Greece Sailing Adventure: 8-Day Island Explorer

What to expect on this itinerary
This 8-day Greece cruise through the stunning paradise of islands has been handcrafted for those in search of a laid-back approach to travel through the use of a comfortable sailing boat equipped with all the modern luxuries. The Greek archipelago has long attracted visitors with its historical legacy and pristine beaches. From Athens to Santorini, enjoy the breathtaking views and ancient ruins that make this location so unique.
Customizable Itinerary
Poros – A Stunning Seascape
A veritable paradise of sandy beaches, volcanic rock formations, and charming villages, the Greek archipelago offers visitors an excellent way to enjoy its abundant supply of history and rich culture while never straying too far from the comfort of a cabana or beautiful vista. You will embark into this charismatic seascape on your cruise today as you depart the port of Athens and make your way to the Agia Marina. Here, you can visit an ancient Greek temple before arriving at the southern section of the Saronic gulf and your destination for the day of Poros.
What's Included:
Kythnos – Perusing the Peloponnesus
Mykonos – The Island of the Winds
Paros – The Island that Time Forgot
Milos – Milos' Volcanic Origins
Folegandros – The Rugged Paths of Folegandros
Ios – The Cycladic Islands
Santorini – The Site of an Ancient Eruption
Trip Highlights
- Stand in the shadows of the ancient ruins on Agia Marina, where visitors are greeted by the rustic ruins and scenic beauty of one of the island's best-preserved archaeological sites
- Enjoy the quiet beauty of Hydra and explore its principal village where cars and motorized vehicles are forbidden
- Witness the ample evidence of the oldest known Mesolithic settlement on the island of Kythnos, which time seems to have forgotten
- Stroll along the picturesque paths of Mykonos and pay a visit to the beautiful balconies of the neighborhood known as Little Venice
- Pay a visit to the original source of utility power on the Island of the Winds as you enjoy the historical perspective of Mykonos' iconic windmills
- Visit the sacred ruins at Delos, which many still consider to be a spiritual center in addition to being one of the Mediterranean world's best-preserved archaeological sites
- Survey the sights of a semi-submerged caldera from the slopes of Santorini, where, in the 16th-century BC, a massive eruption created the current island chain
Starting Price
$7,800 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 656 reviews
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.
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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.
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We had a very good trip to Greece with Zicasso's travel specialist. We traveled to Athens, Mykonos, and Santorini with a group of six (three couples). They did a good job of finding nice and convenient hotels in each location, and we were also pleased with the Acropolis tour, food tours, and catamaran trip we took during the week.
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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.
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Overall, we had an absolutely amazing trip to Greece and Croatia to celebrate our postponed honeymoon. Zicasso’s travel specialist was a joy to work with. Her communication was excellent from start to finish, and she really tried to get to know us as a couple to better plan the perfect trip!
Once we arrived in Europe, she checked in with us via WhatsApp every day, making sure our travels were going to plan and we were enjoying our time. We traveled to Athens, Mykonos, and Santorini in Greece, and Dubrovnik, Split, and Krka National Park in Croatia. Our trip was filled with history, nature, crystal-clear waters, private tours, and lots of adventure.
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I originally reached out to Zicasso to find a travel agent to handle our two-week trip to Greece. Zicasso provided me with three travel company options and, after speaking with each, I decided to work with this travel company. The travel specialist turned out to be the best decision I could have made.
Our travel specialist and the travel company team were absolutely amazing and thorough. We planned the trip for me, my wife, brother, and sister-in-law. Every step of the planning process was informative and the travel specialist gave us her best advice leading up to the trip. She answered many of our questions and researched the things we wanted to do while in Greece.
Once we were on the trip, we communicated almost daily with the travel specialist and she remained readily available. She was extremely responsive. It was always a relief during transfer pick-ups to see the travel company’s signs, so we knew who to connect with.
Our two-week Greece adventure through Athens, Mykonos, Santorini, and Crete was perfect, and we could tell that the work the travel specialist and the team put in ensured that success. This was a vacation dream of a lifetime, thanks to the travel specialist, the travel company, and Zicasso.
Kudos to Zicasso for recommending the travel company at the beginning and I would highly recommend Zicasso and our travel company to anyone interested in traveling to Greece.
Gratitude and appreciation to all for a trip we will never forget!!!!
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