The Best Italy Itinerary Awaits – Discover The Unparalleled Charm!

EVERYTHING you need to know about your trip!

Embark on an unforgettable journey through Italy with the best Italy itinerary, a 2-week adventure that showcases the country’s rich history, stunning landscapes, and mouthwatering cuisine.

Get ready to explore iconic cities like Rome, Florence, and Venice, discover picturesque towns along the Amalfi Coast, and immerse yourself in the beauty of Tuscany. From the ancient ruins to Renaissance masterpieces, from charming canals to rolling vineyards, this itinerary will take you on an extraordinary exploration of the best that Italy has to offer.

When is the Best Time to Visit Italy

The best times to follow the best Italy Itinerary is during spring (April to June) and fall (September to November). During these seasons, the weather is mild, and the crowds are less overwhelming compared to peak summer months.


Avg. Temp

Rainy Days

Special Events



8°C (46°F)

9 days

Epiphany Celebrations and Carnival Festivities



10°C (50°F)

8 days

Venice Carnival and Almond Blossom Festivals



13°C (55°F)

7 days

Rome Marathon and Florence International Handicrafts Fair



16°C (61°F)

7 days

Easter Celebrations and Genoa's Boat Show



20°C (68°F)

7 days

Infiorata Flower Festivals and Giro d'Italia Bicycle Race



24°C (75°F)

5 days

Siena's Palio Horse Race and Festival of San Giovanni



27°C (81°F)

3 days

Luminara of Saint Ranieri and Umbria Jazz Festival



27°C (81°F)

4 days

Assumption Day Celebrations and Opera Festival in Verona



24°C (75°F)

5 days

Venice Film Festival and Grape Harvest Festivals



18°C (64°F)

8 days

Truffle Festivals and Bologna's Motor Show



13°C (55°F)

9 days

All Saints' Day Celebrations and Florence Marathon



9°C (48°F)

9 days

Christmas Markets and Feast of the Immaculate Conception

How Many Days Should You Stay in Italy?

Stay in Italy for at least two weeks to enjoy the best roundtrip experience. This duration allows you to immerse yourself in the country’s rich culture, history, and breathtaking landscapes. Don’t rush your journey; savor each moment as you indulge in Italy’s culinary delights and soak in its unparalleled beauty.

This is the best Italy itinerary for 20 Days!

Lets get ready for the best Italy itinerary of your life and experience the most awesome trip throughout this special country!

Day 1-3: Florence – The Cradle of the Renaissance

Skyline of Florence in Italy at sunset.

Hotel Recommendation: Portrait Firenze ⭐⭐⭐⭐⭐

Florence, the heart of Tuscany, is a living museum of art and architecture. As you wander through its enchanting streets, you’ll be surrounded by awe-inspiring landmarks at every turn. The Florence Cathedral, also known as the Duomo, with its iconic red dome, dominates the city’s skyline and is a masterpiece of Gothic architecture. Inside, you’ll find stunning frescoes and intricate marble work that will leave you in awe.

No visit to Florence is complete without exploring the world-renowned Uffizi Gallery. Home to a vast collection of Renaissance art, including masterpieces by Botticelli, Leonardo da Vinci, and Raphael, this museum is a treasure trove of artistic excellence.

Another must-see is Michelangelo’s David, housed in the Accademia Gallery. The statue’s imposing presence and meticulous attention to detail make it an enduring symbol of human achievement.

After immersing yourself in the city’s cultural heritage, take a leisurely stroll through the Oltrarno district. This neighborhood is known for its artisan workshops, where skilled craftsmen create beautiful leather goods, ceramics, and jewelry. Explore the charming Piazza Santo Spirito, a favorite spot among locals, and indulge in traditional Tuscan cuisine at one of the delightful trattorias.

Day 4-5: Siena – Tuscany’s Timeless Beauty

Siena in Italy

Hotel Recommendation: Grand Hotel Continental ⭐⭐⭐⭐⭐

A short drive from Florence, Siena awaits with its medieval charm and captivating history. The centerpiece of the city is the Piazza del Campo, a beautiful shell-shaped square where the famous Palio horse race takes place twice a year. Surrounded by stunning palaces, this is the perfect spot to immerse yourself in Sienese life.

The Siena Cathedral, a magnificent example of Italian Gothic architecture, is a masterpiece adorned with sculptures and intricate mosaics. Climb the impressive bell tower for breathtaking views of the city and the surrounding Tuscan countryside.

As you wander through the labyrinthine streets, you’ll come across quaint boutiques and artisan workshops, where you can find unique souvenirs and traditional Sienese delicacies.

For a taste of authentic Tuscan cuisine, head to Osteria Le Logge, a charming restaurant known for its mouthwatering dishes made with locally sourced ingredients. Don’t forget to pair your meal with a glass of Chianti, one of the region’s famous wines.

Day 6-7: Rome – The Eternal City

Rome in Fall/Autumn230321162314001

Hotel Recommendation: Hotel Artemide ⭐⭐⭐⭐

Rome, the Eternal City, is a captivating blend of ancient history and modern life. Start your adventure at the Colosseum, where gladiators once battled, and the Roman Forum, the heart of ancient Rome. Marvel at the grandeur of the Pantheon, a perfectly preserved temple dedicated to the gods.

Toss a coin into the Trevi Fountain to ensure your return to Rome, then head to the Spanish Steps to indulge in some retail therapy at the nearby luxury boutiques.

Rome’s culinary scene is a delight for foodies. Visit Trattoria da Teo, a local favorite, to savor classic Roman dishes like cacio e pepe and carbonara. Be sure to treat yourself to some gelato from the city’s delicous gelaterias like Come il Latte.

As the sun sets, the vibrant Trastevere district comes alive with its narrow streets, charming squares, and lively atmosphere. Enjoy a leisurely evening stroll and dine at one of the trattorias, where you can experience the true spirit of Roman hospitality.

Day 8-9: Sorrento – Gateway to the Amalfi Coast

Small fishing boats at harbor Marina Grande in Sorrento, Campania, Amalfi Coast, Italy.

Hotel Recommendation: Grand Hotel Excelsior Vittoria ⭐⭐⭐⭐⭐

Leaving Rome, make your way to Sorrento, the perfect gateway to the enchanting Amalfi Coast. Perched atop cliffs overlooking the azure sea, Sorrento exudes a laid-back Mediterranean charm.

Stroll along the Corso Italia, the main shopping street, and explore the town’s vibrant Piazza Tasso, where you can sip espresso at the Bar del Carmine and watch the world go by.

The picturesque fishing village of Marina Grande is a must-visit for seafood lovers. Here, you can enjoy delectable fresh catches while admiring the colorful boats bobbing in the harbor.

From Sorrento, you can also embark on a guided boat tour to the captivating island of Capri. Known for its stunning beauty, glamorous lifestyle, and turquoise grottoes, Capri is a dream destination. Visit the Gardens of Augustus for panoramic views of the Faraglioni rock formations and the sparkling sea.

Day 10-11: Amalfi – A Gem on the Amalfi Coast

Amalfi at the Amalfi Coast on a sunny day

Hotel Recommendation: Convento di Amalfi Grand Hotel ⭐⭐⭐⭐⭐

Arrive in Amalfi, a hidden gem nestled between cliffs and the azure sea. The town’s stunning Cathedral of St. Andrew is a must-visit, with its ornate architecture and beautiful cloister.

Stroll through the charming historic center and explore the labyrinthine streets lined with boutiques selling local ceramics and handmade souvenirs. Sample a delightful lunch at Ristorante Marina Grande, where fresh seafood dishes are complemented by breathtaking sea views.

A short walk away lies the picturesque town of Atrani, known for its tranquil atmosphere and quaint alleys. Take a hike along the Valle delle Ferriere for a chance to discover lush greenery, cascading waterfalls, and a refreshing natural pool.

Day 12-13: Bari – A Charming Seaside City

Scenic Beach in Bari, Apulien, Italy

Hotel Recommendation: B&B Bari Old Town ⭐⭐⭐⭐⭐

Heading south, you’ll arrive in Bari, a charming city with a rich maritime heritage. The historic old town, known as Bari Vecchia, is a labyrinth of narrow streets and white-washed houses.

Stroll along the Lungomare promenade, where the sea breeze will invigorate your senses. Watch the sunset over the Adriatic Sea and savor the most amazing Gnocchi al Pesto at La Cantina dello Zio.

Bari is famous for its unique pasta shape, orecchiette, and you can’t leave without trying some prepared by a local nonna (grandmother). As you explore the city, you’ll come across lively piazzas, charming churches, and bustling markets, offering a glimpse into authentic Southern Italian life.

Day 14: Vieste – A Coastal Retreat

Vieste Coastline in Italy

Hotel Recommendation: Window on the sea ⭐⭐⭐

Leaving Bari behind, head to Vieste, a hidden gem on the Gargano Peninsula. This coastal paradise boasts pristine beaches, dramatic cliffs, and turquoise waters, making it a perfect retreat for nature lovers.

Start your exploration by visiting Vieste’s iconic Pizzomunno, a stunning limestone monolith that stands majestically on the Spiaggia del Castello beach. Take a boat tour to discover the enchanting sea caves and grottoes that line the coast, such as the Grotta Campana and Grotta dei Pipistrelli.

For panoramic views of the town and the Adriatic Sea, climb up to the Vieste Castle, where you can also learn about the area’s history. Stroll through the historic center with its whitewashed houses, narrow alleys, and charming squares. Don’t miss the opportunity to try some of the region’s fresh seafood at local trattorias.

Gargano National Park, with its lush forests, picturesque lakes, and diverse wildlife, is a haven for hikers and nature enthusiasts. Embark on a trek to explore the beauty of this protected area, which is home to ancient beech forests and unique plant species.

As the sun sets over the horizon, the tranquil ambiance of Vieste will leave you with a sense of peace and awe at the beauty of this coastal paradise.

Day 15-16: Venice – The Floating City

Best Hotels in Venice Italy

Hotel Recommendation: Hotel Antiche Figure ⭐⭐⭐

Your journey takes you to Venice, a city like no other, with its romantic canals and captivating architecture. Explore the maze of alleyways and bridges that make up the historic center and visit St. Mark’s Square, the heart of Venice.

The Venetian Lagoon offers unique experiences, from a gondola ride along the Grand Canal to a visit to the enchanting islands of Murano, known for its glassblowing, and Burano, famous for its colorful houses.

Indulge in a meal at a traditional bacaro, where you can savor cicchetti (small tapas-style dishes) and a glass of Prosecco, a true Venetian tradition. As night falls, the city becomes even more magical, with its historic buildings beautifully illuminated.

Day 17-18: Lake Como – Tranquility Amidst Beauty

Lakeview in Como on the Mountains, Italy

Hotel Recommendation: Hotel Bellavista ⭐⭐⭐

From Venice, head to the stunning shores of Lake Como, a tranquil haven surrounded by mountains. The picturesque villages that dot the lake’s shoreline are postcard-perfect, and exploring them by boat is a must.

Bellagio, often referred to as the “Pearl of Lake Como,” is a charming village with colorful buildings and terraced gardens. Varenna, with its narrow streets and charming cafes, is another gem worth exploring.

Hike along the Greenway del Lago di Como for breathtaking views of the lake and the surrounding landscape. As you traverse this serene pathway, you’ll encounter beautiful villas and gardens that are a testament to the region’s opulent past.

Day 19-20: Milan – Fashion and Culture

Milan in the Summer, Italy

Hotel Recommendation: Bulgari Hotel Milano ⭐⭐⭐⭐⭐

Conclude your Italian journey in Milan, a bustling metropolis that seamlessly blends history, fashion, and culture. Visit the iconic Duomo di Milano, one of the largest cathedrals in the world, and explore the Galleria Vittorio Emanuele II, an elegant shopping arcade.

Milan is a fashion capital, so take some time to browse the haute couture boutiques and experience the latest trends. Enjoy a delightful meal at one of the city’s chic bistros and savor the flavors of Lombard cuisine.

For art enthusiasts, a visit to Leonardo da Vinci’s Last Supper at the Convent of Santa Maria delle Grazie is an absolute must. Marvel at this masterpiece, which continues to captivate visitors with its intricate details and emotive portrayal.

As your adventure comes to an end, reflect on the unforgettable experiences and memories you’ve made during this epic journey through the best of Italy.


What is the best time to visit Italy?

The best time to visit Italy is during the shoulder seasons of spring (April to May) and autumn (September to October). During these months, the weather is pleasant, and tourist crowds are fewer, allowing you to fully enjoy the country’s top destinations without feeling overwhelmed.

What are the must-visit places in Rome?

Rome is brimming with must-visit places. The Colosseum, Roman Forum, Vatican City with St. Peter’s Basilica, and the Pantheon are essential landmarks to explore. Don’t forget to make a wish at the Trevi Fountain and enjoy a relaxing stroll through the charming streets of Trastevere.

Which are the best Amalfi Coast towns to visit?

The Amalfi Coast is dotted with picturesque towns that offer stunning views and delightful experiences. Sorrento, Positano, Amalfi, and Ravello are among the most popular ones. Each town has its own unique charm and captivating beauty that will leave you in awe.

What is the best way to explore Venice?

The best way to explore Venice is on foot and by boat. Wander through the narrow alleyways and charming squares, and don’t be afraid to get lost – it’s all part of the adventure. Take a gondola ride along the Grand Canal, and hop on a vaporetto (water bus) to visit the nearby islands.

What are the must-visit attractions in Milan?

Milan is known for its fashion and culture. The must-visit attractions include the Duomo di Milano, Galleria Vittorio Emanuele II, and Leonardo da Vinci’s Last Supper. Don’t miss the opportunity to indulge in the city’s vibrant dining scene and explore the Navigli district with its charming canals.

Profilbild Jette
About the author

Ich liebe die Vielfalt Europas und kann von Edinburgh, Lissabon und London nicht genug bekommen! Aber mein größtes Glück ist immer noch das schöne Schweden. Eines Tages werde ich nur noch in meiner einsamen Hütte an einem See mitten im Nirgendwo zu finden sein ...

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