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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.
Show More•(11 itineraries)
More About Greece Travel
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.
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.
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.
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