Curator’s statement
Looking to get an overview of Italy? I recommend seeing sights across the country during a 3-week trip. This 21-day itinerary is doable by train and gives you an overview of La Bella Italia. I've included a few of my favorite food cities so you can try everything from Venetian cichetti to homemade orecchiette in Puglia.
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Day 1-4: Venice
Welcome to the captivating country of Italy, a land of art, history, culture and gastronomy. As a first-time visitor, you are in for an unforgettable journey through some of the most iconic cities and regions. This 21-day itinerary will take you from the romantic canals of Venice to the picturesque landscapes of Tuscany and Umbria, and from the ancient wonders of Rome to the breathtaking Amalfi Coast and the charming countryside of Puglia. Get ready to immerse yourself in the Italian way of life, indulge in mouthwatering cuisine, explore historic sites, and savor the beauty of each unique region.
Venetian Romance in Venice
Your adventure begins in Venice, a city built on water and renowned for its stunning architecture and romantic ambiance. Wander through the narrow alleys, cross the iconic Rialto Bridge and visit St. Mark's Square with its impressive Basilica and Campanile.
Take a gondola ride along the Grand Canal, allowing you to admire the magnificent palaces that line the waterways. Explore the lesser-known neighborhoods to discover a more authentic side of Venice.
Day 5-7: Culinary delights in Bologna
From Venice, travel to Bologna, the gastronomic capital of Italy. Bologna is renowned for its rich culinary traditions and you'll have the opportunity to indulge in delectable pasta dishes like handmade tortellini or tagliatelle al ragù (what we in the states call Bolognese sauce).
Visit the Piazza Maggiore, the city's main square, and the nearby Two Towers, the symbols of Bologna. Discover the city's history at the Archaeological Museum of Bologna and the University of Bologna, one of the oldest in the world.
Day 8-10: Art and beauty in Florence
Next on your journey is Florence, the birthplace of the Renaissance and a treasure trove of art and architecture. Explore the Uffizi Gallery, home to masterpieces by Michelangelo, Botticelli and Leonardo da Vinci.
Visit the magnificent Florence Cathedral, known as the Duomo, and climb to the top for panoramic views of the city. Don't miss the Ponte Vecchio, a historic bridge lined with charming shops. And be sure to try lots of gelato since it comes from here!
Day 11-12: Wine and scenic landscapes in Chianti
From Florence, venture into the heart of Tuscany to the region of Chianti, famous for its wine production. Visit local wineries and taste the renowned Chianti Classico wines.
Enjoy leisurely drives through the picturesque countryside, dotted with vineyards, olive groves and medieval villages. Take in the serene beauty of this region that has inspired countless artists and writers.
Day 13-15: Unveiling Umbria
Continue your journey to the lesser-known but equally captivating region of Umbria. Explore the charming town of Perugia, the regional capital, with its historic center and Etruscan remains.
Visit the spiritual town of Assisi, the birthplace of Saint Francis, and marvel at the stunning Basilica of San Francesco. Enjoy the tranquil atmosphere and breathtaking views of the Umbrian countryside.
Day 16-18: Historical marvels in Rome
Your next destination is the eternal city of Rome, a living museum of history and culture. Explore iconic landmarks like the Colosseum, Roman Forum, Pantheon and Trevi Fountain.
Visit Vatican City, home to St. Peter's Basilica and the Vatican Museums, including the renowned Sistine Chapel. Take the time to wander through the cobblestone streets and piazzas, each with its own unique charm. Try pastas like gricia, carbonara and amatriciana.
Day 19-20: Coastal beauty on the Amalfi Coast
Make your way to the stunning Amalfi Coast, a UNESCO World Heritage site renowned for its dramatic cliffs and picturesque towns. Visit the town of Amalfi, with its beautiful cathedral and charming streets.
Take a boat ride to Positano, the jewel of the coast and enjoy the breathtaking views of colorful houses cascading down the cliffs. Don't miss the chance to savor the fresh seafood and delicious limoncello.
Day 21: Exploring Puglia
Conclude your Italian journey in the enchanting region of Puglia. Explore the unique trulli houses in Alberobello, a UNESCO World Heritage site. Visit the picturesque white city of Ostuni, perched on a hilltop.
Discover the historic town of Lecce, known as the "Florence of the South," with its stunning Baroque architecture. Savor the authentic regional cuisine, including fresh seafood, orecchiette pasta and olive oil.
Let's talk about customizing this itinerary for you. Or, about other destinations.
Travel Advisor
Aida Mollenkamp
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Looking for more travel inspo? Check out my guide, Sorrento: A Luxurious Haven for Discerning Travelers.
This guide is part of our ongoing series on travel to Italy.