Cappella di Vitaleta on the hills of Val d'Orcia in Tuscany, Italy.
37,000+ Verified Traveler Reviews

Italy & Greece Trip Planner

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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Beautiful windmill villa in Oia, Santorini, Greece

15 Day Trip IdeaFrom $7,500

Highlights of Greece and Italy Tour

Naples, Sorrento, Isle of Capri, Pompeii, Rome +7 more
San Marco Square in Venice, Italy

14 Day Trip IdeaFrom $13,700

Romantic Getaway to Italy & Greece

Venice,  Lake Como, Cinque Terre, Florence, Santorini
Architecture of landmark Duomo in Florence, Italy

16 Day Trip IdeaFrom $8,000

Tale of Two Empires: Italy & Greece Historical Tour

Rome, Vatican City, Trastevere, Pisa, Florence +9 more
Romantic Santorini island at sunset, Greece

12 Day Trip IdeaFrom $5,200

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

Athens, Santorini, Florence, Vatican City, Venice +1 more
Colorful town of Varenna on Lake Como, Italy

22 Day Trip IdeaFrom $9,400

Adventure and Romance Tour of Italy & Greece

Venice, Lake Como, Bellagio, Portofino, Italian Riviera +5 more
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

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 Italy & Greece Trip Planner

Based on 1938 verified traveler reviews.

Greece Tour Review: Athens, Peloponnese, Santorini, Messinia, Voidokilia, Pylos, Methoni, Monemvasia, Nafplio, Mystras Castle, Polylimnio Waterfalls, Elafonisos, Olive Oil Tasting, Hiking, 10 Nights

We had a wonderful and memorable trip to Greece, thanks to the Zicasso travel specialist’s excellent planning. In addition to exploring Athens, she designed a seamless road trip across the Peloponnese Peninsula that took us to beautiful beaches and ancient castles in Messinia, Voidokilia, Pylos, Methoni, Monemvasia, and Nafplio. She also provided clear directions and recommended great stops to break up our drives, including Mystras Castle and the beautiful Polylimnio Waterfalls.

Our hotel accommodations were excellent throughout the trip and we really enjoyed our stay in beautiful Santorini. We also appreciated her restaurant recommendations, which saved us from having to search for places to eat and always led us to great food. She stayed in touch via WhatsApp the entire time, checking in on us and answering our questions whenever they came up. There is so much to see in Greece that we’ll definitely need to go back for another visit.

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Italy Travel Review: Venice, Florence, Tuscany, Cortona, Sorrento, Amalfi Coast, Capri, Pompeii, Rome, Vatican, Lagoon Boat Trip, Wine Tasting, Cooking Class, 2 Weeks

Our 16-day trip through Venice, Florence, Tuscany, Sorrento and the Amalfi Coast, and Rome was outstanding in every detail. Every transfer ran on time, every guide was knowledgeable and warm, and every hotel was a great choice.

Our favorites were the private lagoon boat trip in Venice, the Brunello wine and cheese tour, the pasta class at a Tuscan farm, Pompeii, the Capri cruise, and the Vatican tour. We couldn’t have asked for better planning or support. We highly recommend Zicasso's travel company.

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Greece Travel Review: Athens, Epidaurus, Nemea, Nafplion, Olympia, Nafpaktos, Delphi, the Temple of Poseidon, Naxos, Santorini, Crete, 3 Weeks

We visited Athens, Epidaurus, Nemea, Nafplion, Olympia, Nafpaktos, Delphi, the Temple of Poseidon, Naxos, Santorini, and Crete in 20 days. Our tour guides were exceptional, all hotels were exceptional except for a minor hiccup in one, and all of our drivers were fantastic. We enjoyed learning about the many ancient civilizations in Greece, including the Mycenaeans, the Minoans, and the ancient Greeks. We enjoyed the Venetian architecture in the islands and the diversity of Santorini.

The travel company, I think, picked the best available hotels and the best available tour guides and drivers. Not every transfer was perfect. There were about three instances where a driver did not meet us due to an incorrect pickup location or incorrect name, or there was confusion about whether we had tickets to one event. But the tour company was available on WhatsApp and responded within 15 minutes when problems occurred. The problems were resolved shortly afterward.

I do not believe there are any trip itineraries that are executed perfectly. In our case, the weather played a role in canceling one excursion and delaying our departure from Naxos to Santorini. While we were on Naxos, strong winds were persistent day and night, forcing the ferry service to cancel rides. Our last day in Naxos did not feel like a vacation. But the tour company commiserated with us, getting us on the last ferry off of Naxos and speaking with us on the phone about our options.

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Italy Trip Review: Sorrento, Naples, Capri, Cooking Class, Boat Ride, Bike Tour, 8 Nights

We had an amazing trip to Sorrento, Naples, and Capri. The tours and people were wonderful. Everything was planned out by Zicasso's travel specialists and not overdone or overbooked. We had an amazing trip and are grateful. Thank you!

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Italy Tour Review: Sorrento, Pompeii, Capri, Amalfi Coast, 2 Weeks

We had a beautiful week in Sorrento, with days in Pompeii, Capri, and the Amalfi Coast. Zicasso’s travel specialist planned the trip exactly as we discussed and we loved every minute!

The one thing that was a bit challenging was that all of our excursions were booked under my middle name, which I do not use, and we had to explain several times to the trip operators.

The hotel was lovely, our room was perfect, and the pool was excellent. Unfortunately, there was a very long ramp required to walk up and down every time we left the hotel, and even though all of the rest of the hotel was excellent, we would have preferred a little less of a distance from the lobby to the street. These items were not at all a big deal, but we are learning what sorts of things to be sure to discuss when planning the next trip.

The travel company was very responsive throughout the trip and communicated with us regularly, which we appreciated!! Overall, I highly recommend this trip and can't wait for the next one!

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Italy Vacation Review: Sorrento, Capri, Naples, Amalfi, Positano, Path of the Gods, Boat Excursion, 9 Days

Zicasso's travel specialist did an amazing job coordinating our trip to the south of Italy. Having our transportation coordinated entirely by her made our time in three different towns (Sorrento, Capri, and Naples) so smooth and stress-free. We had amazing excursions planned privately for us that made great memories.

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