5 Day Greek Island Itinerary

5 Day Greek Island Itinerary

Greece’s stunning islands have always been a sought-after destination for travelers from around the world. With their picturesque landscapes, crystal-clear waters, and rich history, the Greek islands offer a unique and unforgettable experience. Planning a well-structured itinerary is crucial to make the most of your time and explore multiple islands in a limited timeframe. In this article, we present a comprehensive 5-day Greek Island itinerary that will take you through the breathtaking islands of Santorini, Mykonos, and Rhodes, ensuring you have an incredible journey filled with memorable experiences.

The Acropolis illuminated at night, Athens, Attiki, Greece, Europe
The Acropolis illuminated at night, Athens, Attiki, Greece, Europe

Day 1: Arrival in Athens and Ferry to Santorini

Your Greek island adventure begins as you arrive at Athens International Airport. After a long flight, it’s time to make your way to Piraeus Port, where you’ll catch a ferry to the enchanting island of Santorini. The journey from Athens to Santorini takes approximately five hours by ferry, offering you plenty of time to relax and enjoy the beautiful Aegean Sea views.

Upon arriving in Santorini, you’ll be mesmerized by the island’s captivating beauty. Santorini is famous for its whitewashed buildings, blue-domed churches, and dramatic cliffs overlooking the azure sea. A transfer will be arranged to take you to your hotel, where you can settle in and unwind.

In the evening, head to the charming village of Oia to witness one of Santorini’s most iconic sights—the sunset. Find a comfortable spot and watch as the sun paints the sky with vibrant hues, casting a magical glow over the island. Capture this breathtaking moment and create memories that will last a lifetime.

Santorini Island, Greece
Santorini Island, Greece

Day 2: Exploring Santorini

Morning

Wake up refreshed and ready to embark on a day of exploration in Santorini. Start your morning with a delicious breakfast at a local cafe, where you can indulge in freshly baked pastries, Greek yogurt, and aromatic coffee. As you savor your meal, take in the stunning views of the Caldera—the submerged crater that gives Santorini its distinctive landscape.

After breakfast, make your way to Fira, the island’s capital. Here, you’ll find the iconic Blue Dome Church, a postcard-perfect symbol of Santorini. Stroll through the narrow streets of Fira, lined with boutique shops, art galleries, and traditional tavernas. Immerse yourself in the local culture and take in the charming ambiance of this vibrant town.

From Fira, venture to the village of Pyrgos, known for its picturesque alleys and traditional Cycladic architecture. Climb up to the highest point of Pyrgos, where you’ll discover the ruins of a Venetian castle offering panoramic views of the island. Explore the quaint streets, browse local shops, and interact with friendly locals who are always eager to share their island’s stories.

No visit to Santorini would be complete without exploring the ancient ruins of Akrotiri. Often referred to as the “Pompeii of the Aegean,” Akrotiri is a remarkably preserved Minoan settlement that was buried under volcanic ash for centuries. Wander through the excavated site and marvel at the well-preserved buildings, colorful frescoes, and ancient artifacts that provide insight into the island’s past.

Afternoon

By now, your appetite will have surely been whetted, and it’s time to indulge in a leisurely lunch. Choose a seaside restaurant with stunning Caldera views and savor the flavors of traditional Greek cuisine. Treat yourself to mouthwatering dishes such as moussaka, souvlaki, or fresh seafood caught from the surrounding waters.

After lunch, embark on a wine-tasting adventure as you explore the traditional wineries of Santorini. The island’s volcanic soil and unique grape varieties give its wines a distinctive taste. Visit renowned wineries and learn about the winemaking process while enjoying samplings of award-winning wines. Raise a glass and toast to your Greek island journey.

Santorini is also home to some of the most beautiful beaches in Greece. In the afternoon, head to the famous Black Beach of Kamari. Sink your toes into the volcanic black sand, relax under an umbrella, and enjoy the refreshing sea breeze. Take a dip in the crystal-clear waters of the Aegean Sea, or if you’re feeling adventurous, try your hand at water sports such as snorkeling or paddleboarding.

As the sun starts to set, make your way to Amoudi Bay, a picturesque fishing village located below Oia. Indulge in a memorable dinner at one of the seafood tavernas perched on the water’s edge. Delight your taste buds with fresh seafood delicacies while the vibrant colors of the sunset paint the sky above you. It’s a perfect ending to a day filled with exploration and relaxation.

Mykonos
Mykonos

Day 3: Mykonos Island

Morning

On day three, bid farewell to Santorini and embark on a ferry ride to the vibrant island of Mykonos. The journey takes approximately two hours, allowing you to enjoy the scenic beauty of the Aegean Sea as you make your way to this cosmopolitan paradise.

Upon arriving in Mykonos, a transfer will be waiting to take you to your hotel. Mykonos is known for its stunning beaches, vibrant nightlife, and charming Cycladic architecture. Drop off your bags and get ready to explore this famous island.

Start your morning by immersing yourself in the charm of Mykonos Town. Wander through the narrow cobblestone streets, adorned with bougainvillea, and discover the town’s hidden treasures. Visit the iconic Windmills, an iconic landmark of Mykonos, which once powered the island’s agriculture. Climb to the top and admire the panoramic views of the town and the sparkling sea.

Afternoon

After a morning of exploration, treat yourself to a delicious lunch at a seaside taverna in Little Venice. This picturesque neighborhood is known for its colorful buildings that hang over the water’s edge. Indulge in Greek mezes (small plates) and fresh seafood while enjoying the stunning views of the Aegean Sea.

In the afternoon, venture to the village of Ano Mera, located in the heart of Mykonos. Here, you’ll find a traditional and more laid-back side of the island. Visit the Panagia Tourliani Monastery, a beautiful 16th-century monastery known for its intricate marble carvings and stunning courtyard. Take a moment to admire the peaceful atmosphere and learn about the monastery’s history.

No trip to Mykonos is complete without spending time on its world-famous beaches. Head to Paradise Beach or Super Paradise Beach, known for their golden sands and crystal-clear waters. Relax on a sun lounger, soak up the Mediterranean sun, and take refreshing dips in the turquoise sea. Join in beach parties, listen to music, and immerse yourself in the vibrant beach culture that Mykonos is renowned for.

As evening falls, get ready to experience Mykonos’ legendary nightlife. The island is famous for its energetic party scene, with a plethora of clubs and bars catering to all tastes. Dance the night away to the beats of internationally renowned DJs, or enjoy a more relaxed evening sipping cocktails at a beachside bar. Mykonos offers an unforgettable nightlife experience that will keep you entertained until the early hours of the morning.

Agios Nikolaos fortress on the Mandraki harbour of Rhodes
Agios Nikolaos fortress on the Mandraki harbour of Rhodes

Day 4: Delos Island and Rhodes

Morning

On day four, venture beyond Mykonos and take a day trip to the nearby island of Delos. Catch an early morning ferry from Mykonos to Delos, an archaeological gem that holds immense historical significance. Delos is believed to be the birthplace of Apollo, the Greek god of light and music, making it a sacred site in ancient Greek mythology.

Upon arrival, embark on a guided tour of the archaeological site, led by knowledgeable local guides who will bring the ancient ruins to life. Marvel at the well-preserved ancient city, including temples, houses, and marketplaces that date back thousands of years. Explore the Terrace of the Lions, the iconic marble statues that once guarded the sacred island.

As you wander through the ruins, imagine what life was like during the height of Delos’ power. Learn about the island’s importance as a trading center and its role in shaping the ancient Greek world. Delos offers a fascinating glimpse into the past and provides a deeper understanding of Greek history and culture.

Afternoon

After the enriching experience on Delos, return to Mykonos and prepare for your journey to Rhodes. Board a flight from Mykonos Airport to Rhodes, the largest of the Dodecanese islands. Rhodes is a captivating destination with a unique blend of medieval history, vibrant culture, and pristine beaches.

Upon arrival in Rhodes, a transfer will be waiting to take you to your hotel. Check-in and take some time to relax before diving into the island’s rich history.

Start your exploration in the medieval Old Town of Rhodes, a UNESCO World Heritage site. Step back in time as you wander through the fortified walls, narrow cobblestone streets, and charming squares. Visit the Palace of the Grand Master, an impressive castle that showcases the island’s Byzantine and Ottoman influences. Admire the stunning mosaics and architectural details that reflect the grandeur of the past.

Stroll through the Street of the Knights, lined with medieval buildings that once housed the knights of the Order of Saint John. Explore the Archaeological Museum of Rhodes, where you can discover ancient artifacts and learn about the island’s history from the prehistoric era to the Roman period. Immerse yourself in the fascinating stories of Rhodes’ past as you explore its well-preserved historical sites.

Also read: Ultimate Greek Islands Travel Guide: Everything You Need to Know!

Day 5: Rhodes Island and Departure

Morning

As you wake up on your final day of this Greek island adventure, savor a delicious breakfast at your hotel. Today is all about relaxation and enjoying the natural beauty of Rhodes.

Rhodes boasts a plethora of stunning beaches, and no visit would be complete without spending time on one of them. Head to Faliraki Beach, known for its golden sands and crystal-clear waters. Relax on a sunbed, soak up the sun, and take refreshing dips in the Aegean Sea. If you prefer a quieter ambiance, venture to the charming village of Lindos and unwind on its pristine beaches. Enjoy the tranquility and natural beauty that surround you.

For history enthusiasts, a visit to the ancient Acropolis of Lindos is a must. Perched atop a hill, the Acropolis offers breathtaking views of the surrounding landscape. Explore the ancient ruins, including the Temple of Athena Lindia and the Hellenistic stoa. Marvel at the panoramic views of the turquoise sea and the whitewashed village below.

Afternoon

In the afternoon, take a boat trip to the picturesque island of Symi, located just off the coast of Rhodes. Symi is known for its colorful neoclassical houses, charming harbor, and relaxed atmosphere. Explore the narrow streets, browse local shops selling traditional crafts, and indulge in a leisurely lunch at a waterfront taverna. Enjoy the laid-back island vibe and capture the postcard-perfect views that Symi has to offer.

As the day draws to a close, savor a farewell dinner, savoring the flavors of Greek cuisine one last time. Choose a restaurant that specializes in local delicacies, such as moussaka, souvlaki, or freshly caught seafood. Raise a glass of ouzo or local wine and toast to the unforgettable memories you’ve created during your Greek island journey.

After dinner, take a leisurely stroll through the streets of Rhodes Town, enjoying the warm evening ambiance. Visit local boutiques, souvenir shops, and art galleries, and pick up some mementos to remind you of your time in Greece.

Finally, it’s time to bid farewell to the Greek islands. A transfer will take you to Rhodes Airport, where you’ll catch your flight back home or to your next destination. Reflect on the incredible experiences you’ve had, the beautiful places you’ve explored, and the memories you’ve made.

In this 5-day Greek Island itinerary, you’ve embarked on a whirlwind journey through some of Greece’s most stunning destinations. From the enchanting island of Santorini, with its breathtaking sunsets and ancient ruins, to the vibrant nightlife of Mykonos, and the rich history of Rhodes, you’ve experienced the diverse beauty and culture of the Greek islands.

This itinerary has allowed you to make the most of your time, ensuring that you’ve visited the iconic landmarks, indulged in the local cuisine, and relaxed on the picturesque beaches. Whether you’re a first-time visitor to Greece or a seasoned traveler, this itinerary has provided a well-rounded and unforgettable experience.

As you reflect on your Greek island adventure, you’ll carry with you the memories of sun-drenched beaches, whitewashed villages, and the warm hospitality of the Greek people. Plan your next visit to Greece, and explore the countless other islands that await you—each with its own unique charm and allure. The Greek islands are a true paradise, offering an experience that will captivate your heart and soul.

About the author

An adventurer and theme park enthusiast at heart, Mark specialises in family travel content creation, and is a passionate and award-winning travel writer and videographer.