Ultimate 14-Day Greek Islands Itinerary Guide from a Travel Expert

Pack your bags, you’re off to Greece.

Day 1 – USA — Athens

Welcome to Athens. Upon arrival at Eleftherios Venizelos International Airport, you will be greeted by your Hellenic Holidays transfer representative, who will drive you to your hotel. Enjoy the remainder of your day exploring Athens. You might stroll the old neighborhoods of Plaka, which mingle old and new Athens, or explore the vibrant neighborhoods of Monastiraki and Kolonaki.

Day 3 – Athens

After breakfast, your day will begin with your private half-day walking tour. Along with your English-speaking licensed guide, you will visit the Acropolis and the amazing temples of the Parthenon, the Erechtheion, and the Athena Nike. Your walk will continue to the Areopagus, or Hill of Mars. Finally, you will pass the Odeon of Herodes Atticus, where you can still enjoy concerts and theatrical performances in the summer months. The tour will conclude with a visit to the Acropolis Museum, which exhibits the glory of Ancient Athens.

Day 4 – Athens — Milos

After breakfast, your Hellenic Holidays transfer representative will pick you up from your hotel and drive you to the airport or ferry to Milos. Upon arrival, you will be greeted and driven to the hotel. Milos is known as the discovery place of the famous Venus de Milo statue, which is now displayed at the Louvre. Milos has dozens of beaches and picturesque villages that create its dramatic landscapes and charm.

Day 5 – Milos

Milos has beaches and landscapes for all tastes and possesses a relaxing atmosphere that allows you to explore scenic villages like Klima and Plaka while savoring the local color of the island. Pair this experience with visits to stunning beaches like Sarakiniko for a wonderful day. There are dozens of beaches to visit, all different in colors and combinations of sand, stone, and shell, hence the nickname for Milos as the “Island of Colors.” In the evening, visit the port of Adamantas, which boasts a lively waterfront scene with quaint shops and delightful tavernas.

Day 6 – Milos

On your last day in Milos, a must-experience is taking a sailing trip to Kleftiko, a region on the southern side of the island with azure waters and stunning volcanic rock formations. While in Milos, you might consider visiting Plaka and the village of Trypiti with its famous windmills. Plaka is the ideal place for a cinematic sunset, so aim to get there early as many individuals search for the perfect spot. Enjoy a wonderful dinner from one of the recommended restaurants in town.

Day 7 – Milos — Naxos

After breakfast, your Hellenic Holidays transfer representative will pick you up from your hotel and drive you to the port of Milos for your short ferry to Naxos. Upon arrival, you will be greeted and driven to your hotel. Naxos is a historical crossroad, where archaeologists, historians, and scholars have long been drawn by the island’s rich cultural significance. Naxos is also known for its sandy beaches and incredible cuisine.

Day 8 – Naxos

Entice your senses by swimming, sunbathing, and enjoying a range of water sports at some of Naxos’ most beautiful beaches. Naxos has a beach for every activity and taste. Visit Agios Georgios for windsurfing, Mikri Viglia for kite surfing, or Agiassos for a quiet, relaxed beach atmosphere. In the afternoon, consider strolling to Portara, the huge marble gate on the islet in front of the harbor, which captures your eye as soon as you arrive. Enjoy a meal in Chora or at a little seaside taverna to savor a magnificent sunset alongside an authentic meal.

Day 9 – Naxos

On your last day in Naxos, explore the beautiful villages of Apeiranthos and Halki to enjoy the local color. Here you can try the local drink, Kitron, a unique liquor with a greenish tint. The Temple of Demetra is also highly recommended for a visit. After a day of village exploration, enjoy a final swim and a relaxing sunset view with a meal in Chora or at one of the top restaurants.

Day 10 – Naxos — Santorini

Goodbye Naxos, hello Santorini. After breakfast, your Hellenic Holidays transfer representative will drive you to the port of Naxos where you will embark on a one-and-a-half-hour sail aboard a high-speed ferry to Santorini. Santorini is famous for its breathtaking views characterized by layers of red and brown volcanic ash that form its iconic cliffside. You will be driven to your hotel with a spectacular view of the majestic caldera. Spend the rest of the day soaking in the romantic atmosphere of the island, perched on a cliff with stunning views of sunsets and the sea below.

Day 11 – Santorini

After breakfast with views of the caldera, your morning is at leisure. In the early afternoon, you will be driven to the port of Vlichada or Ammoudi to embark on the arranged sailing trip. You will visit the Red and White beaches, the Venetian Lighthouse, and the Sulphur Springs, allowing opportunities to swim and snorkel. You will then sail to a secluded bay for a lavish steak and seafood barbecue with various appetizers and salads to enjoy while you relax.

Day 12 – Santorini

While in Santorini, consider hiking along the picturesque cobblestone pathway from Fira to Imerovigli and then onto Oia. A short ride to the archaeological site of Akrotiri is also worth it, showcasing remnants of this historic village in a beautiful museum. Wine enthusiasts will appreciate a journey through the Santorini wine circuit, exploring the inland villages of Karterados, Monolithos, and Emporio.

Day 13 – Santorini

Your last day in Santorini offers opportunities to visit the famous village of Oia. Some guests enjoy the day with a donkey ride down from Oia to Ammoudi, where they can swim, dine, and then return to Oia to catch one of the world’s stunning sunsets. Others may explore Oia’s local shops or visit artists showcasing their work inspired by the landscape. Conclude your remarkable stay in Greece with a meal at one of the local restaurants, paired with those spectacular views.

Day 14 – Santorini — Athens — Home

Finally, your Hellenic Holidays transfer representative will drive you to the airport for your short flight to Athens, connecting to your flight home.