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

A 12 day trip to Greece & Italy 
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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

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General Information

Detailed Itinerary

Places Visited 

Athens, Santorini, Akrotiri, Italy, Florence, Vatican City, Venice, Murano, Burano, Torcello, Brenta Canal 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

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, airport transfer

Day 2: Athens – Relish a Full Day Spent Exploring the Ancient History of Athens

In the morning, the sunlight will wash over the marble features of the Parthenon, bringing a golden glow to the hilltop more than 500 feet above sea level. At breakfast, the aroma of filo dough and creamy, melting cheese will drift from the bougatsa, a breakfast pastry offering a sweet accompaniment to the strong flavor of Greek coffee. Your guide will meet you in the hotel lobby and introduce you to the incredible history found around Athens, beginning with Temple of the Olympian Zeus.

The remarkable structure was once the largest temple in ancient Greece and stands in view of the dramatically preserved Parthenon. The columns and pediment date back to the 6th century BC but was not completed until the 2nd century AD under the patronage of Roman Emperor Hadrian. 15 of the original marble columns continue to decorate the grounds, representing the enormity of the temple’s original size. The sunlight is warm on your cheeks and shimmers across the pristine marble leading up the Acropolis. You will pass through the Propylaea, the gorgeous gateway framing the plateau. Six Doric columns decorate the doorway in traditional style echoing the proportions of the Parthenon. Set eyes on the magnificent temple dedicated to Athena, the goddess of wisdom, and first erected in the 5th century BC for an inspiring and breathtaking moment as your exploration begin.

What’s Included: accommodation, tour, breakfast

Day 3: Santorini – Travel to Santorini for the Romantic and Inviting Ambiance

In the morning, you can take a romantic stroll through the National Garden as palm trees cast shade over the marble walkways. Daisies and carnations blossom around the waves of emerald grass, and the beauty spreads across the rosy colors stemming from the House of Parliament. After your morning wander, your private transfer will greet you at your hotel when you are ready and escort you to the airport for your brief flight to Santorini.

As you land, the traditional whitewashed homes of the Cycladic villages will glow brightly against the rugged silver volcanic cliffs soaring above the bay. The Aegean Sea shimmers with crystal clear indigo and turquoise hues, splashing against the rocks and lapping lazily against the beaches. Narrow streets wind along the upper ridges of the island, which reaches nearly 1,000 feet above sea level at its highest point. The sea breeze carries a semi-sweet aroma that drifts along with the scent of Greek coffee and souvlaki. The remainder of the day is at your leisure to bask in the beauty of the island and in the luxury of your hotel with unparalleled views of the blue rooftops imitating the glistening sea.

What’s Included: accommodation, transfer, breakfast

Day 4: Santorini – Delight in a Sunset Cruise and Dinner around Santorini

You can take the time for a leisurely romantic breakfast and relish the view of the water that is all around you. The pool offers a tranquil trickling with the gentle breeze brushing through the shading umbrellas while coffee, figs, and grapes bring refreshing aromas to start your day. You can stroll around the quiet shops of Oia in the morning and enjoy the marble walkways and the soft glint of gold and silver jewelry displays in the windows.

Your guide will meet you in the early afternoon and drive you to the small marina to board a luxury catamaran. Glide onto the water and raise the sails for refreshing mists to spray from the hull of the boat and land on your cheeks as you cruise beneath the staggering island cliffs. The boat weighs anchor off the shoreline of the Red Beach, and the pebbly sand creates a thin border between the clear water and the steep red cliffs. You can jump into the water and relax in the cool, refreshing temperature as the sand glows scarlet and orange, contrasting beautifully with the turquoise waters. After a delicious home-cooked dinner featuring the rich flavors of the island, you will sail back to the marina and watch the sunset cast pink, purple, and golden light across the sky.

What’s Included: accommodation, tour, breakfast, dinner

Day 5: Santorini – Relax with a Day of Romance and Charm at your Leisure

In the morning, you can choose to have breakfast in your room and delight in the romance and intimacy of your suite overlooking the Aegean Sea. The day is yours to enjoy the marvels of Santorini at your preferred pace. Stroll along the streets of the island’s biggest village, Fira, or spend time lounging underneath the Mediterranean sun on the soft sands of Kamari Beach. For a unique exploration of the Santorini life and lifestyle, you could also make your way to Akrotiri where the Minoan Bronze Age settlement was covered in volcanic ash and stone after an eruption in the 17th-century BC.

Frescos, ceramic pots, and homes offer insight into the ancient life of the citizens suggesting possible inspiration for Plato’s Atlantis. The scent of baking stone fills the hanger that protects the excavated site from the elements. Artifacts uncovered during archeological digs suggest the island was in contact with Crete, Mainland Greece, Syria, and Egypt. Your private guide will lead you along the designated walkways and immerse you in the elaborate history.

What’s Included: accommodation, tour, breakfast, tour

Day 6: Rome – Travel to Rome for a Passionate Evening Tour of the Historic Sites

The morning light washes over Oia, returning the shimmer to the idyllic whitewashed houses and infinity pools overlooking the caldera. Footpaths weave along the rugged cliffs for spectacular views of the caldera and leading to Fira. Before setting out for the day, enjoy a leisurely breakfast and indulge in the marvelous panoramic view once more, reveling in the perfect company and revitalizing scent of Greek coffee. Your private transfer will then escort you to the airport for your direct flight to Rome.

Take off in your plane and enjoy a perfect view of the glistening Aegean Sea, the spectacular Greek mountains and the golden plains of Italy’s Puglia before touching down at Fiumicino International Airport. You will then reach the heart of historic Rome with your private driver, and be delighted by the city’s bustling streets and incredible charms.

Your gorgeous luxury hotel will provide a terraced view to the terracotta rooftops that decorate the antique buildings across the historical city center. The earthy tones contrast with the whitewashed walls to which you had grown accustomed in Greece. Settle in a bit, and then set out with your guide to experience the passionate ambiance embodied in the stunning artistry of the city. Begin with the main shopping streets of Via Condotti and Via Borgognona as they represent the elegant and luxurious boutique aesthetic of Italian fashion located near the Spanish Steps. Move next to Piazza Navona and watch the many artists with their easels as they capture the beautiful colors and grand fountains, filling the public plaza with romantic ambiance.

What’s Included: accommodation, flight, airport transfer, breakfast

Day 7: Rome – Visit the Ancient Wonders of Rome and Capitoline Hill 

In the early morning, you can have the cobbled lanes to yourself to enjoy the sounds of the trickling waters of the Trevi Fountain while breathing in the aromas of fresh-baked brioche spilling out of the nearby bakeries. The sunlight washes over the city and returns to the glint of the marble angel statues decorating the Sant’Angelo Bridge, which once connected the heart of Rome to the Hadrian’s Tomb, once located on the outskirts of the city.  Join your guide after breakfast ready to delve into the center of the Roman Empire at the Roman Forum.

Alongside the main street that connects the former marketplace and the temples rises the thick, dramatic walls of the Colosseum, which reach nearly 200 feet tall. The amphitheater once held up to 50,000 spectators across rows of seating, staircases, and internal passages but now the sunlight bakes the stone and fills the air with the familiar scent of hot earth. Stand above the hypogeum, which the arena flooring once hid while the two-story tall labyrinth provided training rooms for gladiators and concealed cages for exotic animals. Continue to Capitoline Hill, one of Rome’s Seven Hills standing between the Forum and Campus Martius.

The museum on the hill is one of the world’s oldest, dating back to the 15th century. The sculptures bring an atmosphere of a decorated palace featuring images of the Dying Gaul, Romulus and Remus, along with masterworks by Tintoretto and Caravaggio. Ancient masonry around the courtyard adds a layer of mystique to the collection with a magnificent hand, foot, and head strewed about like garden adornments. The prominent figure of the 5th-century BC bronze wolf represents the legend that birthed the Roman Empire. 

What’s Included: accommodation, tour, breakfast

Day 8: Rome – Traverse the Splendors of Vatican City and the Borghese Gardens

The fragrant orange blossoms in the Garden of the Oranges are most prevalent in the morning. Throughout the day, couples stroll along the edges of the trees and sneak kisses around the terrace or enjoy the beautiful view of the city’s church domes and spires. After breakfast, your guide will bring you to Vatican City at St. Peter’s Piazza where columns outline the incredible plaza that leads to the adorning façade of the celebrated Basilica. Before entering the Vatican Museum, your guide will take you to the base of the central obelisk as the granite statue stands nearly 135 feet tall atop bronze lions an adorned with hieroglyphs.

Near the obelisk is a hidden mark of artist Gian Lorenzo Bernini, who helped design the piazza in the 17th century. The famed artist and architect placed a broken heart in stone, blending his feelings with his masterpiece to forever mark his unrequited love to a Roman woman. The small, simple touch is a romantic secret to share with your lover that most visitors and locals to Rome do not know. The artistic grandeur embodied in St. Peter’s Square presaged the splendor found inside the Vatican Museum. The polished marble floors and opulent walls give way to pristine works of artistic mastery, crowned by Michelangelo’s Sistine Chapel. Upon entering the iconic feature of Vatican City, you look up to find The Birth of Adam, at the center of the paneled stories spanning the ceiling.

What’s Included: accommodation, tour, breakfast

Day 9: Florence – Venture to Florence for a Full Day of Renaissance and Romance

The Renaissance offered a new perspective and the rebirth of humanistic imagery in which the beauty of the world was reflected through the intimacy of human nature. Florence is the best place to explore Renaissance history, and after breakfast, your private transfer will escort you north to the famed landscape of Tuscany. You will quickly find the picturesque verdant hills rolling across the horizon as chestnut and cypress trees decorate the valleys and vineyards while olive orchards grow along the ascending slopes.

Delve into the heart of Florence’s Old City, which embodies the height of the Renaissance in its art, architecture, and preserved culture. Cobbled lanes wind between hidden palaces while the sensational rosy hues of the Cathedral’s brick dome shimmer above the green, white, and pink marble façade. The city offers a fairytale ambiance before you have even entered the museums with the public piazzas for patrons to sip espresso and watch passersby abounding. Jewelry shops on the Ponte Vecchio, the oldest bridge in the city, present elaborate window displays shining with opulent gold, silver, and diamond embellishments.

Enter the Uffizi Gallery, which opened to the public as a museum in the late 18th century, as the marble floors shine in the natural light that pours through the large windows that line the hall. The earthen tones allow the art to stand out in the galleries organized by chronology, and your heart will be racing with excitement as if you have entered an ancient church. You reach Halls 10-14 to find the painting of Botticelli’s Birth of Venus astounding in person, and your every sense will be heightened as you take it in.  Move next to explore the Galleria dell’Accademia and be spellbound by Michelangelo’s David.

What’s Included: accommodation, transfer, tour, breakfast

Day 10: Venice – Enjoy the Fascinating Grandeur of Palaces and Celebrated Canals

Rise early and make your way to Venice via train and enjoy a couple of hours in the Italian country side before arriving at the city of 118 islands. In the morning, the gondolas return to their quiet wading in the narrow canals across the city as the footbridges arch over the waters that connect the land. After some time to settle in, meet your guide and step over the Rialto Bridge to pass through the bustling aisles of the daily Rialto Market. You will likely carry the aroma of plum and cherries with you before reaching the marvels of St. Mark’s Square.

The golden weathervane depicting the angel Gabriel tops the nearly 325-foot tall bell tower known as the Campanile. The bulbous domes of St. Mark’s Basilica represent Byzantine style in the popular design of the 11th century. The Doge had ordered all men returning from the Crusades to bring back treasures from their journeys with which to decorate the newly minted church. Gold mosaics flicker in the archways on the façade as natural light spills through the windows and spreads across the more than 45,600 square feet of decorative mosaics that embellish the interior.  The inlaid marble flooring has an intricate geometrical pattern reminiscent of Muslim artistry of the Middle East, interwoven with floral designs and sporadic depictions of animals.

In the evening, you will board a gondola for an intimate sunset ride through the canals, eventually arriving at a secluded restaurant where a candlelit table awaits, followed by a romantic moonlit walk around the beautiful city.

What’s Included: accommodation, transfer, tour, breakfast, dinner

Day 11: Venice – Choose your Romantic Excursion with a Day at Leisure in Venice

Today you can choose between the stunning glass works of the fabled island of Murano or set out to visit the unique villas that line the former water-highway that connects Padua to Venice. The latter option takes you on a cruise that will explore the Brenta Canal. Nine swing bridges and five locks help to move boats to and from the lagoon over the course of nearly 25 miles, and the tranquil ambiance drifts from the quiet banks on which small towns have grown between the opulent estates. You pass locals enjoying a morning boat ride as the scent of herbaceous jasmine and rich coffee emanates from the open windows of homes as you drift past.

The boat stops at Villa Foscarini, a 17th-century estate that maintains its illustrious stature. The reception floor contains rooms awash in marvelous frescoes, including marble-looking embellishments that were painted rather than built. The upper floors remain the private residence to descendants of the original owner, the Foscari family. In the afternoon, you will reach the former Ducale Villa. The lights flicker against the opulent décor on the walls and ceiling, and you will feel as though you have stepped into a king’s estate in the 18th century. As you settle into the dining room, the food will arrive and fill the room with the aromas of sautéed garlic, zesty basil, and flowing wine all for the two of you to savor and absolutely enjoy.   

What’s Included: accommodation, tour, breakfast

Day 12: Venice – Depart for Home

In the morning, vaporettos, barges, and gondolas return to the Grand Canal, gliding past the wooden plinths and palatial facades. After one last leisurely Italian breakfast, your transfer will greet you on the hotel’s private dock and escort you across the Grand Canal to meet with your water taxi driver. You will then continue onward to Marco Polo International Airport for your flight home. 

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.