Italy in Two Weeks ─ the Best Itinerary

Italy is a country that effortlessly blends the past with the present, where ancient ruins stand as witnesses to centuries of history yet whose cities buzz with ordinary everyday life.

Planning a trip to Italy can feel overwhelming with so much to see and explore, but with this carefully crafted two-week plan, you’ll travel across Italy’s most renowned places, immersing yourself in the art, culture, and flavors that make this country really one-of-a-kind.

So pack your bags and prepare for the adventure of a lifetime as we uncover the best sides of Italy in just fourteen days.

Days from 1 to 3 ─ Venice


The Unparalleled Lifestyle

Start your Italian vacation in Venezia or Venice. On your first day, get lost in the tangle of narrow lanes and canals that make up this distinctive city. Visit famous places and monuments like St. Mark’s Square and the Doge’s Palace, and enjoy a leisurely gondola ride down the Grand Canal.

On your second day, visit the Gallerie dell’Accademia, which contains a great collection of Venetian art from the 14th to 18th centuries. Discover the city’s lesser-known neighborhoods, like Cannaregio and Dorsoduro, which are home to cozy cafes, workshops, and locally appreciated markets.

On your third day in Venice, go to the nearby islands of Murano and Burano. Murano is known for its magnificent glassware, whilst Burano is known for its colorful architecture and very special and intricate lacework. Take the vaporetto to these gorgeous islands and spend the day exploring their scenic neighborhoods.

Days from 4 to 6 ─ Florence


Home to the Renaissance

Next, travel to the heart of Tuscany to experience the artistic magnificence of Florence. Spend your first day visiting and admiring the city’s cultural fortune, beginning at the Uffizi Gallery, which houses masterpieces by Renaissance masters such as Leonardo da Vinci, Michelangelo, and Botticelli.

After this, pass across Florence’s oldest bridge, the Ponte Vecchio, soaking in the vistas of the Arno River.

On your second day, visit the majestic Florence Cathedral, also known as the Duomo, and climb to the top of the dome once again for stunning vistas of the entire city. Consider passing through the picturesque streets of Oltrarno, which are home to artisan workshops, antique shops, and marketplaces.

Spend your third day in Florence exploring the beautiful Tuscan countryside outside of the city boundaries, take a walk, and see the nearby towns Poggibonsi and Volterra. Stop at a local trattoria to savor the local Fiorentina, which is a world-famous traditional Tuscan steak made of a young steer.

Days from 7 to 10 ─ Rome

The Eternal City

No journey to Italy is complete without visiting the stunning city of Rome, the heart of the ancient world and the most famous Italian city.

Spend your day discovering the beautiful landmarks that distinguish this historic city, from a visit to the Colosseum, the worldwide famous icon of Rome, envisioning the gladiator combat that once took place within its walls, to the Roman Forum, which still stands tall as a testimony to the Roman daily life.

After that, explore Rome’s rich background by visiting Vatican City. The Vatican Museums, which house one of the world’s largest art collections, including Michelangelo’s masterpiece, the Sistine Chapel, is one of the most appreciated tourist attractions all over the world.

Take your time to St. Peter’s Basilica, the world’s biggest cathedral, and climb to the top of the dome for panoramic views of Roman surroundings.

Explore the beautiful areas of Trastevere and Monti on your third day in Rome, where the pulse of the city beats with vitality and genuine Italian spirit. Try the varied culinary scene, from hip restaurants to cozy family trattorias serving traditional Roman dishes like fried courgette flowers and pasta carbonara (which is an absolute must-try).

Allow the beautiful streets and enticing scents to lead you on a gastronomic exploration through the core of the Eternal City, and don’t forget to try some exquisite Italian gelato.

Days from 10 to 12 ─ Amalfi Coast


The Paradise Among Us

After discovering the incredible atmosphere of some of the most popular and iconic Italian cities, you’ll be amazed to unwind on the breathtaking Amalfi Coast.

Nestled in the Campania region of Italy, the Amalfi Coast is known for its turquoise waves, villages, and a very special cliffside. The tiny, winding roads that hug the coastline and lead to coves and pebble beaches really captivate visitors.

The area’s ageless appeal as a destination for exploration and relaxation is enhanced by its medieval architecture, antique watchtowers, and lemon trees, all of which bear witness to its rich historical past.

Spend two days bathing in the sun on one of the region’s stunning beaches, Positano or Amalfi. Admire Mediterranean Sea’s crystal-clear waters, inhale the warm and salty sea wind and enjoy panoramic views of the coastal line.

The coast of Amalfi will be one of the most beautiful places you have ever seen.

Day 13-14 ─ Palermo and Taormina


A Taste of the Mediterranean

End your Italian vacation discovering Sicily’s varied scenery beyond the lively areas of Palermo. Pay a visit to the charming city of Taormina, which sits upon a cliff overlooking the seas of the Ionian on your first day there. You can flow through the winding medieval alleyways, explore the ancient Greek theater with its stunning views of Mount Etna, and rest in the overall delightful Sicilian atmosphere.

On the next day, explore the historic city of Syracuse, where Greek and Roman civilizations blend historically. Explore the wonderful archaeological sites, such as the Greek Theater, which still hosts plays today, and the Ear of Dionysius, a unique limestone cave with extraordinary acoustics.

As you can see, Italy is more than just a place somewhere in Europe, it’s a whole experience that never gets boring. This country has an exceptionally rich personality, which is everytime to be discovered like it was the first time.

This itinerary is not the one and only you may follow, but it is for sure designed to be very exciting to be your first visit to the areas. Make sure to visit the most outstanding and researched areas, such as the ones we listed earlier, to fully immerse yourself in this unforgettable experience, and consider to search for the best accommodations to stay on the Retreats website.

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