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

$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.

4.9

Verified Traveler Reviews

Based on 975 reviews

Greece Vacation Review: Naxos, Athens, Cuisine, Walking Tour, 10 Nights

Zicasso's travel company made our bucket-list trip to Greece come to life! They organised all our tours and transportation, worked with us to provide activities that were in line with our interests, and even gave detailed information on suggested itineraries for our free days.

Some highlights included the walking tour(s) of Athens, our trip to see Santorini, and the best steak I have ever had at a beach hotel in Naxos! Our only suggestion is that we went on a day tour to Delos which was self-guided. There is so much history there though that a guided tour would have been helpful. I would definitely recommend booking your tour with them!

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Greece Luxury Vacation Review: Mykonos, Paros, Santorini, Athens, History, Culture, Catamaran Cruise, Local Cuisine, 10 Nights
"I recently had the pleasure of experiencing the most unforgettable vacation with my family, all thanks to Zicasso’s travel agent."

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Italy Trip Review: Rome, Florence, Tuscany, Amalfi Coast, Pope Francis’ Funeral, Wine, Cuisine, Culture, Museums, Relaxation, 10 Nights

Zicasso’s tour operator planned the most amazing trip to Italy for us! My requirements were culture, romance, and relaxation. She delivered on every aspect. Although we missed our tour of the Vatican due to the Pope's funeral, my husband and I actually attended his funeral!! Our hotel, though planned many months before, was next to the basilica where Pope Francis was laid to rest. Talk about being a part of history!

We stayed in a beautiful converted villa to boutique hotel in Florence; got whisked away through the Tuscan countryside in a vintage Fiat 500; took cooking classes; sipped lovely wine, accompanied by excellent lunches on our winery tours; soaked in Italy's rich culture and museum scene; and even ticked the relaxation box by spending time by the pool, in the spa, and resting on our large deck overlooking the Amalfi coastline.

Every tour guide was extremely knowledgeable and personable, and it was evident they loved their jobs. Between memories of the boat ride along the Amalfi Coast, tips from the cooking classes I have already started using at home, and the cases of wine we are eagerly awaiting delivery of, my husband and I will forever hold Italy in our hearts and la dolce vita it provided us. 

Talk with our tour operator; you will be glad you did!

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Greece Tour Review: Athens, Mykonos, Santorini, Horseback Riding, Food Tours, 10 Days

We had a wonderful time in Greece. We spent 10 days there and went to Athens, Mykonos, and Santorini. The accommodations were great and the planned excursions were fantastic. The weather was perfect.

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Greece Tour Review: Athens, Naxos, Santorini, 9 Nights

From start to finish, our experience with Zicasso's travel expert was top-notch! To date, it was the best trip we have taken. After talking to our agent on the phone to get what type of trip we were looking for, she put together an itinerary that suited us perfectly. Our trip included Athens, Naxos, and Santorini. All of our vehicle transportation, in-country flights, ferries, hotels, and tour guides were planned out for us. All we had to do was show up. We enjoyed all the tours planned out for us and it kept us from wandering unknowingly into the tourist traps. I can't express enough what a wonderful experience we had, thanks to our agent's expertise. The trip was absolutely seamless!

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Greece Tour Review: Athens, Santorini, Mykonos, History, Culture, Tradition, Local Cuisine, Shopping, 8 Nights

If you're considering a trip to Greece, look no further than Zicasso. Our travel expert planned an unforgettable journey for our family; Athens, Mykonos, and Santorini, and every detail was executed with care, expertise, and passion. 

From the moment we arrived in Athens, we were immersed in the country’s warm hospitality. Our agent made sure we had the perfect balance of sightseeing and relaxation. The historical sites in Athens, like the Acropolis and the ancient Agora, were must-sees.

Mykonos is vibrant yet relaxed. The beaches were beautiful. Every meal on this trip was a highlight. Fresh seafood, local cheeses, olive oil, and delicious pastries—each bite told a story of Greece’s deep culinary heritage.

In Santorini, we were captivated by the island’s charm—whitewashed buildings, breathtaking sunsets, and the deep blue Aegean Sea. We visited traditional villages, giving us a glimpse into the rich cultural traditions that are still very much alive.

Throughout the trip, what stood out most—beyond the stunning landscapes and ancient history—was the friendliness of the Greek people. Their warmth and pride in their culture made every moment feel welcoming and genuine.

Our agent didn’t just plan a vacation—he created an experience rooted in history, tradition, and hospitality. I can’t recommend him and Zicasso highly enough.

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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