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

Santorini, Greece

What to expect on this itinerary

Discover history, culture, and natural beauty during your two-week best of Italy and Greece tour. From the Colosseum in Rome to the Parthenon in Athens and from Venice’s canals to Santorini’s Caldera, you will have an experience that immerses you in over 3,000 years of Western Civilization and contemporary luxury. Specialized guided tours, private transfers, and gorgeous accommodations help bring the best of the Mediterranean to light.

Countries Visited

Greece, Italy

Places Visited

Rome, Florence, Venice, Athens, Mykonos, Santorini

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

Rome – Introductory Tour of Rome

Historic Rome collides with contemporary culture as the layers of ancient, medieval, Renaissance, and Baroque architecture rise above the cobblestone streets. Your flight will land at Fiumicino Airport, where your private transfer will greet you at customs and escort you to your accommodation. After you settle in to the comforts of your new surroundings, your guide will meet you in the lobby to lead you on an immersive monuments tour, beginning with the Trevi Fountain. The water will trickle into the waiting pool as you find the iconic image of Oceanus at the heart of the fountains.

What's Included:

Transfer
Accommodation
Tour
Day 2

Rome – Ancient Rome and the Vatican

Day 3

Rome – The Appian Way and Borghese Villa

Day 4

Florence – Historical Tour of Florence

Day 5

Florence – Renaissance Art and Cooking Class

Day 6

Venice – Padua and the Brenta Canal

Day 7

Venice – Venice’s Charms and History

Day 8

Athens – Immersive City Tour of Athens

Day 9

Athens – The Islands of Hydra and Poros

Day 10

Mykonos – A Day for Self-Exploration

Day 11

Mykonos – Delos’ and Mykonos’ Beaches

Day 12

Santorini – Oia and a Sunset Cruise

Day 13

Santorini – History and Wines of Santorini

Day 14

Santorini – Depart for Home

Trip Highlights

  • Embrace the Renaissance when touring the preserved grandeur of Michelangelo’s Sistine Chapel
  • Delight in the immersive history of Athens on a private tour that brings you to the remarkable Parthenon
  • Witness the breathtaking detail of Michelangelo’s David during a private tour of the Accademia Gallery
  • Sample the authentic flavors of Italy and the special ingredients of Tuscany with a private cooking class in Florence
  • Find elements of the divine when visiting the ruins of ancient Delos, which is the birthplace of Apollo and Artemis
  • Bask in the beauty of the unique red sand of Santorini when enjoying a sunset cruise
  • View the enchanting design and embodiment of the history of St. Mark’s Basilica when discovering the treasures of Venice
  • Traverse the beauty of the Brenta Canal to view elegant villas that possess unique artistic details
  • Discover the depth of history in Santorini on a private tour of Akrotiri, which is a Minoan civilization that has been preserved under layers of volcanic ash
  • Experience the spirit of Florence on a private walking tour that uncovers the particular layers and characteristics of the Renaissance city

Starting Price

$7,000 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.

4.9

Verified Traveler Reviews

Based on 7801 reviews

Vicki P.
Greece Tour Review: Athens, Santorini, Mykonos, History, Culture, Tradition, Local Cuisine, Shopping, 8 Nights

If you're considering a trip to Greece, look no further than Zicasso. Our travel expert planned an unforgettable journey for our family; Athens, Mykonos, and Santorini, and every detail was executed with care, expertise, and passion. 

From the moment we arrived in Athens, we were immersed in the country’s warm hospitality. Our agent made sure we had the perfect balance of sightseeing and relaxation. The historical sites in Athens, like the Acropolis and the ancient Agora, were must-sees.

Mykonos is vibrant yet relaxed. The beaches were beautiful. Every meal on this trip was a highlight. Fresh seafood, local cheeses, olive oil, and delicious pastries—each bite told a story of Greece’s deep culinary heritage.

In Santorini, we were captivated by the island’s charm—whitewashed buildings, breathtaking sunsets, and the deep blue Aegean Sea. We visited traditional villages, giving us a glimpse into the rich cultural traditions that are still very much alive.

Throughout the trip, what stood out most—beyond the stunning landscapes and ancient history—was the friendliness of the Greek people. Their warmth and pride in their culture made every moment feel welcoming and genuine.

Our agent didn’t just plan a vacation—he created an experience rooted in history, tradition, and hospitality. I can’t recommend him and Zicasso highly enough.

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Chris T.
Greece Vacation Review: History, Culture, Biking, Cuisine, Beaches, Olive Oil Experience, Family Time, 2 Weeks

We had an amazing experience working with Zicasso's travel specialist and her company's team for our two-week trip to Greece. The itinerary was thoughtful, family-friendly, and beautifully balanced, with just the right mix of cultural experiences, local flavor, recreation, and downtime. It was clear from the start that a great deal of care and collaboration went into planning this journey and the result was a trip perfectly suited to our family. Every stop, activity, and transition reflected a deep understanding of what would engage and inspire us.

What truly set our tour company apart was the exceptional Traveler Care team. Throughout the entire trip, they were consistently attentive, warm, and impressively responsive, often going above and beyond, even outside regular hours. Their real-time guidance and reassuring presence gave us complete peace of mind, allowing us to fully relax and enjoy the journey without ever feeling uncertain or unsupported.

We never once felt unsure or alone while navigating a multi-stop itinerary across several islands and regions. Thanks to the travel company, we were able to focus entirely on what mattered most: being present and making lifelong memories with our children.

If you’re planning a trip to Greece and want something truly unforgettable — not just a vacation, but a seamlessly orchestrated, soul-stirring, memory-making journey — you must work with this company! They took the time to truly understand our family and crafted an experience that felt uniquely ours at every step. Their combination of deep local expertise, personalized care, and flawless execution is nothing short of world-class. Every family should be so fortunate — the company is, quite simply, in a league of its own.

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Grace B.
Italy, Greece Honeymoon Review: Culture, Cuisine, Snorkeling, Cooking Class, 12 Nights

My husband and I went through Zicasso to plan our honeymoon to Italy and Greece. This was the best decision ever! We worked closely with our travel specialist to plan our trip and she was absolutely phenomenal. This was our first international trip outside of the US, so we were a bit nervous at first! However, our specialist ensured every aspect of the trip was organized and that we were taken care of every step of the way.

The biggest relief was transportation. We did not have to give a second thought as to how we were getting places; we had drivers set up at every destination and for nearly every activity. Also, we had 24/7 support if anything were to go wrong, which gave us peace of mind.

If you are hesitant to use Zicasso for your next trip, I want you to know that I was too, but it was the best decision! We were able to personalize and tailor our trip to our needs without the hassle of dealing with the details.

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Tom O.
Greece Travel Review: Athens, Nafplio, Paros, Food Tour, Cooking Class, Private Catamaran Ride, Fortress, 12 Nights

Our Zicasso travel specialist and the team were great; helpful, immediately available when needed, and they ensured everything was as planned. The trip was wonderful, with great diversity in accommodations, activities, and locations. We really loved our time.

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Cristie S.
Greece Vacation Review: Santorini, 15-Day Trip

I cannot recommend Zicasso's trip planner enough for her exceptional travel planning services! As frequent travelers, with experience working with various travel agents, we can confidently say she is by far the best we’ve ever encountered. From the very beginning, she took the time to learn our likes and dislikes, crafting a personalized itinerary that perfectly suited our preferences.

She coordinated a dream trip for us to Greece, planning two completely different weeks for our vacation. The first week was spent touring classical Greece, where we were fortunate to have a university professor as our tour guide, enriching our experience with incredible insights. The second week included a beautiful journey through the stunning islands of Greece. Every detail was planned exceptionally well and we felt fully taken care of throughout our trip.

In the past, we’ve faced issues with travel agents, where things fell through once we were on vacation. However, that was never the case with her. She was personally available to contact during our trip, which proved invaluable when our flight was delayed. In fact, she even helped us extend our trip by a day with only four days left, allowing us to visit Santorini, which was a highlight of our journey!

Her passion for her work shines through in every interaction. She genuinely cares about her clients and possesses amazing knowledge of travel destinations. Trust her and her recommendations to take care of your travel needs, and you will not be disappointed. Thanks to her for an unforgettable trip of a lifetime!

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komal P.
Italy, Malta Trip Review: City Tour, 20 Days

I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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