Sailing around Kleftiko Bay in Milos Island, Greece

Ultimate Three Week Greek Island Vacation

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Customizable Itinerary

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

Countries Visited


Places Visited

Mykonos, Santorini, Naxos, Paros...

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Suggested Duration

21 Days

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

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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

Detailed Description

Your handcrafted Greek Island escape will begin in Santorini, where you will enjoy three days of exploration. On your first day, you will be treated to an enjoyable tour of the island’s highlights. The following day will then find you flying among the clouds in a helicopter on a private sightseeing tour. You will then have a day on a yacht, which will allow you to swim, snorkel, and more. Your final day in Santorini will be filled with a private oceanside yoga session and a catamaran cruise to Nea Kameni Island.

Day five will have you heading to Naxos, where you will enjoy three days. During your time on the island, an expert guide will make sure that you thoroughly explore it. On the morning of day nine, you will make your way to the island of Paros. Here, you will enjoy several days of exploration and enjoy the wonders of Parikia, Naoussa, and Antiparos. You will even be treated to an authentic cooking class with a local chef.

Ios’ idyllic shores will be your next destination. Here, you will spend your first day sightseeing the island on a speedboat tour. The following day will then find you embarking on an island-hopping adventure to Sikinos for a wine tour. On day fifteen, you will make your way to Mykonos. For your first evening on the island, you can enjoy a sunset dinner sail. The following day, you will witness the island’s best sights with a local guide before participating in a private cooking class. The following day, you will take a private helicopter ride above Mykonos before a tour of the South Coast.

On day nineteen, you will transfer to Milos. Upon your arrival, you can enjoya private yoga session before venturing on a food tour of the island. Your final day will provide you with a sailing excursion to the Kleftiko Caves.

Starting Price

$5,455 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

The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.

Reviews of Zicasso's Referral Service

4.92 stars based on 1103 reviews.

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