the gentle, homely Palombara Piccola, one of our most exquisite luxury villas in Puglia, warm brick amid the sparkling emerald of the surrounding olive groves, between the brilliant white of Ostuni and the twinkling turquoise of the Adriatic Sea.

From here, travel to the rocky shores of Corfu - linked to Italy by its time under Venetian rule, but still recognisably Greek and undeniably its own in its architecture, culture, and soul. Here, you’ll spend your time in the laid-back setting of Olika, perched above the golden sands of Prasoudi Beach in one of our very best luxury villas in Corfu.

Skip through the Med - Sicily Island-hopping

Posidonia to Antika

Scattered across the seas to the north of Sicily lie the Aeolian Islands, emerging from the waters of the Tyrrhenian Sea like volcanic gemstones. The largest of the seven significant Aeolian Islands, Lipari is an ideal base from which to explore the entire chain, and features their best-served port. The town of Lipari itself is a pretty pastel-coloured cluster of winding streets, alive with restaurants, shops and bars in the summer months. On Lipari, you’ll find Posidonia, gazing out over the ocean, with eyes too on Lipari town’s historic castle and harbour.

Sail across the sea and on to Panarea, smallest of the inhabited Aeolian Islands. With fewer than 300 year-round residents, it’s the perfect place to find true tranquillity - and there is no accommodation on the island better to experience this than Antika, ‘where the garden meets the sea’.

Jump across the Aegean - Greek Island-hopping

Simone (Mykonos) to Enyalos (Tinos)

The ease with which travellers can go from one island to another has always made the Cyclades one of the most alluring destinations for multi-destination holidays in Europe.

The laidback ease of Simone makes the perfect base from which to explore the bright and buzzy island of Mykonos. Then, after a vibrant cosmopolitan week of fun, it’s just 30 minutes by boat to the traditional treasure trove of Tinos, where windmills and white marble dot the landscape, and the subtle stone of Enyalos rises as if from the earth itself.

Citrus (Hydra) to Cleonice (Spetses)

From the timeless elegance of Hydra, situated just over an hour by ferry from Athens, where the streets are cobbled and the use of cars is banned, to the pine-scented breeze and maritime stylings of Spetses, a multi-destination holiday to Greece offers a wide variety of experience in just the one trip. On Hydra, you will see Donkeys roaming the quaint streets - transporting goods, supplies, and even people up and down. Donkeys in Hydra are well cared for and part of the Island's iconic history and charm.

On Hydra, Citrus boasts a prime location with a pebbled beach literally on your doorstep, accessed by a gate from the villa’s private garden. On Spetses, meanwhile, Cleonice offers privacy and seclusion just a short walk from the modest but lively Spetses Town centre.

Beach to beach, sea to sea

Azalea (Skiathos) to Kolokithi Bay (Alonissos)

If you can’t get enough of translucent blue waters, golden sands and secret coves, book a pair of villas with direct sea access.

Skiathos stands out for the stunning sights of its sandy beaches, as well as its easy-access international airport, and the summer house of Azalea complements the island’s natural beauty perfectly, surrounded on all sides by glimmering green gardens.

Just across the water, you’ll find Alonissos. Ferries between these two Islands are very accessible, with 3 daily sailings and journey time between 1.5 - 2 hours. Over on Alonissos, where small seafront towns greet you with easy peace, you’ll find the striking modern gem that is Kolokithi Bay.

From buzz to blissful peace

Live like a local in a historic town or village before retiring to a country retreat or a beachfront hideaway.

Palazzo Alvear to Angheli

Back to Sicily now, where Palazzo Alvear offers both interior luxury and al fresco space in the very heart of the bustling baroque city of Noto.

Once you’ve seen and sampled all that Noto has to offer, move out to the stunning beauty of the municipality of Menfi, home to the Belice Nature Reserve, where the smell of orange blossoms adds a tang to the air as you wander the walled courtyards of Angheli.

Castello di Caprarica to Villa Elia

Castello di Caprarica dates back to the early sixteenth century, and seeing it for the first time is striking, as the imposing walls and turrets still stand. Despite the space and seclusion it offers, it’s also just an easy walk from the town centre of Tricase.

Further out, in the rambling fields and golden plains of the Puglian countryside, you’ll find Villa Elia, an extensive masseria spread out among extensive gardens, with everything from its own tennis court to a cinema and even a hammam.

Start small, grow bigger

Begin with a romantic break, than have a week of convivial fun with family and friends.

Casa Rosemary to Madreterra

With its lush landscapes, rugged cliffs, and popularity among water sport lovers, the Greek island of Lefkada is the perfect place for a multi-week holiday that begins as a couple’s getaway and ends as an adventure.

Beguiling and beautiful, Casa Rosemary offers incredible views of both the Ionian Sea and the Greek mainland, with sleek and soothing contemporary design. Madreterra, meanwhile, sits within the pine woods of the island’s northwestern coast, with generous open spaces both inside and out that make it perfect for large groups.

Ibid to Ersi

Designed for just two guests, Ibid is perfectly suited to couples seeking serenity and seclusion in Zakynthos’s almost untouched northern countryside.

On the neighbouring island of Kefalonia, Ersi, by contrast, has enough space for family and friends across its three buildings, where multicoloured flowers spill up and over the doorways and windows, almost overwhelming the eye with their natural beauty.

Architectural variations

From classic to contemporary, masserie, enjoy a combination of beautiful design and evocative traditions.

Trullo del Sale to Masseria delle Gnizze

One of the best attractions of our luxury villas is the way that many of them build on and update classical architectural styles. And multi-destination trips give you the chance to immerse yourself in the surroundings of not just one style but many.

Trullo del Sale maintains the classic style of the famous Puglian trulli, with contemporary elements blended in tastefully - a delicate mix perfectly exemplified in the age-old olive trees that line the bright white pool.

Over on Puglia’s southwestern coast, Masseria delle Gnizze brings the grace and grandeur of a Salentine masseria into the modern day.

Maistros to Adina

Over to the Greek islands of Skopelos and Zakynthos now, where two very different contemporary classics offer the chance for a multi-destination holiday with a difference.

Perched high on a cliff on Skopelos’s northeast coast sits Maistros, brainchild of French architect Marc Held, where clean lines and vaulted ceilings welcome you with light and luxury.

From the Aegean Sea to the Ionian, and the island of Zakynthos, home to the modern and stylish Adina, which offers everything from a 20m-long infinity pool to its own private beach. that’s perfect for you.