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 2538 verified traveler reviews.
We traveled to Greece in September 2025 for an 18-day trip to five locations. We went through Zicasso and were paired with the primary travel company and the local partner. I cannot express how wonderful our trip was. It was apparent that every detail was carefully tailored to meet all of our wants and needs. From the transfers to the tours, and the hotel accommodations and locations, everything about it was just perfect! Highly recommended if you want a worry-free trip.
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It was an excellent experience. Zicasso's travel designer worked with me every step of the way to plan an ideal trip.
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Zicasso's travel company was an absolute joy to work with. Our travel expert and her team listened to every bit of information we shared regarding what we were looking for in a trip to Greece. No one else paid as close attention.
The hotels, tours, and transportation were exceptional. They were always on time and delivered what they promised. The 24/7 concierge service we received was awesome, no matter how insignificant our questions were. They stayed on top of things that might impact our travel, like a strike, and communicated with us and made new arrangements efficiently. We would give more than five stars if we could.
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Zicasso's travel company was wonderful to work with and super-responsive. Our trip ticked all of the boxes; small island to large, relaxation and history, restful boutique hotels to our personalized stay on an olive farm.
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We were very pleased with our recent travel experience with Zicasso's tour company. Their communication was excellent, keeping us updated and responding to our questions quickly. The trip was well organized, smooth, and carefully planned. The destinations were unique and thoughtfully selected, making the itinerary memorable. We highly recommend this company to anyone seeking a hassle-free and unforgettable travel experience.
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Zicasso's travel specialists did an excellent job. We loved the hotel in Santorini.
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