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 3137 reviews
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!
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Zicasso's travel expert was very professional. She answered all my questions promptly and made sure to book the tours and hotels that fit our needs. Highly recommend.
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Our 11-day honeymoon in Greece was nothing short of magical—and we owe so much of that to our Zicasso travel specialist and the entire team at her company. From the very start, they worked within our budget and offered a flexible payment plan that made planning feel manageable and stress-free.
As our trip approached, we had a thorough planning call with our specialist. She walked us through every detail of our itinerary, which completely put us at ease. That level of preparation meant we could focus on enjoying the moment instead of worrying about logistics.
Once we landed in Athens, the travel company was just a WhatsApp message away. Anytime we had a question—no matter how small—they responded within minutes. That kind of real-time support made us feel cared for the entire time.
The accommodations they booked were absolutely out of this world. Each hotel felt handpicked just for us—luxurious, romantic, and incredibly welcoming. It was clear the company has strong relationships with local vendors because we were treated like royalty everywhere we went.
As a gay couple, we also appreciated how safe, inclusive, and celebrated we felt throughout the trip. Every detail was thoughtfully planned with us in mind.
We’d recommend our travel company 1,000 times out of 10. If you're planning a gay honeymoon—or any trip to Greece—look no further. This was truly the trip of a lifetime.
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Zicasso's travel specialist and her company did an amazing job of planning the most incredible and memorable trip for my family of five.
Every detail was meticulously thought out and perfectly executed. Every transfer was spacious and, thankfully, air conditioned. Each boutique hotel booked was unique and beautiful, with stunning views and amenities offered. Every excursion with English-speaking guides was incredible. The guides were knowledgeable and super-friendly.
We can't thank our travel specialist and her team enough for this amazing trip. We have memories for a lifetime!! I highly recommend using her for your next trip to Greece or Europe.
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It was our family's first time visiting Greece. We've always wanted to see the country and there were so many good things we'd heard about Greece.
There were a couple of things that made this trip very special. First, our youngest daughter's request for her 16th birthday was to go as a family and celebrate it in Greece. Second, none of us had ever been to Greece (on our previous trips, either my husband and/or I had been there or it was our family's second time there), so experiencing it together for the first time was really special.
Zicasso gave us two very good Greek travel companies. Both presented interesting itineraries to us. It was a year of planning and I'd gone back and forth with both travel companies with revisions of itineraries and, of course, the cost.
What made us choose this travel company was that the specialist was very honest, upfront, and very accommodating. He gave his honest opinion when I asked him about certain excursion activities or even restaurants (social media makes it really look good, especially for people who have not been there), and he did not pressure or force us into doing activities that did not interest us. He wanted to make sure we got to experience the best, but he was also very mindful of the costs. I had many back and forth conversations with him via texts, emails, or phone calls. He wanted to get to know our family. When I told him about our daughter's 16th birthday requests, he made sure he got every detail of what would make her birthday special. He also asked me about the interests of our eldest daughter because he wanted to surprise her with something special from Greece. That says a lot about the travel specialist and his company; they are personal and it's not just pure business for them.
A few days before we left the US, he called us so we could reschedule our flights (Santorini to Athens) to an earlier time going back home because he was concerned we may miss our connecting flights. Who does that? This just shows he checks every detail and wanted to make sure that even before we left the US, up to the time we arrived back home, everything was taken care of.
We had the best vacation in Greece. We did not worry about anything the entire time. The travel company was in constant communication with us. They created a WhatsApp group chat which made it so much easier. They gave us daily reminders and they arranged everything for us. We felt that the entire trip was customized for our family. The "Mamma Mia" island tour and birthday celebration for our daughter was perfect. The restaurant in Kolios was a great recommendation, and when I asked him to reserve the specific table and have a little birthday decoration for my daughter, it was accomplished.
Chania was amazing; both me and my husband loved this place. The view from our hotel room on Zampeliou Street, overlooking the old harbour and the Cretan Sea with the lighthouse, was breathtaking. We enjoyed walking through the streets of the Old Town of Chania.
We thought Santorini would be overcrowded, but we had a great tour guide who knew where to take us first to avoid crowds, and he gave us really helpful advice to go around the island. He took us to the little hidden alleys and showed how locals live. We ended up really loving the island.
We enjoyed every activity planned for us. We enjoyed our stay at our hotels. Mine and my husband's favorite were the hotel in Kalamata and the one in Chania. We really liked the view of the Acropolis from our rooms at the hotel in Athina, and that hotel was very convenient. We also enjoyed their breakfast there. The girls enjoyed the hotel in Skiathos because of how close it was to the beach, and they loved the "Mamma Mia" boat tour.
We each have our own favorite activities/tour/tour guides, but overall, our family had an amazing time in Greece – the way the travel agent and the entire team did a phenomenal job. The way the itinerary was put together and the timing for each place/island was just perfect for us. They exceeded our expectations. We fell in love with Greece, the culture, and the people, who were all so kind, nice, and very hospitable (not once did we have a bad encounter). We will definitely go back; there is so much more to explore and we'll definitely be working with this travel company in the future.
We only have good things to say about our Greece vacation and we highly recommend this travel agency. We've been to other countries and worked with other travel companies. In our opinion, this one was the best travel company we've ever worked with.
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Zicasso's travel agent took great care of my family, planning an excellent trip, with revisions based on our interests, and was quick to respond to my emails. He took care of the necessary arrangements when the ferry was unexpectedly cancelled.
We stayed in beautiful hotels and enjoyed our tours with knowledgeable guides and drivers. Our trip to Delphi and Meteora was a highlight of our trip. We had a great driver there.
Highly recommend!
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