21 Days Exploring Italy's Iconic Cities Itinerary

Begin your second day with a visit to Brera Art Gallery (Pinacoteca di Brera). This renowned art museum houses an impressive collection of Italian Renaissance art. Take your time to appreciate masterpieces by artists like Caravaggio and Raphael.

After immersing yourself in art, head to Church of Santa Maria delle Grazie (Chiesa di Santa Maria delle Grazie) to see Leonardo da Vinci's famous mural, The Last Supper. Make sure to book tickets in advance as it is highly popular. For lunch, try a nearby trattoria for some authentic Milanese cuisine.

In the evening, visit La Scala Opera House (Teatro alla Scala), one of the most famous opera houses in the world. If you can, catch a performance or simply take a guided tour to learn about its rich history and architectural beauty.

Start your day with a visit to the Church of San Maurizio al Monastero Maggiore (Chiesa di San Maurizio al Monastero Maggiore). Known as the 'Sistine Chapel of Milan,' this church is adorned with stunning frescoes that are sure to captivate you.

After exploring the church, head to Brera, a charming district known for its artistic atmosphere. Enjoy lunch at one of the local cafes and then visit the Brera Art Gallery (Pinacoteca di Brera) to see an impressive collection of Italian Renaissance art.

In the evening, take a leisurely stroll through Sempione Park (Parco Sempione). This beautiful park is perfect for a relaxing walk and offers great views of the city. End your day with dinner at a nearby restaurant.

Arrive in Venice and start your exploration at St. Mark's Square (Piazza San Marco). Visit St. Mark's Basilica (Basilica di San Marco) with its stunning mosaics and opulent design. Don't miss climbing up St. Mark's Campanile for panoramic views of Venice.

For lunch, enjoy Venetian cuisine at one of the cafes around St. Mark's Square before heading to Doge's Palace (Palazzo Ducale). This Gothic masterpiece was once the residence of the Doge of Venice and now serves as a museum showcasing Venetian history.

In the evening, take a romantic gondola ride through Venice’s canals starting from Rialto Bridge (Ponte di Rialto). Afterward, dine at Trattoria Antiche Carampane, known for its traditional Venetian dishes.

Begin your day with a visit to Peggy Guggenheim Collection (Collezione Peggy Guggenheim), an outstanding modern art museum located on the Grand Canal. The collection includes works by Picasso, Pollock, and Dalí among others.

Afterward, explore more artistic treasures at Venice Accademia Gallery (Gallerie dell'Accademia). Have lunch nearby before visiting Bridge of Sighs, which connects Doge’s Palace with old prisons—a must-see for history enthusiasts.

Conclude your day by visiting Da Fiore for dinner—a Michelin-starred restaurant offering exquisite Venetian cuisine.

Scuola Grande di San Rocco is your first stop today. This historic building houses an incredible collection of paintings by Tintoretto.

Frari Church (Basilica dei Frari) awaits you next. This impressive church features works by Titian and other renowned artists. For lunch, try a local trattoria nearby.

Trattoria da Romano is perfect for dinner tonight. Located on Burano Island, this restaurant offers delicious Venetian cuisine in a charming setting.

Start your day in Florence with a visit to the Florence Duomo (Cattedrale di Santa Maria dei Fiori). This iconic cathedral is known for its stunning dome designed by Brunelleschi. Climb to the top for breathtaking views of the city.

After exploring the Duomo, head to Uffizi Galleries (Gallerie degli Uffizi). This world-renowned museum houses an incredible collection of Renaissance art, including works by Botticelli, Michelangelo, and Leonardo da Vinci. For lunch, try All'Antico Vinaio, famous for its delicious sandwiches.

In the evening, take a leisurely stroll across the Ponte Vecchio, Florence's oldest and most picturesque bridge. Enjoy dinner at La Giostra, known for its romantic ambiance and Tuscan cuisine.

Begin your day with a visit to the Accademia Gallery (Galleria dell'Accademia), home to Michelangelo's David. Spend some time admiring this masterpiece and other notable works of art.

Next, explore the historic Palazzo Vecchio, Florence's town hall that offers fascinating insights into the city's political history. For lunch, dine at Trattoria Mario, a beloved local spot known for its hearty Tuscan dishes.

In the evening, visit the beautiful Basilica of Santa Croce (Basilica di Santa Croce), where many famous Italians are buried, including Michelangelo and Galileo. End your day with dinner at Osteria Santo Spirito, which offers delightful Italian cuisine in a cozy setting.

Boboli Gardens (Giardino di Boboli) is your starting point today. These beautifully landscaped gardens offer stunning views over Florence and are perfect for a morning stroll.

Palazzo Pitti awaits you next. This grand palace houses several museums and galleries showcasing art, fashion, and history. For lunch, dine at Cibreo Ristorante, known for its creative Tuscan dishes.

Gustapizza is ideal for dinner tonight—a beloved local spot offering some of Florence’s best pizza.

Arrive in Rome and start your exploration at the iconic Colosseum (Colosseo). Take a guided tour to learn about its history as an ancient gladiatorial arena.

After visiting the Colosseum, head to the nearby Roman Forum and Palatine Hill. These ancient sites offer fascinating glimpses into Rome's past. For lunch, enjoy traditional Roman dishes at Roscioli, known for its exceptional pasta.

In the evening, visit the stunning Trevi Fountain (Fontana di Trevi). Toss a coin into the fountain to ensure your return to Rome. Dine at Armando al Pantheon, located near another iconic landmark—the Pantheon.

Begin your day with a visit to Vatican City. Explore St. Peter's Basilica and marvel at its grandeur. Don't miss climbing up to St. Peter's Dome for panoramic views of Rome.

Next, head to the Vatican Museums where you can see an extensive collection of art and historical artifacts, including Michelangelo’s Sistine Chapel ceiling frescoes. For lunch, try nearby restaurant Pizzarium Bonci for some of Rome’s best pizza.

Conclude your day by visiting Castel Sant'Angelo—a fortress with rich history and stunning views over Rome from its terrace. Enjoy dinner at Ristorante Aroma at Palazzo Manfredi, offering exquisite dining with views of the Colosseum.

Begin your day with a visit to the Pantheon. This ancient temple-turned-church is one of Rome’s best-preserved monuments.

Next, head to Piazza Navona, one of Rome’s most beautiful squares featuring stunning fountains and lively street performers. For lunch, try Osteria da Fortunata, known for its handmade pasta.

La Pergola offers an unforgettable dining experience with panoramic views over Rome—perfect for ending your day on a high note.

Start your day in Naples with a visit to the Naples National Archaeological Museum (Museo Archeologico Nazionale). This museum houses one of the most extensive collections of Greco-Roman antiquities, including artifacts from Pompeii and Herculaneum.

After the museum, head to Spanish Quarter (Quartieri Spagnoli) for a taste of local life. Wander through its narrow streets and enjoy lunch at Pizzeria Starita, famous for its delicious Neapolitan pizza.

In the evening, take a stroll along the waterfront to Castel dell'Ovo, an ancient castle offering stunning views of the Bay of Naples. End your day with dinner at Veritas Restaurant, known for its modern take on traditional Neapolitan cuisine.

Herculaneum Archaeological Park (Parco Archeologico di Ercolano) is your first stop today. This ancient Roman town was buried by the same eruption that destroyed Pompeii but is better preserved.

Pompeii Archaeological Site awaits you next. Spend your afternoon exploring this vast site, which offers an incredible glimpse into daily life in ancient Rome. For lunch, try a local trattoria near the entrance.

Ristorante Don Alfonso 1890 is perfect for dinner tonight. Located in nearby Sant'Agata sui Due Golfi, this Michelin-starred restaurant offers exquisite Mediterranean cuisine.

Start your final day with a visit to the Royal Palace of Naples (Palazzo Reale). This historic palace offers a glimpse into the opulent lifestyle of the Bourbon kings and features beautiful rooms and gardens.

After exploring the palace, head to Castel Nuovo (Maschio Angioino), a medieval castle that now houses a museum. For lunch, enjoy traditional Neapolitan cuisine at Ristorante Mattozzi, known for its delicious seafood dishes.

In the evening, take a leisurely stroll along the waterfront promenade to Castel dell'Ovo. This ancient castle offers stunning views of the Bay of Naples. End your day with dinner at Il Comandante, a Michelin-starred restaurant offering exquisite Mediterranean cuisine.

Path of the Gods (Sentiero Degli Dei) is a must-do hike offering breathtaking views of the Amalfi Coast. Start early to avoid the midday heat and enjoy this scenic trail.

Amalfi Cathedral (Cattedrale di Sant'Andrea) is your next stop. This stunning cathedral features beautiful mosaics and a fascinating history. For lunch, dine at a local café in Amalfi town.

Caruso Roof Garden Restaurant offers an unforgettable dining experience with panoramic views over the coast. Enjoy delicious Italian cuisine as you watch the sunset.

Correale di Terranova Museum (Museo Correale di Terranova). This museum showcases fine art and historical artifacts from Sorrento's past.

La Cantina dei Mille for dinner tonight—a highly-rated restaurant known for its fresh seafood dishes.

Start your day with a visit to the Valley of the Temples (Valle dei Templi). This archaeological site is one of Sicily's most important and features well-preserved ancient Greek temples. Take your time exploring the ruins and learning about their history.

After the Valley of the Temples, head to Agrigento Archaeological Museum (Museo Archeologico Regionale "Pietro Griffo"). This museum houses an extensive collection of artifacts from the ancient city of Akragas. For lunch, try a nearby trattoria for some authentic Sicilian cuisine.

In the evening, visit Duomo for dinner. This Michelin-starred restaurant offers exquisite Sicilian dishes made with fresh local ingredients.

Begin your day with an excursion to Mt. Etna (Monte Etna). Explore this active volcano through guided tours that take you to its craters and lava fields.

After exploring Mount Etna, head to Gambino Winery (Vini Gambino) for a wine tasting experience featuring local wines produced from volcanic soil grapes.

Conclude your day with dinner at Il Consiglio di Sicilia, known for its exceptional Sicilian dishes made from locally sourced ingredients.

Palermo Cathedral (Cattedrale di Palermo) is your first stop today. This stunning cathedral features a mix of architectural styles and offers beautiful views from its rooftop terrace.

Massimo Opera House (Teatro Massimo) awaits you next. Take a guided tour of this grand opera house, which is one of the largest in Europe. For lunch, dine at Antica Focacceria San Francesco, known for its traditional Sicilian street food.

Vucciria Market (La Vucciria) is perfect for an evening stroll. This historic market comes alive at night with food stalls and lively bars. Enjoy dinner at Osteria dei Vespri, offering delicious Sicilian cuisine in a charming setting.

Taormina Piazza Duomo is your starting point today. Explore this picturesque square and visit the nearby Taormina Cathedral.

Giardini della Villa Comunale is next on your list. These beautiful gardens offer stunning views over the coast and Mount Etna. For lunch, try Trattoria da Nino, known for its fresh seafood dishes.

Greek Theatre (Teatro Greco) is a must-visit in Taormina. This ancient theatre offers breathtaking views and hosts various performances throughout the year. End your day with dinner at La Capinera, a Michelin-starred restaurant offering exquisite Mediterranean cuisine.