Greek Island Itinerary for the Ages: Crete, Santorini, Milos & More

What to expect on this itinerary
Discover the fascinating history and explore the breathtaking scenery of Greece on this spellbinding 13-day tour that takes you from Athens to Milos. Your adventures will take you back in time as you visit Ancient Greek monuments, expand your culinary horizons, and spend moments under the Mediterranean sun on the beautiful shores of idyllic islands.
Customizable Itinerary
Athens - Special Scenes of the City
The former capital of the ancient world, Athens, is now a city where history and modernity are consolidated to create the fascinating destination that exists today. While you transfer from the airport to your accommodation, you will witness your first views of Greece. Locals chat lazily under the sun in open plazas that frame gushing fountains, and Byzantine churches squat along cobbled streets. Welcome to a city that is steeped in history and spotlights said history in all its grace.
What's Included:
Athens - Authentic Athenian Eats
Crete - Venetian and Ottoman Origins
Crete - Across the Samaria Gorge
Crete - The Birthplace of the Minoans
Crete - The Birthplace of Zeus
Santorini - Beneath the Caldera
Santorini - Smooth Sailing
Santorini - The Flavors of Firostefani and Fira
Milos - The Blue Water of Milos
Milos - Picturesque Scenes
Milos - A Toast to the Greek Islands
Athens - Bid Your Farewells
Trip Highlights
- Ascend to the Acropolis and learn more about Ancient Greek civilization as you tour its grounds and venerated monuments
- Deepen your sensory experience of Athens with a gastronomic tour of the city’s culinary hotspots
- Stroll the forested headlands of the Cretan Caldera and venture from village to village in the emerald expanse of the Samaria gorge
- Step foot on the soils that ancient Minoans once stood upon on a tour of the birthplace of the civilization, Knossos
- Expand your understanding of Ancient Greek mythology within the Dikteon Cave, the birthplace of Zeus
- Set sail across the sea for passionate panoramas of the flaming sunset that illuminates the Mediterranean in the evening
- Further your flavorful journey in Greece as you indulge in a taste tour in the endearing villages of Firostefani and Fira
- Swim off the shores of Milos and at the idyllic islands of Polyaigos and Kleftiko, where geological formations dominate the landscape
Starting Price
$5,800 per person (excluding international flights)
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 85 reviews
Me and my five friends did a girls' trip to Greece for 11 nights. I was nervous about planning a trip that far and did my research online. Zicasso received great reviews and I thought it was great to connect with a travel team in Greece. We worked with our travel agent for months to plan our trip of a lifetime. She took the time to listen to our needs with patience and also asked lots of questions to determine what the best itinerary for our vacation would be. She was amazing.
The transportation company that picked us up from locations and took us from hotel to hotel was amazing too.
We stayed in Athens the first few days and that was a great hotel. The rooms were spacious and we were right in the middle of town. We could walk anywhere we wanted to go, even to the Acropolis. We had wonderful tour guides, doing mostly private tours, and the guides felt like family at the end of our trip. We loved Athens, all the shopping and food and hustle and bustle of the city.
Our next adventure was Chania. That hotel was fabulous too. We loved the city and again, our hotel was within walking distance to everything. Our agent also provided us with ideas for restaurants the days we didn't have tours planned, as well as other things to see. Chania was one of our favorites, especially the tour of the 7 Villages of Apokoronas. What a beautiful tour, and we got to stop at a cheese factory, try cheese, hike, and learn about the olive trees and history. Our tour guide was amazing; so full of knowledge and such a wonderful and friendly personality.
Our next leg was the town of Rethymno. We loved it. It was so quaint and our hotel was the most beautiful boutique hotel, with so much history. We also did a walking tour of Rethymno Old Town and learned about the town and its historical places while snacking on Greek cookies and coffee. Our guide was amazing too. We had another private tour the next day of the Eleftherna and Rethymno villages, which were amazing to visit. Our agent kept us busy with lots of tours and we loved every minute of it.
We saw monasteries and also visited Heraklion, where we did a food and wine tour. That was so amazing too. The food in Greece and all the villages was also fresh and delicious. Every place we visited was fabulous. Our tour guide and his team did an amazing job.
We did a Heraklion Village tour and toured the Lasithi Plateau, which was beautiful. We stopped at a little café for coffee and ate lunch at a wonderful restaurant the tour company's owner suggested. It was the best food ever.
The hotels we stayed in were all top-notch. We requested four- and five-star hotels, which we got. Our drivers were always on time and went out of their way to make us happy. The breakfast in every hotel was amazing and delicious.
I had never been to a country that was so stress-free and where everyone was so nice and accommodating. I felt like we needed to stay another two weeks, but we will be back. Our agent was in touch with us the entire time and we appreciated that. She went above and beyond to ensure we were happy and having a great trip. We had no mishaps and can't wait to go back.
Thank you, Zicasso and our travel company, agent, and teams, for making the trip a memorable one and the trip of a lifetime. We love you all and you are family now.
Yamas!! Roxanne, Barbara, Nora, Frances, and Annette – California girls and Texas girls!
See more
Thodoris provided us with an amazing trip to Greece. After a conversation about what we wanted to do and see, he planned everything for us and took care of all of the details for our entire trip. We started out in Athens where we spent four days at a wonderful boutique hotel in the heart of Athens. Thodoris met us and made sure all of our needs were met. He arranged an amazing private tour of the acropolis and the Acropolis Museum. Kiki, our tour guide, was incredible and a great source of information and geared the tour to our interests. Our second tour, to Delphi, was also amazing with Penny as another very knowledgeable and interesting tour guide. All of our pick-ups and deliveries, from the airport to the hotel, each tour, and from the hotel to the airport were provided with no issues or delays. We also had plenty of time to explore Athens on our own, which is what we requested. It was a truly wonderful experience.
We left Athens and went to Chania, on Crete. There we stayed at another adorable boutique hotel with amazing customer service. Thodoris arranged a tour of the traditional villages of Chania where a true local, Dometri (sp?) showed around his villages. You could tell that he knew and loved the area very much. We also had plenty of time to explore Chania on our own. After three nights, Dometri drove us to Knossos. George was our tour guide at Knossos and he was also wonderful. The crowds were a little heavy, so George offered to wait until later in the day to tour the museum, since the line was around the block, which we took him up on and we went on our own to get lunch and when we went to the museum later in the day, the crowd was much improved. Knossos was just outside Heraklion and the museum was within walking distance to the hotel. We then caught the high-speed ferry to Mykonos the next morning.
On Mykonos, we stayed at another beautiful hotel. We had a day trip to see Delos, the birthplace of Apollo and Artimus lead by another excellent tour guide. We had plenty of time to explore, relax and enjoy the Spa at Petasos! Then it was on to Santorini for the grand finale. We stayed in Oia at a spectacular place overlooking the Caldera. We had an amazing wine tour with Steve as our very energetic and entertaining guide. We were not sure we really wanted to do this tour, but it was one of our favorites and we got to see three wineries in different parts of the island. The last stop provided dinner with paired wines and our first incredible sunset view. We then had a free day on Santorini and ended our trip the next day with an incredible sunset cruise which took us to the red beach, the black beach, and the white beach with opportunities to swim and experience the warm springs. Another wonderful meal on the catamaran followed by an amazing view of the sunset on the water.
Thodoris took care of every detail and we did not have to worry about anything other than enjoying ourselves. All transfers and pick-ups were from our hotel and everyone was right on time and very professionally handled. We were free to totally enjoy ourselves and was a completely stress-free vacation. I would highly recommend Thodoris and his travel company to plan a once-in-a-lifetime trip. I hope that we will have an opportunity to use them again on another trip.
See more
See more
See more
See more
My husband and I had an amazing trip to Greece. He worked with our Zicasso agent to set up sightseeing in Athens, the Peloponnese and, finally, on the island of Rhodes. Our agent worked with us for weeks to pin down the perfect balance of hotels, tours, and restaurants. She even helped us make dinner reservations.
All of our tour guides at each destination were top-notch and able to answer my husband's questions and give us new information.
Our agent was in touch with us throughout the 10 days and even met us in person in Athens for a brief drink on our first full day. This was our second trip booked with Zicasso and it has set the bar even higher. We can't wait to get back to Greece and will definitely be in touch with our agent.
See more





