Enchanting Three Week Island Tour of Greece

Greek Church in Oia Village in Santorini, Greece

What to expect on this itinerary

This 3-week Greek Islands tour captures the allure and romance for which this region is known. From Santorini and Mykonos, to Milos and Naxos, experience some of the most idyllic island havens the world has to offer. Enjoy a cycling tour through the countryside, venture on a scuba diving excursion, and sail along the southern coast of Mykonos.

Countries Visited

Greece

Places Visited

Mykonos, Santorini, Naxos, Paros, Milos, Delos

Suggested Duration

21 Days

Customizable Itinerary

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Day 1 - 3

Santorini – Hike, Sail, and Sightsee

When you land on Santorini, a private driver will greet and escort you to your luxurious accommodation. Upon your arrival, you will have some time to relax and settle in to your new surroundings after your long flight. When you are ready, your private guide will lead you on an evening hike along Santorini’s caldera rim. The following day will find you setting sail for the Cyclades Islands, where you will sightsee, swim, snorkel. A kayaking excursion will begin your next day and will be followed by a food tour.

What's Included:

Transfer
Accommodation
Tour
Breakfast
Day 4 - 5

Santorini – Oceanside Yoga

Day 6 - 8

Naxos – Naxos’ Island Treasures

Day 9 - 11

Paros – Paros, Parikia, and Lefkes

Day 12 - 13

Mykonos – Scuba Dive and Couples Massage

Day 14 - 15

Mykonos – The Mystique of Mykonos

Day 16 - 18

Mykonos –Delicious Island Fare

Day 19 - 20

Milos – The Kleftiko Caves

Day 21

Milos – Departure

Trip Highlights

  • Witness the wonders of Santorini and embark on an evening caldera hike
  • Sail to the Cyclades Islands to sightsee, swim, snorkel and bask in the sunshine
  • Explore Delos, traverse its ruins, and learn about Greek mythology
  • Partake in a private seaside yoga session in Santorini
  • Enjoy a e-bike tour that will lead you through Santorini’s countryside
  • Indulge in a culinary tour in Mykonos of the island’s tasty delicacies
  • Discover the Kleftiko Caves and stop for a picnic at sunset
  • Scuba dive and sail into the sunset in Mykonos
  • Spend a day snorkeling and sailing along the southern coast of Mykonos

Detailed Description

Your handcrafted romantic Greek Island vacation starts in Santorini with a sunset caldera hike that will leave you breathless from witnessing such stunning beauty. You will spend the following day sailing to the Small Cyclades Islands with a private guide. An exhilarating sea kayak excursion and a gourmet food tour fill your third day in Santorini, and on day four, you will be treated to a morning couple’s yoga session by the sea before wheeling around the island countryside on a scenic bike tour. Your final day in Santorini finds the two of you escaping on a private yacht to while away your remaining hours together, simply relaxing and enjoying each other’s company.

You will make your way to Naxos on day six and spend your first evening visiting a marble quarry and learning how to sculpt marble from a local master. A day trip to Delos awaits on day seven, followed by a private luxury cruise to the outer islands on day eight.

Departing Naxos on day nine, you will journey to Paros and be led on a lovely walking tour of charming Naoussa town. The following day, you will be introduced the the highlights of the island, including the picturesque locales of Parikia and Lefkes before embarking on a bike ride in the idyllic countryside. Your final day in Paros starts with a sea kayak excursion, followed by a private cooking class taught by a local master chef.

Mykonos awaits your arrival on day twelve, and after checking in to your luxury accommodations, you will enjoy a couple’s massage and candlelit dinner in your suite. Scuba diving and sailing into the sunset are on the agenda for day thirteen, followed by a Mykonos highlights tour and a private wine tasting excursion. A gourmet food tour fills your day sixteen, before you are swept away to sail and snorkel along the stunning South Coast. Your final day in Mykonos will be spent just the two of you on a luxury private yacht, relaxing and basking in one another’s presence in paradise.

Day nineteen finds you journeying to Milos and enjoying a romantic sunset dinner sail, before spending your final hours in this heavenly haven paddling through the pristine seas on a kayak and indulging in a gourmet picnic at sunset after witnessing the Kleftiko Caves.

Throughout your romantic escape, you will stay in luxury accommodations and have every detail of your vacation handled for you, including all private transfers to and from every destination and airport. All that you have to do is pack your bags and get on that plane, together.

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 1384 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! 

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Review: Anniversary Vacation in Greece, Athens, Santorini, Mykonos, Crete, Delos, Knossos Palace, Acropolis Tour, Catamaran Cruise

We booked a 2 week vacation to Greece with this agent and travel company for the end of May.   Our travel agent helped us plan the perfect vacation for our 25th wedding anniversary. It was the most incredible trip, more than we could ever have imagined! She planned accommodations, excursions and tours at each place we visited that highlighted each place.  We started our trip in Athens for 3 nights, Crete 3 nights, Mykonos 3 nights and Santorini for 4 nights.

We were met promptly at the Athens airport by our driver taken to our Hotel in Athens where we were met by our agent personally to give us all of our tickets and instructions for our stay in Greece. As well she gave us a cell phone programmed with her number and the travel agency in case we had any issues during our time in Greece.

We stayed at the foot of the Acropolis in Athens at a wonderful boutique hotel. Our trip started with a private tour(highly recommend)  of the Archeological museum of Athens ,the Acropolis and the area surrounding. Truly specials and unforgettable! A romantic dinner at a beautiful restaurant in the center of Athens.  Watching the sun set on the Acropolis with all of Athens at our feet...stunning. A free day to explore a bit of the ancient and beautiful city then onto Crete.

We were met by a delightful young man, who was our guide for all 3 days on this amazing island. Wine tours, Palace of King Mynos at Knossos, ancient cities Rhethmynon and Chania, beautiful beaches and stunning views. We fell in love with Crete.

Then Mykonos. A beautiful little jewel of an island with beautiful beaches and ancient cities once attacked by pirates. A romantic dinner, tour of the island of Delos (incredible!) and getting lost in the maze of streets that make up Mykonos town.

Then onto Santorini. A jewel in the beauty of the Aegean Sea. Stunning hotel on the cliffs with a view that you never tired of, wine tours, a full day Catamaran sail to beaches and the Caldera ending with a magnificent sunset at Land's End. Santorini was the cherry on top of the trip. Truly a stunning island.

And everywhere we went the friendly, hospitable and welcoming Greek people.  We can't say enough on how well orchestrated this trip was. We had flawless connections, over-the-top accommodations, incredible guides, amazing excursions that did not disappoint at any of our island visits.  "More than we could have ever imagined" is how we describe this trip to friends and family.  We highly recommend this company and the travel agent who planned a trip exactly to fit us personally.

Thank you Zicasso for your stellar travel agents and fantastic job of Jackie who paired us up with such great agents to choose from.

Tanya and Ross

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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.

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Greece Travel Review: Luxury Family Cylclades Islands Tour, Sailboat Trip to Delia & Rhenia, Athens, Views & Olive Oil
Overall it was a relaxing trip very much needed and our travel agent did a splendid job of organizing a great trip. We visited 3 islands in the Cyclades, Mykonos, Santorini and Naxos. Spent a day in Athens. All of the accommodations were top notch! The hotels in Mykonos and Santorini had spectacular views from the rooms and it was well ventilated given the concerns of ventilation during the pandemic. The sail boat trip to Delia and Rhenia was excellent. It was a hot day in Delia but the overall trip made up for it. the trips were well organized given our family's needs and we were very pleased. Would certainly recommend this travel company to anyone else who is contemplating a trip to Greece.

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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! 

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Review: Luxury Greece Vacation, Mykonos, Crete, Santorini, Delos, Chania, Athens, Acropolis, Constitution Square, Knossos Palace

This Greece travel company did a great job setting us up at ideal locations in Athens, Mykonos and Santorini. All were located in the central area, right near the center of each town for shopping and restaurants. The people at the hotels were really nice and everything was very organized that we did not have to worry about anything.

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews