The blue lagoon village Veli Losinj on sunny day in Croatia.
30,000+ Verified Traveler Reviews

Two Week Mediterranean Itineraries

A vast array of ecosystems, cultures, and experiences can be found in this special place on Earth. From ancient monuments and island paradises to amazing cuisine and colorful landscapes, a two week Mediterranean itinerary from one of Zicasso’s travel specialists will be a vacation unlike any other. Your exploration of this incredible region is made better through a personalized trip.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Santorini, Greece

14 Day Trip IdeaFrom $7,000

Gems of the Mediterranean: 14-Day Italy and Greece Tour

Rome, Florence, Venice, Athens, Mykonos +1 more
Ancient theater in Delphi, Greece

14 Day Trip IdeaFrom $5,700

Two-Week Greece Tour: Wine, History & Legends

Athens, Cape Sounion, Delphi, Spetses, Epidaurus +7 more
Bridge and river in Toledo, Spain with the Alcazar fortification in background

14 Day Trip IdeaFrom $5,500

Immersive 2 Weeks in Spain Tour: History, Culture & Food

Barcelona, Montjuic, Eixample, Tarragona, Valencia +13 more

14 Day Trip IdeaFrom $6,300

14-Day Ultimate Italy Highlights Tour

Naples, Rome, Vatican City, Castelli Romani, Tuscany +11 more
St Mark's Basilica in Venice, Italy

14 Day Trip IdeaFrom $6,300

Luxury Italy Tour in 14 Days

Milan, Como, Venice, Florence, Pisa +19 more
Cathedral of Palermo in Italy

14 Day Trip IdeaFrom $6,300

Two-Week Highlights of Southern Italy Tour

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 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. 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. 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.

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4.9

Reviews of Zicasso's Two Week Mediterranean Itineraries

Based on 1204 verified traveler reviews.

Greece Luxury Tour Review: Athens, Crete, Santorini, Mykonos, Delos, Historical Sites, Local Cuisine, Sunset Catamaran Cruise
"Zicasso’s trip planner and her company provided my wife and me with the ultimate Greek vacation. I would definitely recommend her and her company."

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Greece Trip Review: Crete, Chania, Athens, Santorini, Naxos, Villages, Private Guides, Hiking, Wine Tasting, History, 2 Weeks

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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Greece Tour Review: Athens, Mykonos, Santorini, Horseback Riding, Food Tours, 10 Days

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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The Netherlands, Greece, Switzerland, Croatia Travel Review: Athens, Venice, Amsterdam, Basel, Dubrovnik, Split, 19-Day Tour

Our trip was fabulous. The cruise from Athens to Venice was nice, but we much preferred the one from Amsterdam to Basel. This one was much nicer and just more intimate and welcoming. The staff were excellent.

Zicasso's travel agent did a wonderful job planning our pre- and post-cruise itinerary.

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Greece Solo Vacation Review: Athens, Mykonos, Santorini, Crete, Acropolis, Minoan Civilization, Museums, 10 Nights
"I very highly recommend the services of Zicasso’s travel company for a wonderful, memorable trip to Greece."

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Greece Tour Review: Athens, Naxos, Santorini, Crete, Cuisine, RIB Experience, Cooking Class. 10 Nights

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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