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 2565 reviews
We had a fantastic trip, in large part because of the planning assistance and execution by Zicasso's travel company!
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We have used Zicasso twice to find local travel agents in Greece. Two different trips, the first to island hop and the second to concentrate on Crete. Both agencies we ended up working with were excellent! We could not have been more pleased.
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Working with Zicasso’s travel company was a wonderful experience, from the initial intake of my request to brainstorming ideas to fit my budget and itinerary, and prepping us for every day of our honeymoon. Every single guide and vendor they booked for us was absolutely wonderful. I would recommend them without hesitation!
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If I could give them more than five stars, I would. I cannot recommend Zicasso's tour operator enough!!! Our agents were amazing and created the most perfect honeymoon for my husband and I!! We went to Paros, Santorini, Crete, and Athens and loved them all. It was amazing not to have to worry about a thing. We had zero issues and we had the best time.
We went to wonderful restaurants and beautiful hotels, had two fun boat trips, a beautiful tour throughout Kissamos, Crete, and the best tour guide for the Acropolis/Athens.
If you want an amazing trip with beautiful memories and zero worries, I would absolutely use this tour operator!!!
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Our trip was wonderful!!! I can't say enough about Zicasso and our travel specialist. She planned our trip so perfectly, based on our interests and requests. She had so many useful tips and suggestions that helped us tremendously throughout the trip! Everything went very smoothly and according to plan, right down to the last detail. There was not one issue or hiccup; something I have never been able to say very often after travel! The accommodations, tours, tour guides, transportation arrangements, drivers, etc., were all amazing.
My family and I are beyond pleased with everything and would not hesitate to use Zicasso or the travel company for any future travel plans. Thank you so much to our travel specialist!!!
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This trip was amazing! Zicasso's travel company took care of every detail. They created a wonderful itinerary and coordinated it seamlessly. They communicated with us all along the way; there was absolutely nothing amiss from the first day to the last.
Our accommodations were wonderful. Our guides were top-notch, incredibly experienced and knowledgeable, and all very enjoyable people. They felt like friends almost immediately! Each of them went above and beyond to make sure our experiences were everything we hoped for and more! Our drivers were attentive and professional as well.
We're seasoned travelers, but we couldn't possibly have planned and executed this trip on our own. We're so appreciative of the travel company's excellent staff and services. They created a trip that we'll remember forever.
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