Two-Week Greece Tour: Wine, History & Legends

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.

This was one of the best-organized trips my wife and I have taken in Europe. Zicasso had put us in touch with Zicasso's travel specialist. She called us to ask about the dates, interests, islands we wanted to see, sights, etc. She formulated a travel plan including hotels, transfers, and tours (including food tours). We discussed the plan, chose hotels based on our budget, and finalized a tour plan with her.

Right from the moment we arrived at Athens airport, everything was taken care of for us. We had a limo waiting, even though it took time to go through the EU's new immigration system. Our hotel in Athens was right next to the city center, with a beautiful Acropolis view from our balcony. The room was comfortable and spacious, and ready when we arrived at 2 pm. Our travel specialist even suggested a restaurant to celebrate our anniversary and made reservations for us, as we were unable to do it online.

The next day, we had a tour of the Acropolis conducted by a professional tour guide. It was a good two-hour walking tour and we enjoyed it very much. The tour guide was very knowledgeable, took time to explain the history, which we are interested in, and also took some amazing pictures for us. We had free time to go to the city center to shop and try out some of the Greek taverns.

From Athens, we went to Mykonos by ferry. Ferry tickets were sent on a WhatsApp group chat created by her. Our limo came at the designated time and our ferry trip was easy and very enjoyable. On arrival, our limo was waiting to take us to our hotel in Mykonos, located on top of the hill, with a balcony overlooking the central area and a scenic sea view. It was easy to go down and see the shops, windmills, Little Venice, and explore the city center that day. Nighttime was party night, with almost everything open late.

The next day, we had a private Jeep tour of the island. We went to different parts of the island to explore. Our driver and tour guide were very thorough and patient, and it was a very enjoyable tour.

The following day, we were taken by a tour bus to the port, where we went on a private tour of the Delos and Rhenia islands. The tour guide was very knowledgeable and pointed out the sights of an ancient civilization. Lunch on the boat was basic, but on the whole, it was a very informative tour.

We then left for Santorini by ferry. Again, ferry tickets arrived a day before on WhatsApp. We requested an upgrade from basic tickets to Club Class/Platinum Class for the rest of the tour, which was immediately arranged and payment was accepted by credit card. In Santorini, we stayed at our hotel, which had a beautiful view from the balcony and the breakfast was superb, made to order, with the rooftop restaurant having spectacular views of the caldera. It was just awesome! In the afternoon, a tour guide took us in a van and showed us the sights, including the Three Bells of Fira. We did not have to wait anywhere, as the guide knew exactly how and where to go to see the sights and take photos. We learned a bit of history of the island.

The next day, we had two wine-tasting tours, first to a premium vineyard and then to the oldest winery in Santorini. Our tour guide and van arrived on time everywhere for a well-conducted and planned private tour.

On the third day, we went on a semi-private sunset cruise to the volcano, hot springs, and beaches. It was a well-conducted tour with a BBQ on the boat! The crew even accommodated my shellfish allergy by cooking the chicken before cooking the seafood on the BBQ. The food was good and, more importantly, the crew was friendly and very caring. The crew members took some beautiful pictures of us against the spectacular Santorini sunset.

We left for Crete the following morning by ferry. Everywhere, we had private transfers waiting to take us and we did not wait anywhere to be transferred. In Heraklion, we were staying at our hotel in the city center and therefore had access to some very nice traditional Greek restaurants where the locals went for dinner. The following day, we had a private tour of Knossos Palace with a very friendly and knowledgeable tour guide. On our return, our limo was waiting for us to take us to Chania in Crete.

Our journey to Chania took us two hours and was very informative and enjoyable, as our driver pointed out a number of sights on the way. Our check-in at our hotel in Chania was quick and efficient. The hotel even sent us a bellboy to the drop-off point (cars are not allowed inside) to help with our luggage. The hotel room was spacious and had a balcony overlooking the waterfront, the lighthouse, and all the restaurants in the area. The next day, we were taken on a private olive oil tour and, in the evening, a food tour with a tour guide who spoke seven languages and knew the city inside and out!

The following day, a private limo and a private boat took us to Glyka Nera, Loutro, and Marmara. We were able to swim and see some of the beautiful azure-blue water and sights, again in the company of the same tour guide from the previous night. Lunch in Marmara was exceptional. At no time during this tour were we rushed and everything moved at a very easy pace. We checked out from the hotel the following morning for a flight to Athens. The hotel manager helped us with our luggage to the pickup point. Boarding passes were sent on WhatsApp and our check-in and travel were smooth. Everything went like clockwork. Our limo was waiting on arrival and we were taken back to our hotel in Athens, where we stayed the night before our travel home the following day.

At all the sites we visited, our travel specialist even suggested some restaurants to try. These were special in their own ways and not touristy. This tour was very detailed, meticulously planned, and executed by her and the team, who kept in touch with us every day throughout the tour to make sure we had a great time. Thank you for making this a memorable, special, and personalized tour.

This was our 35th-anniversary celebration trip and, thanks to Zicasso's travel specialist and the team, it was a memorable trip for us.

Excellent! Everything was meticulously planned. All of our tours were very interesting and the drivers were courteous. We went to Athens, Naxos, and Santorini during our 11-day trip. Overall, I think our favorite place was Naxos, with Athens and the Acropolis being second, although the weather that morning was not the best. But our guide was excellent and kept us engaged while fighting rain and wind. As I mentioned, all the drivers and guides were excellent and I would highly recommend this trip. Santorini was beautiful too and the wine tour was extremely interesting. We highly recommend Zicasso.

Our trip to Greece was exceptional, thanks to the careful planning by our travel company! They had every detail planned out and made sure we were well taken care of.

I traveled with my husband (50s) and my parents (80s). We had a general idea of some places we wanted to see and told the travel planner our interests. She ran with it and planned us the perfect trip for the pace we wanted and the types of experiences we were looking for. She suggested places that weren't even on our radar and they fit perfectly with our interests.

Our trip was 12 days, broken up into four nights in Chania, Crete, three nights in Santorini, and four nights in Athens. This was the right amount of time in each place (though my husband said he could spend a week in Santorini just to relax).

The travel planner met us at the airport and gave us a burner phone for our use during the trip, as well as a packet with tickets and boarding passes that we would need. The phone was very helpful because it had an app with our itinerary for each day, as well as contact numbers for her, drivers, tour guides, etc. This was great because we had what we needed at our fingertips and didn't have to pay for an international plan on our cell phones.

Each location we went to offered very different experiences.

Chania, Crete, was fantastic and my personal favorite spot. Our travel planner recommended it and I'm so glad she did. It was rich with history and culture, without feeling like a tourist trap.

Santorini: When we first arrived, it was a bit of a jolt because all the buildings are white and boxy (only the churches have blue roofs), and I was missing the color and vibrance of Chania. We went into Fira while we waited for our rooms to be ready and it was a total tourist trap, with people swarming around and souvenir shops and fast food restaurants. I was wondering if it was a mistake to come to this island. However, once we were settled into our hotel and saw the spectacular views and experienced the calmness, I understood why people come here. The nature and beauty won me over (and I just avoided the cities).

Athens was amazing because of the history and hospitality of the people. Everyone was so welcoming and kind. The ruins do not disappoint and we marveled at how they were just everywhere in Old Town.

Delphi: We took a day trip from Athens to Delphi and toured the ruins and museum, and had a wonderful lunch overlooking the mountains and valleys.

We went on several incredible tours during our trip. Two food tours (Chania and Athens), three archaeology/ruin-focused tours (Santorini, Athens, and Delphi), one tour of the mountains in Chania, and one sunset catamaran boat ride in Santorini. Every one of them was unique and interesting.

Our travel planner arranged several lunches and dinners for us. Each place was outstanding and the views were spectacular. We would just tell them we were with the travel company and they gave us the best seats in the restaurants and outstanding service.

We could not have asked for a more perfectly planned out trip!

The itinerary is not the best for the price we paid and for a family with two children. We thought we could come back to Greece, but after this trip, we might not come back or even use Zicasso again. Here are the reasons: 1. The hotels are subpar for the price we paid for this tour. Our hotel in Athens felt like a 2-star. Our hotel in Santorini has a great view, but it's just a view, no pool, etc. nearby. Our hotel in Crete is not near a beach, a 20-minute walk. 2. Too much time was wasted on travel from one location to the next (Santorini to Crete and Crete to Athens). 3. Four nights in Santorini with two children is overkill since there is not much to do other than take photos, hike, and that's basically it. 4. Some of the tours are okay but nothing special, i.e., the hiking tour in Crete where they call the "little forest" is merely just for the name. It has nothing to do with the tour guides. All tour guides are great. However, we feel the tour company is crafting ordinary tours, labels it special, and calls it private. 5. In Delphi, we could have had more time to look around after the two hours. If any of the tours were great, it was the tours we had in Athens and Delphi. If we had known this type of tour we received, we could have done an all-inclusive resort in Greece and done our own without having to go through Zicasso and the tour company.

This was a dream vacation made reality–five stars!

We just returned from the most unforgettable two-week adventure through Greece, all thanks to the exceptional planning and care of Zicasso's travel operator and her team! From the moment we landed until our final farewell in Athens, every detail was flawlessly executed.

Our journey began in Crete, where we were welcomed by a warm, knowledgeable guide who brought Chania's rich history to life during all of our many activities. From touring the many villages to hiking Imbros Gorge to the Palace of Knossos, we felt immersed in the true spirit of Crete.

Next was Santorini, where the sunsets were just as magical as we’d hoped. Our stay was filled with stunning cliffside views, wine tastings, and personalized recommendations that made it feel like we were exploring the island with a local friend.

Naxos was an unexpected gem—less touristy, but bursting with charm. The tour guide here was particularly fantastic, taking us to authentic villages, ancient ruins, and serene beaches that felt like our own private paradise.

Our final days in Athens were the perfect ending to this epic journey. The historical sites were breathtaking and our guide’s passion for Greek history made every moment at the Acropolis and the museums feel deeply meaningful.

What truly set this experience apart was how responsive and supportive our agent and her team were throughout the trip. Any time we had a question—whether about transportation, recommendations, or small changes in plans—they replied quickly and helpfully, making us feel completely at ease and well cared for.

Throughout the trip, the logistics were seamless—beautiful accommodations, smooth transfers, and thoughtfully curated excursions. Every guide was not only professional and knowledgeable, but also incredibly kind and engaging. It felt like we were traveling with friends who truly cared about our experience.

We can’t thank our agent enough for crafting such a memorable and enriching vacation. Greece was always on our bucket list and now we’re already dreaming of our return!

Highly, highly recommended!