Planning a Romantic Italian Getaway: The Perfect Itinerary for Two

Italy is synonymous with romance. From the cobblestone streets of Rome to the rolling hills of Tuscany and the shimmering canals of Venice, it's a destination that enchants lovers from around the world. If you’re dreaming of a romantic getaway, Italy offers a perfect blend of history, culture, delicious cuisine, and breathtaking scenery. Here’s a guide to planning the ultimate romantic Italian itinerary that will create memories to last a lifetime.

Day 1-3: Rome – The Eternal City

A romantic couple in front of St. Peter's Basilica in Rome

Begin your journey in Rome, the city where ancient history meets modern romance. Stay in a charming boutique hotel near the Spanish Steps or the Trevi Fountain to be in the heart of the city's most romantic sights. Start your days with a leisurely breakfast at a local cafe, followed by a guided tour of the Colosseum, Roman Forum, and the Pantheon.

In the evenings, stroll through the romantic streets of Trastevere, a neighborhood filled with cobblestone paths, charming piazzas, and intimate trattorias. Don’t miss a sunset at the Pincio Terrace in Villa Borghese, where you can enjoy a panoramic view of the city. End your Rome experience with a private dinner at a rooftop restaurant, savoring the city lights over a glass of Italian wine.

Day 4-6: Florence and Tuscany – Art, Wine, and Rolling Hills

A narrow cobblestone street in a Tuscan village

Next, head to Florence, the cradle of the Renaissance. Choose a luxury hotel along the Arno River with views of the Ponte Vecchio for a perfect romantic ambiance. Spend your days visiting world-famous art museums like the Uffizi Gallery and the Accademia, where Michelangelo’s David awaits.

Take a day trip to the Tuscan countryside, where you can visit picturesque villages like Siena or San Gimignano. Arrange a private wine-tasting tour in the Chianti region, complete with a gourmet picnic among the vineyards. As the sun sets, return to Florence for a sunset stroll along the river, and enjoy a candlelit dinner with views of the Duomo.

Day 7-8: Venice – A City of Romance on Water

A couple in front of colorful houses in Burano, Italy

No romantic trip to Italy is complete without visiting Venice. Take a high-speed train from Florence to Venice and check into a historic palazzo overlooking the Grand Canal. Begin your Venetian experience with a gondola ride through the winding canals. Wander hand-in-hand through the city's narrow streets, discovering hidden gems around every corner.

Visit St. Mark's Basilica and the Doge's Palace, and take a moment to enjoy a coffee at Caffè Florian, one of the oldest coffee houses in Europe. In the evening, treat yourselves to a private boat tour of the Venetian lagoon, ending with a romantic dinner at a Michelin-starred restaurant. Venice is also a favorite destination of the Castaway Crew - in case you missed it, click here to read Addison’s blog post all about her favorite city!

Day 9-10: The Amalfi Coast – Sunsets and Seaside Beauty

Castaway Clients, Andy and Nikki, enjoying lunch in Positano, Italy

For the final leg of your trip, head south to the stunning Amalfi Coast, a place where colorful cliffside villages meet the sparkling Mediterranean Sea. Stay in a luxury hotel in Positano or Ravello with sweeping ocean views. Spend your days exploring the charming towns of Amalfi and Atrani or take a boat tour around the island of Capri.

Relax on sun-soaked terraces, swim in hidden coves, and dine on fresh seafood by the sea. End your journey with a romantic sunset cruise along the coast, toasting to your unforgettable Italian adventure. You can read more about Capri in our blog post 10 Islands Every Luxury Traveler Should Visit: Part 1.

A couple holding hands while walking down a cobblestone street in Verona

Italy offers countless opportunities for romance, from its historic cities to its scenic countryside and coastlines. Whether it's your honeymoon, anniversary, or simply a getaway for two, this romantic itinerary promises an unforgettable Italian experience that you’ll cherish for years to come.

Ready to plan your romantic Italian escape? Contact me today, and let’s make your dream trip a reality! 🌹✨