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Greek Island Hopping Itineraries

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The Aegean Sea holds a wealth of treasures. Enjoy serene beaches that look out upon azure waters, an ancient history that harkens back to the roots of Western Civilization, and unforgettable cuisine full of tantalizing flavors. From the most popular destinations to lesser-known gems, an island-hopping itinerary from Zicasso will provide you with the perfect Greece vacation.

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Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Village of Oia at sunset in Greece

Island-Hopping Tour of Mykonos, Naxos, Santorini

8 Day Custom Tour

From $2,075

The Greek Islands will awaken your senses on this bewitching 8-day tour, starting in Naxos and ending in Athens. Delight in the sumptuous flavors of authentic Greek cuisine, spend time luxuriating on the white-sand beaches that hug the coastline of Naxos, escape to the secluded beaches of Koufonisia, bask in Santorini's serenity, and satiate your hunger for all ancient history in Athens.

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Sailing the coast of Milos island, Greece

Glamorous Grecian Getaway to Athens, Naxos, Milos, and Santorini

12 Day Custom Tour

From $6,595

Culture, architecture, and cuisine collide on this glamorous 12-day couples' getaway to Athens, Naxos, Milos, and Santorini in Greece. Explore the astonishing works of architectural art that signify the height of Ancient Greece in Athens, make your way to the ruins that pepper parts of Naxos, sail the deep-blue waters surrounding Milos, and uncover the untold stories of Santorini on spectacular private tours.

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Potara Gates overlooks Naxos.

Spectacular Island Tour of Greece's Charm

9 Day Custom Tour

From $2,380

The Greek Islands are breathtaking and boast beautiful beaches as well as luxuriant landscapes for you to discover on this 9-day self-drive exploration from Crete to Naxos. Along the way, scenes of the spectacular seascape and moments of indulging in Ancient Greek heritage will fill you with an appreciation of the picturesque encounters and fascinating historical discoveries that await you.

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Venetian Quay of Chania with Kucuk Hasan Pasha Mosque during twilight blue hour, Crete, Greece

Greek Island Itinerary for the Ages

13 Day Custom Tour

From $3,505

Discover the fascinating history and explore the breathtaking scenery of Greece on this spellbinding 13-day tour that takes you from Athens to Milos. Your adventures will take you back in time as you visit Ancient Greek monuments, expand your culinary horizons, and spend moments under the Mediterranean sun on the beautiful shores of idyllic islands.

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Enjoy a delightful sunset on a boat cruise around Santorini

Family Friendly Greek Island Hopping Vacation

9 Day Custom Tour

From $2,245

The gorgeous Greek Islands are the perfect destination for a memorable and luxurious family vacation. Begin with a stay in Athens to discover the ancient sites of Greece’s capital city. The amazing Acropolis and sight of the Parthenon will leave you in awe before you depart via a private, high-speed boat for the exotic islands of Mykonos, Naxos, and Santorini. Pristine beaches, historical sites, and engaging family activities will be found on every island, and you can discover the best of the Greek Islands during this immersive and unforgettable, 9-day family vacation.

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Admire the Theater of Dionysus, the first theater in the world, on your Acropolis tour in Athens.

Romantic Greece Island Hopping Tour

7 Day Custom Tour

From $1,745

When one thinks of beautiful and romantic locations, the stunning Greek islands most likely come to the forefront of your mind. This luxurious, 7-day excursion to Greece’s premier islands is designed especially for couples. A brief stay in Athens begins your trip before you travel in luxury to the gorgeous islands of Mykonos, Paros, and Santorini. Exclusive tours, dinners for two, and spectacular sea views will be found on every island. Add in the delicious food and idyllic beaches, and you have a true paradise on your hands. During this luxurious and memorable adventure for two, experience some of the best that the Greek islands have to offer.

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The Island of Los is one of the most beautiful islands in Greece.

Best of Greece Island Hopping Itinerary

8 Day Custom Tour

From $1,995

Amazing views, beautiful waters, and delicious cuisine are just a few things that you should expect during your 8-day, highlights tour through Greece. The islands of Greece are renowned for their beauty and remarkable location, and you will discover the best of these islands. Begin in the capital city of Athens, which is full of history and culture, before embarking via private boat for the islands of Mykonos, Santorini, and Ios. From golden beaches with sparkling waters to historic attractions and mouthwatering restaurants, your stay on each Greek island will be unforgettable. Experience the essential and breathtaking highlights of these islands during this luxurious and memorable 8-day trip through Greece.

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Temples of Paestum, archeological area in Italy

Island Hop Through History: Unique Greek Island Hopping Itinerary

9 Day Custom Tour

From $2,335

During this luxurious 9-day excursion to Delos, Tinos, and Nea Kameni have been arranged for you to uncover the beauty, history, and culture of the remarkable Greek Islands. This vacation immerses you in the history and culture of each destination. Explore the iconic sites of the Acropolis, traverse the ruins of Akrotiri, venture to the charming island of Tinos, and uncover the diverse ancient history of Greece.

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Indulge in the islands’ savory food and wine

Greek Island Paradise and Gourmet Gastronomy Tour

7 Day Custom Tour

From $1,815

This immersive 7-day vacation will allow you to explore the gorgeous islands of Mykonos, Naxos, and Santorini. Indulge in the islands’ savory food and wine. The cuisine of Greece has been perfected over thousands of years, and the delicious flavors of the country can be experienced with a trip to its premier islands. Indulge in the flavors of Greece and its celebrated islands, learn the techniques of traditional Greek cooking, and savor the delicious wines of Santorini.

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View of old town Agora in Athens in Greece

Essential Aegean Gems: Perfect Greece Tour

12 Day Custom Tour

From $3,115

Submerge yourself in the cradle of Western Civilization on this 12-day tour of Greece. Visits to Athens, Santorini, Naxos, and Crete ensure that nothing is missed in each of these attractive locations. Witness the abundance of history on display, appreciate the culture of modern Greece, and enjoy this distinct corner of the Mediterranean world.

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Romantic Greece Vacation: Athens & Island Hopping

8 Day Custom Tour

From $1,995

Romance overtakes you and wonders enrapture you on this custom tailored tour that will take you through the fantastic Greek Isles. From the glassy waters of a Mykonos beach to the immaculate whitewashed walls of a Santorini village, the rising pillars of the Parthenon to the birthplace of Apollo, there is no end to the beauty that has captivated the world for thousands of years. Come see the passion. Come see the grandeur. Come see Greece.

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Windmill and white house with clear blue sky and ocean in Santorini

Best Greek Island Hopping Vacation for Travelers Over 50

8 Day Custom Tour

From $2,075

Your relaxing 8-day Greece vacation for travelers over 50 takes you across the luxurious lifestyles and enchanting scenery of the Greek islands. The ancient wonders of Athens will emerge from the Acropolis while divine images continue to decorate the island of Delos. You can swim in hot springs inside Santorini’s caldera and delight in views of the famous windmills on Mykonos as you bask in Greece’s beauty, prestige, and majesty.

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History and Culture of Greece: 10-Day Island Hopping Tour

10 Day Custom Tour

From$2,595

This luxurious 10-day journey of Greece and its islands is designed to uncover the best historical and cultural attractions. The islands of Greece are the ideal combination of beauty and history. Steeped in centuries of culture, they are the ultimate destination for an immersive vacation. Sail across the Aegean Sea, explore the Acropolis, and bask in the tranquility of Greece’s hot springs.

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Greece Sailing Adventure: Island Explorer

8 Day Custom Tour

From$4,795

This 8-day Greece cruise through the stunning paradise of islands has been handcrafted for those in search of a laid-back approach to travel through the use of a comfortable sailing boat equipped with all the modern luxuries. The Greek archipelago has long attracted visitors with its historical legacy and pristine beaches. From Athens to Santorini, enjoy the breathtaking views and ancient ruins that make this location so unique.

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Greece Island Explorer: Crete, Naxos, Mykonos & More

14 Day Custom Tour

From$3,495

Explore and experience iconic beaches and enchanting panoramas during your 14-day Greece island-hopping vacation. You will travel to four islands known for their combination of pink and white beaches, whitewashed villages, and fascinating ancient ruins. Your tour will be custom-tailored to immerse you in Greece’s history and heritage as you traverse the marvels of Crete, Mykonos, Naxos, and Santorini for an unforgettable Mediterranean getaway.

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Greece Island Hopping Tour in 10 Days

10 Day Custom Tour

From$2,495

Explore six exquisite islands on this 10-day tour through the Cyclades and beyond. Each island has its own appeal, be it the quiet beaches on Naxos, Santorini’s whitewashed villages, the history of Crete, the waters around Elafonisi, chic Mykonos, or the archaeological Delos. Handcrafted to provide the complete island hopping experience for those relatively short on time, these are ten days of endless highlights and impressions. And just like the Aegean Sea, it’s as laid-back as it can be.

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Unforgettable Greece Diving Exploration

10 Day Custom Tour

From$2,815

From Greece’s idyllic island landscapes to the fascinating marine wonders that lie below the glimmering surface of the Mediterranean Sea, this 10-day tour for scuba divers reveals the ethereal qualities of this enchanting country. Discover the marvels of Mykonos, the surreal scenes of Santorini, and the captivating coral reefs of Chania on this exciting adventure. Book your tour today!

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Best Greek Islands Vacation in 8 Days

8 Day Custom Tour

From$1,995

This is your custom tailored vacation through the Greek Islands that will bring you to the precipice of grandeur. Look out over the never-ending wonder of Greece, where famous philosophers and humanity thrived, and get ready for an unforgettable vacation designed specifically to highlight the famous Greek islands and Athens.

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Ultimate Three Week Greek Island Vacation

21 Day Custom Tour

From$5,455

This 3-week Greek Islands tour will allow you to immerse yourself in their luxurious allure and relaxing atmosphere. Witness Santorini from the unique vantage point of a private helicopter, choose from a variety of watersports in Mykonos, embark on a sailing trip to Sikinos, and indulge in the delicious fare that the Greek Islands have to offer.

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Idyllic Greek Islands Itinerary for Seniors

10 Day Custom Tour

From$2,595

Experience much of the best that Greece has to offer and more during this immersive 10-day getaway to the idyllic haven of the Greek Isles. The Greek Islands are imbued with beautiful landscapes, delicious food, intriguing history, and a captivating culture. Explore famous such like the Acropolis, bask in the relaxing hot springs of Nea Kameni, and immerse yourself in the region’s delicious food and wine.

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Romantic Greek Trip: Island-Hopping Getaway

10 Day Custom Tour

From$2,595

Beautiful sunsets, captivating landscapes, delicious cuisine, and enchanting panoramas will provide you with endless memories during your 10-day romantic Greece vacation. You will bask in the luxuries of the idyllic Greek islands of Mykonos, Naxos, and Santorini where you can embrace ancient history and enjoy local culture. With private sailing excursions, exceptional seaside dining, and luxurious accommodations, your island-hopping gateway will reveal the best of Greece's passionate spirit.

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Ultimate Greek Island Hopping Getaway for Seniors

8 Day Custom Tour

From$2,075

This 8-day island-hopping tour of Greece has been handcrafted to allow you to partake in some of the most incredible experiences that an island-hopping excursion can afford. From the famed shores of Santorini and Paros to Naxos and Mykonos, this epic journey will immerse you in volcanic landscapes, natural hot springs, charming fishing villages, amazing cuisine, and much more.

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Three Weeks of Family Fun in the Gorgeous Greek Islands

21 Day Custom Tour

From$5,455

This 3-week tour of the Greek island offers your family some of the best experiences that Mykonos, Naxos, Paros, and Milos have to offer. From translucent seas to pristine beaches and unique activities, the Greek Islands offer an immersive experience that can be enjoyed by everyone in your family. Venture on a sailing tour, have a scavenger hunt-themed tour of Paros, and partake in a food tour in Santorini.

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More About Greece Travel

Greece Travel Guide
Agios Nikolaos, Greece
Greece Travel Guide

Explore the ancient world and enjoy modern comforts in the ideal destination of Greece.

With our Greece Travel Guide you can access the details and inspiration you need to create the perfect vacation.

From island paradises and cultural wonders to culinary delights, your customized trip to Greece will be made even better when you plan with the experts. Get connected with a travel specialist to learn more.

Read More    >
10 Best Greek Islands to Visit
Lindos on Rhodes Island, Greece
10 Best Greek Islands to Visit

The best Greek islands to visit embody the timeless beauty of nature and effortless preservation of culture.

Each can ignite your imagination or settle you into the comforts of a luxurious view, connect you to an ancient myth or uncover the essential flavors of the land and sea. Greece’s islands can satisfy the appetites of any traveler by giving you access to active exploration, stunning beaches, or a legacy of Mediterranean cuisine with a distinctive Greek twist.

You can embrace the past, enjoy island life, and embrace the splendor of simple pleasures on any island that you choose.

Read More    >
Best Time to Visit the Greek Islands
Red Beach on Santorini Island, Greece
Best Time to Visit the Greek Islands

The best time to visit the Greek Islands is from April to October, but it really depends on your goals and preferences during your trip.

The islands across Greece offer diverse beauty, culture, and activities, with each new destination promising a new perspective, no matter the season. Many Greek islands have become year-round destinations for travelers, with promises of romance, adventure, or relaxation beyond the treasured beaches.

Whether looking for an off-the-beaten-path island in summer or the perfect family escape in spring, eager to visit ancient ruins or enticed by a dream of sailing the Aegean, the best time to visit the Greek Islands depends on the experiences you wish to have.

Read More    >

Reviews of Zicasso's Referral Service

4.92 stars based on 1141 reviews.

Greece Review: Mykonos Island Tour, Sailing, Food Tours,...
"The tour guides were fabulous, and some of the best we...

Reviewed By Jennifer J.

Greek Islands Honeymoon Review: Greece, Naxos and Santorini...
"I highly recommend you book a trip like this with the travel...

Reviewed By Emily E.

Luxury Greece Trip Review: Naxos, Santorini, Crete, Peloponnese...
"We are extremely pleased with our travel agency. The owner,...

Reviewed By Michael H.

Luxury Greece Vacation Review: Athens, Crete, Santorini,...
"[...] I would recommend this company 100% because I think...

Reviewed By Nicolas H.

Luxury Greece Honeymoon Review: Athens, Mykonos, Santorini,...
"We had an amazing honeymoon in Greece with our travel agency!"

Reviewed By Madison H.

Luxury Greece Vacation Review: Crete, Santorini, Naxos,...
"Our travel planner worked with us to put together a special...

Reviewed By Nancy H.