Ultimate Three Week Greek Island Vacation

The Temple of Demeter in Naxos, Greece

What to expect on this itinerary

This 3-week Greek Islands tour will allow you to immerse yourself in their luxurious allure and relaxing atmosphere. Witness Santorini from the unique vantage point of a private helicopter, choose from a variety of watersports in Mykonos, embark on a sailing trip to Sikinos, and indulge in the delicious fare that the Greek Islands have to offer.

Countries Visited

Greece

Places Visited

Mykonos, Santorini, Naxos, Paros, Ios, Milos

Suggested Duration

21 Days

Customizable Itinerary

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Day 1 - 2

Santorini – Land, Air, and Sea

When you arrive in Santorini, a private driver will be waiting to greet and transfer you to your accommodation in the heart of the city. Upon your arrival, you will have some time to relax and settle in after your long flight. When you are ready, your guide will lead you on a sunset dinner cruise. The following morning, you will go on a thorough tour of the island’s highlights. Afterward, your guide can provide you with excellent dining recommendations so that you can tuck into some authentic Greek fare.

What's Included:

Transfer
Accommodation
Tour
Breakfast
Day 3 - 4

Santorini – Morning Yoga Session

Day 5 - 6

Naxos – The Stunning South Coast

Day 7 - 8

Naxos – Island-Hopping

Day 9 - 11

Paros – Paros & Antiparos

Day 12 - 14

Ios – Private Wine Tour

Day 15 - 16

Mykonos – The Wonders of Mykonos

Day 17 - 18

Mykonos – Views from the Sky

Day 19 - 20

Milos – The Kleftiko Caves

Day 21

Milos – Departure

Trip Highlights

  • Witness Santorini from above during an private helicopter tour
  • Explore Naxos and the Cyclades Islands and make your way among idyllic island havens
  • Discover the unique island gems of Parikia and Naoussa on a tour of Paros and Antiparos
  • Sightsee by speedboat before escaping to Sikinos for a wine tour
  • Snorkel, swim, and sightsee among the shores of Mykonos
  • Escape to Milos and learn how to create an authentic Greek meal from a local chef during a private cooking course
  • Discover the Kleftiko Caves and set sail on a luxurious excursion
  • Sample the best flavors of Milos during a gourmet gastro tour
  • Embark on an island-hopping adventure to Sikinos for a wine tour
  • Glide along the sea on a sunset dinner sail

Starting Price

$23,900 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

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.

4.9

Verified Traveler Reviews

Based on 618 reviews

Greece Anniversary Vacation Review: Athens, Mykonos, Santorini, Crete, Catamaran Cruise, Cooking Class, Wine Tasting, Hiking, Local Cuisine, 2-Week Trip

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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Greece Trip Review: Athens, Mykonos, Santorini, Crete, 12 Nights

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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Greece Tour Review: Athens, Paros, Antiparos, Naxos, Santorini, Crete, Olive Oil Tasting, Wine Tasting, 18 Days

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!

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Greece Vacation Review: Athens, Santorini, Paros, Naoussa, Pottery Class, Sunset Cruise, Cooking Class, Beaches, Water Sports, 13-Day Trip

We thoroughly enjoyed our 13-day trip (June 8-21) to Athens, Santorini, and Paros, Greece, with our three grandchildren (ages 16, 14, and 12). Planning our dream trip was so easy with the help of Zicasso's travel specialist! We were super-impressed with his pre-trip planning. He took the time to gather information about us and our grandchildren to plan the perfect trip, taking into account our interests and travel expectations. It was especially beneficial to have his expertise as a long-time resident of the area.

From accommodations to tours to transportation, everything was perfectly planned and executed. The few mishaps we experienced were addressed immediately. It was wonderful to have the digital itinerary he prepared on all of our devices, so each participant could see and read about what we would be doing each day! We had access to the travel company's team 24/7 if we needed to contact them (which we did) and they were very attentive to our requests. I would highly recommend this travel company!

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Greece Vacation Review: Athens, Naxos, Santorini, Acropolis, Wine Tasting, 11-Day Trip

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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Greece Trip Review: Athens, Crete, Chania, Santorini, Paros, Ferry Ride, Wine Tasting, 12 Nights

We loved our Greece trip and had so much fun with our activities. Of the referred travel companies from Zicasso, we gravitated to this travel company because of its personal attention to detail regarding our vacation wishes. Our travel specialist took the time to listen and tailored an itinerary that captured our interests. It did not disappoint. This was our second trip through Zicasso and, as with the first, the guides, drivers, and support were on point.

The travel company lined up excursions with the nicest and most engaging people. From our arrival at the airport, they made us feel welcomed and special. We went to the head of the line again and again, and avoided much wasted time. The guides and drivers were genuinely glad we were there and our enjoyment was of the utmost importance. They always seemed to go above and beyond expectations with the knowledge they imparted and the amount of personal attention they provided.

In general, we found the people of Greece to be so nice and that really made the difference on this trip. Need a restaurant suggestion, just text our guide, as he was always right. Need a reservation, just text the travel company through WhatsApp and it was made. We are still texting a couple of the guides for additional information and recommendations for friends traveling to Greece.

Traveling by boat was one of the best decisions we made. The overnight ferry from Athens to Crete was an unexpected pleasure, and we would recommend it over air travel anytime, as it was very relaxed. Chania was engaging, Santorini was beautiful, and Paros was the ultimate place to chill out before traveling home.

We can't stop talking about how much fun we had in Greece. Thank you, the travel company, our travel specialist, and Zicasso. We will be in touch about our next adventure!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

32,000+ Verified Traveler Reviews