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How to plan a dream Greek-island trip, according to the experts

The heavenly pool at Parilio on the Greek island of Paros

From majestic landscapes and glittering seas to ancient architecture and famous hospitality, Greece never goes out of style for the island-hopping adventures and unparalleled relaxation it offers. But where do those in the know go for a Greek-island experience like no other? KATIE BERRINGTON asks four owners of incredible Greek retreats to share their secrets – for when it’s possible to visit again


Kalia Eliopoulos, owner of Parilio on Paros and Istoria on Santorini

My favorite spots on Paros and Santorini

“Megalochori on Santorini is my happy place – an unspoiled, traditional little village where life has changed very little throughout the years. It’s a carefree place where children can play in the streets and every neighbor is a friend. I also adore Naoussa town on Paros. It is the island’s undisputed lifestyle and nightlife hub, which bustles day and night, and attracts visitors to its many bars, tavernas and boutiques. Its small churches, fishing boats and busy main square also offer plenty to explore.”

The once-in-a-lifetime experiences

“When on Paros, take a boat trip to Despotiko, a small island that preserves all the mystery and magic of a place that’s pristine and almost impenetrable. The Delion Sanctuary of Apollo and Artemis sparkles under the Cycladic sun, surrounded by the turquoise waters, at the heart of the archipelago. What was once the gathering place for crowds of believers is now an illustration of Ancient Greek beauty.

“On Santorini, nothing can compare to endorsing the local culture and lifestyle. Explore the picturesque villages of Pyrgos and Emporio, which are off the beaten tourist trail and inhabited only by locals. Visit a winery for exceptional Assyrtiko wine and sit back at a traditional ‘kafenio’ to mingle with the community. It is an experience that will imbue you with a sense of authentic Cycladic life.”

Parilio does alfresco dining in laid-back but luxurious style

Where to drink and dine

“Most locals will tell you to try ouzo, a traditional aniseed-flavored aperitif that is very popular here. But I insist you try a Greek beer instead. Santorini is known for Yellow Donkey, a fresh ‘lagered ale’, while Paros is proud to produce 56 Isles – a ‘Wit’ with Aegean heart. As for food, well, apart from the genuine Greek salad, seafood freshly caught from the Aegean sea is best eaten raw. Just choose a seafront taverna, sit back and enjoy while listening to the soothing sound of the waves breaking beside you. My personal favorites are To Psaraki taverna on Santorini and Mario Restaurant on Paros.”

Where to shop

“When I am on Paros, I love taking a walk through the bougainvillea-flourished alleyways of Naoussa, which are filled with small boutiques (my favorites are Leto and Electric). One can find true treasures there, from handcrafted jewelry to ceramics and kaftans by Greek designers.”

Something only the locals know

“Santorini is an island that has been widely discovered, yet there are so many spots that remain known only to the locals. The most peaceful place to watch the island’s magnificent sunset and feel a true connection with nature is Profitis Ilias, a small church on the caldera between Oia and the village of Finikia. Hanging from the cliff, the panoramic views it offers over the island and volcano are breathtaking.

“I never stop discovering ancient and Byzantine ruins that are spread around Paros and make it feel like an open museum. I recently visited Marathi Marble Quarries, a place where one of the finest varieties of marble is found, and it was an unforgettable experience. Some of the world’s greatest all-time masterpieces, including Venus de Milo and Hermes, were sculpted using this Parian marble.”

Kalia Eliopoulos and her husband are the owners of Parilio, on the island of Paros, and Istoria, on Santorini

There are many hidden gems, such as this ancient cliffside church, to discover while staying at Mèlisses on the island of Andros

Allegra Pomilio, Mèlisses on Andros

My favorite spot on Andros

“I have traveled far and wide across the Greek islands and, in the end, most of my best memories lie under the water rather than above. This is why I fell in love with Greece in the first place: the sea – so full of life and wonders. Combined with my love for history and cultural heritage, I think there’s no more special place for me than the submerged harbor of Paleopoli, Andros. I love snorkeling and exploring each corner of the bay, where I see red mullets nesting under immaculate white marble columns or carved rocks protecting sea urchins.”

The once-in-a-lifetime experience

“Rent a boat and explore the island on water. It offers a completely different feel, and you’ll be amazed by how many wonderful coves there are that are completely unspoiled. For an even more authentic experience, find a local to take you round. Their knowledge of the sea is undisputed.”

Where to drink and dine

“There are many places I love, and each of them is truly unique and authentic. I fell in love with the Agia Marina tavernas, located in the most picture-perfect corner of Andros. A dip in the sea followed by a glass of cold beer and Greek salad is pure bliss. For the best lamb chops of your life, remember this name: O Kossis, a farm-to-table restaurant on the hills above Gavrio. Last but not least, if you’re looking for something truly authentic, seasonal and comforting, Katerina from Tou Josef will make you fall in love with her food.”

Where to shop

“My friend Kiki owns the most charming shop on the island – Waikiki, which sells an eclectic mix of objects, clothing and accessories from independent designers, including herself. Sotiris is the owner of To Tsoubleki, a small gem in the streets of Chora. He has all sorts of traditional ceramics, glassware and vintage finds sourced on the island. For little gourmet gifts, I like Rodozakari, which sells the island’s best herbs, dried fruits and produce.”

Something only the locals know

“The old abbot of Panachrantou monastery is a legendary cook, and his food has become well known across Greece. He once taught me how to make traditional semolina halva, step by step. Still, today, if you’re lucky and happen to visit the monastery at the right time, the priests may invite you in for a meal or coffee – the quintessence of Greek hospitality.”

Allegra Pomilio owns Mèlisses on the island of Andros

Every meal at Mèlisses is a celebration of Mediterranean produce and flavors
The terrace at the Aristide Hotel offers the most spectacular views of the island of Syros – and beyond

Oana Aristide, Aristide Hotel on Syros

My favorite spot on Syros

“One of my favorite places in the entire world is the urban beach in the old town of Vaporia – especially in the mornings. The backdrop of the neoclassical architecture is glorious and, combined with the clear water and that quiet time of day, it is something special. Sometimes, an elderly man, who whiles away the hours on the jetty, will play a wonderfully tranquil piece by Hatzidakis. That, for me, has become the epitome of a morning swim in Greece; I never want to leave.”

The once-in-a-lifetime experience

“Attend one of the many street festivals and parties that take place mostly out of season. The capital, Hermoupolis, morphs into a kind of mini Mediterranean Rio, with the streets full of dancing and singing – day and night.”

The Aristide Hotel combines old-world elegance and contemporary design

Where to drink and dine

“Greece has an extraordinarily varied cuisine, and all the islands have their own dishes and ingredients. The best way to avoid ‘generic’ Greek food is to go to restaurants or tavernas that offer local dishes. On Syros, two tavernas that serve wonderful local food are Tsipouradiko Mirsini in Hermoupolis and Dyo Tzitzikia by the beach in Kini. For drinks, I would suggest Hotel Aristide’s rooftop bar, which has an extensive Greek and Cycladic wine list, with a focus on Greek grape varieties.”

Something only the locals know

“The north of Syros is a nature reserve and is wonderful for walks to some of the secluded beaches that can only be accessed on foot or by boat. And these walks are spectacular at night as well. The clear Greek sky and a full moon are more than enough for lighting the paths, and the scenery at night is otherworldly.”

Oana Aristide runs Syros’s Aristide Hotel with her mother and sister

Each of the villas at Vora provides the perfect spot to sit and watch one of Santorini’s famously sensational sunsets

Yannis Bellonias, Vora on Santorini

My favorite spot on Santorini

“I have so many, but my very favorite would have to be the private verandas of Vora, in Imerovigli. I am biased, but the view and the feeling you get here is amazing. It is literally on the edge of the caldera, with one of the most breathtaking vantage points on the island. No matter how many times you see this view, it is always like the first time.”

The once-in-a-lifetime experience

“Stay on the beach until sunset, and watch the sun go down with the sea salt still on your skin. Order a fresh fish dish with Assyrtiko wine and have dinner on the beach.”

Vora’s heavenly setting guarantees magnificent views and total tranquillity

Where to drink and dine

“Definitely try the delicious local products that you find only here, such as the white eggplant, the fava beans, the famous volcanic wine varieties and the anhydrous small Santorini tomato. The best places to try these are local, family owned taverns that keep the tradition alive from one generation to the other, such as Bacchus taverna in Kamari – a place where Mrs Rita still cooks the tastes of our grandmothers’ cooking.”

Something only the locals know

“The great historical and archaeological background of Santorini. Large settlements were here in ancient times and, after archaeological excavations, a whole city was discovered. You can visit and see one of the oldest aqueducts in the world, a feat of ancient design. Santorini is not just about the beauty, the views and the glamour (although we do those very well) – it has a truly fascinating history if you delve deeper.”

Yannis Bellonias owns Vora, a collection of luxury villas on the island of Santorini

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