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Private cove exploring Greek islands

Luxury Greek Island Tours made for you

Luxury Greek Island holidays and private tours

Tailor-made luxury Greek Island tours

There are some 6,000 Greek Islands scattered between the Aegean and Ionian seas – 200 of them inhabited – and our travel designers have unrivalled expertise on the best of them. 

Explore crescent-shaped Santorini with its dramatic cliffs and sunset cruises and Mykonos where luxury yachts deliver you to exclusive beach clubs. Family-friendly Crete is home to the beautiful Samaria Gorge National Park and the forests of Lasithi and then peaceful Paros, with its traditional villages, kite surfing and the tiny neighbouring island of Antiparos.

Travel to off-the-beaten-path islands. Discover some of the country’s most beautiful beaches on the island of Milos and explore Folegandros with its medieval clifftop town of Chora. Then there’s Spetses, a car-free island with a handful of elegant boutique hotels.

Depending on your interests and pace, your luxury Greek Island vacation will include several destinations, often beginning in the capital city of Athens. Our travel designers will guide you to the best yacht charters between islands, and to secret swimming spots and idyllic beaches. 

Speak with our specialists who can arrange a perfect luxury Greece honeymoon, with private tastings of Santorini’s beautiful wines, or a luxury Greece family trip with hiking, swimming and cycling around Paros. We’ll recommend the best private villas and share our first-hand restaurant recommendations, so you can discover the culinary specialities of each island.

  • A tourist mother and her daughter looking at the whitewashed houses of Santorini
  • Romantic dinner for two
  • Drying octopus arms in restaurant on Santorini island, Oia village, traditional greek seafood prepared on a grill, Greece.
  • The famous Tsigrado beach with crystal clear waters and rocks. Milos Greece
  • Private Greek island tour in clear sands and turquoise waters
  • boat tour around the Greek island
  • Couple at sunset Santorini, adventure, attractive, boat, caucasian, couple, cruise, cruising, dusk, freedom, greece, happiness, happy, holiday, honeymoon, love, luxury, man, ocean, people, romantic, sail, sailboat, sailing, sea, summer, sunset, travel, trip, vacation, wealth, woman, yacht, yachting, young Romantic couple on yacht at sunset
  • Zagoria hiking in Greece for family trips
  • Temple of Isis Ruins Delos
  • Man with a pile of green olives in his hands freshly collected during the harvesting.
  • exploring Greek islands

From our experts

Experiences picked by our Greek islands specialists

Cruise Santorini at sunset

Enjoy a romantic private cruise of Santorini at sunset, sailing to the volcano and hot springs

Spend a day at Scorpios beach club on Mykonos

Spend a day at Scorpios beach club on the sun-drenched southern peninsula of the island of Mykonos

Take a rib boat to the Small Cyclades

Board a luxury rib boat from Paros to cruise the breathtaking bays and sparkling waters of the ‘Small Cyclades’

Eat at Pollonia, Milos's fishing village

Discover the culinary capital of Milos in Pollonia, a small fishing village on the island’s northeastern tip

Uncover Minoan history at Knossos Palace

Learn Crete’s fascinating history at Knossos Palace and the Archaeological Museum of Heraklion

A word from one of our experts

A Greek Island hopping tour offers the perfect mix of relaxation, cuisine, adventure and culture, all rolled into one amazing sun-drenched trip. As most of the islands are so close together, it’s easy to cruise between them.

Dan Rhodes Travel Designer

Luxury accommodation in the Greek Islands

There are many incredible places to stay in the Greek Islands. Here are some of our favourites, handpicked by our travel designers:

Why book with Jacada?

  • Personalised design

    We’ll plan your trip around your specific interests, tastes and preferences, providing helpful tips and honest advice based on first-hand knowledge of the destination.

  • Authentic experiences

    Our expert guides and brilliant travel concierges are hand-picked to provide a genuine experience, bringing your destination to life with care and passion.

  • Responsible travel

    Our luxury trips are designed with responsible travel principles that prioritise travel experiences that are both good for you and good for the planet.

Greek Islands trip inspiration

Get inspired with our Greek Island example trips and then get in touch to plan your own adventure

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Luxury Greece Highlights

Embark on a luxurious 12-day journey through Greece, visiting Athens, Crete and Santorini. In Athens, explore the Acropolis and Plaka with a private guide and…

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A Luxury Honeymoon to Greece

Discover beautiful beaches, romantic islands and ancient architecture on a luxurious ten-day honeymoon in Greece. There are few sights more idyllic than the ev…

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Family Adventure to Greece

Greece is a wonderful destination for families and we’ve handpicked our favourite experiences that will surprise and delight everyone from kids to grandparents…

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Adventurous Greece

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Ready to plan your adventure?

Whatever you want from your Greek Islands tour, our team of expert travel designers are ready to help.

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Where to go in the Greek Islands

Meet your Europe team

When to visit the Greek Islands

For fewer crowds, visit Greece in late spring (April and May) or early autumn (October and November). These shoulder months offer pleasant temperatures and far quieter islands than peak summer, letting you explore at a more relaxed pace with comfortable weather. That said, July and August have their appeal if you enjoy the buzz. Summer brings Greece’s liveliest festivals – from the August Moon Festival to vibrant Panigiria (or Panegyria) celebrations honouring local saints. During these busier months, we’d recommend choosing a quieter island like Folegandros, or the northern northern islands of Samothrace and Thassos, to escape the heaviest tourist traffic.

Hiking and cycling

April–May, October–November

A beach break

June–September

Festivities

March–April (Easter)

When Is the Best Time to Visit Greece?

Travel guides

Plan your trip to the Greek Islands

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Don't take our word for it

“We enjoyed our first trip with Jacada…”

We enjoyed our first trip with Jacada and it surely won't be our last! Every detail and moment of our trip was perfectly planned. We were met every step of the way with courteous and knowledgeable drivers and guides. We really appreciated the local guides and the commitment they had to make every day special. Thank you Jacada for the…

Amy Schulz Trustpilot ★★★★★

“heavenly honeymoon”

My wife and I used Jacada to plan our honeymoon to French Polynesia. Working with the Jacada team was fantastic and effortless. Every question was quickly answered. Every hiccup was quickly addressed. We felt like we were in the hands of experts who are equally passionate about travel, and who were committed to helping us have the trip of a…

MJ Trustpilot ★★★★★

“Jacada Travel has been outstanding”

We enjoy traveling and we have used Jacada Travel for some wonderful trips over several years. We have never been disappointed. In 2024 we took a Safari in Botswana Africa and walked with the gorillas in Rwanda planned by Jacada and the itinerary was amazing. In 2025 we had planned a trip to Antartica ( with another company ) but…

Lisa Schrage Trustpilot ★★★★★

“Communication and organization were…”

Communication and organization were excellent. The Jacada team was helpful and genuinely interested in our experience. The guides were personable, knowledgeable, and clearly enjoy their work. Vehicles were spotless, timely, and coordinators managed our every need brilliantly. I will recommend Jacada to friends and family. The only way to travel!

Andrew Woodcock Trustpilot ★★★★★

“Iceland 8 Days”

We had a wonderful trip planned through Jacada. We enjoyed the venues and the excursions. This is a beautiful place we'd recommend to anyone who wants to go on a new adventure.

The Reynolds Trustpilot ★★★★★

Your trip, your story

We craft trips deeply personal, delightfully surprising and entirely one of a kind. Every Jacada journey begins in conversation with a travel designer, a specialist in their destination of expertise. Behind each journey is a wealth of insight, gathered over years of on-the-ground exploration.

Once you’re booked, you’ll meet your concierge. Based in the region you’re visiting, they’ll take care of all the details so your mind is at rest. They make the trip truly special – and truly yours.

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