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
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:
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)
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.
Reviews of Zicasso's Referral Service
4.94 stars based on 2452 reviews.
The trip was simply incredible! When I shared with Zicasso’s travel company that I was looking for a trip that combined sightseeing with relaxation, they listened! They planned an incredible trip, with exceptional attention to detail. Nothing was overlooked.
From our driver in Athens to our guides who showed us the archaeological sites and gave us an unforgettable food experience to our incredible driver in Milos!
The travel company was also available every time I messaged them a quick question. Thank you for the best vacation ever!
Reviewed By Dawn K.
We had been waiting over 25 years to take a trip to Greece and this did not disappoint! Zicasso's travel company was in constant communication with us to make sure everything was perfect and we were enjoying our trip.
Reviewed By Sarita G.
I would give Zicasso's travel agency 10 stars if I could! Our travel specialist was fantastic. I connected with her through Zicasso and we had a conversation about what I had in mind for my trip to Greece. She made excellent suggestions, I did a little research on my own, then ended up following all her suggestions, and I'm so glad I did. She was very knowledgeable about Greece and helpful to me in creating the kind of trip I was looking for.
We stayed on the island of Naxos. The hotel was very nice. The excursions our specialist booked for us (a food tour of the island and an all-day boat tour) were just right. The transportation she arranged for us was great. And best of all, she was easily accessible via messaging and always helpful when I had a question or needed guidance or reassurance on any part of the trip.
I loved that she also followed up after our tours and checked in periodically to make sure everything was going well. I really appreciated knowing that I had someone I could reach out to if needed. I highly recommend our great travel agent and really appreciate how she made our trip to Greece go so smoothly.
Reviewed By Mary P.
Zicasso’s travel consultant and his entire team from Zicasso's travel agency were truly spectacular. We spent a long time planning a very involved trip and had many discussions with the travel consultant about very specific needs, wants, and desires long before we stepped on a plane.
We went to Greece and Italy, and all of the hotels, transports, and adventures were as good or better than we imagined. As a family, we were hoping for a trip of a lifetime and that is exactly what we got. He went above and beyond each step of the way. He even joined us one evening in Athens and took us on a private tour of some of his favorite places there!
I cannot thank and recommend him and his team enough. It’s a bit of a gamble planning such an intricate and expensive trip long distance. It was a magical time and all of it was due to the professionalism of the travel consultant. We are forever grateful!
Reviewed By Woody W.
From start to finish, working with our Zicasso travel specialist and her company was an absolute pleasure. The planning process was seamless and once we arrived in Greece, communication was effortless, even while abroad. Every detail was handled with care, resulting in a truly luxurious trip.
The private drivers and tour guides were exceptional—punctual, knowledgeable, and genuinely warm—making every transfer and excursion feel effortless. The hotels were absolutely stunning, each offering unique character and world-class amenities.
One moment that really stood out was when we accidentally left our bathing suits on a hotel balcony in Crete. Without hesitation, our travel company arranged for a staff member to retrieve them, wash them, and ship them all the way back to our home in the United States. This level of thoughtfulness and service went far beyond our expectations.
If you’re looking for a flawlessly coordinated, luxurious, and highly personalized Greek vacation, I can’t recommend this travel company enough.
Reviewed By Brian L.
I would give Zicasso's travel agent and her team 100 stars if I could. The trip far exceeded our expectations. Everyone was so kind, professional, and friendly, and we were supported in every possible way, above and beyond what we expected. It was the trip of a lifetime!
Reviewed By Erinn R.
