Romance for Two: From Rome to Santorini

Your travels through Italy and Greece start with your arrival in Rome, where you’ll be greeted at the airport and escorted by private transfer to your centrally located hotel. After settling in, a relaxed afternoon and evening is a great way to ease into the timeless rhythm of the city.

Stretch your legs with a stroll, perhaps discovering ancient landmarks in the area that surrounds your hotel, pausing for a creamy gelato or enjoying a front-row seat for people-watching while sipping wine in an enticing piazza.

When it’s time to dine, follow the aroma of fresh pasta and wood-fired pizza drifting from a neighborhood trattoria.

Explore Rome on a privately guided half-day stroll through its storied, ancient center. Begin at the Pantheon, a former pagan temple, now a church. Built in 27 BC, it’s the most well-preserved from the city’s earliest days, particularly renowned for its remarkable dome and open oculus that floods the interior with natural light. From there, wander to lively Piazza Navona to admire Bernini’s dramatic Fountain of the Four Rivers, then continue to the Spanish Steps, linking the piazza below with Trinità dei Monti above.

Conclude at the ornate Baroque-style Trevi Fountain, where tradition invites you to toss a coin and wish for a future return.

Meals Included:
Breakfast

Experience Included:
Private Highlights of Ancient Rome Tour

With a day at leisure, you might visit some of the other top attractions in Rome. Perhaps visit Vatican City, where you can marvel at the staggering opulence of St. Peter’s Basilica, the world’s largest church. This is also where you’ll find Michelangelo’s remarkable works in the stunning Sistine Chapel, the famous Raphael Rooms in the Vatican Palace, and much more. Or, explore Villa Borghese Park with its beautifully landscaped gardens.

It’s also home to a must-visit for art lovers: Galleria Borghese. Set within a magnificent 17th-century building, it’s a treasure trove of Renaissance and Baroque art, including works by Raphael, Rubens, Canova, and Bernini.

Meals Included:
Breakfast

Having explored many of the highlights in the Eternal City, it’s time to return to the airport, where you’ll catch your flight to Venice. After checking out of your Rome hotel, you’ll meet up with our driver for a private airport transfer. Another driver will be waiting for you upon arrival in Venice to provide a private transfer to your Venice hotel.

After settling in, the remainder of the day is all yours, but we highly recommend taking a stroll to soak up the enchanting atmosphere, followed by dining on authentic Venetian fare and wine by the Grand Canal at one of our recommended restaurants.

Meals Included:
Breakfast

Savor two of the most timeless traditions in Venice on a private tour that pairs a classic gondola ride with a guided tasting experience. Drift through the serene canals and beneath elegant bridges while admiring the unique blend of Venetian Gothic, Renaissance, and Baroque architecture, including ornate palaces inaccessible on foot.

As your gondolier navigates the waterways, note the city’s layered past, reflected in the façades and hidden passageways. Afterward, meet a wine expert while visiting a traditional bacaro.

You’ll sample regional wines or a classic spritz alongside cicchetti (small savory bites), while learning about the customs that shape Venetian culinary heritage and social life.

Meals Included:
Breakfast

Experience Included:

Private Gondola Ride & Venetian Aperitivo with Sommelier Guide

After a few busy days of exploring, enjoy the day at your leisure, perhaps wandering through Venice to see what you can discover. Two of the top attractions are in St. Mark’s Square. The 11th-century St. Mark’s Basilica is one of the world’s finest examples of Byzantine architecture and includes a bell tower that can be climbed for a spectacular view.

The adjacent Doge’s Palace dates to the 14th century and includes the prison that once held Casanova. Or, join our optional day tour to Verona, which includes visiting the well-preserved Verona Arena and the famous balcony at Juliet’s House, along with a guided wine tasting.

Meals Included:
Breakfast

Welcome to Greece! Upon arrival at Athens International Airport, our driver will be there to provide a private transfer to your hotel in the city center. After settling in, you can join our Unforgettable Greece Exclusive led by an expert local guide. It’s the ideal way to get a feel for daily life, the atmosphere, and the layout of the city streets.

Significant landmarks will be pointed out while you gain insight into Athens’ stories and its people, going well beyond your typical sightseeing tour. Conclude by grabbing your reserved dinner table, relaxing over drinks, and enjoying a delicious meal overlooking Acropolis and the Parthenon. 

Meals Included:
Breakfast

Experience Included:

Private welcome tour in Athens and Dinner reservation with Acropolis View

Explore Athens’ legends and legacy alongside your private guide on an immersive half-day tour, starting near the Temple of Olympian Zeus. Ascend the slopes of the Acropolis to uncover the myths behind the landmark monuments, including the Theatre of Dionysus, the Temple of Athena Nike, and the iconic Parthenon, guarding the city for some 2,500 years. From here, you’ll also have a panoramic view of the city that stretches out to the sea.

Continue to the Ancient Agora, once the vibrant heart of civic life, where great thinkers shaped democratic ideals, all while gaining insight into how Athens influenced the course of Western civilization.

Meals Included:
Breakfast

Experience Included:

Private Mythology tour of Athens including Acropolis and Ancient Agora

It will soon be time to head to the final destination on this romantic itinerary: Santorini. One of the most popular islands for honeymooners and romance-seekers of all types, you’ll begin your journey with a private transfer to Athens International Airport. Catch your flight to Santorini, where, upon arrival, you’ll see another driver waiting to provide the private transfer to your hotel. After checking in, the rest of the day is all yours.

With the scenery so dazzling, many guests prefer to simply unwind with a glass of Santorini wine complemented by an epic view of the caldera cliffs and the brilliant blue Aegean.

Meals Included:
Breakfast

With a day of leisure, the adventurous might enjoy hiking the trail that connects Fira and Oia. Following the edge of the caldera cliffs on a just over six-mile route, you’ll take in some of the most breathtaking sea and coastal views. Oia is famously picturesque with its maze of narrow alleyways and streets lined with whitewashed buildings home to enticing art galleries, boutiques, and tavernas.

Designed for wine enthusiasts, we highly recommend our optional tour that visits the historic, family-owned Argyros Estate winery. You’ll explore the production facilities, vineyards, and enjoy a guided tasting of six estate wines paired with regional delicacies.

Meals Included:
Breakfast

Set sail on a private sunset catamaran tour that sails alongside Santorini’s dramatic coast, departing from Vlychada. You’ll cruise toward magnificent Ammoudi Bay, which lies beneath Oia village, famous for its sunsets. A bespoke voyage, enjoy personalized service and a relaxed pace, stopping to swim in geothermally warmed hot springs and snorkel in crystal-clear waters off the renowned shores of the famous Red and White beaches. Between stops, soak up the Mediterranean sun while taking in sweeping views of the sea and coast. A freshly prepared barbecue featuring seafood, meats, salads, and complimentary drinks will be enjoyed onboard, with a glorious sunset completing the experience.

Meals Included:
Breakfast

BBQ meal

Experience Included:
Private Sunset Boat tour

With another day at leisure, you can relax and savor the awe-inspiring scenery or head out to explore more on your own. You might visit the Pompei-like archaeological site of Akrotiri or one of the lesser-known villages, like Imerovigli, with its tranquil streets and iconic castle.

A hike to the remains of the once-imposing fortress is rewarded with a panoramic view over the island and the Aegean. Or, take our optional farm-to-table hands-on cooking class. A guided hands-on experience, you’ll learn how to prepare traditional Santorini dishes using seasonal farm ingredients before sitting down to enjoy the delicious meal you helped to make.

Meals Included:
Breakfast

As your journey draws to a close, reflect on some of the unforgettable moments: tossing a coin into Rome’s Trevi Fountain, drifting along Venice’s canals, standing atop Athens’ Acropolis, and watching the sun melt into the sea in Santorini.

Upon your hotel checkout, our driver will provide a private transfer to Santorini Airport for your short flight to Athens. From there, you can begin your journey home or continue exploring with the help of our travel specialists. As an international gateway, Athens offers easy connections to many Greek island groups from the Dodecanese to the Ionians, as well as nearby favorites like Turkey and Croatia.

Customize This Trip

All of the itineraries we create are fully customized and can be tailored to your exact preferences. If you would like to extend your stay in any of the destinations or add/remove any experiences, simply mention this to our travel specialists.