The best places to stay in the Greek islands - from backpacking to barefoot luxury

From backpacking to barefoot luxury, writer Maria Boyle retraces her fondly-remembered first Greek island-hopping trip in the Cyclades, this time with her family in tow.

One of the best summers in my early twenties was spent backpacking around the Greek islands with university friends.

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With a budget of £500 to cover travel, accommodation, food and going out, we survived on slices of Spanakopita pie (a Greek staple involving layers of crispy, flaky phyllo dough and a rich spinach and feta cheese filling), spent the days lounging on the beach, ‘dined’ on Tzatziki and crisps, and then partied the nights away.

Fast forward some 20 years, husband and daughters in tow, we decided to revisit the islands, ditching basic backpacking accommodation for some of the best places to stay on the Greek islands.

Sunset dining in SantoriniSunset dining in Santorini
Sunset dining in Santorini

First stop: Santorini. The island is the most famous of the Cyclades, known for its plunging cliffs dripping with picturesque, whitewashed houses, blue dome churches, winding paths and its incredible sunsets.

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We stayed in Oia, the most northern part of the island, and booked in to Adronis Arcadia (www.andronis.com/hotels/andronis-arcadia), which is located on the fringes of the village. The five star hotel has a contemporary design, its 53 suites each have earthy interiors and chic luxury touches (85 per cent of the furniture is hand made locally), together with outdoor seating and your own private pool.

Activity wise, visitors to the island can do a spot of wine tasting, visit the historic site of Akrotiri, ‘the Pompeii of the Aegean’, now excavated from its ashen tomb, or explore the capital Fira and take a tour of Museum Megaro Gyzi which was built in 1700s. The Museum is located in a house that belonged to a Venezian family and is one of the few that survived the earthquake on 1956.

It is well worth the three Euro entrance fee as it provides a fascinating insight in to the history of Santorini, a chance to see old documents charting life on the island and photos and newspaper cutting detailing the volcanic eruptions on the island over the last 100 years.

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Villa Flo NaxosVilla Flo Naxos
Villa Flo Naxos

Santorini’s food offering is excellent and the foodie highlight of our stay on the island was dinner at Lyacabettus Restaurant (www.lycabettusrestaurant.com). We enjoyed cocktails and mocktails in what has to be one of the best cliff top locations in the world, and then devoured an incredible menu of dishes created by chef Chris Karagiannis.

Second stop: Naxos. Naxos is the largest of the Cycladic islands, known for its stunning Venetian castle, captivating history, traditional mountain villages, immaculate sandy beaches and great food. We hired a car to explore the island and booked Villa Flo (www.travelstaytion.com/rooms/348730), located 30 minutes from Naxos Town. Chora, the capital of Naxos, was the first place we visited.

We headed to the Old Market, which is densely packed with restaurants and boutique shops tucked under archways, in tunnels, and stacked over multiple levels. We dined al fresco at Kastro, which was located just under the town’s historic monastery. The restaurant serves traditional Greek fare and seafood with a contemporary twist as well as an excellent choice of vegetarian and vegan dishes, it was a real hit with all the family.

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One of the coolest spots we went to was a café and wine bar called Avaton, located in the old Ursuline Monastery which was built 1739. It served an excellent selection of creative cocktails on its rooftop in the evenings and in the day, the building houses the Archaeological Museum of Naxos. Beaches in Naxos are Carribean like and one of the best we found was just 10 minutes from the villa called Plaka Beach.

Villa Flo NaxosVilla Flo Naxos
Villa Flo Naxos

Tortuga (www.tortuganaxos.com) beach bar and club serves an excellent lunch of fresh seafood, Naxian potatoes, guacamole with watermelon salad. All we then had to do was flop on the beach and enjoy the crystal clear waters. On our final evening, private chef Babis Tsamadias from No Reservations No Recipes (nrnr.gr) came to cook for us. We left Naxos with full stomachs and heavy hearts and all agreed we would definitely return.

Final stop - Mykonos. A short 45-minute ferry trip led us to our fourth and final stop, Mykonos, otherwise known as the island of the winds. Our base was Harmony Hotel (www.harmonyhotel.gr) a 22-room boutique hotel with a pool just located by the old port and a two-minute walk in to Mykonos Town. While the island has a reputation as the Ibiza of the Aegean, it’s also incredibly laid back.

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Mykonos Old Town is worth a visit and fun to get lost in the narrow alleyways. Retaining its historic charm, the stone windmills of Mykonos Town are a must see as is Little Venice which you will recognise from the familiar images associated with the island.

The island once again delivers on all things foodie. Kalita (kalitamykonos.com), located in a pretty courtyard in the heart of the old town, serves modern Greek cuisine that is Michelin standard.

Another day we bought a ticket (20 euros return, stops at multiple beaches) and jumped on a wooden motorised boat service run by a co-op of local fisherman’s family and stopped at a number of the island’s beaches before chilling at Platis Gialos with its crystal clear water and beach bars and cafes.

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For our last evening, we visited Bill & Coo Beef Bar https://www.bill-coo-hotel.com/beefbar-mykonos/, located on Agios Ioannis Beach under the mulberry trees. The spacious restaurant has an excellent menu (Beef Bar fans will be familiar) with added Greek inspired dishes including Tarana Tuna with yuzu, grilled fish and jumbo prawns, and the only Kobe beef gyros in the world.

As we reminisced about our epic Greek odyssey over cocktails, fireworks lit up the sky. We had enjoyed four mini holidays in one and loved every island. We just need to return to explore the other 223 inhabited islands……perhaps next year’s holiday is already sorted?