Cappella di Vitaleta on the hills of Val d'Orcia in Tuscany, Italy.
31,000+ 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 1757 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 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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Italy Trip Review: Venice, Amalfi, Capri, Sorrento, Pompeii, Rome, Colosseum, Roman Forum, 12 Days

Italy was fantastic! We visited Venice, Amalfi, Capri, Sorrento, Pompeii, and Rome.

Zicasso’s travel specialist was knowledgeable and patient with me when planning the trip. She was amazing at taking in the information I shared about my family and creating an itinerary that worked well for our family of five (our three children, ages 20, 20, and 22), including food-allergy limitations.

The chosen tours and tour guides were incredible, knowledgeable, engaging, attentive, thoughtful, and a pleasure with which to spend the day or half-day.

When we were in Italy, our travel specialists quickly responded to inquiries and to new requests for transportation needs resulting from unanticipated and good “extra” opportunities.

I highly recommend the travel company and our travel specialists.

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Greece, Croatia Honeymoon Review: Athens, Mykonos, Santorini, Dubrovnik, Split, Krka National Park, Acropolis, Elaphiti Islands, Wine Pairing, 2 Weeks

Overall, we had an absolutely amazing trip to Greece and Croatia to celebrate our postponed honeymoon. Zicasso’s travel specialist was a joy to work with. Her communication was excellent from start to finish, and she really tried to get to know us as a couple to better plan the perfect trip!

Once we arrived in Europe, she checked in with us via WhatsApp every day, making sure our travels were going to plan and we were enjoying our time. We traveled to Athens, Mykonos, and Santorini in Greece, and Dubrovnik, Split, and Krka National Park in Croatia. Our trip was filled with history, nature, crystal-clear waters, private tours, and lots of adventure.

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Italy Trip Review: Naples, Amalfi Coast, Sorrento, Capri, Positano, Rome, Boat Ride, Cooking Class, Wine Tasting, Colosseum, 12 Days

I recently completed an incredible 12-day vacation in Italy, arranged by Zicasso’s travel company, and it was one of the best vacations I have ever had. From the initial planning with the travel specialist and her team to the seamless execution on the ground, everything exceeded my expectations for a luxury custom trip.

We started in Italy, where we were immediately met at the airport by a hostess who got us through all the lines in record time and into a Mercedes Sprinter van that took us to Naples. Naples offered us a really vibrant, authentic Italian feel, and the incredible food that the travel specialist recommended from the movie "Eat Pray Love" was the best pizza I’ve ever eaten in my life. I don’t think I can eat pizza in the United States anymore. The private drivers and guides made this whole trip stress-free.

Our next incredible experience was the dream-like Amalfi, Sorrento, and the Isle of Capri. The hotel in Positano was beautiful. We were enchanted with all the colorful cliffs, the boutique shopping, and the stunning view from our balcony room. Sorrento was my favorite city of all. It was very relaxed, with lemon groves everywhere and beautiful sunsets, and our hotel had balconies that opened up on the Mediterranean. The highlight of our trip was the island of Capri. The boat ride was just fantastic and we started at the top of the mountain and did the chairlift so we had a whole view of the city.

The highlights of the trip for me were the boat ride along the Amalfi Coast, the cooking class and wine experience at the female venture, and the wine by Mount Vesuvius.

Our last two nights were back in Rome and it was kind of hard to go from the low-key vibes of Sorrento to the action-packed atmosphere of Rome, but the hotel the travel specialist picked was just perfect. It was 10 minutes from the Spanish Steps and she arranged a tour of the underground Colosseum. I learned so much about everything in that area. All the guides, the drivers, everything was magical. I would highly recommend this travel specialist and the travel company.

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Italy Trip Review: Amalfi Coast, Herculaneum, Vatican, Capri, Pompeii, Naples, Sorrento, Pantheon, Boat Ride, Street Food Tour, History, Culture, Local Cuisine, 10 Days

We had a fantastic time and Zicasso's tour operator did an excellent job organizing every detail of our trip. Drivers and guides were always punctual, and the itinerary was perfectly balanced—full days, without ever feeling rushed.

Some real highlights for us were Herculaneum, the Pantheon, the Vatican, and our unforgettable Capri boat tour. Our guide brought Pompeii's history to life in a way that made it feel like stepping back in time and the Naples street food tour was delicious and nostalgic—her pizza fritta instantly took me back to the calzones I grew up with in Niles, Ohio. Our driver was with us for several days and made every transfer feel effortless.

There was a small hiccup at the very end with a trip planner, but it was minor compared to the overall quality of the trip. The organization, communication, and attention to detail throughout made this a truly memorable experience and we wouldn’t hesitate to book with this tour agency again. We had a fantastic time and the tour company did an excellent job organizing every detail of our trip.

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