How To Plan A Dream Greek-Island Trip, According To The Experts

Soak up summer in style in the whitewashed glow of Kalesma Artemis Villa, Mykonos

From majestic landscapes and glittering seas to ancient architecture and famous hospitality, Greece never goes out of style. But where do those in the know go for a Greek-island experience like no other? KATIE BERRINGTON asks five owners of incredible Greek retreats to share their secrets

Fashion editor Millie Parry
Expect sun-drenched spaces inside and out at Istoria on Santorini

Kalia Eliopoulos, Parīlio 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. I also adore Naoussa town on Paros. It is the island’s undisputed lifestyle and nightlife hub, which bustles day and night. The 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, 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.”

Parīlio does alfresco dining in laid-back but luxurious style

Where to drink and dine

“I insist you try a Greek beer – 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, 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.”

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. 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 that hugs the cliff on the caldera between Oia and the village of Finikia. The panoramic views it offers over the island and volcano are breathtaking.

“I also 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 – 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 Parīlio on the island of Paros, and Istoria on Santorini

The best way to explore Andros is by boat, according to Allegra Pomilio

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. 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.”

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.”

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. 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
Design-led, sophisticated spaces come as standard at Kalesma Mykonos

Aby Saltiel, Kalesma Mykonos

My favorite Greek islands

“There are so many islands and each has [a] different vibe, [but] I love the Cycladic islands, of course. Mykonos is top because it provides visitors with so many choices and has the best beaches, restaurants and entertainment. Paros is a great island, too. Then I like Ios and Koufonisia, [which are] small but with the Mykonos vibes of the ’70s.”

Where to dine

“Locals love to eat on the square in Ano Mera, [where] there are great old-style restaurants. My favorite is Tsaf – the fish is amazing.”

The once-in-a-lifetime experience

“See the sunset at Kalesma – facing Delos island, there is an incredible energy [here]. And [experience] Scorpios on a Saturday.”

Aby Saltiel is co-owner of Kalesma Mykonos

The terrace at the Aristide Hotel offers the most spectacular views of the island of Syros and beyond
Chartering a boat is a great way to explore the Greek islands at your own pace

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.”

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.”

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. For drinks, I would suggest Aristide Hotel’s rooftop bar, which has an extensive Greek and Cycladic wine list.”

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 Vòra provides the perfect spot to sit and watch one of Santorini’s famously sensational sunsets

Yannis Bellonias, Vòra on Santorini

My favorite spot on Santorini

“I have so many, but my very favorite would have to be the private verandas of Vòra, 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.”