The Ultimate Island-Hopping Itinerary: 14 Days in Greece

By | November 17, 2025

The Ultimate Island-Hopping Itinerary: 14 Days in Greece

Are you ready for the ultimate island-hopping adventure? Look no further than the crystal-clear waters and stunning landscapes of Greece. With a plethora of islands to explore, delicious cuisine to savor, and a rich history to discover, Greece is the perfect destination for an unforgettable island-hopping journey. In this article, we’ll take you on a 14-day itinerary through some of the most breathtaking islands in the region, showcasing the best of what Greece has to offer.

Day 1-2: Mykonos

Our journey begins on the vibrant island of Mykonos, known for its picturesque whitewashed houses, vibrant nightlife, and stunning beaches. Spend your days exploring the narrow streets of Mykonos Town, visiting the famous windmills, and enjoying the island’s beautiful beaches, such as Paradise Beach and Super Paradise Beach. In the evenings, experience the island’s legendary nightlife, with a plethora of bars, clubs, and restaurants to choose from.

Day 3-4: Santorini

From Mykonos, we sail to the breathtaking island of Santorini, with its picturesque villages perched on cliffs, stunning sunsets, and breathtaking views of the caldera. Explore the charming village of Oia, visit the famous black sand beach of Perissa, and enjoy a romantic dinner at one of the many cliffside restaurants. Don’t miss the opportunity to visit the ancient city of Akrotiri, a UNESCO World Heritage Site, and take a scenic hike from Fira to Oia for breathtaking views of the island.

Day 5-6: Ios

Next, we head to the tranquil island of Ios, a hidden gem with a rich history and stunning natural beauty. Visit the ancient city of Skarkos, explore the picturesque village of Chora, and enjoy the island’s beautiful beaches, such as Mylopota and Maganari. Ios is also a great spot for water sports, such as snorkeling, kayaking, and paddleboarding.

Day 7-8: Crete

From Ios, we sail to the largest island in Greece, Crete, with its rich history, stunning landscapes, and delicious cuisine. Visit the ancient palace of Knossos, explore the charming old town of Chania, and enjoy the island’s beautiful beaches, such as Elafonisi and Balos. Don’t miss the opportunity to try some of the island’s local specialties, such as moussaka, souvlaki, and fresh seafood.

Day 9-10: Rhodes

Our next destination is the beautiful island of Rhodes, with its stunning medieval town, beautiful beaches, and rich history. Explore the UNESCO World Heritage Site of the Acropolis of Rhodes, visit the Palace of the Grand Master of the Knights of Rhodes, and enjoy the island’s beautiful beaches, such as Faliraki and Lindos. Don’t miss the opportunity to visit the ancient city of Lindos, with its stunning acropolis and breathtaking views of the island.

Day 11-12: Symi

From Rhodes, we sail to the charming island of Symi, with its picturesque harbor, stunning beaches, and rich history. Visit the charming village of Gialos, explore the ancient ruins of the Castle of the Knights, and enjoy the island’s beautiful beaches, such as Panormitis and Nimborio. Symi is also a great spot for hiking and exploring the island’s stunning natural beauty.

Day 13-14: Karpathos

Our final destination is the beautiful island of Karpathos, with its stunning beaches, charming villages, and rich history. Visit the charming village of Pigadia, explore the ancient ruins of the Castle of Aperi, and enjoy the island’s beautiful beaches, such as Apella and Kyra Panagia. Karpathos is also a great spot for water sports, such as snorkeling, kayaking, and paddleboarding.

Getting Around

The best way to get around the islands is by ferry, with frequent departures from each island. You can also rent a boat or take a guided tour to explore the islands and their surrounding waters.

Accommodation

Greece offers a wide range of accommodation options, from budget-friendly guesthouses to luxury hotels and villas. Be sure to book your accommodation in advance, especially during peak season.

Tips and Essentials

    • Best time to visit: May to October, with warm weather and calm seas.
    • Language: Greek, but most locals speak English.
    • Currency: Euro.
    • Food: Delicious Greek cuisine, with plenty of fresh seafood, moussaka, souvlaki, and traditional desserts.
    • Activities: Snorkeling, kayaking, paddleboarding, hiking, and exploring the islands’ rich history and culture.

In conclusion, our 14-day island-hopping itinerary in Greece is the ultimate adventure for anyone looking to explore the best of what this stunning region has to offer. With its crystal-clear waters, stunning landscapes, rich history, and delicious cuisine, Greece is the perfect destination for an unforgettable island-hopping journey. So pack your bags, grab your sunscreen, and get ready for the ultimate Greek island adventure!