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

What to expect on this itinerary
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.
Customizable Itinerary
Athens – Arrive in the Enchanting Historical Center of Athens, Greece
Athens is a city of philosophy and ancient wisdom with a modern edge. Lively cafes line streets that are paved with marble while the white stones featured on the facades of historic structures shine in the light of the Mediterranean. The fabled Parthenon crowns the Acropolis, viewable from around the city below. Your private transfer will greet you upon your arrival and drive you into the city. The savory aroma of olives drifts from the groves that grow around the edges of Greece’s largest city while the bittersweet scent of Greek coffee drifts from the open doors of the small cafes.
To settle into the charms of the city and Greek life, you will first make your way to Kolonaki, a neighborhood in the center of the city along the southern slopes of Lycabettus Hill. Shop windows offer quiet delights in the form of elaborate displays of bags, clothing, and shoes while the jewelry glistens in the fading sunlight on Voukourestiou Street. The scent of tangy feta and xynotyro fill the cheese plate accompanying the aromas of plum and sour cherry emanating from your wine glass as you toast to one another and the weeks ahead.
What's Included:
Athens – Relish a Full Day Spent Exploring the Ancient History of Athens
Santorini – Travel to Santorini for the Romantic and Inviting Ambiance
Santorini – Delight in a Sunset Cruise and Dinner around Santorini
Santorini – Relax with a Day of Romance and Charm at your Leisure
Rome – Travel to Rome for a Passionate Evening Tour of the Historic Sites
Rome – Visit the Ancient Wonders of Rome and Capitoline Hill
Rome – Traverse the Splendors of Vatican City and the Borghese Gardens
Florence – Venture to Florence for a Full Day of Renaissance and Romance
Venice – Enjoy the Fascinating Grandeur of Palaces and Celebrated Canals
Venice – Choose your Romantic Excursion with a Day at Leisure in Venice
Venice – Depart for Home
Trip Highlights
- Luxuriate in your romantic hotel suite in the charming town of Oia on the atmospheric Greek island of Santorini
- Embrace over the hidden broken heart of St. Peter’s Square, giving a romantic undertone to the legend behind Vatican’ City’s architectural design
- Bask in the grandeur of the Venetian Republic with a multi-course meal held inside the 18th century home of the Venetian aristocracy
- Delight in the breathtaking image of the Parthenon, the icon of Athens’s Golden Age and the mark of Western European civilization
- Board a catamaran to glide across the indigo waters of Santorini’s caldera for an unforgettable Greek island sunset
- Admire the grand design of the Colosseum on a private guided tour of Rome, taking you from the Forum to the masterpieces in the Capitoline Hill Museum
- Share in the experience of the rush of emotion when viewing Botticelli’s masterwork, The Birth of Venus, on display in Florence’s Uffizi Gallery
- Relish the romantic ride of your life on a sunset gondola winding between the narrow canals of Venice before arriving at a secluded candlelit restaurant
Detailed Description
Greece offers endless romance in the quiet and secluded islands that span the Aegean Sea while Italy is known for cities that embrace the passion and nurture love. Your 12-day romantic getaway will follow in the footsteps of Eros and Cupid to bring the perfect romantic getaway accentuated by enchanting history. Your tour to Greece and Italy will begin with your arrival at the airport as your private transfer will escort you into the heart of the ancient city and near the historic neighborhood of the Plaka. Enjoy the atmosphere of the city found along the cobblestone streets and open cafes that flicker with candlelight.
While in Athens, you can discover the splendors of the past through the ruins that predate those of Ancient Rome. Visit the Parthenon, and then watch the sunset over the Aegean Sea at the Temple of Poseidon on Cape Sounion. Santorini is one of Greece’s most popular islands for couples to visit, and you will quickly embrace the romantic ambiance that emanates from the seaside views that look into the caldera. Charm abounds with the whitewashed homes with blue rooftops, and the days are yours to indulge in the secluded sense of romance at your leisure. Enjoy a sunset cruise on the clear indigo water, visit the ancient ruins of Akrotiri, or lounge on the beaches that are known for their red and black sand.
Continue to Rome for a change of pace as the stunning city is enhanced by the presence of both ancient and Baroque histories with modern life woven throughout. Romance is around the hidden gardens and throughout the masterful art. Tour the impressive palaces, fountains, and public piazzas, and then wander the grand halls of the Vatican Museums to find works by Raphael, Michelangelo, and Giotto. Embrace the terraced views and restaurants that are isolated by the antique architecture, and find charm around every corner.
Move next to Florence and discover the majesty of the Renaissance and the splendor of a sunset seen from Piazza Michelangelo. You will have a sensational view of the Florentine skyline and the idyllic rolling hills of Tuscany. Travel on to Venice, a unique city on the water where you can indulge in the grandeur of the former republic and its touted romantic ether. Enjoy a sunset gondola ride, discover the pristine restaurants in the labyrinthine streets, and then follow your private guide through the landmarks at St. Mark’s Square. You will have the opportunity to choose between visiting the famous islands of Burano, Murano, and Torcello or cruising down the Brenta canal to explore the opulent villas. Not ready to end your tour yet? Consider reading some of our travelers’ Italy honeymoon tour reviews for more ideas to perfect your dream Italy vacation.
Starting Price
$5,200 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
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 1383 reviews
Excellent! Everything was meticulously planned. All of our tours were very interesting and the drivers were courteous. We went to Athens, Naxos, and Santorini during our 11-day trip. Overall, I think our favorite place was Naxos, with Athens and the Acropolis being second, although the weather that morning was not the best. But our guide was excellent and kept us engaged while fighting rain and wind. As I mentioned, all the drivers and guides were excellent and I would highly recommend this trip. Santorini was beautiful too and the wine tour was extremely interesting. We highly recommend Zicasso.
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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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We had a very good trip to Greece with Zicasso's travel specialist. We traveled to Athens, Mykonos, and Santorini with a group of six (three couples). They did a good job of finding nice and convenient hotels in each location, and we were also pleased with the Acropolis tour, food tours, and catamaran trip we took during the week.
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We recently returned from an incredible two-week Coral Anniversary trip to Greece and it exceeded every expectation. From the ancient wonders of Athens to the whitewashed villages of Mykonos, the dramatic cliffs of Santorini, and the authentic traditions of Crete, every stop offered something unique and unforgettable. Most importantly, the people we met along the way transformed a beautiful vacation into a truly special experience. The journey took us through Athens, Mykonos, Santorini, and Crete.
Outstanding Planning and Service
Every transfer, hotel, tour, ferry, flight, restaurant reservation, and activity was flawlessly coordinated by Zicasso's travel partner. The itinerary struck a perfect balance between guided experiences and personal exploration, allowing us to enjoy Greece without ever worrying about logistics.
Athens – History, Culture, and Exceptional Hospitality
Our stay at our hotel in Athens gave us incredible Acropolis views and a perfect base for exploring the city. Walking through the Acropolis with our guide and standing before the Parthenon was breathtaking. The Acropolis Museum and city highlights tour helped bring thousands of years of history to life.
One of the highlights of our anniversary celebration was dinner at a restaurant atop Lycabettus Hill. Watching the sun set behind the Acropolis while enjoying excellent Greek cuisine and wine was a magical experience and one we'll never forget.
We would especially like to recognize our driver in Athens. He was professional, knowledgeable, and genuinely invested in making our trip memorable. During our day exploring the Argolis region, Epidaurus, Mycenae, and the Nemea wine country, he provided insights that helped us better appreciate the history and culture of Greece.
What truly distinguished our driver was his attention to detail. While we were traveling along the Athenian Riviera toward Cape Sounion and the Temple of Poseidon, he realized we were hoping for a true seaside lunch experience. Without being asked, he contacted the travel company and coordinated everything to make a last-minute adjustment so we could enjoy lunch by the sea. That thoughtful gesture perfectly reflects the level of service he provided throughout our stay. It turned a wonderful day into one of our favorite memories of Athens.
Mykonos – Relaxation and the Beauty of the Aegean
Mykonos provided the perfect contrast to the historical focus of Athens. Staying at our hotel in Mykonos overlooking the Aegean Sea allowed us to fully appreciate the island's beauty.
We spent time exploring the charming streets of Mykonos Town, admiring the famous windmills, and enjoying the relaxed island atmosphere. A major highlight was our private catamaran cruise to Delos and Rhenia. Sailing through the crystal-clear waters of the Aegean while visiting the UNESCO World Heritage Site of Delos gave us a fascinating glimpse into one of the ancient world's most important religious centers. The secluded waters around Rhenia were stunning and provided some of the most beautiful scenery of our trip.
Santorini – Spectacular Views and Unforgettable Sunsets
Santorini is every bit as beautiful as the photographs suggest and somehow even more impressive in person. Our stay in Oia overlooking the caldera was breathtaking. Whether enjoying breakfast with panoramic views or simply walking through the village, every moment felt special.
The wine-tasting experiences at a winery were outstanding. Sampling the island's distinctive Assyrtiko wines while learning about Santorini's unique volcanic terroir gave us a new appreciation for Greek winemaking. The carefully paired food-and-wine experiences were among the culinary highlights of the entire trip.
Our private sunset catamaran cruise around the caldera, White Beach, Red Beach, Black Beach, hot springs, and the volcano was another unforgettable experience. Watching the sunset from the water while enjoying dinner and local wine created one of the most memorable evenings of our anniversary trip.
Crete – The Heart of Greece
As amazing as Athens, Mykonos, and Santorini were, Crete became our favorite part of the journey.
Our quick stop at Knossos Palace and the historic city of Rethymnon allowed us to learn about the Minoan civilization and experience the rich blend of Venetian and Ottoman influences that define the island. The old Venetian harbor in Chania was equally impressive and provided a spectacular setting for our stay.
Samaria Gorge
One of the most rewarding experiences of our entire trip was hiking the Samaria Gorge. Covering 11 miles through one of Europe's most spectacular natural settings was challenging and incredibly rewarding. The dramatic cliffs, pristine landscape, and sheer scale of the gorge were unlike anything we had experienced before.
A tremendous part of that experience was our guide. Our guide brought expertise, enthusiasm, and a genuine passion for Crete that elevated the hike far beyond a typical excursion. His knowledge of the region, local culture, and natural environment made every step more meaningful.
Kissamos Villages and Cooking Class
Our final full day in Crete may have been the most authentic and memorable day of the entire trip.
The tour of the traditional villages of Kissamos provided a fascinating look at everyday Cretan life. Learning about olive oil production, tasting regional products, and experiencing rural villages gave us a perspective on Crete that most visitors never see.
The cooking class that followed was exceptional. Our host created an atmosphere that felt less like a tour and more like spending a day with friends. Together with his mother, he shared not only recipes, but the stories, traditions, and values that make Cretan culture so special.
For anyone traveling to Crete, we cannot recommend this tour company highly enough. Their commitment to authentic local experiences is truly outstanding.
This trip exceeded our expectations in every possible way. We experienced world-famous historical sites, breathtaking landscapes, incredible food and wine, beautiful hotels, and unforgettable adventures. Yet what we will remember most are the people who made the experience so special.
We returned home with wonderful memories, a deeper appreciation for Greek culture, and gratitude for everyone who helped make our anniversary celebration the trip of a lifetime.
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This was one of the best-organized trips my wife and I have taken in Europe. Zicasso had put us in touch with Zicasso's travel specialist. She called us to ask about the dates, interests, islands we wanted to see, sights, etc. She formulated a travel plan including hotels, transfers, and tours (including food tours). We discussed the plan, chose hotels based on our budget, and finalized a tour plan with her.
Right from the moment we arrived at Athens airport, everything was taken care of for us. We had a limo waiting, even though it took time to go through the EU's new immigration system. Our hotel in Athens was right next to the city center, with a beautiful Acropolis view from our balcony. The room was comfortable and spacious, and ready when we arrived at 2 pm. Our travel specialist even suggested a restaurant to celebrate our anniversary and made reservations for us, as we were unable to do it online.
The next day, we had a tour of the Acropolis conducted by a professional tour guide. It was a good two-hour walking tour and we enjoyed it very much. The tour guide was very knowledgeable, took time to explain the history, which we are interested in, and also took some amazing pictures for us. We had free time to go to the city center to shop and try out some of the Greek taverns.
From Athens, we went to Mykonos by ferry. Ferry tickets were sent on a WhatsApp group chat created by her. Our limo came at the designated time and our ferry trip was easy and very enjoyable. On arrival, our limo was waiting to take us to our hotel in Mykonos, located on top of the hill, with a balcony overlooking the central area and a scenic sea view. It was easy to go down and see the shops, windmills, Little Venice, and explore the city center that day. Nighttime was party night, with almost everything open late.
The next day, we had a private Jeep tour of the island. We went to different parts of the island to explore. Our driver and tour guide were very thorough and patient, and it was a very enjoyable tour.
The following day, we were taken by a tour bus to the port, where we went on a private tour of the Delos and Rhenia islands. The tour guide was very knowledgeable and pointed out the sights of an ancient civilization. Lunch on the boat was basic, but on the whole, it was a very informative tour.
We then left for Santorini by ferry. Again, ferry tickets arrived a day before on WhatsApp. We requested an upgrade from basic tickets to Club Class/Platinum Class for the rest of the tour, which was immediately arranged and payment was accepted by credit card. In Santorini, we stayed at our hotel, which had a beautiful view from the balcony and the breakfast was superb, made to order, with the rooftop restaurant having spectacular views of the caldera. It was just awesome! In the afternoon, a tour guide took us in a van and showed us the sights, including the Three Bells of Fira. We did not have to wait anywhere, as the guide knew exactly how and where to go to see the sights and take photos. We learned a bit of history of the island.
The next day, we had two wine-tasting tours, first to a premium vineyard and then to the oldest winery in Santorini. Our tour guide and van arrived on time everywhere for a well-conducted and planned private tour.
On the third day, we went on a semi-private sunset cruise to the volcano, hot springs, and beaches. It was a well-conducted tour with a BBQ on the boat! The crew even accommodated my shellfish allergy by cooking the chicken before cooking the seafood on the BBQ. The food was good and, more importantly, the crew was friendly and very caring. The crew members took some beautiful pictures of us against the spectacular Santorini sunset.
We left for Crete the following morning by ferry. Everywhere, we had private transfers waiting to take us and we did not wait anywhere to be transferred. In Heraklion, we were staying at our hotel in the city center and therefore had access to some very nice traditional Greek restaurants where the locals went for dinner. The following day, we had a private tour of Knossos Palace with a very friendly and knowledgeable tour guide. On our return, our limo was waiting for us to take us to Chania in Crete.
Our journey to Chania took us two hours and was very informative and enjoyable, as our driver pointed out a number of sights on the way. Our check-in at our hotel in Chania was quick and efficient. The hotel even sent us a bellboy to the drop-off point (cars are not allowed inside) to help with our luggage. The hotel room was spacious and had a balcony overlooking the waterfront, the lighthouse, and all the restaurants in the area. The next day, we were taken on a private olive oil tour and, in the evening, a food tour with a tour guide who spoke seven languages and knew the city inside and out!
The following day, a private limo and a private boat took us to Glyka Nera, Loutro, and Marmara. We were able to swim and see some of the beautiful azure-blue water and sights, again in the company of the same tour guide from the previous night. Lunch in Marmara was exceptional. At no time during this tour were we rushed and everything moved at a very easy pace. We checked out from the hotel the following morning for a flight to Athens. The hotel manager helped us with our luggage to the pickup point. Boarding passes were sent on WhatsApp and our check-in and travel were smooth. Everything went like clockwork. Our limo was waiting on arrival and we were taken back to our hotel in Athens, where we stayed the night before our travel home the following day.
At all the sites we visited, our travel specialist even suggested some restaurants to try. These were special in their own ways and not touristy. This tour was very detailed, meticulously planned, and executed by her and the team, who kept in touch with us every day throughout the tour to make sure we had a great time. Thank you for making this a memorable, special, and personalized tour.
This was our 35th-anniversary celebration trip and, thanks to Zicasso's travel specialist and the team, it was a memorable trip for us.
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We thoroughly enjoyed our 13-day trip (June 8-21) to Athens, Santorini, and Paros, Greece, with our three grandchildren (ages 16, 14, and 12). Planning our dream trip was so easy with the help of Zicasso's travel specialist! We were super-impressed with his pre-trip planning. He took the time to gather information about us and our grandchildren to plan the perfect trip, taking into account our interests and travel expectations. It was especially beneficial to have his expertise as a long-time resident of the area.
From accommodations to tours to transportation, everything was perfectly planned and executed. The few mishaps we experienced were addressed immediately. It was wonderful to have the digital itinerary he prepared on all of our devices, so each participant could see and read about what we would be doing each day! We had access to the travel company's team 24/7 if we needed to contact them (which we did) and they were very attentive to our requests. I would highly recommend this travel company!
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