How to select the ideal Mediterranean holiday destination based on your dream getaway

The regions of the Mediterranean may share an enviable climate and a certain romance, but within this daydream-inducing destination, there is also extraordinary cultural, historical and geographical richness. From the rolling rural beauty of Puglia on the ‘heel’ of Italy, to the myth-wreathed sparkling islands of the Ionian Sea on Greece’s west coast, each corner of the Mediterranean has its own distinct flavour.

Where to go in the Mediterranean on your next holiday

When you fantasise about your dream Mediterranean getaway, do you picture bustling local markets and bold regional flavours, or pristine golden beaches where you can escape the hubbub of everyday life? Do you see yourself sipping ouzo in a charming seaside village as the stars come out over the harbour, or are you out exploring rugged coves on a snorkelling expedition from a privately chartered boat? Whatever your fantasy, we’re confident that we can help you find the best place to go in the Mediterranean to make your dreams a reality.

Sailing holidays in the Mediterranean

The Mediterranean boasts no end of options for water-lovers, from the rugged coastline of Puglia (interspersed with soft, sandy beaches) on Italy’s mainland, to the diverse islands which pepper the sparkling waters of this region, those looking for sailing holidays in the Mediterranean are truly spoiled for choice. Some of our favourite Mediterreanean islands for sailing holidays include:

1. Sicily, Italy

This distinctive Italian island has a strong, colourful identity, entirely separate to the mainland. Alongside extraordinary gastronomy, vibrant culture and astonishing natural beauty, this large island also boasts a mesmerising coastline.

We love the Sicilian coast so much that we have designed an Experience to share it with our guests. Book a private chartered boat tour of the area surrounding the historic city of Syracuse, including the Plemmirio Nature Reserve and the adjoining island of Ortigia, which is home to a wealth of ancient Greek relics. Your private chartered boat will include everything you could want from a magical day on the water, including delicious locally prepared lunch, fresh towels and snorkelling equipment. Set sail from a The Thinking Traveller villa in Sicily, like the spectacular Isola Blu (with panoramic views across Syracuse to Mount Etna) and Ortigia (which lie on the coast of the ancient island of Ortigia itself).

Discover our luxury villas in Sicily

2. Lefkada, the Ionian Islands, Greece

The Ionian Islands are something very special indeed. Dotted off the west coast of mainland Greece, they are quite literally the stuff of legends. Ithaki is the supposed home of Homer’s ancient hero Odysseyus - although archaeologists now believe the mythological Ithaca was in fact found on the island of Lefkada. In fact, Lefkada is one of our very favourite Ionian gems. A little off the beaten track, it is an island of turquoise waters, dramatic cliffs, hidden coves, fascinating archaeology and delicious, Italian-influenced Greek cuisine.

Exploring Lefkada - as well as neighbouring islands like Meganissi - via motorboat is perhaps the finest way to take in the very best the Ionian Islands have to offer. Booking our private Lefkada motorboat Experience allows you to tour the region at your own pace, uncovering gem-like bays and beaches which are only accessible from the water, or stopping at charming waterside tavernas to sample local specialities. Boats of up to 30hp can be rented without a license, and your Local Specialist will ensure that everything you might require is on board. We can even arrange for your boat to be delivered to a mooring near your villa. Our Lefkada villa collection includes spectacular coastal properties, including Penio (which boasts an infinity pool that seems to stretch out into the Ionian Sea, and offers rocky sea access) and Madreterra (just steps from a glorious beach with sparkling waters and an enchanting sunset).

3. Valle d'Itria in Puglia, Italy

One of Puglia's most attractive regions, the central area of the Valle d'Itria is known for its vast rolling countryside, olive groves, vineyards, unique trulli and picturesque towns, including the UNESCO World Heritage Site of Alberobello. Its easy reach of the beaches of the Adriatic and the Ionian seas make it a wonderful place to explore by boat.

Our Valle d'Itria private charter Experiences embark from Monopoli and Polignano a Mare, touring spectacular coastal scenery, fascinating grottos or ideal spots for snorkelling. These voyages can be accessed from many of our villas in the Valle d'Itria, including some of the very best of Puglia's converted trulli and masserie.

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The best Mediterranean family holidays

If you think you know Corfu, think again. From the informal open-air museum which has preserved the untouched mountain village of Old Perithia on the northern slopes of Mount Pantokrator, and the fortresses of historic Corfu Town (which is a UNESCO World Heritage Site), to the natural paradise around Lake Korrison (home to tortoises, flamingos and orchids), there so is much more to the largest Ionian island than beach resorts.

With so much to do on the island, our Corfu villas are the perfect base for a Mediterranean family holiday, while our Local Specialists can recommend all manner of ‘off the beaten track’ activities. We think families staying at Iola (a sea-view, 5-bedroom villa in walking distance of Spilios beach) will particularly love exploring the secret beaches and nature havens of northern Corfu on horseback. Ask us about this exhilarating Experience.

Quiet Mediterranean holidays

If your idea of heaven is a beach all to yourself, and nothing but olive groves and lapping waves for miles around, Antipaxos will surely be your ultimate quiet Mediterranean holiday destination. In 2011, the resident population of this tiny Greek Island was just 20, and there are no shops on the island, so our Local Specialists will arrange provisions for your stay. For a true slice of relaxation, you could even arrange an in-villa cook and book a wine delivery.

We recommend two tranquil villas on Antipaxos. The romantic two-bedroom Iremia (boasting a private pool and hypnotic views) and the three-bedroom Oneiro (a truly enchanting hilltop villa at the heart of the island).

Activity holidays in the Mediterranean

Widely (yet somewhat quietly) held to be one the finest destinations in the Mediterranean, Corsica is an adventure-lover’s paradise.  If you consider yourself a skilled hiker, the 70 kilometre GR20 hiking route will challenge you, while taking your breath away (both physically and figuratively). Experienced hikers take two weeks to make this strenuous hike along Corsica’s spine, but fit explorers can certainly take on a small stretch of this naturally beautiful route. For a somewhat less demanding trek, book a walking tour of Corsica’s interior.

If you favour water-based activities, Corsica’s coast is a mecca for kite-surfers, wind-surfers and kayakers. We can arrange a watersports Experience near your Corsican villa. Charming, four-bedroom A Torra boasts beach access through its garden gate, making it the perfect villa from which to enjoy southern Corsica’s best beaches for watersports.

The Med Awaits...

Which Mediterranean holiday destination has captured your imagination? Contact The Thinking Traveller for villa recommendations and to arrange Experiences that will take you beyond the surface of these magical locations across the Mediterranean. Our Local Specialists are matchless in their knowledge of their specialist regions, so allow us to recommend secret bays to visit via motorboat, tavernas serving the finest local cuisine (which only the locals know about) and authentic experiences which will stay with you for a lifetime. Browse our Mediterranean villa collection today.