• Gazing out at  an ancient volcanic caldera-turned-harbor from the deck of a small taverna perched above Santorini’s sheer cliffs
• Having a drink by the sea amid the whitewashed houses and traditional windmills on trendy Mykonos
• Wandering among the ancient ruins on the small island of Delos, once considered sacred to the god Apollo
• Exploring the Turkish and Knights Templar-influenced architecture on the island of Rhodes
• Sampling the fragrant wines on the verdant island of Samos, just off the Turkish coast
• Discovering the charms of lesser-known Cycladic islands such as Folegandros, Milos or Amorgos
• Touring the large island of Crete, savoring the beauty, the sunshine, the history, and the beaches
• Hiking and dining on the gorgeous mountainous island of Naxos
• Retracing the literary footsteps of Lawrence Durrell on the lush Ionian island of Corfu

As you might imagine, touring the Greek Islands involves some extent of water transportation, ranging from sailing, to small cruise ship touring, to large cruise line travel.

However, when browsing Greek Island tours you'll find there is an abundance of travel styles, itineraries, and activities to choose from. These range from active hiking and outdoor activity-packed excursions, to relaxing cruises filled with all there is to love about Greek culture, history, and food. Search through the 25 tour companies on Stride to find the perfect Greek Island trip for you!

Greek Islands in 1 Week

One week touring the Greek Islands gives you a taste of all the beauty the iconic region has to offer. Greek Islands tours lasting one week hit the main tourist attractions and historical landmarks the make up the Greek Islands.

Days 1-2, Athens: Explore the Panathenaic Stadium, where the first Olympic Games of modern times were held in 1896. Visit the famous ancient buildings of the mighty Acropolis.

Days 3-4, Santorini: Bask in the sun on the beaches of the famous island of Santorini, and explore the picturesque capital city of Fira. Don’t miss the iconic photo-op spot of the white and blue covered hills of Oia!

Days 5-6, Mykonos: Party it up in the lively Mykonos! Enjoy the sandy beaches and quaint town during the day, and dance the night away at a popular Mykonos party in the evening!

Day 7, Athens: Take a ferry to end your trip back in the historic Athens.

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Greek Island in 2 Weeks

Two weeks allows for a more thorough exploration of the magnificent Greek Islands. With two weeks’ time, you can explore all that the islands have to offer, while also including some historic tours and authentic Greek activities in your itinerary.

Days 1-2, Athens: Start your trip off in Greece’s capital city of Athens. Tour the ancient ruins of 5th-century BC landmarks such as the Acropolis and the Parthenon.

Day 3, Delphi: Explore the archeological sites of Delphi, including the 4th-century BC Temple of Apollo and Athenian Treasury.

Days 4-5, Kea/Delos/Mykonos: Explore the quaint island of Kea before sailing to the uninhabited archaeological site of Delos to tour the remarkable ancient ruins. Spend the night docked in Mykonos and enjoy the lively nightlife this island has to offer!

Day 6, Santorini: Venture to the most popular of the Cyclades Islands for a day to remember in picturesque Santorini! View the whitewashed buildings cascading over the cliffs overlooking the caldera.

Day 7, Rethymnon, Crete/­Knossos: The largest of the Greek Islands, Crete, is home to the ancient city of Knossos. Here you will explore the largest Bronze Age archaeological site, which is also considered Europe’s largest city.

Day 8, Kythira: Take a swim and enjoy the wonderful crystal-clear waters of Kythira. Soak up the sun on the beach for a relaxing Greek Island getaway day.

Day 9, Monemvasia/Nafplio: Located on a small island off the east coast of the Peloponnese, Monemvasia is a prominent medieval town with unique, well-preserved architecture. Explore the town of Monemvasia before sailing to the seaport town of Nafplio in The Peloponnese.

Day 10, Mycenae/Hydra: Tour the ­UNESCO World Heritage site, the striking ruins at ­Mycenae, before heading to the car-free, traditional town of Hydra.

Day 11, Piraeus/Athens: End your tour in the imposing, Athens, with a tour of the Benaki Museum and a farewell dinner to toast the end of a perfect trip.

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Greek Islands Small Ship Cruises

Small ship Cruises are a great way to get an up close and personal Greek Islands experience. Many Greek Islands small ship cruises focus on adventure-packed island excursions and activities and exciting nightlife parties and dancing. These cruises usually explore the main sailing sights to see in the Greek Islands, lasting an average of 8-9 days.

Days 1-2, Santorini: Kick off your cruise in the wonderous, Santorini. Explore the caldera’s famous cliffs for a picture-perfect view.

Day 3, Ios: This island is most famously known for its nightlife and party scene. Enjoy a cocktail and dance the night away on the lively, Ios!

Day 4, Koufonisia: Explore this hidden gem and smallest island of the Cyclades. Experience the calmness and peace that the majestic beaches of Koufonisia provide.

Day 5, Naxos: Enjoy the rocky terrain and long stretch of beaches that the largest island in the Cyclades has to offer. Soak in the beautiful sunset in Naxos before embarking on your next destination.

Day 6, Paros: Famous for its water sports, have an active water day in Paros. If you’re more interested in a relaxing day, lay out on the beach before hitting the vibrant clubs at night.

Days 7-8, Mykonos: End your cruise in the most anticipated party destination in the Greek Islands. Experience all that the world-famous Mykonos nightlife has to offer!

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