Romantic Rendezvous: Captivating Italy & Greece Highlights

Embark on a timeless journey through Italy and Greece, where romance whispers in every winding street, and history and culture permeate through each picturesque town.


15 days

Trip Type



Rome, Florence, Cinque Terre, Athens, Naxos & Santorini

Preferred Travel Months



€ 4200/person

About this trip

This 15-day trip will captivate your five senses with its romance, beauty, and charm. You’ll start in the enchanting city of Rome, where ancient ruins and savory cuisine await you. Then, discover the birthplace of the Renaissance, Florence, where every corner is a work of art. Next up is Cinque Terre, a series of five colorful coastal villages that will take your breath away with its serene beauty. After exploring Italy, it’s time to head to Greece and immerse yourself in the vibrant city of Athens—the cultural and historical hub of Western civilization. Finally, you’ll wind down on the islands of Naxos and Santorini to fall even more in love with the Mediterranean lifestyle.


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Map & Itinerary


Day to Day

  • Day 1: Arrival at Rome
  • Day 2: Rome Colosseum Tour
  • Day 3: Complete Vatican Tour
  • Day 4: Train to Florence
  • Day 5: Florence Walking Tour
  • Day 6: Free Day in Florence
  • Day 7: Car Transfer to Cinque Terre
  • Day 8: Free Day in Cinque Terre
  • Day 9: Car transfer to airport, flight to Athens
  • Day 10: Athens Mythology Tour
  • Day 11: Flight to Naxos
  • Day 12: Naxos Highlights Tour
  • Day 13: Ferry to Santorini Day
  • Day 14: Santorini Highlights Tour
  • Day 15: Departure

Picture Yourself

Romantic Rendezvous: Captivating Italy & Greece Highlights
Joining guided tours across the destinations you visit to introduce yourself to the local culture and history.
Romantic Rendezvous: Captivating Italy & Greece Highlights
Catching a whimsical sunset in Santorini and enjoying the ultimate romantic experience.
Romantic Rendezvous: Captivating Italy & Greece Highlights
Admiring precious archaeological sites like the Acropolis with its fascinating monuments.
Romantic Rendezvous: Captivating Italy & Greece Highlights
Enjoying the company of your beloved in a romantic setting.

DAY 1-3: Rome

Arrive in the eternal city of Rome and prepare to be swept away by its romantic charm. Your private driver will be waiting to transfer you to your hotel so you can relax and unwind after your journey.

Once you’ve settled in, head out and explore the winding streets of historic ruins and enjoy your first Italian meal.

On the morning of your second day, you’ll join a licensed guide as you delve into the heart of an empire. Explore the awe-inspiring Colosseum, Roman Forum, and Palatine Hill on this once-in-a-lifetime experience.

Your guide will tell tales of gladiators, emperors, and epic battles that will transport you back in time.

After a morning of ancient history, spend the afternoon indulging in delicious Italian cuisine and wandering through the city’s charming neighborhoods.

Stop at the Trevi Fountain to toss a coin and make a wish, visit the iconic Pantheon, or simply relax at a sidewalk cafe and enjoy a delicious cacio e pepe and a limoncello.

For your last day in Rome, head to Vatican City for a tour of the world-renowned museums and St. Peter’s Basilica. Marvel at masterpieces by Michelangelo, Raphael, and Bernini as your guide sweeps you up in the art and history of this holy city.

In the evening, we recommend venturing to the Trastevere neighborhood for a romantic dinner in one of its many quaint restaurants.

As the sun sets over the Tiber River, soak in the ambiance and enjoy a taste of la dolce vita.

DAY 4-6: Florence

In the morning, your private driver will be waiting to take you to the train station to continue your journey to the picturesque city of Florence. Upon arrival, you’ll be met by your driver, who will take you to get settled into your new hotel.

After getting refreshed and rejuvenated, head out to explore Florence’s charming streets, lined with beautiful architecture and bustling markets. Stop for a delicious gelato or espresso as you soak in the beauty of this city.

On your second day in Florence, you’ll experience the best of the Renaissance with a guided tour of the city’s top sights.

Visit the iconic Duomo, admire Michelangelo’s David in the Accademia Gallery, and cross the Ponte Vecchio bridge.

As you walk through the city, your guide will bring this era of art and culture to life with fascinating stories and insights.

In the evening, take a romantic stroll along the Arno River and watch the sunset over the city. Treat yourself to a classic Florentine dish such as bistecca alla Fiorentina or ribollita for dinner.

Day six is all yours to explore the city as you wish. Spend the morning like a local, sipping cappuccinos and eating pastries at a café.

You can also visit the Uffizi Gallery, which houses famous works such as Botticelli’s ‘The Birth of Venus’ and Da Vinci’s ‘Annunciation.’

End your day with a glass of Chianti wine while you take in a gorgeous sunset view from Piazzale Michelangelo.

DAY 7-8: Cinque Terre

In the morning, your private driver will pick you up from your hotel in Florence to transfer you to the charming coastal villages of Cinque Terre.

These five colorful towns are nestled among rocky cliffs and are the perfect place for your romantic rendezvous.

After checking into your hotel, spend your first day exploring the winding streets, stopping for delicious seafood dishes at local restaurants, and enjoying the stunning views. You can spend the afternoon lounging on the beach or taking a boat ride along the coast.

You can do as you please on your second day in Cinque Terre. We recommend heading out early for one of the most scenic hikes in Cinque Terre, the Blue Trail.

This hike will take you to three villages and offer breathtaking views of the coastline. Stop for juice and gelato along the way, and remember to snap some photos for lasting memories.

For your last night in Cinque Terre and Itlay, watch the colorful buildings light up at sunset and enjoy a romantic dinner with some Cinque Terre wine.

DAY 9-10: Athens

On day nine, you are saying goodbye to Italy and hello to Greece.

Your driver will transport you to the airport to catch your flight to Athens. Upon arrival, you’ll be taken to your hotel, where you can freshen up before heading into the vibrant city.

Spend the evening getting lost in the bustling streets of Athens, filled with a mix of ancient ruins and modern shops and restaurants. Try traditional Greek dishes, like moussaka or souvlaki, and sip on some ouzo to feel like a local.

The next day, immerse yourself in the history of Athens by joining a tour of magic and mystery. Get a glimpse of the city’s ancient past as you visit the Acropolis, the Acropolis Museum, Parthenon, and other significant landmarks.

You’ll discover the captivating mythology of ancient Greek civilization as your guide unveils stories of conquests, mythical creatures, heinous crimes, betrayals, and acts of heroism.

In the evening, head to the lively Plaka neighborhood, known for its charming streets and traditional Greek tavernas.

Spend your last night in Athens indulging in delicious food and drinks while watching street performers and soaking up the vibrant culture.

DAY 11-12: Naxos

After a traditional Greek breakfast, your driver will be waiting to take you to the Athens Airport for your flight to Naxos. Once you arrive, you’ll be taken to your hotel to enjoy the laid-back island vibes.

Spend the rest of your day strolling along the picturesque beaches, swimming in the crystal clear waters, and soaking up the warm sun. In the evening, head to Naxos Town for a delightful dinner overlooking the sea.

On your only full day in Naxos, You’ll be swept away by the best of Naxos on a private tour, exploring picturesque villages, immersing in the island’s rich history and traditions, and indulging in local food and wine tastings.

This tour combines ancient heritage and modern lifestyle, giving you a glimpse into the authentic Greek way of life.

We recommend ending your last day in Naxos with a sunset cruise around the island, admiring the stunning views while enjoying a glass of wine.

And if you’re lucky, you might even catch a glimpse of dolphins swimming alongside the boat.

DAY 13-14: Santorini

On day thirteen, it’s time for your last stop on your trip. Your driver will transport you to the ferry port for a scenic ride to Santorini.

Upon arrival, your driver will take you to your hotel, where you can unpack your bags and head out for a day relaxing at the beach.

Take some time to relax and enjoy the island’s beauty before heading to the charming village of Oia in the evening to catch one of Santorini’s famous sunsets and enjoy a romantic dinner overlooking the picturesque caldera.

For your last full day in Greece, you are getting the best of Santorini on a private tour. With a little bit of all the island has to offer, this tour will take you to the most stunning viewpoints, volcanic beaches, and must-see locations while giving you a taste of local cuisine and wine.

Your guide will take you on a whimsical journey, showcasing the beauty of Santorini’s landscapes and rich history.

On your final night, we recommend returning to Oia for one last sunset experience. With the golden hues reflecting on the white-washed buildings and blue-domed churches, it’s a sight that will stay with you forever.

DAY 15: Departure

The day has come to say goodbye to Greece and all it has offered you on this romantic journey. Your driver will take you to the airport, where you will begin your journey home.

After an incredible two weeks of getting lost in the love and beauty of Italy and Greece, your newfound romance for the art, history, and culture of these countries will remain with you forever.

And we know that long after the flight home, these memories will continue to sweep you off your feet for the years to come.


  • Boutique 4-5* accommodation
  • All private tours with excellent licensed guides, as described in the itinerary
  • All private transfers with professional drivers and luxury vehicles
  • All domestic and international flights/trains/ferries
  • Skip the line entrance fees at all sites
  • All taxes and VAT


  • Meals, unless mentioned in the itinerary
  • Personal travel insurance
  • Personal expenses
  • Gratuities
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