Italy—a country of timeless beauty, rich history, and world-renowned cuisine. From the romantic canals of Venice to the rolling hills of Tuscany and the ancient ruins of Rome, Italy offers a diverse array of experiences that capture the hearts of travelers. If you’re planning a two-week trip to Italy, you’re in for a treat. This itinerary is designed to help you explore the very best of what this enchanting country has to offer, with a perfect blend of iconic sights, cultural experiences, and hidden gems.

Let’s embark on a journey through Italy that will take you from the vibrant streets of Rome to the serene landscapes of the Amalfi Coast, ensuring that every day is filled with unforgettable memories.

Day 1-3: Rome—The Eternal City

Day 1: Arrival and Introduction to Rome

Welcome to Rome, the Eternal City! After arriving at Fiumicino Airport, make your way to your accommodation and take some time to relax and settle in. Once you’re ready, start your Roman adventure with a leisurely stroll through the city’s historic center. Begin at the Spanish Steps, where you can enjoy the lively atmosphere and beautiful views, then make your way to the nearby Trevi Fountain. Don’t forget to toss a coin into the fountain to ensure your return to Rome!

• Tip: Consider staying in the historic center, near landmarks like the Pantheon or Piazza Navona, for easy access to Rome’s top sights.

Day 2: Ancient Rome—The Colosseum, Roman Forum, and Palatine Hill

Dedicate your second day in Rome to exploring the city’s ancient history. Start with a visit to the Colosseum, the iconic amphitheater where gladiators once fought for glory. Next, head to the Roman Forum and Palatine Hill, where you can wander among the ruins of ancient temples, basilicas, and public spaces that were once the heart of Roman civilization.

• Must-See Spots:
  • Colosseum: One of the most famous landmarks in the world, offering a glimpse into the grandeur and brutality of ancient Roman entertainment.
  • Roman Forum: A sprawling archaeological site filled with the remnants of Rome’s ancient government buildings, temples, and marketplaces.
  • Palatine Hill: One of Rome’s seven hills, offering panoramic views of the city and a chance to explore the ruins of imperial palaces.

Day 3: Vatican City—The Vatican Museums, St. Peter’s Basilica, and the Sistine Chapel

Spend your third day in Rome exploring Vatican City, the smallest independent state in the world and the spiritual heart of the Catholic Church. Begin with a visit to the Vatican Museums, where you can marvel at an incredible collection of art and artifacts, culminating in Michelangelo’s masterpiece, the Sistine Chapel. Afterward, visit St. Peter’s Basilica, one of the most magnificent churches in the world, and climb to the top of the dome for breathtaking views of Rome.

• Tip: Book your tickets to the Vatican Museums online in advance to skip the long lines, and consider taking a guided tour to fully appreciate the art and history on display.
• Evening: For your last night in Rome, enjoy a traditional Italian dinner in the Trastevere neighborhood, known for its charming cobblestone streets and lively atmosphere.

Day 4-5: Florence—The Cradle of the Renaissance

Day 4: Arrival in Florence and Introduction to the City

Take a morning train from Rome to Florence, the birthplace of the Renaissance. After arriving in Florence, check into your accommodation and start your exploration of this artistic city. Begin at the Piazza del Duomo, where you can admire the stunning Florence Cathedral (Duomo) with its iconic red-tiled dome designed by Brunelleschi. Climb to the top of the dome or the adjacent bell tower for panoramic views of the city.

• Must-See Spots:
  • Florence Cathedral (Duomo): An architectural masterpiece with a breathtaking interior and spectacular views from the top.
  • Baptistery of St. John: Famous for its bronze doors, including the “Gates of Paradise” by Ghiberti.

Day 5: Art and History—Uffizi Gallery, Ponte Vecchio, and Michelangelo’s David

Dedicate your second day in Florence to exploring the city’s incredible art and history. Start with a visit to the Uffizi Gallery, home to an unparalleled collection of Renaissance art, including works by Botticelli, Leonardo da Vinci, and Michelangelo. Afterward, take a leisurely walk across the Ponte Vecchio, Florence’s famous medieval bridge lined with jewelry shops.

In the afternoon, visit the Accademia Gallery to see Michelangelo’s David, one of the most iconic sculptures in the world. End your day with a visit to the Piazzale Michelangelo, a hilltop square that offers stunning views of Florence, especially at sunset.

• Tip: Book tickets to the Uffizi and Accademia galleries in advance to avoid long lines.
• Dining Suggestion: For dinner, enjoy a classic Florentine steak (bistecca alla Fiorentina) at one of the city’s traditional trattorias.

Day 6-7: Tuscany—Chianti, Siena, and San Gimignano

Day 6: Exploring the Tuscan Countryside

Leave the city behind and venture into the rolling hills of Tuscany. Rent a car in Florence and drive through the scenic Chianti region, famous for its vineyards, olive groves, and charming villages. Stop at a local winery for a wine tasting and a tour of the vineyards, and enjoy a leisurely lunch with views of the Tuscan countryside.

• Must-See Spots:
  • Greve in Chianti: A charming village in the heart of the Chianti region, known for its wine production and picturesque town square.
  • Castello di Brolio: A historic castle and winery offering tours, tastings, and beautiful views of the surrounding vineyards.

Day 7: Siena and San Gimignano

On your second day in Tuscany, visit the medieval city of Siena, known for its stunning Gothic architecture and the famous Palio horse race. Explore the magnificent Siena Cathedral, with its intricate façade and richly decorated interior, and visit the Piazza del Campo, one of the most beautiful squares in Italy.

In the afternoon, drive to the hilltop town of San Gimignano, often referred to as the “Medieval Manhattan” due to its many tall towers. Wander through the town’s narrow streets, visit the Duomo, and enjoy some of the best gelato in Italy at Gelateria Dondoli.

• Tip: Both Siena and San Gimignano are pedestrian-friendly, so park your car outside the city walls and explore on foot.
• Dining Suggestion: Enjoy a traditional Tuscan dinner at a local osteria, featuring dishes like pappardelle with wild boar ragu and ribollita, a hearty vegetable and bread soup.

Day 8-9: Venice—The City of Canals

Day 8: Arrival in Venice and Exploring the Grand Canal

Take a morning train from Florence to Venice, one of the most romantic and unique cities in the world. After arriving in Venice, check into your accommodation and begin your exploration of this enchanting city. Start with a vaporetto (water bus) ride along the Grand Canal, Venice’s main waterway, lined with beautiful palazzi and historic buildings.

Disembark at St. Mark’s Square, the heart of Venice, and visit St. Mark’s Basilica, a stunning example of Byzantine architecture. Climb to the top of the Campanile (bell tower) for panoramic views of the city and the lagoon.

• Must-See Spots:
  • St. Mark’s Basilica: A masterpiece of Byzantine architecture, with its gilded mosaics and stunning domes.
  • Doge’s Palace: A Gothic palace that was the residence of the Doge of Venice, offering a fascinating glimpse into the city’s history.

Day 9: Venice’s Hidden Gems—Rialto, Dorsoduro, and Cannaregio

Spend your second day in Venice exploring some of the city’s lesser-known neighborhoods. Start with a visit to the Rialto Market, where you can browse the stalls of fresh seafood, fruits, and vegetables, and enjoy a morning coffee at a nearby café. Cross the iconic Rialto Bridge and wander through the narrow streets of the San Polo district.

In the afternoon, head to the Dorsoduro neighborhood, home to the Peggy Guggenheim Collection, a modern art museum housed in a beautiful palazzo along the Grand Canal. Afterward, explore the Cannaregio district, a quieter area of Venice where you can visit the historic Jewish Ghetto and enjoy a peaceful stroll along the canals.

• Tip: Venice can be crowded, especially in the main tourist areas. Consider exploring early in the morning or later in the evening to experience a more tranquil side of the city.
• Dining Suggestion: For dinner, enjoy Venetian specialties like risotto al nero di seppia (squid ink risotto) or sarde in saor (sweet and sour sardines) at a traditional trattoria.

Day 10-12: The Amalfi Coast—Sorrento, Positano, and Capri

Day 10: Arrival in Sorrento and Exploring the Town

Take a morning train from Venice to Naples, followed by a short drive or train ride to Sorrento, the gateway to the Amalfi Coast. After checking into your accommodation, spend the afternoon exploring the charming town of Sorrento. Stroll through the Piazza Tasso, visit the historic Cathedral of Sorrento, and enjoy a walk along the scenic clifftop promenade with views of the Bay of Naples.

• Must-See Spots:
  • Marina Grande: A picturesque fishing village within Sorrento, known for its colorful boats and seafood restaurants.
  • Limoncello Tasting: Sorrento is famous for its lemons, so be sure to try some locally made limoncello, a delicious lemon liqueur.

Day 11: Positano and Amalfi

Spend your second day exploring the stunning Amalfi Coast, known for its dramatic cliffs, colorful villages, and crystal-clear waters. Start with a visit to Positano, one of the most iconic and photogenic towns on the coast. Wander through the narrow streets, relax on the beach, and enjoy lunch at a seaside restaurant.

In the afternoon, continue your drive along the coast to the town of Amalfi, where you can visit the impressive Amalfi Cathedral and explore the town’s charming streets and squares.

• Tip: The roads along the Amalfi Coast can be narrow and winding, so take your time and enjoy the views. Consider taking a boat tour for a different perspective of the coastline.
• Dining Suggestion: Enjoy fresh seafood and Italian specialties at a beachfront restaurant in Positano or Amalfi, with stunning views of the Mediterranean.

Day 12: Capri and the Blue Grotto

On your third day on the Amalfi Coast, take a ferry from Sorrento or Positano to the island of Capri, a glamorous destination known for its rugged landscapes, upscale boutiques, and celebrity visitors. Start your day with a boat tour of the island, including a visit to the famous Blue Grotto, a sea cave known for its mesmerizing blue light.

Afterward, explore the island’s main town, Capri, where you can visit the Gardens of Augustus for panoramic views of the Faraglioni rock formations and the Marina Piccola. In the afternoon, take the chairlift to the top of Monte Solaro, the highest point on the island, for breathtaking views of the Bay of Naples and the Amalfi Coast.

• Tip: The Blue Grotto can be crowded, especially in the summer months. Visit early in the morning or later in the afternoon for a more peaceful experience.
• Dining Suggestion: Enjoy a leisurely lunch at a seaside restaurant in Capri, savoring local specialties like insalata caprese (Caprese salad) and ravioli capresi (Capri-style ravioli).

Day 13-14: Milan and Lake Como—The Elegance of Northern Italy

Day 13: Arrival in Milan and Exploring the City

Take a morning train from Naples to Milan, the fashion and design capital of Italy. After arriving in Milan, check into your accommodation and start your exploration of the city. Begin with a visit to the iconic Milan Cathedral (Duomo di Milano), one of the largest and most impressive Gothic cathedrals in the world. Climb to the rooftop for stunning views of the city and the surrounding Alps.

Next, visit the Galleria Vittorio Emanuele II, a historic shopping arcade known for its beautiful glass dome and high-end boutiques. Continue to the nearby La Scala Opera House, one of the most famous opera houses in the world, where you can take a guided tour or attend a performance.

• Must-See Spots:
  • Milan Cathedral (Duomo di Milano): A magnificent Gothic cathedral with a stunning façade and rooftop views.
  • Galleria Vittorio Emanuele II: A historic shopping arcade filled with luxury stores, cafes, and restaurants.

Day 14: Day Trip to Lake Como

On your final day in Italy, take a day trip to Lake Como, one of the most beautiful and luxurious destinations in Northern Italy. Just a short train ride from Milan, Lake Como is known for its stunning scenery, elegant villas, and charming lakeside towns.

Start your day in the town of Como, where you can visit the Como Cathedral and explore the town’s historic center. From Como, take a boat tour of the lake, stopping at the picturesque towns of Bellagio and Varenna. Wander through the narrow streets, visit the beautiful gardens of Villa Melzi in Bellagio, and enjoy a lakeside lunch with views of the water.

• Tip: Consider renting a boat or taking a guided tour to fully appreciate the beauty of Lake Como from the water.
• Evening: Return to Milan in the evening and enjoy a farewell dinner at a traditional Milanese restaurant, savoring dishes like risotto alla Milanese or ossobuco.

Conclusion: Arrivederci, Italia!

After two unforgettable weeks exploring Italy, it’s time to say arrivederci. From the ancient ruins of Rome to the romantic canals of Venice, the artistic treasures of Florence, and the stunning landscapes of the Amalfi Coast and Lake Como, you’ve experienced the very best that Italy has to offer.

As you reflect on your journey, you’ll carry with you memories of breathtaking sights, delicious food, and the warmth and hospitality of the Italian people. Whether you’re leaving with a newfound appreciation for art and history or a deeper love for Italian cuisine and culture, one thing is certain: Italy will always have a special place in your heart.

Until next time—arrivederci e buon viaggio!