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 579 reviews
See more
This was a dream vacation made reality–five stars!
We just returned from the most unforgettable two-week adventure through Greece, all thanks to the exceptional planning and care of Zicasso's travel operator and her team! From the moment we landed until our final farewell in Athens, every detail was flawlessly executed.
Our journey began in Crete, where we were welcomed by a warm, knowledgeable guide who brought Chania's rich history to life during all of our many activities. From touring the many villages to hiking Imbros Gorge to the Palace of Knossos, we felt immersed in the true spirit of Crete.
Next was Santorini, where the sunsets were just as magical as we’d hoped. Our stay was filled with stunning cliffside views, wine tastings, and personalized recommendations that made it feel like we were exploring the island with a local friend.
Naxos was an unexpected gem—less touristy, but bursting with charm. The tour guide here was particularly fantastic, taking us to authentic villages, ancient ruins, and serene beaches that felt like our own private paradise.
Our final days in Athens were the perfect ending to this epic journey. The historical sites were breathtaking and our guide’s passion for Greek history made every moment at the Acropolis and the museums feel deeply meaningful.
What truly set this experience apart was how responsive and supportive our agent and her team were throughout the trip. Any time we had a question—whether about transportation, recommendations, or small changes in plans—they replied quickly and helpfully, making us feel completely at ease and well cared for.
Throughout the trip, the logistics were seamless—beautiful accommodations, smooth transfers, and thoughtfully curated excursions. Every guide was not only professional and knowledgeable, but also incredibly kind and engaging. It felt like we were traveling with friends who truly cared about our experience.
We can’t thank our agent enough for crafting such a memorable and enriching vacation. Greece was always on our bucket list and now we’re already dreaming of our return!
Highly, highly recommended!
See more
If you're considering a trip to Greece, look no further than Zicasso. Our travel expert planned an unforgettable journey for our family; Athens, Mykonos, and Santorini, and every detail was executed with care, expertise, and passion.
From the moment we arrived in Athens, we were immersed in the country’s warm hospitality. Our agent made sure we had the perfect balance of sightseeing and relaxation. The historical sites in Athens, like the Acropolis and the ancient Agora, were must-sees.
Mykonos is vibrant yet relaxed. The beaches were beautiful. Every meal on this trip was a highlight. Fresh seafood, local cheeses, olive oil, and delicious pastries—each bite told a story of Greece’s deep culinary heritage.
In Santorini, we were captivated by the island’s charm—whitewashed buildings, breathtaking sunsets, and the deep blue Aegean Sea. We visited traditional villages, giving us a glimpse into the rich cultural traditions that are still very much alive.
Throughout the trip, what stood out most—beyond the stunning landscapes and ancient history—was the friendliness of the Greek people. Their warmth and pride in their culture made every moment feel welcoming and genuine.
Our agent didn’t just plan a vacation—he created an experience rooted in history, tradition, and hospitality. I can’t recommend him and Zicasso highly enough.
See more
We had a wonderful time in Greece. We spent 10 days there and went to Athens, Mykonos, and Santorini. The accommodations were great and the planned excursions were fantastic. The weather was perfect.
See more
We had a wonderful experience with our Zicasso travel specialist while planning our vacation in Greece. We had a group that consisted of two families; in total, eight people. Our travel specialist gave us recommendations based on the types of activities we wanted to do and the types of islands we were hoping to experience.
We stayed two nights in Athens, three nights on Naxos, and three nights in Santorini. The accommodations were fantastic! Every tour guide and driver was helpful and so kind.
When we wanted to add a stop in Naxos for an impromptu lunch, our guide was happy to detour and bring us to a place with the best gyros that the locals really enjoy! Everyone made us feel at home. Thank you for a beautiful trip and all the lovely memories!
See more
Zicasso's travel specialist went above and beyond to curate a fantastic, scenic, exciting, and restful vacation for us and was sure to provide us the best possible accommodations at each destination (Athens, Mykonos, Santorini). We didn't have to worry about one single detail for the entire trip as all of our transport was covered, we had a local contact in each location, and all hotels were pre-paid and perfect. We loved every single second of the trip and would absolutely recommend our specialist for anyone seeking a wonderful visit to Greece!
See more





