STAGE 1 - Chios
The fifth largest of the Greek Islands, Chios actually lies close to the Turkish coast. Its fame as an exporter of mastic gum probably isn’t relevant to your holiday but its beautiful 11th century monastery Nea Moni, a UNESCO World Heritage Site, will be.
The stunning mosaics that still remain are among the best in all of Greece.
Chios has all the Instagram-winning views you could hope for, including a picturesque medieval castle and villages, heavily decorated buildings, cosy little bays and whitewashed houses scattered down the hillside.
WHERE TO STAY: The Argentikon Luxury Suites - named one of the top 100 villas in the world - reflects the rich history of Chios. Built in the 16th century by the Genoese Argenti family, today, the mansion has just eight luxury suites, all with period furniture but the latest technology. Relax in the formal gardens - an authentic legacy of its Genoese founders - or indulge in the in-room massage and beauty treatments.
WHERE TO STAY
Argentikon Luxury Suites
Kambos, Chios Island, North Aegean Islands, Greece
STAGE 2 - Rhodes
WHERE TO STAY: The Allegory Boutique Hotel lies in the historic Knights’ Quarter and strikes a balance between modern design and the original architecture of the stone building.
Each of the six suites is named after a character from Greek mythology and combines antique furniture with cutting edge design in confident colours. This is the ultimate in chic Greece.
From Chios, sail south to Rhodes, the largest of the Dodecanese islands and a tourist mecca since the Colossus of Rhodes was destroyed by a devastating earthquake in 226BC.
That’s some impressive history, so it’s not surprising that antiquities are everywhere in Rhodes. Whether you want to marvel at sites such as the Acropolis of Lindos and the Knights’ Quarter, or tuck into moussaka at a candlelit harbourside restaurant, there’s something for everyone.
WHERE TO STAY
Allegory Boutique Hotel
Rhodes Island
STAGE 3 - Santorini
West of Rhodes, in the middle of the Aegean, you’ll find glamorous Santorini. Its soaring cliffs spoon a huge volcanic crater and create the perfect foil for those Greek sugar-cube houses that cling to the hillsides.
Santorini is actually a series of islands but all the action is on the main land mass, Thira. As a Greek island, bucket-loads of history goes without saying - check out the Minoan site of Akrotiri.
But it’s also a very forward-looking destination, with some of the area’s best accommodation and restaurants. Or just ignore everything and kick back on one of the black, volcanic beaches.
WHERE TO STAY: Esperas Santorini was named Historic Hotels of Europe’s most romantic hotel last year - and one look at its breathtaking views will show you why.
High on the rocky cliffs, in the village of Oia, the traditional island houses are actually carved into the rock, with a private terrace overlooking the volcanic sea below.
When the Greek sun gets too much, stroll down for a dip in Esperas Santorini’s swimming pool - it’s also carved out of the solid rock.
Alternatively, the Aigialos Hotel Santorini is another gorgeously romantic hotel. The 16 neoclassical houses were renovated in 2009, by master masons using local volcanic stone.
The interiors blend antiques and modern touches, while outside, they’re linked by charming cobbled pathways.
WHERE TO STAY
Aigialos Hotel Santorini
Santorini Island, Fira Town, Cyclades Islands, Greece
Esperas Santorini
Village of Oia, Santorini Island, Cyclades Islands, Greece
STAGE 4 - Crete
WHERE TO STAY: The team at the Kapsaliana Village Hotel is rightly proud of its unique heritage. The neighbouring Arkadi monastery, the most important on Crete, built an olive oil mill in 1763 and a whole community sprang up around it.
Today, Kapsaliana’s 12 original houses have been converted into a luxurious hotel, carrying on the high standards set by the monks all those years ago.
Also on Crete is the Avli Lounge Apartments, which have been home to a Venetian lord, an olive press, a soap factory and a tannery. Today, guests stay in seven distinctive suites with historic details that tell the story of the relationship between the island and its Venetian neighbours.
And the Cretan treasures don’t stop there. Another delightful place to stay is the Kalimera Archanes, a cluster of three traditional houses dating back to the early 19th century.
If you want to experience real Cretan design - and hospitality - this is the hotel for you.
Head south now, to the largest Greek island, Crete, with a 1,000km long coastline harbouring coves and beaches galore.
Yes, there are sandy beaches but there’s so much more to Crete, from bustling urban restaurants to sleepy mountain villages, ancient Minoan ruins to hiking routes worth a few blisters. Its geographic position - between Africa, Europe and Asia Minor - led to a long and tumultuous history for the island, much of which is still evident today.
Medieval towns such as Réthymno and Haniá show the Venetian and Ottoman influences on Crete’s history - and don’t miss the Samarian Gorge. It’s busy - but worth the walk; the vertiginous walls are an impressively rugged reminder of the unstoppable forces of nature. WHERE TO STAY
Kapsaliana Village
Kapsaliana Village, Arkadi Rethymnon, Crete Island, Greece
Avli Lounge Apartments
Rethymnon Old City, West Crete, Crete Island, Greece
Kalimera Archanes
Archanes Village, Heraklion Area, Crete Island, Greece
STAGE 5 - Hydra
Further north and just off the mainland, Hydra is a complete contrast to bustling Crete. The small island is blissfully free from motor vehicles, so it will be a mule clip-clopping your luggage around on the marble pavements.
Hollywood discovered the island in the late 1950s, revealing its beauty to the world in A Girl in Black and Sophia Loren picture, Boy on a Dolphin. But even before the resulting celebrity attention, Hydra was a wealthy place, thanks to its sea-faring success.
Also unlike Crete, there are no hugely important sites or museums here. Hydra is simply about strolling in the sun, relaxing. The perfect end to a busy holiday.
WHERE TO STAY: Cotommatae 1810 is just as small and peaceful as the island on which it sits. It’s just 200m from Hydra’s famous amphitheatre-style port and features traditional white-washed walls and charming country style decor. Its five suites and two bedrooms can be booked individually or as a whole for a larger group.
WHERE TO STAY
Cotommatae 1810
Hydra Island, Saronic Gulf Islands, Greece