Sail into Love: A Summer Adventure in Italy & Greece

Dive headfirst into a whirlwind romance this summer as you voyage through the enchanting cities of Italy and Greece.


14 days

Trip Type



Lake Como, Portofino, Florence, Athens, and Paros

Preferred Travel Months



€ 3900/person

About this trip

This 14-day itinerary is everything you need for a summer filled with love and adventure. Starting with the sparkling waters of Lake Como, sweeping you away with the charm and beauty of this enchanting destination. From there, you will sail to Portofino to get lost in the winding streets and picturesque views. Then immerse yourself in the rich art and history of Florence, where the past comes alive, before venturing to Athens, the birthplace of democracy and ancient Greek culture, where mythical stories unfold before your eyes. Finally, surrender to the allure of Paros, a paradise of white sandy beaches, where the sun’s embrace and the crystal-clear waters create a blissful escape.


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Map & Itinerary


Day to Day

  • Day 1: Lake Como | Car transfer from Milan airport to Lake Como
  • Day 2: Lake Como | Boat Tour with Venetian Limousine
  • Day 3: Lake Como | Free day
  • Day 4: Portofino | Car transfer to Portofino
  • Day 5: Portofino | Ferry to Santa Margherita, Highlights of Portofino Tour with Pesto Cooking Class
  • Day 6: Florence | Car transfer to Florence
  • Day 7: Florence | Florence in a Day with David, Duomo, Uffizi & Walking Tour
  • Day 8: Florence | The Chianti Experience: Small Group Half-Day Wine Tour from Florence (afternoon)
  • Day 9: Athens | Car transfer to airport, Flight to Athens, Evening Highlights tour with Dinner
  • Day 10: Athens | Sunset Acropolis tour
  • Day 11: Paros | Car transfer to airport, flight to Paros
  • Day 12: Paros | Paros and Small Cyclades Full-day Sailing Adventure
  • Day 13: Paros | Free day
  • Day 14: Departure

Picture Yourself

Sail into Love: A Summer Adventure in Italy & Greece
Swimming in the turquoise waters of Paros Island.
Sail into Love: A Summer Adventure in Italy & Greece
Drinking local Italian wine alongside your parter.
Sail into Love: A Summer Adventure in Italy & Greece
Admiring the mesmerizing views of the Greek and Italian coastline.
Sail into Love: A Summer Adventure in Italy & Greece
Strolling the streets of Greece and Italy while getting insight into the local cultures.

DAY 1-3: Lake Como

On day one, you’ll arrive at the Milan airport, where your private transfer will take you to your hotel on Lake Como. Once you arrive, spend some time relaxing before heading out to enjoy the beautiful views of the lake.

On day two, wake up and have coffee on your balcony overlooking the lake before setting out on a romantic boat tour with Venetian Limousine.

Your driver will take you to all of the best spots on the lake to see stunning villas and gardens as you bask in the beautiful Italian sun.

Experience the evening charm of Lake Como by dining at one of its exquisite restaurants, where you can relish the finest seafood and pasta in the country. As the sun sets over the glistening lake, savor each sip of Italian wine and enjoy the warm summer night.

Day three is all yours to explore the charming towns and villages around Lake Como at your own pace. We recommend visiting the Bellagio village, known for its captivating atmosphere and stunning views of the lake.

Take a stroll through the streets, indulge in some gelato, or rent a bike to explore further. End the day with a romantic dinner by the lake, taking in the peaceful ambiance of this enchanting destination.

Day 4-5: Portofino

After a delicious breakfast in Lake Como, you’ll be picked up by your private driver to embark on a scenic drive to Portofino. This picturesque fishing village is known for its brightly colored houses and quaint cafes.

Check into your hotel and settle in before walking the Portofino Harbor. It’s lined with rows of boats and yachts, capturing the essence of a small Italian fishing village.

On day five, you’ll board the ferry to the neighboring village of Santa Margherita Ligure to join a 3-hour tour of Portofino.

Discover the highlights, learn to make pesto the traditional way, and soak in the beauty of the Italian Riviera’s coastline. You’ll explore Portofino’s charming streets, try some local focaccia, and enjoy a panoramic view from San Giorgio’s Church.

After a waterfront lunch, you’ll have the afternoon to catch some sun on one of Portonfinos’ beautiful beaches or relax at your hotel. In the evening, take a romantic stroll along the harbor and indulge in some fresh seafood at one of its many restaurants with a stunning view of the Mediterranean Sea.

DAY 6-8: Florence

On the morning of your sixth day, your private driver will pick you up from your hotel and drive you to the historical city of Florence. Check in to your hotel and get settled for the next three days.

When you’re ready to explore the city, we recommend spending your first night discovering the Oltrarno neighborhood, where you’ll find some of the best local restaurants and bars.

In the morning, you’ll join a walking tour that will mesmerize you with its beautiful architecture, art, and history.

You’ll visit the world-famous Duomo and the iconic Michelangelo’s David in the Accademia Gallery and take in Renaissance masterpieces at the Uffizi Gallery.

In the evening, take your time wandering the charming streets of Florence, sipping on a glass of Chianti, and basking in the romantic atmosphere.

Then, head to Piazzale Michelangelo for a stunning view of the sunset over Florence’s skyline.

For your last day in Florence, you can spend the morning like a local, enjoying a cappuccino and cornetto at a cafe before browsing the city’s vibrant markets for souvenirs.

And don’t forget to stroll across the Ponte Vecchio, the city’s oldest bridge, for some breathtaking views of the Arno River.

In the afternoon, you’ll join a half-day tour in the glorious hills of Chianti, where you’ll be whisked away to two of the best wineries in the area.

You’ll indulge in five different wines that are perfectly paired with local delicacies for a burst of flavors.

As the tour ends, you’ll be dropped off at your hotel to pack and get ready for a new destination in the morning.

DAY 9-10: Athens

On day nine, you’ll be picked up at your hotel in Florence and transferred to the airport for your flight to Athens.

Upon arrival, you’ll be transported to your hotel to rest up until your evening tour and dinner.

As the sun is going down, you’ll join a guided tour to explore Athens in a different light. Your expert local guide will tell enchanting tales of ancient Greek mythology as you stroll through the city’s illuminated streets.

You’ll head to Syntagma Square to discover iconic landmarks like the Greek Parliament, the Temple of Olympian Zeus, and the Arch of Hadrian.

The tour will wind through the charming Plaka neighborhood, marvel at the Tower of the Winds, and catch a glimpse of the awe-inspiring Acropolis at sunset.

As the night sets in, you’ll head over to Monastiraki Square for a traditional Greek mezze dinner and savor sips of wine while immersing yourself in the lively atmosphere of Athens.

Take day ten to immerse yourself in the city and explore at your own pace. You can visit the National Archeological Museum, home to some of the most fascinating ancient Greek artifacts and statues.

You can also take a walk through the bustling Monastiraki flea market to pick up some souvenirs for loved ones back home. Enjoy some of Greece’s finest Greek cuisine at a local taverna and take in the city’s vibrant culture.

In the evening, you’ll join an Acropolis tour. You’ll ascend the hill to reach the iconic Parthenon, where you’ll witness a breathtaking sunset over the city of Athens.

Your knowledgeable guide will share stories and facts about this ancient citadel as you soak in the stunning views.

Afterward, you can have dinner at one of the many rooftop restaurants with a view of the Acropolis before heading back to your hotel.

DAY 11-13: Paros

On day eleven, you are headed to your last destination. You’ll be picked up by your private drive and taken to the Athens airport to catch your flight to the stunning island of Paros. Upon arrival, you’ll be transferred to your hotel, where you can relax and enjoy this idyllic island’s beauty.

Your first full day in Paros is for sailing and island hopping. Embark on a private boat tour with your captain and explore the riches of Paros and the Small Cyclades while sailing in the Aegean Sea.

Start from Piso Livadi and visit impressive seascapes like Iraklia, Schoinousa, and Koufonissia. Swim in turquoise-colored waters and enjoy a delicious lunch on board. End the day exploring the waters in south Naxos as the waters turn to shimmering gold with the setting sun.

After a long day on the water, spend your evening relaxing over a candlelit dinner at a charming seaside restaurant. Enjoy fresh seafood and local eats as you listen to the calming sound of waves crashing against the shore.

On your last day in Paros and the last full day of your summer adventure, spend the day however you like.

Paros is one of the most beautiful islands in the Cyclades and offers so many things to do. Visit the charming fishing village of Naoussa, stroll through the cobblestone streets of Parikia, or swim in the crystal-clear waters on one of Paros’ famous beaches.

Whether you spend your day soaking up the sun or exploring ancient ruins, enjoy the last bits of paradise before saying goodbye to this magical place.

DAY 14: Departure

Sadly, your two-week summer adventure has come to an end. Your private driver will be waiting to transfer you to the Athens airport to catch your flight home. 

As you set sail on your journey home, we know you’ll be flooded with memories of your time in these two countries.

From the stunning landscapes of Lake Como to the charming villages of Portofino and the rich history of Athens, you have experienced the best of Italy and Greece, and your heart will be bursting with love and appreciation for these two incredible places. 


  • 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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