Expansive Greece Itinerary: Athens, Rhodes, Crete, Santorini

We visited Athens, Epidaurus, Nemea, Nafplion, Olympia, Nafpaktos, Delphi, the Temple of Poseidon, Naxos, Santorini, and Crete in 20 days. Our tour guides were exceptional, all hotels were exceptional except for a minor hiccup in one, and all of our drivers were fantastic. We enjoyed learning about the many ancient civilizations in Greece, including the Mycenaeans, the Minoans, and the ancient Greeks. We enjoyed the Venetian architecture in the islands and the diversity of Santorini.

The travel company, I think, picked the best available hotels and the best available tour guides and drivers. Not every transfer was perfect. There were about three instances where a driver did not meet us due to an incorrect pickup location or incorrect name, or there was confusion about whether we had tickets to one event. But the tour company was available on WhatsApp and responded within 15 minutes when problems occurred. The problems were resolved shortly afterward.

I do not believe there are any trip itineraries that are executed perfectly. In our case, the weather played a role in canceling one excursion and delaying our departure from Naxos to Santorini. While we were on Naxos, strong winds were persistent day and night, forcing the ferry service to cancel rides. Our last day in Naxos did not feel like a vacation. But the tour company commiserated with us, getting us on the last ferry off of Naxos and speaking with us on the phone about our options.

We recently returned from an incredible two-week Coral Anniversary trip to Greece and it exceeded every expectation. From the ancient wonders of Athens to the whitewashed villages of Mykonos, the dramatic cliffs of Santorini, and the authentic traditions of Crete, every stop offered something unique and unforgettable. Most importantly, the people we met along the way transformed a beautiful vacation into a truly special experience. The journey took us through Athens, Mykonos, Santorini, and Crete.

Outstanding Planning and Service

Every transfer, hotel, tour, ferry, flight, restaurant reservation, and activity was flawlessly coordinated by Zicasso's travel partner. The itinerary struck a perfect balance between guided experiences and personal exploration, allowing us to enjoy Greece without ever worrying about logistics.

Athens – History, Culture, and Exceptional Hospitality

Our stay at our hotel in Athens gave us incredible Acropolis views and a perfect base for exploring the city. Walking through the Acropolis with our guide and standing before the Parthenon was breathtaking. The Acropolis Museum and city highlights tour helped bring thousands of years of history to life.

One of the highlights of our anniversary celebration was dinner at a restaurant atop Lycabettus Hill. Watching the sun set behind the Acropolis while enjoying excellent Greek cuisine and wine was a magical experience and one we'll never forget.

We would especially like to recognize our driver in Athens. He was professional, knowledgeable, and genuinely invested in making our trip memorable. During our day exploring the Argolis region, Epidaurus, Mycenae, and the Nemea wine country, he provided insights that helped us better appreciate the history and culture of Greece.

What truly distinguished our driver was his attention to detail. While we were traveling along the Athenian Riviera toward Cape Sounion and the Temple of Poseidon, he realized we were hoping for a true seaside lunch experience. Without being asked, he contacted the travel company and coordinated everything to make a last-minute adjustment so we could enjoy lunch by the sea. That thoughtful gesture perfectly reflects the level of service he provided throughout our stay. It turned a wonderful day into one of our favorite memories of Athens.

Mykonos – Relaxation and the Beauty of the Aegean

Mykonos provided the perfect contrast to the historical focus of Athens. Staying at our hotel in Mykonos overlooking the Aegean Sea allowed us to fully appreciate the island's beauty.

We spent time exploring the charming streets of Mykonos Town, admiring the famous windmills, and enjoying the relaxed island atmosphere. A major highlight was our private catamaran cruise to Delos and Rhenia. Sailing through the crystal-clear waters of the Aegean while visiting the UNESCO World Heritage Site of Delos gave us a fascinating glimpse into one of the ancient world's most important religious centers. The secluded waters around Rhenia were stunning and provided some of the most beautiful scenery of our trip.

Santorini – Spectacular Views and Unforgettable Sunsets

Santorini is every bit as beautiful as the photographs suggest and somehow even more impressive in person. Our stay in Oia overlooking the caldera was breathtaking. Whether enjoying breakfast with panoramic views or simply walking through the village, every moment felt special.

The wine-tasting experiences at a winery were outstanding. Sampling the island's distinctive Assyrtiko wines while learning about Santorini's unique volcanic terroir gave us a new appreciation for Greek winemaking. The carefully paired food-and-wine experiences were among the culinary highlights of the entire trip.

Our private sunset catamaran cruise around the caldera, White Beach, Red Beach, Black Beach, hot springs, and the volcano was another unforgettable experience. Watching the sunset from the water while enjoying dinner and local wine created one of the most memorable evenings of our anniversary trip.

Crete – The Heart of Greece

As amazing as Athens, Mykonos, and Santorini were, Crete became our favorite part of the journey.

Our quick stop at Knossos Palace and the historic city of Rethymnon allowed us to learn about the Minoan civilization and experience the rich blend of Venetian and Ottoman influences that define the island. The old Venetian harbor in Chania was equally impressive and provided a spectacular setting for our stay.

Samaria Gorge

One of the most rewarding experiences of our entire trip was hiking the Samaria Gorge. Covering 11 miles through one of Europe's most spectacular natural settings was challenging and incredibly rewarding. The dramatic cliffs, pristine landscape, and sheer scale of the gorge were unlike anything we had experienced before.

A tremendous part of that experience was our guide. Our guide brought expertise, enthusiasm, and a genuine passion for Crete that elevated the hike far beyond a typical excursion. His knowledge of the region, local culture, and natural environment made every step more meaningful.

Kissamos Villages and Cooking Class

Our final full day in Crete may have been the most authentic and memorable day of the entire trip.

The tour of the traditional villages of Kissamos provided a fascinating look at everyday Cretan life. Learning about olive oil production, tasting regional products, and experiencing rural villages gave us a perspective on Crete that most visitors never see.

The cooking class that followed was exceptional. Our host created an atmosphere that felt less like a tour and more like spending a day with friends. Together with his mother, he shared not only recipes, but the stories, traditions, and values that make Cretan culture so special.

For anyone traveling to Crete, we cannot recommend this tour company highly enough. Their commitment to authentic local experiences is truly outstanding.

This trip exceeded our expectations in every possible way. We experienced world-famous historical sites, breathtaking landscapes, incredible food and wine, beautiful hotels, and unforgettable adventures. Yet what we will remember most are the people who made the experience so special.

We returned home with wonderful memories, a deeper appreciation for Greek culture, and gratitude for everyone who helped make our anniversary celebration the trip of a lifetime.

We had a wonderful and memorable trip to Greece, thanks to the Zicasso travel specialist’s excellent planning. In addition to exploring Athens, she designed a seamless road trip across the Peloponnese Peninsula that took us to beautiful beaches and ancient castles in Messinia, Voidokilia, Pylos, Methoni, Monemvasia, and Nafplio. She also provided clear directions and recommended great stops to break up our drives, including Mystras Castle and the beautiful Polylimnio Waterfalls.

Our hotel accommodations were excellent throughout the trip and we really enjoyed our stay in beautiful Santorini. We also appreciated her restaurant recommendations, which saved us from having to search for places to eat and always led us to great food. She stayed in touch via WhatsApp the entire time, checking in on us and answering our questions whenever they came up. There is so much to see in Greece that we’ll definitely need to go back for another visit.

This was a fantastic experience! Shout-out to our wonderful travel specialist for crafting an amazing itinerary. We could only do eight days in Greece and our specialist provided wonderful recommendations. All the ferry rides, excursions, and travel outside of getting to and from Greece were provided.

In addition, the hotel selections were spectacular. Our hotels in Santorini and Mykonos both overlooked the Aegean Sea and the staff was absolutely wonderful. Our specialist was also super attentive to our requests mid-trip, which we were extremely grateful for. My favorite excursion was the catamaran/snorkeling/sunset cruise in the Aegean Sea. An incredible experience.

On the last leg of our trip to Athens we had ferry delays and hit traffic, but once again our specialist coordinated with our private guide at the Acropolis, who patiently waited for us and provided a wonderful tour. The last day in Athens we took a tour to the Temple of Poseidon. It was a longer than expected bus tour that took around six hours. In hindsight, we would probably have not chosen to do that; however, it is hard to complain as we had dinner watching the sunset over the ancient ruins.

We had a wonderful experience and truly appreciate Zicasso's wonderful team for making Greece a trip of a lifetime!

I could not ask for a better partner and travel company than this one. I reached out on short notice, looking to plan a two-and-a-half-week trip to Greece to explore Athens and some islands (Paros, Antiparos, Naxos, Santorini, Crete). I provided our Zicasso travel specialist with some of my interests, guidelines for my travel style, and the kind of trip I was looking to plan, and she delivered all of that and more!

She developed an itinerary that provided me with exactly what I was looking for and gave me some specific recommendations for restaurants, experiences, and things to do in each location. It was an absolutely incredible trip, all made possible by our travel specialist and her team. Her assistance, guidance, and the time and attention to detail that she put in made it an amazing journey. She was incredibly responsive and even checked in with me throughout the trip to make sure everything was okay and to provide me with any updates. Everyone should only be so lucky to have our travel specialist help plan such a wonderful experience, and I can't wait to work with her again to plan another fantastic adventure!

I greatly enjoyed my two-week trip to Greece, including Athens and four islands.

Zicasso's travel specialist was extremely patient when planning my trip and answering all of my questions. I greatly enjoyed all of the tours she put together, which allowed me to see the Acropolis in Athens, a food walk in Mykonos, a tour of Delos, a guided hike in Paros, a sunset cruise in Santorini, and a tour of Knossos Palace in Crete.

The hotels she booked for my trip were well located and provided a good experience in each island. I definitely recommend Zicasso's travel company for trips to Greece, and also enjoyed my experience dealing with Zicasso!