
Greek Island Hopping Itineraries & Vacation Packages
The Aegean Sea holds a wealth of treasures. Enjoy serene beaches that look out upon azure waters, an ancient history that harkens back to the roots of Western Civilization, and unforgettable cuisine full of tantalizing flavors. From the most popular destinations to lesser-known gems, an island-hopping itinerary from Zicasso will provide you with the perfect Greece vacation.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

8 Day Trip IdeaFrom $3,400
Island-Hopping Tour of Naxos & Santorini With Athens

12 Day Trip IdeaFrom $10,600
Glamorous 12-Day Getaway to Athens, Naxos, Milos, and Santorini

9 Day Trip IdeaFrom $3,900
Spectacular Island Tour of Greece's Charm

13 Day Trip IdeaFrom $5,800
Greek Island Itinerary for the Ages: Crete, Santorini, Milos & More

9 Day Trip IdeaFrom $3,700
Family Friendly Greek Island Hopping Vacation

9 Day Trip IdeaFrom $3,700
A Perfect Greece Vacation Package: Mykonos, Santorini, and More
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
3.Design Your Perfect Journey
Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

9 Day Trip IdeaFrom $3,900
Island Hop Through History: Unique Greek Island Hopping Itinerary

7 Day Trip IdeaFrom $3,000
Greek Island Paradise and Gourmet Gastronomy Tour

12 Day Trip IdeaFrom $5,100
Essential Aegean Gems: Athens, Santorini, Crete and Naxos

8 Day Trip IdeaFrom $3,300
Romantic Greece Vacation: Athens & Island Hopping
More Popular Greek Island Vacations
Reviews of Zicasso's Greek Island Hopping Itineraries & Vacation Packages
Based on 2430 verified traveler reviews.
We have just returned from our week in Greece and it was everything we dreamed of and more! Zicasso’s travel company, from booking to execution, was superb and provided us a stress-free, first-class experience that gave us memories to cherish for a lifetime.
We will absolutely use this travel company again and refer them to friends for any future Greece and/or Italy travel!!
THANK YOU to everyone on the team! Greece has secured a big place in our hearts!
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Our trip was absolutely amazing, thanks to the excellent planning and organization by Zicasso's travel specialist. It provided us with everything from stress-free pick-ups and drop-offs to a variety of experiences with the most wonderful excursions. It far exceeded our expectations. We were kept informed of any changes that happened and all of the guides were wonderful, knowledgeable, and very welcoming. Thank you for providing us with a trip of a lifetime!
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Zicasso’s travel company was fantastic to work with! They immediately responded to our requests and helped us with booking restaurant reservations during the trip. This was a huge help, as we didn't want to waste time on our trip calling restaurants to see what was available. The trip overall was amazing and we enjoyed every minute of it!
The only thing I would call out is that we expected the catamaran tour to be a smaller group than it was. On the itinerary, it was labeled as "small group," which we thought meant around three other couples, so a total of eight guests on the boat. Instead, there were 14 of us and it felt a bit crowded/not as premium of an experience as we were expecting.
Thank you!
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We had a great time! The trip was really well planned. The highlight was the quality of guides Zicasso’s travel company selected. They really helped provide a great experience. We would have liked to have known that the Hagia Sophia was under renovation. Nevertheless, it was a fantastic family vacation.
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It was a pleasure working with Zicasso’s travel company to create a wonderful trip that included a diverse collection of requests that was enjoyed by everyone in the family. We discussed places we wanted to see and overall physical rigor, as well as if we needed breaks in the schedule and the particular interests of each child. They then organized everything, including every transfer and hotel for the entire trip, including mainland Greece, as well as islands (Santorini and Crete), with everything planned outside of flights to and from Greece.
They arranged private tour guides who often were archaeologists who also grew up there, which added additional depth in understanding the historical and cultural relevance of the sights, making it easy to understand for all members of the family. We could not have asked for a more personal and pleasurable experience.
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I knew that visiting Greece would be lots of fun, but Zicasso’s travel specialist (and team) made many suggestions that made it absolutely magical! While I gave her a list of what we wanted to do and to see in Greece (which she provided to us), she also sent me what she would propose if she were going on vacation, which was 50% different. Wow! That made all of the difference and made it a much, much better itinerary and experience than the one that I was contemplating. It also differentiated her suggestions compared with the second travel agency, which also sent me a proposal.
While I'm an experienced international traveler, she made some suggestions that I wouldn't have thought of independently and I loved that her team was accessible 24/7 during our entire visit via Whatsapp. I also appreciate the additional details and suggestions that I received from her team every evening for the next day. I rated the travel company five stars, but if I could, I'd give them 10 stars! Thank you to the team!!!
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