Ultimate Three Week Greek Island Vacation

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.
Customizable Itinerary
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:
Santorini – Morning Yoga Session
Naxos – The Stunning South Coast
Naxos – Island-Hopping
Paros – Paros & Antiparos
Ios – Private Wine Tour
Mykonos – The Wonders of Mykonos
Mykonos – Views from the Sky
Milos – The Kleftiko Caves
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)
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 2570 reviews
Everything was planned according to the itinerary set by Zicasso’s travel specialist and experienced to full pleasure. I cannot express how great of a time I had in Greece, even during the off-season.
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Our trip was incredible! We were so impressed with the professionalism of Zicasso’s travel agent and the guides we had during our tours. Greece has been a long-dreamed-of destination and our time in Naxos, Santorini, and Athens exceeded our expectations. It was an easy process to give some guidance on what we liked to do and have a curated trip for our preferences. We would recommend the travel company to anyone needing help planning a trip!
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We highly recommend Zicasso’s tour operator. They were able to plan a tour for us around the dates we had available. They listened to what we were looking for in our travels and everything was spot-on. Many highlights were unanticipated. Everything was perfect, from our driver to our tour guides and our stay at an olive grove estate. We could not have asked for more. We will definitely use the travel company again.
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After planning a destination wedding, my husband and I were not looking forward to also planning our honeymoon. So we felt so fortunate to work with the lovely travel agents at Zicasso's tour operator.
Our agent and the team at the tour operator made this process so seamless and easy. We were able to clearly communicate our hopes and dreams for our honeymoon and our ideal budget, and she took that and created the most perfect itinerary. The thorough plan was perfect. We especially appreciated the 24-hour white-glove service, where we were able to ask any questions we wanted at any time and someone answered quickly.
I could not recommend them enough! We would not have had the honeymoon of our dreams without the travel company.
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If I could give 10 stars, I would. As an older woman traveling alone, I felt completely comfortable and well cared for throughout the trip, as if I were part of the family of the team at Zicasso's travel company. Every single detail of the complex and densely packed five days in Naxos and four in Athens unfolded perfectly. The travel specialist personally knew a number of the guides, drivers, and restaurateurs, and all spoke glowingly of this travel company.
From sharing honey with bees at a tiny apiary to touring the Acropolis with an archaeologist, to squeezing the whey out of cheese at a family farm and meeting the goats who provided the milk, to hiking from village to village with a guide who knew the name and medicinal use of every plant we passed, to learning to make phyllo dough, it was simply terrific! If you're thinking of visiting Greece, connect with this travel company and enjoy the trip of a lifetime.
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We had a fantastic trip, in large part because of the planning assistance and execution by Zicasso's travel company!
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