Cappella di Vitaleta on the hills of Val d'Orcia in Tuscany, Italy.

Italy & Greece Trip Planner

Ratings of Zicasso's Service

The draw of the Mediterranean is palpable, from the ancient mythology and intriguing culture to delectable cuisine and enchanting landscapes. With the Italy and Greece trip planner from Zicasso, you can have your dream vacation brought to life by local specialists. When you submit a trip request, your fantasy will be encapsulated with the aid of an expert.

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    Describe your dream trip.

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    We match you with top travel specialists. They compete to plan your vacation.

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    Book the trip when you are satisfied.

Ratings of Zicasso's Service

Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Beautiful windmill villa in Oia, Santorini, Greece

Highlights of Greece and Italy Tour

15 Day Custom Tour

From $3,925

Footsteps on cobbles, aromas of coffee, back street pizzerias, and whitewashed villages are the charms that seal your experience across Italy and Greece. This highlights tour brings many of the iconic sights including Rome, Athens, Capri and Mycenae, your handcrafted selection of destinations will evoke the small pleasures that make these countries so unique while Sorrento, Naples, Nauplia and Santorini all provide their distinctive atmospheres and pleasures.

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Scour the romantic streets of Venice, from Saint Mark’s Square, to the labyrinthine streets

Romantic Getaway to Italy & Greece

14 Day Custom Tour

From $3,663

You can never have enough romance on this 14-day tour through Italy and Greece meant for honeymooners and passion seekers, lovers and explorers, adventurers and romantics. Spend your days traversing cities that have inspired passion; landscapes take your breath away and the luxuries rejuvenate your soul. Traverse Italy’s vibrant coasts and stunning countryside, along with Greece’s majestic island, where each city offers you a unique treasure to take with you, hiding within the dreamy quality of the architecture and sea, the hills and the sunset, making your fantasy come to life.

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Architecture of landmark Duomo in Florence, Italy

Tale of Two Empires: Italy & Greece Historical Tour

16 Day Custom Tour

From $4,187

From the Pantheon to the Parthenon, Florence to Venice to Olympia, this is a journey to the heart of empire and civilization. You will explore places that changed the world, including the oldest Greek ruins and medieval Tuscany. Immerse yourself in the atmosphere of cities that live and breathe history. Lose yourself in archaeological sites and the redolent wonder of ruins. These are the countries of legend, and this two-week journey will take you far back in time.

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Romantic Santorini island at sunset, Greece

From Eros to Cupid: A Romantic Tour of Greece and Italy

12 Day Custom Tour

From $3,139

Ancient Greeks had words to describe different kinds of love while Italians can declare their passion in hundreds of different ways. Express your love with a grand romantic gesture of a custom-tailored Greece and Italy tour that will provide you both with the perfect outlet for your affections. Enjoy both a sunset cruise around Santorini and a sumptuous meal in a Venetian villa. Wander the hidden orange orchards together and find a little cozy little cove for a rest as you explore the Vatican City. Whisper sweet infatuations beneath the striking image of Venus and be in awe together as you stand underneath the grandeur of Michelangelo’s Sistine Chapel.

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Colorful town of Varenna on Lake Como, Italy

Adventure and Romance Tour of Italy & Greece

22 Day Custom Tour

From $5,759

Lose yourself in luxury, history and romance as you effortlessly drift through Italy and Greece on this three-week tour. Beginning in the Venetian canals, we lead you through the hearts of opulence in Lake Como and the Italian Riviera before you find yourself at peace on the whitewashed island of Santorini in the Aegean Sea. Complemented by authentic Tuscan feasts and quiet seaside Italian towns, this three-week tour will reveal all that is magical, timeless and positively cherished in these two quintessential European countries.

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Santorini, Greece

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

14 Day Custom Tour

From $3,845

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.

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Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.

Helpful Content

Reviews of Zicasso's Referral Service

4.89 stars based on 133 reviews.

Travel Review: Spain, Greece, & Italy Birthday Trip,...
"Robert definitely went above and beyond with keeping the...

Reviewed By Ashley a.

Italy, Greece & Egypt Trip Review: 2-Week Honeymoon...
"Mary Bai was phenomenal to work with. I highly recommend...

Reviewed By Brooke G.

Italy, Greece, & Turkey Travel Review: Istanbul, Vatican,...
"I would recommend this travel agency and Zicasso to anyone...

Reviewed By John H.

Luxury Italy & Greece Vacation Review: Cinque Terre,...
"Highly recommend this travel company for your next trip...

Reviewed By Brian G.

Italy & Greece Family Vacation Review: Sailing the Aegean...
"Our travel agent was wonderful to work with!"

Reviewed By Lara S.

Travel Review: Italy & Greece Vacation, Tuscany, Rome,...
"Our travel agent thought of everything"

Reviewed By Cynthia B.