5-day Trip to Santorini, Greece Itinerary

Start your day with a leisurely stroll through the charming streets of Oia. Admire the iconic blue-domed churches, white-washed buildings, and breathtaking views of the Aegean Sea. Stop by Naoussa Restaurant for a delicious breakfast with a view.

Embark on the Fira–Oia Hike, a scenic trail that offers panoramic views of the island. Take your time to enjoy the picturesque landscapes and make your way to the Skaros Rock, a natural rock formation with stunning views.

Indulge in a romantic dinner at Koukoumavlos, a fine dining restaurant known for its creative Greek cuisine. After dinner, head to the White Door Theater (White Door Theatro) for an evening of live performances and entertainment.

Visit the Monastery of Profitis Ilias (Moni Profitou Iliou), located at the highest point of the island. Explore the monastery and enjoy panoramic views of Santorini. Afterward, head to Pyrgos (Pyrgos Kallistis), a traditional village known for its Cycladic architecture.

Experience a wine tasting tour at Artemis Karamolegos Winery, where you can sample a variety of local wines and learn about the winemaking process. After the tasting, relax at Perivolos Beach, a beautiful black sand beach with beachfront cafes and lounges.

Enjoy dinner at Kyprida Greek Restaurant, a cozy restaurant known for its authentic Greek dishes. Afterward, head to Fira Kalamia for a relaxing evening of cocktails and live music.

Start your day by exploring the Ancient Thera, an ancient city perched on a hilltop. Discover the ruins and enjoy panoramic views of the island. Afterward, visit the Port of Santorini (Athinios Port) and watch the boats come and go.

Spend the afternoon relaxing at Kamari Beach, a popular black sand beach with beachfront bars and restaurants. Enjoy swimming in the clear waters and soak up the sun. In the evening, take a leisurely walk along the Fira, the main town of Santorini, known for its stunning views and vibrant atmosphere.

Enjoy a delicious dinner at Metaxi Mas, a traditional Greek taverna known for its authentic flavors. After dinner, head to Sphinx Restaurant for a rooftop cocktail with panoramic views of the caldera.

Embark on a Santorini Luxury Small Group Catamaran w/ Meal & Open Bar to explore the beautiful coastline of Santorini. Enjoy swimming in secluded bays, snorkeling, and sunbathing on the catamaran. Indulge in a delicious meal and refreshing drinks on board.

After the cruise, visit the charming village of Thirasia (Therasia), located on a neighboring island. Explore the traditional houses and enjoy a leisurely lunch at Ammoudi Fish Tavern, known for its fresh seafood.

For your last evening in Santorini, dine at Selene Restaurant, a Michelin-starred restaurant known for its innovative Greek cuisine. After dinner, head to Katharos Lounge for a relaxing evening of cocktails and stunning sunset views.