A Perfect 14-day Itinerary to the Greek Islands From a T+L Travel Expert
Petros G. Zissimos is a member of Travel + Leisure’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. He is the founder of Hellenic Holidays, which specializes in the best of the best Greece has to offer. Below is an example of the type of itineraries he creates.
To work with Petros, you can contact him directly at firstname.lastname@example.org.
Day 1 – USA — Athens
Pack your bags, you're off to Greece.
Day 2 – 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 awesome temples of the Parthenon, the Erechtheion, and the Athena Nike. Your walk will continue to the Areopagus, or Hill of Mars. Finally, you 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 exhibiting 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 great beaches like Sarakiniko for a wonderful day. There are dozens of beaches to visit, all different colors and all different combinations of sand, stone, and shell, hence the nickname for Milos as the “Island of Colors.” In the evening, visit the port of Adamantas. Adamantas has a lively waterfront scene with quaint shops and wonderful tavernas.
Day 6 – Milos
Today is your last day in Milos. A must experience while in Milos is to take a sailing trip to Kleftiko, a region on the southern side of the island with azure waters and amazing volcanic rock formations. While in Milos, you might consider visiting Plaka, another charming village that will lead you to the village of Trypiti with its famous windmills. Plaka is the place to visit a truly cinematic sunset but try to get there early as many people try to find the perfect spot for the sunset. Enjoy a wonderful dinner from one of our restaurant recommendations 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 and always has been a crossroad, where archaeologists, historians, and scholars of all kinds can meet, drawn by the importance of the culture which has flourished on the island down the centuries. Naxos is also known for its sandy beaches and spectacular 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 all activities and tastes. Visit Agios Georgios for windsurfing, Mikri Viglia for kite surfing, or Agiassos for a quiet and relaxed beach atmosphere. In the afternoon, consider strolling into Portara, on the islet in front of the harbor which you spot as soon as you arrive in Naxos, as the huge marble gate captures your eye. Enjoy a meal in Chora or at a little seaside taverna where you can enjoy a magnificent sunset and an authentic meal.
Day 9 – Naxos
Today is your last day in Naxos. Explore the beautiful villages of Apeiranthos and Halki and enjoy the local color of these villages. There you can even try the local drink, a liquor named Kitron with a greenish tint. There is the Temple of Demetra that should be visited. Enjoy a final swim after your day of village exploration and enjoy a relaxing sunset view and meal from Chora or one of our restaurant recommendations.
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 embark on a one-and-half-hour sail aboard a high-speed ferry to Santorini. Santorini is most known for its breathtaking views of the red and brown layers of volcanic ash that makes its famous cliffside. You will be driven to your hotel overlooking the majestic caldera. Spend the rest of the day enjoying the romantic atmosphere of the island. Perched on a cliff with breathtaking views of the sunsets and the sea below creates the perfect setting for the next few days.
Day 11 – Santorini
After breakfast enjoying caldera views, your morning is at leisure. In the early afternoon, you will be driven to the port of Vlichada or Ammoudi where you will embark on the sailing trip that we have arranged. You will sail to the Red and White beaches, the Venetian Lighthouse, and the Sulphur Springs. During these visits, you will have the opportunity to swim and snorkel. You will then sail to a secluded bay where while you swim or relax, a lavish steak and seafood barbecue with many appetizers and salads is being prepared for you to enjoy.
Day 12 – Santorini
While in Santorini, consider hiking along the cobblestone pathway from Fira to Imerovigli and then on to Oia. You can also take a short ride and visit the archaeological site of Akrotiri, seeing the remnants of this village in its beautiful museum. Wine connoisseurs will enjoy a journey down the Santorini wine circuit through the inland villages of Karterados, Monolithos, and Emporio.
Day 13 – Santorini
Your last day in Santorini. You might consider visiting the famous village of Oia. Some enjoy the day by taking a donkey ride down from Oia to Ammoudi where they swim, eat, and then return to Oia to take in one of the world’s famous sunsets. Others explore Oia’s local souvenir shops or visit some of the local artists who display their work of the landscape. What better way to end your stay in Greece, by dining at one of the local restaurants we recommend with those majestic views.
Day 14 – Santorini — Athens — Home
Your Hellenic Holidays transfer representative will drive you to the airport for your short flight to Athens connecting to your flight home.