
2 Week Greece Itineraries & Tours
Indulge in a vacation that encompasses a lavish lifestyle. Savor fine food and wine, unwind on pristine island beaches, and get lost in your imagination when you encounter Greece’s enchanting ancient history. From Athens to Crete, your ideal 2-week Greece vacation starts with Zicasso’s local experts. Design your perfect Aegean getaway today.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

14 Day Trip IdeaFrom $5,700
Greece Island Explorer: Crete, Naxos, Mykonos & More

16 Day Trip IdeaFrom $14,000
Luxurious Cultural Greece Tour: Athens, Nafplio, and More

14 Day Trip IdeaFrom $5,700
Epic Culinary Tour of Aegean Flavors

15 Day Trip IdeaFrom $6,200
Spirit of Greece Tour: History, Grandeur & Romance

14 Day Trip IdeaFrom $5,700
Delights of Deities: Greece Cultural Tour

14 Day Trip IdeaFrom $5,900
The Great Aegean Escape: Greece & Turkey Vacation
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.

14 Day Trip IdeaFrom $5,700
Two-Week Family Vacation: Myths & Wonders of Greece

14 Day Trip IdeaFrom $5,700
Two-Week Greece Tour: Wine, History & Legends

14 Day Trip IdeaFrom $5,700
Mainland & Island Hopping Greece Adventure Tour

13 Day Trip IdeaFrom $11,500
2-Week Luxury Tour of Mainland Greece
Reviews of Zicasso's 2 Week Greece Itineraries & Tours
Based on 513 verified traveler reviews.
This was a dream vacation made reality–five stars!
We just returned from the most unforgettable two-week adventure through Greece, all thanks to the exceptional planning and care of Zicasso's travel operator and her team! From the moment we landed until our final farewell in Athens, every detail was flawlessly executed.
Our journey began in Crete, where we were welcomed by a warm, knowledgeable guide who brought Chania's rich history to life during all of our many activities. From touring the many villages to hiking Imbros Gorge to the Palace of Knossos, we felt immersed in the true spirit of Crete.
Next was Santorini, where the sunsets were just as magical as we’d hoped. Our stay was filled with stunning cliffside views, wine tastings, and personalized recommendations that made it feel like we were exploring the island with a local friend.
Naxos was an unexpected gem—less touristy, but bursting with charm. The tour guide here was particularly fantastic, taking us to authentic villages, ancient ruins, and serene beaches that felt like our own private paradise.
Our final days in Athens were the perfect ending to this epic journey. The historical sites were breathtaking and our guide’s passion for Greek history made every moment at the Acropolis and the museums feel deeply meaningful.
What truly set this experience apart was how responsive and supportive our agent and her team were throughout the trip. Any time we had a question—whether about transportation, recommendations, or small changes in plans—they replied quickly and helpfully, making us feel completely at ease and well cared for.
Throughout the trip, the logistics were seamless—beautiful accommodations, smooth transfers, and thoughtfully curated excursions. Every guide was not only professional and knowledgeable, but also incredibly kind and engaging. It felt like we were traveling with friends who truly cared about our experience.
We can’t thank our agent enough for crafting such a memorable and enriching vacation. Greece was always on our bucket list and now we’re already dreaming of our return!
Highly, highly recommended!
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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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Fabulous, Fantastic, Fun! We had an absolutely amazing 10 days traveling in Athens, Naxos, Santorini, and Crete. We were traveling with four 20somethings with varied interests. Zicasso's tour planner listened to my description of what we were looking for and created a masterpiece of a trip!
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This was my husband’s and my first trip to Greece and, like any incredible country, it was so tough to decide what to see and do. Luckily, we found Zicasso's tour specialist and, suddenly, our dream trip became a reality. She worked with us for about a year to customize an itinerary that met all our needs, while introducing us to hidden gems we might never have discovered on our own.
We spent 11 unforgettable days exploring Athens, Delphi, Nafplio, and the island of Naxos. Each day was thoughtfully planned, offering a fantastic mix of excursions, dining experiences, and cultural activities. From touring breathtaking archaeological sites to indulging in cheese and olive tastings, taking an amazing cooking class, and visiting the Citron distillery, every experience was uniquely special. Despite the busy schedule, we still had plenty of time to wander, soak in additional sights, and relax on Naxos' stunning beaches.
What truly set this trip apart was the exceptional service. The drivers were friendly and polite, and our tour guides were so knowledgeable and so engaging, making us feel at home in each destination. Wherever we went, the guides enriched our experience with captivating insights and expertly answered all our questions. Their warmth and professionalism made us feel completely at ease.
Once we arrived in Greece, her team remained incredibly accessible. When a flight delay between Naxos and Athens Airport put our connection at risk, we reached out to her. She and her team immediately arranged for someone to meet us at the Athens airport, helping us navigate smoothly and ensuring we caught our flight.
They truly went above and beyond to ensure that our trip was fun, enriching and seamless! We highly, highly recommend this tour company.
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