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

Expand All
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

$19,200 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 1362 reviews

Luxury Vacation Review: Greece, Crete, Naxos Villages & Winery, Mykonos, Santorini, Athens, History
I consider myself a traveler but had never been to Greece before and wanted to ‘do it right’. I had a three week timeframe to spend in the islands.  Of course Mykonos and Santorini were on my list and I looked to this travel team for additional recommendations.  They suggested Crete and Naxos.  It was a wonderful and interesting mix.  From our Acropolis tour in Athens, authentic Naxos tour of villages and winery, every detail was meticulously tended to and this travel team checked in with me multiple times throughout my journey.  All transfers and guides were timely, knowledgeable and very nice people. Several of the guides felt like friends by the time we concluded.  The travel planner of this team was responsive to my inquiries and did a very good job of delivering the best Greece had to offer! 

See more

Travel Review: Luxury Honeymoon in Greece, Naxos, Crete, Athens, Mykonos, Santorini, Archaeology, History, Food & Wine

This travel agent is fantastic! She was super friendly and extremely easy to work with. Using them again on our next trip is a no brainer. If you have the opportunity or interest, we strongly suggest visiting Greece, it was simply amazing and WAY better than we could have ever imagined. We visited Athens, Crete, Santorini, Naxos, and Mykonos. Each was awesome in their own right, Athens for the history and archeological sites. Crete, for the fresh food, wine, and olive oil. Santorini, for the amazing sunsets, villages, and the beautiful water. Naxos, for it's authenticity and beaches. Mykonos, for it's night life and entertainment.

See more

Luxury Greece Group Vacation Review: Athens, Greek Islands, Walking Tour, Markets, Olives
The trip planner was remarkable! Our 10 days met or exceeded our expectations. His intimate knowledge of the islands and tours available ensured we received outstanding service and interesting outings. We had a group of 6 adults - transportation was timely and comfortable. Tour guides in Athens, Santorini and Naxos were all wonderful. This was no cookie-cutter experience. Each guide asked questions and altered the tours to meet our needs. Our accommodations were excellent also. The hotel in Athens gave wonderful views and easy walks to Parliament, shopping/restaurants and the Acropolis. The vacation rental on Santorini was in the perfect location - central, excellent views of the sea and island. The staff was extremely helpful with reservations and local transportation. Our hotel in Mykonos was beautiful and walking distance from the port, windmills, etc. We all agreed the entire trip was great, but Naxos was our favorite part. We met locals, could drive freely/safely, and the beaches are beautiful. I must add that the customer service provided by our planner went way above the norm. When a member of our group left valuables in a room safe in Athens - not only did our trip planner coordinate pick up, he also arranged for the items to be hand delivered to Naxos. AMAZING! 

See more

Greece Luxury Vacation Review: Mykonos, Paros, Santorini, Athens, History, Culture, Catamaran Cruise, Local Cuisine, 10 Nights

I recently had the pleasure of experiencing the most unforgettable vacation with my family, all thanks to the exceptional planning and coordination by Zicasso’s travel agent. Our trip to Greece, covering the beautiful islands of Mykonos, Paros, Santorini, and the vibrant city of Athens, was nothing short of magical.

Mykonos: The Perfect Start. Our journey began in Mykonos, where we were greeted with stunning beaches, charming alleys, and vibrant nightlife. The accommodations arranged by our agent were luxurious and perfectly located. We loved exploring the iconic windmills, Little Venice, and indulging in the local cuisine.

Paros: A Hidden Gem. Next, we ventured to Paros, which quickly became a favorite. The island’s serene beaches and picturesque villages offered a more laidback atmosphere. The boutique hotel we stayed in was charming and welcoming, with fantastic views and excellent service. Our agent's recommendations for a semi-private all-day catamaran cruise made our stay in Paros even more special.

Santorini: A Romantic Escape. It was everything we imagined and more. The breathtaking sunsets, iconic white-washed buildings, and crystal-clear waters were simply stunning. Our agent ensured we had the best views, with our accommodation perched on the caldera’s edge. The private wine tour and morning cruise they arranged were highlights of our trip, offering unique experiences that we will cherish forever.

Athens: A Historical Finale. Our trip concluded in Athens, where we immersed ourselves in the rich history and culture of Greece. From the awe-inspiring Acropolis to the bustling streets of Plaka, every moment was captivating. Our agent’s detailed itinerary allowed us to maximize our time, ensuring we didn't miss any of the key attractions. The guided tours provided deep insights and made our experience even more enriching.

Overall Experience: From start to finish, our agent exceeded our expectations. Her meticulous planning, attention to detail, and personalized recommendations made our trip seamless and memorable. Every flight, ferry, transfer, tour, and accommodation was perfectly coordinated, allowing us to relax and enjoy our vacation to the fullest.

We can’t thank her enough for making our dream trip to Greece a reality. We highly recommend the company’s services to anyone looking to explore the wonders of Greece. This was truly a once-in-a-lifetime experience that we will cherish forever.

Thank you to our travel company for an extraordinary journey!

See more

Greece Luxury Travel Review: Athens, Mykonos, Naxos, Santorini, Acropolis, Sunset Catamaran Cruise, 10 Nights
"We had the most amazing trip. The Zicasso travel agency was top-notch, with every detail meticulously planned and implemented flawlessly."

See more

Greece Travel Review: Athens, Milos, Santorini, Mykonos, 10 Nights
We really enjoyed our trip to Greece and the entire itinerary in Athens, Milos, Santorini, and Mykonos. The transfers and activities were conducted in a timely and pleasant manner, and the accommodations were also wonderfully planned! We were so happy with Zicasso and the agent. We can't wait to plan our next trip!

See more

Customizable Itinerary

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

28,000+ Verified Traveler Reviews