Luxury Greek Island Holidays

Sun-drenched beaches, azure waters and cobbled streets lined with white-washed buildings. Greece's many rugged islands have an indescribable allure.

  • Tailor-made Greek island holidays
  • Exclusive experiences with local private guides
  • Award-winning travel experts
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Greek Island Holidays

Sit back and watch the waves lap against the shore as you tuck into delicious gyros or souvlaki, served with lashings of tzatziki and a cold beer. This is relaxed island life at its finest and it's the simplicity that we love the most.

From the rugged beauty and sleepy fishing villages of Sifnos to the luxurious private villas on Zakynthos, Greek island holidays allow you to discover each place's unique charm. These enticing islands are ideal for an early summer getaway in May and June when the temperatures are warming up but the summer crowds haven't arrived yet.

Whether you're after a tailor-made island-hopping adventure or prefer to unwind at a single hotel for a week, our specialists will ensure your trip ticks all the boxes.

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Corfu

Located in the Ionian Sea just off the northwest coast of mainland Greece, lies the Greek Island of Corfu. Synonymous with British and European travellers for decades, it's an island of contrast, with a rugged interior and shoreline littered with beautiful coves, bays and a mix of hotels, B&Bs and villas. An eclectic island, with an architectural style defined by Italian, French and British rule.

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Crete

Lying in the Aegean Sea, Crete is a mountainous island with spectacular rocky coasts, vast sandy beaches, pebble shores and pristine crystal-clear Mediterranean waters. The interior is equally stunning, with green, lush, mountainous terrain. Rich in history and culture, with impressive architecture in its towns and villages and many archaeological sites, Crete is well worth a visit.

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Mykonos

The small Greek island of Mykonos makes up part of the Cyclades island group. The Greek destination of choice for jet-setters and honeymooners, Mykonos is known for its glamorous night-life, luxurious resorts, white-washed villages and sparkling blue sea. However away from the busier beach clubs, you'll find pristine sands, secluded coves and hidden bays waiting to be explored.

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Naxos

Naxos is the largest island in the Cyclades, boasting history, culture and pristine beaches. From the soft sands found along the coastline to the hilltop villages of the island's interior, Naxos offers something for both sun worshippers and culture lovers. A wealth of local produce is grown on this unusually green island, ensuring Naxos also boasts a fantastic foodie scene.

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Milos

With its wealth of natural beauty, fine cuisine and unquestionable charm, the island of Milos is a must-visit destination on a luxury holiday to Greece.

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Paros

The picturesque island of Paros is home to spectacular sandy beaches and enchanting towns. The third largest island in the Cyclades, Paros is renowned worldwide for its beautiful marble, which helped put the island on the map. Whitewashed villages lead to the stunning coast, where the surrounding islands are scattered across the horizon.

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Santorini

Santorini is possibly the most picturesque of the Cycladic islands, famed for its spectacular sunsets, whitewashed houses, blue-domed churches and legendary romantic appeal. Beaches of multicoloured volcanic sand can be found in the south-east of the island while along the western coast calm, clear waters lap the pebble beaches.

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Zakynthos

Set just off the west coast of mainland Greece in the crystal clear Ionian Sea, Zakynthos is one of the country's most beautiful islands. Mentioned in Homer's The Iliad and The Odyssey and for many centuries it was the crossroads for numerous nations and cultures the island has a wealth of history and tradition.

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Sifnos

The rugged island of Sifnos is an outdoor lover's paradise, where spectacular scenery and breathtaking views meet picturesque whitewashed villages. This mountainous island offers fantastic hiking trails, as well as the opportunity to discover a more authentic side of Greece. Paired with delicious local cuisine, Sifnos is a true hidden gem of the Cycladic islands.

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1 - 5 of 5 Hotels
Grace Santorini, Auberge Resorts Collection

Grace Santorini, Auberge Resorts Collection

Santorini, Greece

Grace Santorini, Auberge Resorts Collection is a luxurious boutique hotel perched high on the cliffs of this volcanic island, offering spectacular views over the caldera. Located in peaceful Imerovigli, it is one of the most exclusive hotels on Santorini.

Couples Culture
Santa Marina, a Luxury Collection Resort, Mykonos

Santa Marina, a Luxury Collection Resort, Mykonos

Mykonos, Greece

Set on a private beach on the island of Mykonos in Greece is Santa Marina. With a selection of hotel rooms, suites and villas, this secluded resort offers a luxurious island retreat, ideal for both families or couples.

Beach Spa & health Villa
Naxian Collection

Naxian Collection

Agios Prokopios, Naxos, Greece

Located in western Naxos, just a short drive from Chora, Naxian Collection is a boutique hotel comprised of 16 suites and villas. Close to the beaches and sights of the island, this is an ideal base for both families and couples looking to explore Naxos.

Seven Santa Maria

Seven Santa Maria

Santa Maria, Paros, Greece

Located in the north of Paros, Seven Santa Maria is a beachfront boutique property with just seven rooms. Surrounded by fragrant gardens and with the sandy beach just a short walk away, Seven Santa Maria is a secluded and peaceful hotel.

Milos Breeze

Milos Breeze

Pollonia, Milos, Greece

Just outside the charming town of Pollonia, Milos Breeze is a boutique hotel perched on a hilltop, overlooking the beautiful bay below. This peaceful retreat offers a relaxing stay and is the ideal base from which to explore the island of Milos.

1 - 5 of 5 Hotels
1 - 4 of 4 Tour Ideas
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10 nights
Honeymoon in the Greek Islands

Honeymoon in the Greek Islands

Athens, Milos, Sifnos & Santorini

Discover the beauty and romance of the Cyclades islands on this spectacular Greece tour. Soak up the history of Athens and then go off the beaten track to admire the incredible landscapes of Milos and the rugged beauty of Sifnos. End your voyage on Greece’s most romantic island, Santorini, with breathtaking caldera views and glorious sunsets.

Couples Beach Culture

SGD $14,900 pp

CHOICE
11 nights
Epic Greek Islands

Epic Greek Islands

Athens, Milos, Sifnos & Naxos

Epic island hopping off the beaten track. Experience the unique Greek isles like never before on this luxury tour of Greece's iconic Cycladic cluster. Stunning vistas, secret hideaways, sublime cuisine, and all with pure authenticity. You'll get under the skin of local traditions, visit secluded islands and soak up the sun on paradise beaches.

Couples

SGD $10,900 pp

9 nights
Family Fun in the Greek Islands

Family Fun in the Greek Islands

Athens, Kea, Paros & Vouliagmeni

Greece is a fantastic destination for families. There's history, culture and beautiful beaches in abundance, plus plenty for children of all ages. On this touring holiday in Greece, you'll take in the spectacular scenery and ancient traditions of Sifnos and Paros, two authentic Cycladic islands, and then relax in ultimate luxury on the mainland.

Beach Culture Off the beaten track

SGD $10,100 pp

7 nights
Extraordinary Mykonos & Santorini

Extraordinary Mykonos & Santorini

Mykonos & Santorini

Immerse yourself in the glamour of these stunning islands. This itinerary boasts boutique hotels overlooking the sparkling waters of the Aegean Sea, iconic whitewashed streets and blue-domed churches, plus sun-drenched beaches and exclusive clubs. Lap it up in your private jacuzzi, dine at the best restaurants or relax on a sublime sunset cruise.

Couples Beach

SGD $11,100 pp

1 - 4 of 4 Tour Ideas
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The Best Greek Islands for…

Whether you’re after the outdoors hiking the rural landscapes or spending time with a Greek family learning about their culture and traditions all wrapped in a gorgeous homecooked meal, here’s where to go for your ideal trip.

Meet our Greece Expert

Our team of specialists are waiting to help you book your next adventure. Contact us today to start planning your tailor-made trip.

FAQs for Greek Island Holidays

  • Is Greek Island-hopping worth it?

    Definitely! It's such a great way to see all that Greece has to offer and experience the different islands’ variety of cultures and foods. Whether your interests lie in history, adventure or simply relaxing on the beach, these islands have something for everyone.

    And with our tailor-made tours, we’ll craft a Greek Island holiday that feels uniquely yours.

  • What is the most elegant island in Greece?

    We recommend Paros as the most elegant island in Greece.

    Expect traditional whitewashed hillside towns and sleepy tavernas serving the catch of the day. With plenty of white sand beaches to choose from, Paros is also a foodie-loving haven. Anti-Paros, a small island just a short boat ride away from Paros, is ideal for those who seek total peace and quiet – a rare thing in Greece during the summer months! For the best beaches, Milos has plenty to offer.  A great spot for couples, Milos is evolving into one of the Mediterranean’s most sought-after destinations.

  • Which is the prettiest and quietest Greek island?

    The prettiest and quietest Greek island has to be Sifnos. With towering mountains, crystal clear water and incredible food, this island is a must for all who are seeking complete relaxation. The breathtaking whitewashed villages are full of friendly locals who want to show travellers what their lovely island has to offer. This island is ideal for couples, as well as families, a truly hidden gem undiscovered by mass tourism.

Corinth, Greece
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Why Choose Scott Dunn for Luxury Holidays to Greece?

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Unique to you

  • We listen to your travel goals and craft unique trips that are bespoke to you.
  • We’re with you every step of your life’s travel journey, from honeymoons to family trips and beyond.

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Seamless Service
Seamless Service

  • Global offices in the UK, US, and Singapore for 24/7 seamless service.
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Carefully Curated Collection
Curated Collection

  • We’ve curated an elevated collection of accommodation, experiences, and guides.
  • Committed to fostering close global relationships to continue bringing you unique experiences.

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Luxury in Every Sense
Luxury in every sense

  • We deliver a sense of luxury that matters most to you.
  • Awarded Condé Nast Traveller’s Top Travel Specialists in the World 12 years in a row.
     
     

Call us on 212 660 0228 to start planning your holiday

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