Enchanting Three Week Island Tour of 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.
Customizable Itinerary
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:
Santorini – Oceanside Yoga
Naxos – Naxos’ Island Treasures
Paros – Paros, Parikia, and Lefkes
Mykonos – Scuba Dive and Couples Massage
Mykonos – The Mystique of Mykonos
Mykonos –Delicious Island Fare
Milos – The Kleftiko Caves
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)
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 759 reviews
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.
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Zicasso's travel company made our bucket-list trip to Greece come to life! They organised all our tours and transportation, worked with us to provide activities that were in line with our interests, and even gave detailed information on suggested itineraries for our free days.
Some highlights included the walking tour(s) of Athens, our trip to see Santorini, and the best steak I have ever had at a beach hotel in Naxos! Our only suggestion is that we went on a day tour to Delos which was self-guided. There is so much history there though that a guided tour would have been helpful. I would definitely recommend booking your tour with them!
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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.
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Zicasso's travel planner and her company gave me one of the most phenomenal vacations I have ever had. This trip can be labelled as the trip of a lifetime. She had every detail completed.
Our flights, our transfers, and our ferry tickets were waiting for us at the hotel front desk on every island. We had incredible tours set up, with the most incredible tour guides. We laughed, drank, ate, and celebrated in the most decadent locations in Naxos, Santorini, Crete, and Athens.
We encountered only one hiccup and she was on it within minutes of receiving my email. She stood by her word and solved my issue with professionalism and expedited the correction. I cannot emphasize enough how awesome she is. I cannot wait to plan my trip for next year. I highly recommend her and her company. Thank you for the lifelong memories!!!! You're the best!!
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