14 Day Italy Itinerary: Best Way To Spend Two Weeks In Italy


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Italy is a dream destination that captivates travelers with its irresistible charm. From the grandeur of ancient Rome to the romantic charm of Venice’s canals, this country offers an enchanting blend of history, art, and natural beauty. Immerse yourself in the rich cultural heritage, exploring iconic landmarks like the Colosseum, Vatican City, and the leaning tower of Pisa. Discover the masterpieces of Renaissance art in Florence and marvel at the architectural wonders of Venice. The rolling hills of Tuscany, provide the perfect backdrop for unforgettable experiences.

And let’s not forget the food! Indulge in delectable pasta, pizza, and gelato, savoring the authentic flavors of Italian cuisine. Whether you seek history, romance, or simply a taste of la dolce vita, Italy promises a journey of a lifetime. If you are wondering how much time do you need in Italy, then two weeks in Italy is enough for you to absorb its marvels, so read on to know how to spend two weeks in Italy.

How We Structured The 14 Day Trip To Italy

The 14 day trip includes spending 4 days in Rome, 3 days in Florence, 3 days in Tuscany region, 2 days in Venice and 2 days in Milan, for a total of two weeks in Italy. Rome is the best destination to have as the starting point for the trip. You can choose to fly out from Milan to your home destination, or head back to Rome for your return flight. Scroll down for a view of the Google map that will help you visualize the entire path for the trip.

How To Get Around In Italy

One of the best things about the country is the solid transportation infrastructure. Getting around the city can be done using trains, trams, buses and cabs. Traveling in their super-fast train service is best suited when traveling between cities. If you want to visit the Tuscany hill region, then it is best you rent a car and drive around on your own, which is also very easy. Just be mindful of their traffic signs posted along the roads. Read on to discover the best way to spend two weeks in Italy.

Best Way To Spend Two Weeks In Italy

Day 1: Rome – Explore the Vatican Museums and Sistine Chapel

Today, you will explore the Vatican Museums and Sistine Chapel, that are extraordinary gems of human artistry and historical significance. Housed within the Vatican City, these renowned attractions hold an unparalleled collection of artistic treasures from various eras. The Vatican Museums and Sistine Chapel hold deep religious and cultural importance, serving as a symbol of the Catholic Church’s legacy and the preservation of humanity’s artistic heritage.

two weeks in Italy
Inside the Vatican Museums’ grounds

The Sistine Chapel, with its awe-inspiring frescoes by Michelangelo depicting biblical scenes, stands as a pinnacle of Renaissance art. The masterpieces within these museums showcase the brilliance of artists like Raphael, Leonardo da Vinci, and Caravaggio, creating a mesmerizing journey through the evolution of human creativity. Photography is forbidden inside the chapel, so be mindful of that.

Inside one of the halls at the Vatican Museums

Plan to spend half a day here. Tickets are required with timed entry, so you need to book them well in advance.

Magnificent work on the ceiling at Vatican Museums

Afterwards, plan to visit the Trevi Fountain, a magnificent Baroque masterpiece, featuring stunning sculptures, cascading water, and intricate architectural details. Its historical significance, romantic allure, and the tradition of coin tossing make it a beloved and iconic landmark in the heart of Rome. This place is absolutely packed all the time with tourists due to its popularity.

Trevi Fountain

The area around the fountain is filled with restaurants and cafes, and some luxury shops as well. Plan to have dinner here before heading back to your hotel.

Day 2: Rome – Visit the Colosseum and Pantheon

Today, you will visit one of the marvels in the world, the Colosseum. The Colosseum, Palatine Hill, and Roman Forum collectively form an extraordinary archaeological complex that showcases the rich history and grandeur of ancient Rome.

The Colosseum

The Colosseum, an iconic amphitheater, is a symbol of Roman engineering and entertainment, having hosted epic gladiatorial contests and spectacles for thousands of spectators.

Inside The Colosseum
Palatine Hill

Palatine Hill, the legendary birthplace of Rome, boasts breathtaking panoramic views and holds the ruins of opulent palaces, immersing visitors in the lives of emperors and aristocrats.

The Roman Forum

The Roman Forum, once the heart of the Roman Empire, brims with impressive temples, arches, and civic buildings, offering a glimpse into the political, religious, and social life of ancient Rome.

Together, these historical landmarks provide an awe-inspiring journey through time, leaving visitors with a profound appreciation for the grandeur and enduring legacy of the Roman civilization. The complex is huge, and with the immense volume of visitors, plan to spend half a day here. Tickets are required with timed entry, so book in advance.

The Pantheon

Next, head to the Pantheon, an architectural marvel and a testament to ancient Roman engineering prowess, with its iconic domed structure and perfectly preserved interior. Its remarkable oculus at the center of the dome allows natural light to filter into the temple, creating a mesmerizing play of light and shadows, adding to the ethereal ambience that has captivated visitors for centuries.

Piazza Navona

Your last stop for the day is at Piazza Navona, a charming public square in Rome known for its vibrant atmosphere and stunning Baroque architecture. Its unique oval shape, adorned with elegant fountains, including the famous Fontana dei Quattro Fiumi by Bernini, and impressive sculptures, creates a picturesque setting that has inspired artists and visitors alike for generations. Plan to have dinner at one of the several restaurants at the piazza, before heading back to the hotel.

Day 3: Rome – Visit St. Peter’s Basilica

Today, you will visit one of the most important places in Rome, the St. Peter’s Basilica. This located inside of Vatican City and is a place of extraordinary beauty and profound religious significance. As the largest church in the world, it showcases magnificent architecture, stunning artworks, and intricate details that leave visitors in awe. The basilica’s historical importance as the burial site of St. Peter, one of the apostles of Jesus Christ, adds to its sacred aura.

St. Peter’s Basilica

It is best to visit the basilica as part of a tour, since the place is packed at all times, and getting inside could take up to several hours if visiting independently. After spending a few hours visiting the dome and the basilica, head to Castel Sant’Angelo.

Castel Sant’Angelo

Castel Sant’Angelo was built as a mausoleum for the Roman Emperor Hadrian and his family, and later served as a fortress and a papal residence. The castle’s commanding presence on the banks of the Tiber River, its cylindrical shape, and its iconic statue of the Archangel Michael atop the building make it a distinctive landmark in Rome. You will get to explore its underground passages, fortified walls, sumptuous Renaissance-era chambers and panoramic views of the entire city from its terraces.

Inside the Trastevere neighborhood

Your last stop for the day will be at Trastevere, widely known as the best foodie neighborhood in Rome. Trastevere is a charming and enchanting district that exudes an authentic and bohemian atmosphere. Its narrow cobblestone streets are lined with quaint, colorful buildings, and it is known for its lively ambience and vibrant nightlife. It is a hub of local life, offering a plethora of trattorias, cafes, and artisan shops, where visitors can savor traditional Roman cuisine and soak in the conviviality of the locals. Read our recommendations on the 7 best hotels in Trastevere Rome.

Day 4: Florence – View Michelangelo’s David

Continue your two weeks in Italy trip by traveling from Rome to Florence on one of their high-speed trains. After checking in at your hotel in Florence, grab lunch and then head to the Accademia Gallery. The gallery holds one of the world’s most renowned masterpieces, Michelangelo’s David. This iconic sculpture, standing at an imposing height, showcases the artist’s unparalleled skill and attention to detail.

Michelangelo’s David

Beyond David, the gallery houses a collection of exceptional Renaissance artworks, including Michelangelo’s unfinished sculptures, known as the Prisoners or Slaves, and a remarkable collection of religious paintings.

The rest of the day is for you to explore the city; some of the places we recommend visiting are Piazza della Repubblica, Palazzo Vecchio and Ponte Vecchio.

Ponte Vecchio

Day 5: Florence – Visit Cathedral of Santa Maria del Fiore

Today, you will visit the most sought after attraction in Florence, the Cathedral of Santa Maria del Fiore, also known as the Duomo. It is an iconic symbol and the most popular sight in all of Florence. The cathedral’s intricate façade, adorned with elaborate marble work and stunning sculptures, reflects the artistic brilliance of the Renaissance era. Inside, you can marvel at the grandeur of the nave and soak in the beauty of the stained glass windows and frescoes.

Cathedral of Santa Maria del Fiore by Joseph Quam

If you climb to the top of the dome, you will be rewarded with a breathtaking panorama of the city’s iconic landmarks.

Giotto’s Bell Tower

After exploring all the sights (Baptistery of San Giovanni, Giotto’s Bell Tower, Brunelleschi’s Dome, the Opera del Duomo Museum and the ancient basilica of Santa Reparata) that are included in the Cathedral’s entry ticket, explore the city at your leisure. Uffizi Gallery and Piazza della Signoria are our recommendations for you.

Day 6: Pisa – Explore the Leaning Tower of Pisa

Start your day by taking a quick 1 hour train ride to Pisa, home to one of the most unbelievable architectural wonders of the world, the Leaning Tower of Pisa.

Leaning Tower of Pisa

This structure is part of the Piazza dei Miracoli complex, that includes the Baptistery, Camposanto, Sinopie Museum, Opera del Duomo Museum. You can visit them depending on the type of ticket that you have purchased. Do not miss the opportunity to climb to the top of the tower, and experience the lean as you ascend the tower’s spiral staircase.

Inside the Camposanto

Spend half a day visiting all the areas inside the complex and have lunch at one of the cafes overseeing the tower. Bid goodbye to the tower and take a return train back to Florence.

Exploring the streets of Florence

Rest of the day is for you to explore the streets of Florence, or go shopping at the luxury boutiques along Via de’ Tornabuoni.

Day 7: Head to the Tuscany region

Today, you will be heading to the magical rolling hills of Tuscany, where every view is picture-perfect, right out of a postcard! There are several towns to choose from for your stay over the next few days in the region, the most famous ones being Pienza, Monticchiello and Montepulciano, to name a few. You can choose to stay at either of these towns, or at a villa near these towns, but you can’t go wrong either way.

We recommend staying at a villa near Pienza, which puts you close to sight-seeing attractions, and also lets you have a relaxed vacation in your villa in the middle of nowhere. Whatever you choose, make sure you book several months in advance, as these are the most sought after areas in the region.

View from our Tuscany villa

Since you will be heading to a small town on the Tuscany hills, we recommend you rent a car from the Florence airport, since there will be no public transportation at these small towns. Most of the day will be spent getting to your destination and settling in at your accomodation.

Day 8: Relax at your villa

As you complete a portion of your two weeks in Italy vacation, it is going to be one of those days where you do nothing besides basking in the sun at your villa, or grabbing a swim in the pool, or lounging in the garden with your favorite book and cocktail. Enjoy the scenic beauty of the Tuscany region, and the tranquility and serenity of the space, while being mesmerized by the stunning landscapes around you.

Day 9: Explore Pienza

Head to Pienza today and spend time exploring the cobblestone streets, absorb the breathtaking landscapes of rolling hills and vineyards, and indulge in some delicious Pecorino cheese.

Exploring Pienza

We definitely recommend you go wine tasting at one of the fantastic vineyards in the area, but advance booking is recommended. Enjoy the many flavors of wine, while you continue to be fascinated by the landscape all around.

Day 10: Head to Venice

It is time to bid goodbye to the rolling hills of Tuscany, and head back to Florence to return your rental car. Most of the day is going to be spent in travel since you will catch a train from Florence to Venice, after dropping off your car.

Once you reach Venice, you can either use the public motor boat service, or hire a water taxi to take you to your hotel. Check in to your hotel and explore the nearby area for the rest of the day.

Day 11: Venice – Explore St. Mark’s Square

Spend the entire morning exploring the most famous public square of Venice, the St. Mark’s Square, or Piazza San Marco. The square is home to St. Mark’s Basilica, the majestic building with its intricate mosaics and Byzantine design. The Doge’s Palace, or Palazzo Ducale, is also located here and is a magnificent Gothic-style palace that served as the residence of the Doge (the chief magistrate) of Venice and the seat of Venetian government.

Palazzo Ducale

The area is surrounded with cafes and restaurants, for you to have lunch at. Later during the afternoon, do not forget to see the Rialto Bridge and experience a gondola ride in Venice! It is certainly a romantic experience, drifting along the picturesque canals and under charming bridges. The rest of the day is for you to explore Venice and its labyrinthine streets and picturesque bridges.

Experiencing a gondola ride

Day 12: Explore Milan

Your last destination in this magical two weeks in Italy vacation will be Milan. The first half of the day will be spent traveling from Venice to Milan by train. After checking in at your hotel, head to Piazza del Duomo, the main piazza of Milan. Prepare to be mesmerized by Duomo di Milano, Italy’s largest church that’s located here.

Duomo di Milano

The square is also home to Galleria Vittorio Emanuele II, a shopping arcade with soaring glass ceiling, intricate mosaics, and luxurious storefronts.

Galleria Vittorio Emanuele II

This is one of the best sights in Milan that you can ask for. The area is packed with elegant cafes, restaurants, and bars, so plan to have dinner here before heading back to the hotel.

Day 13: Shopping in Milan

No visit to Milan is complete without shopping here! Widely considered as one of the fashion and shopping capitals in the world, Milan hosts the best and prestigious luxury brands across the world. Milan is home to upscale fashion districts, such as the Quadrilatero della Moda (Fashion Quadrangle), which includes famous shopping streets like Via Montenapoleone, Via della Spiga, and Via Manzoni. These streets are lined with high-end boutiques, luxury brands, and designer showrooms, offering an unparalleled shopping experience.

Spend the entire day shopping at the luxury boutiques, people watching and enjoying some delectable food and drinks as you wrap your day in Milan.

Day 14: Head back to Rome

This is your last day of the magical two weeks in Italy vacation, so it’s time to head back to Rome. Depending on when your return flight is, you can plan to explore the city before bidding farewell until next time.

Your 14 Day Italy Itinerary Map

Plan Your Two Weeks In Italy Vacation

Now that you know how to explore the charming cities and towns in Italy, go ahead and start planning your next vacation! Email us and we will help put together a relaxing and luxurious itinerary just for you!

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