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

Romantic Santorini island at sunset, Greece

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.

Countries Visited

Greece, Italy, Vatican City

Places Visited

Athens, Santorini, Florence, Vatican City, Venice, Rome

Suggested Duration

12 Days

Customizable Itinerary

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Day 1

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:

Accommodation
Transfer
Day 2

Athens – Relish a Full Day Spent Exploring the Ancient History of Athens

Day 3

Santorini – Travel to Santorini for the Romantic and Inviting Ambiance

Day 4

Santorini – Delight in a Sunset Cruise and Dinner around Santorini

Day 5

Santorini – Relax with a Day of Romance and Charm at your Leisure

Day 6

Rome – Travel to Rome for a Passionate Evening Tour of the Historic Sites

Day 7

Rome – Visit the Ancient Wonders of Rome and Capitoline Hill

Day 8

Rome – Traverse the Splendors of Vatican City and the Borghese Gardens

Day 9

Florence – Venture to Florence for a Full Day of Renaissance and Romance

Day 10

Venice – Enjoy the Fascinating Grandeur of Palaces and Celebrated Canals

Day 11

Venice – Choose your Romantic Excursion with a Day at Leisure in Venice

Day 12

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

$4,100 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.

4.9

Verified Traveler Reviews

Based on 1151 reviews

Italy, Greece 45th Anniversary Review: Rome, Athens, Santorini, Florence, Colosseum, Vatican, Parthenon, Walking Food Tour, Tuscan Wine Region, 10 Nights

We enjoyed all of the planned tours in Italy and Greece. Favorites included the Vatican, Colosseum, Roman walking food tour, and a day exploring the Tuscany wine region.

We loved all of our hotels (favorites being our hotel on Via Emilia in Rome and then our hotel on Nikodimou Street in Athens). All of our drivers at our various locales were always on time, even early, and were friendly and engaging.

We did have various questions come up and any time of day/night, Zicasso's travel professional and the tour company were responsive and so helpful.

Our long-awaited 45th anniversary trip came off seamlessly. I appreciate all of the time and planning that went into planning our venture. I will happily recommend you to our friends and family.

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Greece Travel Review: Naxos, Santorini, Athens, 11-Day Trip

Our trip was incredible! We were so impressed with the professionalism of Zicasso’s travel agent and the guides we had during our tours. Greece has been a long-dreamed-of destination and our time in Naxos, Santorini, and Athens exceeded our expectations. It was an easy process to give some guidance on what we liked to do and have a curated trip for our preferences. We would recommend the travel company to anyone needing help planning a trip!

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Greece Honeymoon Review: Paros, Santorini, Crete, Athens, Acropolis, Boat Ride, 11 Nights

If I could give them more than five stars, I would. I cannot recommend Zicasso's tour operator enough!!! Our agents were amazing and created the most perfect honeymoon for my husband and I!! We went to Paros, Santorini, Crete, and Athens and loved them all. It was amazing not to have to worry about a thing. We had zero issues and we had the best time.

We went to wonderful restaurants and beautiful hotels, had two fun boat trips, a beautiful tour throughout Kissamos, Crete, and the best tour guide for the Acropolis/Athens.

If you want an amazing trip with beautiful memories and zero worries, I would absolutely use this tour operator!!!

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Greece Honeymoon Review: Athens, Crete, Santorini, Naxos, 10 Nights

My husband and I had the most amazing honeymoon and owe it all to Zicasso’s travel specialists. We visited Athens, Crete, Santorini, and Naxos. We had an amazing experience in each location and were constantly in awe of the hotels and experiences that had been booked for us. Zicasso’s travel specialist responded to messages almost immediately and sent us our ferry/plane boarding passes before we had even thought of them. We only got home a few days ago and are already looking forward to planning another trip with Zicasso.

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Greece Vacation Review: Santorini, Corfu, Crete, Athens, Syros, Wine Tasting, 18-Day Trip

We traveled to Greece in September 2025 for an 18-day trip to five locations. We went through Zicasso and were paired with the primary travel company and the local partner. I cannot express how wonderful our trip was. It was apparent that every detail was carefully tailored to meet all of our wants and needs. From the transfers to the tours, and the hotel accommodations and locations, everything about it was just perfect! Highly recommended if you want a worry-free trip.

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Italy Travel Review: Rome, Florence, Naples, Ischia, Vatican Museums, Skywalk, Wine Tasting, Olive Oil Sampling, 2 Weeks

Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.

The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.

In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.

Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.

At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.

Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.

We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.

We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.

We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.

I can’t wait to use the travel company again next year.

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Customizable Itinerary

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

30,000+ Verified Traveler Reviews