Dreaming of Italy

Ah, Italia! A land filled with rich history, breathtaking art, and delicious cuisine. If ever there was a country to ignite your wanderlust, Italy is the one. In this two-week itinerary, we’ll guide you through a dreamy experience where dreams come to life. Every day is packed with things to see, do, eat, and drink in the charming cities of Rome, Florence, Siena, Pisa, Cinque Terre, Milan, and Venice.
Day 1: Arrive in Rome – Colosseum & Trevi Fountain Welcome to Rome, the Eternal City! Our journey begins by touring the iconic Colosseum, a gladiatorial arena where history whispers from every corner. Post this memorable experience, relax at a nearby café and enjoy a delightful cup of Italian coffee, paired with heavenly tiramisu. Once rejuvenated, take a stroll to the enchanting Trevi Fountain. As twilight falls, indulge in Rome’s culinary wonders with a traditional pizza dinner and a glass of fine Italian wine.
Day 2: Rome – Visit the Vatican An early start to explore the Vatican City is a must, as a day full of awe-inspiring art and history lies ahead. Discover the breathtaking Vatican Museums, the Sistine Chapel, and St. Peter’s Basilica. Lunch at a cozy trattoria offers a chance to sample fresh pasta with a rich, homemade tomato sauce. Post-lunch, explore the charming streets of Rome and experience the unique vibe of the vibrant city. End the day with a sumptuous dinner of creamy risotto and a glass of Prosecco.
Day 3: Rome – Pantheon & Fori Romani Begin the day exploring the ancient Pantheon, a true architectural marvel. Afterward, amble over to the Fori Romani, an impressive collection of Roman forums. A visit to Rome isn’t complete without savoring the famous Roman Supplì — rice balls filled with cheese — perfect as a midday snack. As the sun sets, unwind at a local enoteca with a cozy atmosphere, and treat yourself to a delicious plate of pasta carbonara and a full-bodied red wine.

Day 4: Travel from Rome to Florence Today, board a high-speed train and ride from Rome to the Renaissance city of Florence. Upon arrival, check into your accommodation, freshen up, and explore your surroundings. Stop by a gelateria, indulge in a scoop (or two!) of authentic Italian gelato, and stroll along the Arno River, taking in the remarkable vistas. In the evening, dine at a traditional Florentine steakhouse for a taste of the mouthwatering Bistecca alla Fiorentina.
Day 5: Florence – Gallery and Gardens Start your day with a visit to the marvelous Uffizi Gallery, where enchanting works of Leonardo da Vinci and Michelangelo come alive. Later, meander through the lush Boboli Gardens, and enjoy a well-deserved panino for lunch. As the day comes to an end, make sure to experience Florence’s lively Aperitivo culture, offering a selection of pre-dinner drinks and appetizing finger foods.
Day 6: Explore the Old Town of Siena Time to visit the charming town of Siena. A short bus ride from Florence transports you into a world rich in history and culture. Get lost in Siena’s narrow cobblestone streets, admire the breathtaking architecture, and delve into the iconic Piazza del Campo. Lunch in Siena features Pici pasta with a heavenly Cacio e Pepe sauce; afterward, wash down a slice of Panforte – a delicious local candy – with an espresso.
Day 7: Travel to Pisa & explore Piazza dei Miracoli Board a train to the picturesque city of Pisa. Upon arrival, head immediately to the Piazza dei Miracoli, home to the legendary Leaning Tower. Once the photoshoot is complete, grab a warm-and-crunchy focaccia sandwich and a cooling limoncello to continue exploring Pisa’s beauty. In the evening, gorge on a delectable bowl of pasta with pesto while reminiscing about the day’s adventures.

Day 8: Pisa to Cinque Terre Take a train from Pisa to Cinque Terre, a string of stunning coastal villages. Upon your arrival, bask in the idyllic scenery and savor a hearty meal of fresh seafood paired with a glass of local white wine. End the day with a gentle seaside stroll, soaking in the romantic atmosphere of this unique destination.
Day 9: Hike the Sentiero Azzurro in Cinque Terre Day nine challenges you with a thrilling hike along the dazzling Sentiero Azzurro trail. Revel in the breathtaking views of the Mediterranean and Cinque Terre’s vibrant villages. Treat yourself to a much-deserved break with a plate of Focaccia di Recco, topped with creamy cheese. Catch the coastal sunset over a dinner of Trofie al Pesto and a refreshing local white wine.
Day 10: Cinque Terre to Milan Time to bid adieu to the enchanting Cinque Terre and embark on a train journey to Milan, Italy’s fashion capital. Once settled in, meander through the city and indulge in a slice of authentic Milanese panettone. In the evening, choose a trendy wine bar to relish Milan’s vibrant nightlife with a sophisticated Negroni in hand.
Day 11: Explore Piazza del Duomo in Milan Begin your Milanese adventure at the iconic Piazza del Duomo, home to the jaw-dropping Milan Cathedral. Once you’ve absorbed your fair share of architectural brilliance, pamper your taste buds with a traditional dish of Osso Buco and Risotto alla Milanese. Wrap up the day with an after-dinner amaretto, toasting to your unforgettable Italian experience.

Day 12: Travel from Milan to Venice Board a comfortable train and leave the bustling city of Milan for the dreamy canals of Venice. Upon arrival, take in the city’s magical atmosphere and settle into your accommodation. Venetian dining calls for local Black Squid Ink Risotto and a divine Bellini cocktail, overlooking the canals as the sky deepens into twilight.
Day 13: Explore Venice Your final full day begins with a visit to the majestic Saint Mark’s Square. Glide through the bewitching canals by gondola, a bucket-list experience many travelers dream about. Once your enchanting ride ends, enjoy Italy’s iconic cicchetti at a Bacari wine bar, as you recount your favorite moments from the trip with a glass of Venetian Spritz in hand.
Day 14: Fly home from Venice or extend your trip As this fantastic journey draws to a close, board your Venice-bound flight for a heartfelt “Arrivederci, Italia!” Alternatively, if you can’t bear to say goodbye just yet, extend your trip and uncover more of Italy’s hidden treasures.
Over these unforgettable two weeks, you’ll have explored the awe-inspiring art, history, and flavors of Italy’s most magical cities. With every twist, turn, and taste, your love for this captivating country will have grown exponentially, ensuring a lifelong bond with la dolce vita.

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