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3 Weeks in Italy: Embracing La Dolce Vita from Rome to Milan

Rome, Florence, Sienna, Pisa, La Spezia, Cinque Terre, Bologna, Ravenna, Venice, Verona, Milan

Planning a grand adventure for 3 weeks in Italy, I envisioned a journey filled with rich history, breathtaking landscapes, and unforgettable culinary experiences. This dream became a thrilling reality as I embarked on a meticulously planned 3-week Italian escapade. Every day, from the ancient streets of Rome to the fashion-forward avenues of Milan, a new chapter in this Italian saga unfolded. Exploring Italy over three weeks allows for an immersive experience into the heart and soul of its varied regions, each offering a unique blend of culture, history, and flavors.

How to Get Around Italy

Navigating through Italy is an adventure in itself. The country boasts an extensive and efficient train network, making intercity travel a breeze. These convenient train rides connect major cities like Rome, Florence, and Milan, offering a scenic and comfortable journey. Within the cities, I highly recommend walking. There’s something magical about getting lost in the cobblestoned alleyways of Italy’s urban landscapes. Each turn brings a new discovery, whether a quaint café, a hidden piazza, or a stunning piece of street art. For longer distances or when time is a factor, regional buses and domestic flights are also available options. However, trains and walking provide the most authentic and enjoyable way to experience Italy’s charm.

Where/How to Buy Train/Bus Tickets 

Getting around Europe is a breeze with many options. First, Trainline and Rail Europe make train journeys easy. Then, OMIO offers the choice of train, bus, or plane, giving you flexibility. Also, Expedia is great for booking flights to zip across countries. For bus travelers, BusBud connects you to various destinations, while FlixBus offers comfy rides at low prices. So, whether by train, bus, or plane, exploring Europe is simple and fun. So start booking and enjoy the ride!

This itinerary lets you explore Rome efficiently, minimizing travel time and maximizing your experience in each neighborhood. Enjoy your Roman adventure!

3 Weeks Itinerary in Italy; 4 Days in Rome
3 Weeks Itinerary in Italy; 4 Days in Rome

Day 1: Ancient Rome and Colosseum Area

  • Visit the Colosseum, Roman Forum, and Palatine Hill.
  • Explore the Arch of Constantine.
  • Stroll around the Capitoline Hill and visit the Capitoline Museums.
  • Enjoy traditional Roman cuisine at a local trattoria nearby. Try Trattoria Luzzi or Pasta Chef Monti.

I highly recommend that you join a tour to get to know Ancient Rome. Unless you are a visitor for the sake of social media content, then you are free to do so. But isn’t it amazing to know its history from someone who breathes Roman history? You can join the tour here. It’s also a good idea to buy the ticket ahead if you’re impatient in lining up there.

Day 2: Vatican City and Surroundings

  • Tour St. Peter’s Basilica and climb to its dome for a panoramic city view.
  • Visit the Vatican Museums and the Sistine Chapel.
  • Walk along the Via della Conciliazione.
  • Dine in the Prati district, known for its eateries and gelaterias.

Day 3: Historic Center (Centro Storico)

  • Toss a coin in the Trevi Fountain.
  • Visit the Pantheon.
  • Explore Piazza Navona and its surrounding streets.
  • Enjoy a meal in one of the cozy restaurants in the area. Check out: Osteria della Suburr, Trattoria Dal Cavalier Gino, and Cacio e Pepe “da Gianni.

Day 4: Trastevere and the Jewish Ghetto

  • Wander through the cobblestone streets of Trastevere.
  • Visit the Basilica of Santa Maria in Trastevere.
  • Explore the historic Jewish Ghetto and visit the Great Synagogue.
  • Sample local street food and Roman Jewish delicacies. Try Nonna Betta or Fonzi the Burger’s House.

In Rome, accommodation options cater to all tastes and budgets. Budget travelers can stay at the YellowSquare Hostel, known for its lively atmosphere and central location. For a mid-range option, Hotel Artemide offers comfortable rooms and excellent service, just a short walk from major attractions. Luxury seekers will find sophistication and elegance at the Hotel Hassler Roma, perched atop the Spanish Steps.

This itinerary comprehensively explores Florence’s and Siena’s key neighborhoods and attractions, with minimal travel between sites. Enjoy your time in the heart of Tuscany!

3 weeks in italy travel itinerary florence
3 weeks in italy travel itinerary – Florence

Day 5: Santa Maria del Fiore and Surroundings

  • Visit Florence Cathedral (Cattedrale di Santa Maria del Fiore) and climb the dome.
  • See Giotto’s Campanile and the Baptistery of Saint John.
  • Explore Piazza del Duomo and its surrounding streets.
  • Enjoy a traditional Florentine lunch at a nearby trattoria.

Day 6: Uffizi and Ponte Vecchio Area

  • Tour the Uffizi Gallery, home to Renaissance masterpieces. Buy your ticket in advance, and you’ll thank me later.
  • Walk across the Ponte Vecchio and browse the jewelry shops.
  • Visit the Palazzo Vecchio and Piazza della Signoria.
  • Sample gelato near the Arno River.

Day 7: Accademia and San Lorenzo Area

  • See Michelangelo’s David at the Accademia Gallery. (I wasted 2.5 hours here lining up because I didn’t buy a ticket ahead. So, I urge you to purchase in advance.
  • Stroll through the San Lorenzo Market.
  • Visit the Medici Chapels and Basilica di San Lorenzo.
  • Try a famous Florentine steak for dinner in this area.

Day 8: Day Trip to Siena (from Florence)

I highly recommend that you join a one-day tour here for easy transport and a great way to maximize your day. I did this awesome tour.

  • Explore Siena’s historic center, a UNESCO World Heritage site.
  • Visit the Siena Cathedral and Piazza del Campo.
  • Enjoy traditional Sienese cuisine at a local osteria.

In Florence, there’s a range of accommodations to suit every traveler. For those on a budget, Hostel Archi Rossi is a great choice, offering a friendly atmosphere and is close to Florence’s main train station. Mid-range travelers can enjoy the comforts of Hotel Orto de’ Medici, which boasts a fantastic location near key attractions. For a luxurious stay, the Portrait Firenze offers exquisite rooms and exceptional service, right by the iconic Ponte Vecchio.

This itinerary will allow you to experience the best of Pisa’s central sights and flavors without needing to travel far between locations. Enjoy your time in this charming Tuscan city!

Day 9: Pisa Central Sights

  • Visit the iconic Leaning Tower of Pisa in Piazza dei Miracoli.
  • Explore the Pisa Cathedral and the Baptistery.
  • Stroll around the Camposanto Monumentale (Monumental Cemetery).
  • Relax in the green lawns of Piazza dei Miracoli.
  • Enjoy lunch at a local trattoria, trying specialties like cecina (chickpea pancake).
  • Walk along the Arno River and admire the views.
  • Visit the Church of Santa Maria della Spina on the riverbank.
  • Explore the lively streets and squares of the city center.
  • Have a gelato from a local gelateria as you wander.
3 weeks in Italy travel itinerary Pisa One Day
3 Weeks in Italy travel itinerary: A Day in Pisa

In Pisa, travelers have a variety of accommodation options. Budget-conscious visitors can choose the centrally located Hostel Pisa, known for its vibrant atmosphere and convenience. Hotel Bologna offers excellent facilities for a comfortable, mid-range stay and is just a short walk from the Leaning Tower. Upscale travelers can indulge in luxury at the Allegroitalia Pisa Tower Plaza, which boasts stunning views of the city and top-notch amenities.

This itinerary allows you to immerse yourself in the unique atmosphere and beauty of La Spezia and each Cinque Terre village with minimal travel and maximum enjoyment.

Day 10: La Spezia

  • Visit the Naval Museum (Museo Tecnico Navale) for maritime history.
  • Explore Castello San Giorgio and enjoy panoramic views.
  • Stroll along the La Spezia waterfront and Passeggiata Morin.
  • Enjoy a lunch of local seafood specialties.
  • Visit the Lia Museum for art and archaeology.
  • Explore the city’s shops and boutiques.
  • Dine in a traditional trattoria, trying Ligurian dishes like trofie al pesto.
3 weeks in Italy travel itinerary cinque terre
3 weeks in Italy travel itinerary

Day 11: Cinque Terre

  • Take a train to Riomaggiore, the first of the Cinque Terre villages.
  • Walk the Via dell’Amore (Lover’s Lane) towards Manarola.
  • Explore Manarola, known for its wine and scenic views.
  • Continue to Corniglia, the only village not directly by the sea.
  • Have a lunch of local cuisine in Corniglia.
  • Visit Vernazza, with its picturesque harbor and castle.
  • End the day in Monterosso al Mare, the largest of the five villages.
  • Relax on the beach or take a dip in the sea.
  • Enjoy a dinner with local seafood and Cinque Terre wine.

Accommodation choices in La Spezia cater to a range of preferences. For those on a budget, the Grand Hostel Manin offers a friendly and comfortable stay, conveniently located for exploring the area. Mid-range travelers can enjoy the hospitality of CDH Hotel La Spezia, known for its modern amenities and proximity to the train station. Luxury seekers should consider the NH La Spezia, which offers elegant rooms and splendid sea views.

This itinerary thoroughly explores Bologna’s diverse neighborhoods and key attractions, along with a culturally rich day in Ravenna, minimizing travel and maximizing your Italian experience.

Day 12: Historic Center of Bologna

  • Visit Piazza Maggiore and see the Fountain of Neptune.
  • Explore the Basilica of San Petronio and its panoramic terrace.
  • Stroll through the medieval market area, Quadrilatero.
  • Enjoy a traditional Bolognese lunch, like tagliatelle al ragù. Go to La Prosciutteria Bologna or Breaking Toast.

Day 13: University Area and Towers

  • Visit the University of Bologna, the oldest in the Western world.
  • Climb the Asinelli Tower for city views.
  • Explore the Museum of the History of Bologna. Try local street food, like piadina or mortadella. Check out Zenzero Bistrot or Eataly Ambasciatori.
3 weeks in Italy travel itinerary bologna

Day 14: Santo Stefano and Surroundings

  • Visit the Basilica di Santo Stefano complex.
  • Stroll through the Giardini Margherita.
  • Explore the local shops and cafés.
  • Dine in an osteria, trying dishes like tortellini in brodo. Try Osteria dell’Orsa or To Steki. 

Day 15: Day Trip to Ravenna

  • Visit the Basilica of San Vitale and marvel at its mosaics.
  • Explore the Mausoleum of Galla Placidia.
  • See Dante’s Tomb and the nearby Dante Museum.
  • Have lunch with local specialties like cappelletti.
  • Visit the Arian Baptistry and the Basilica of Sant’Apollinare Nuovo.
  • Enjoy a gelato before heading back to Bologna.

In Bologna, there’s a perfect place to stay for every type of traveler. Budget-conscious visitors can enjoy Dopa Hostel, known for its modern amenities and central location. For a mid-range option, Hotel Metropolitan offers a stylish stay with excellent service, just steps away from Bologna’s historic center. Luxurious travelers can indulge at the Grand Hotel Majestic “già Baglioni”, an elegant hotel renowned for its classic decor and impeccable service.

This itinerary allows you to fully immerse yourself in the distinct character of each neighborhood in Venice, minimizing travel time and maximizing your experience of the city’s rich culture and history.

Day 16: San Marco District

  • Visit St. Mark’s Basilica and climb its Campanile for city views.
  • Explore Doge’s Palace and the Bridge of Sighs.
  • Stroll around St. Mark’s Square and watch the world go by.
  • Have a coffee at one of the historic cafés in the square.
  • Enjoy a Venetian dinner, perhaps trying seafood risotto or squid ink pasta.

Day 17: Dorsoduro and Giudecca

  • Visit the Gallerie dell’Accademia for Venetian art.
  • Explore the Peggy Guggenheim Collection for modern art.
  • Stroll along the Zattere promenade for scenic views.
  • Take a vaporetto to the Giudecca island and enjoy a quiet stroll.
  • Dine in a local trattoria, sampling dishes like sarde in saor.
3 weeks in Italy
Venice travel itinerary

Day 18: Rialto and Cannaregio

  • Explore the Rialto Market in the morning.
  • Walk across the Rialto Bridge and browse the shops.
  • Visit the Ca’ d’Oro and its gallery.
  • Stroll through the Cannaregio district and visit the Jewish Ghetto.
  • Enjoy an evening cicchetti tour, tasting Venice’s version of tapas.

I missed Burano – so, go and explore it for me! Burano is a small island near Venice, Italy. It’s known for its colorful houses and handmade lace. People visit Burano to see its bright buildings, watch lace-making, and enjoy a quiet, beautiful place. It’s different from Venice, more relaxed, and very pretty, making it a great place to see.

In Venice, you’ll find accommodations that cater to all preferences and budgets. For budget travelers, the Generator Venice offers a stylish and affordable stay with a great location on Giudecca Island. Mid-range visitors can enjoy Hotel Sant’Antonin, praised for its charming ambiance and convenient proximity to major sights. For those seeking luxury, the Hotel Firenze provides an exquisite experience with its elegant rooms and exceptional service near St. Mark’s Square.

This itinerary provides a compact exploration of Verona’s historic center, allowing you to enjoy its key sights and flavors without extensive travel across the city. Enjoy your day in this romantic city!

Day 19: Verona City Center

  • Visit the Verona Arena, a well-preserved ancient Roman amphitheater.
  • See Juliet’s House (Casa di Giulietta) and the famous balcony.
  • Stroll through Piazza delle Erbe and Piazza dei Signori.
  • Visit the Verona Cathedral (Duomo di Verona).
  • Walk across the Ponte Pietra, Verona’s oldest bridge.
  • Have lunch at a local osteria, trying specialties like risotto all’Amarone.
  • Explore the Castelvecchio Museum and its bridge.
  • Enjoy a gelato in one of the city’s charming squares.
  • Dine in the city center, possibly trying Veronese horse meat dishes, if adventurous.

Verona offers diverse accommodation options for all travelers. Budget guests can stay at The Hostello, noted for its welcoming atmosphere and central location. Mid-range visitors might prefer Hotel Milano & Spa, conveniently situated near the Arena, offering modern comforts. For a touch of luxury, Palazzo Victoria provides an elegant experience, blending rich history with contemporary amenities.

This itinerary allows you to experience Milan’s diverse neighborhoods, from historic sights to modern urban developments, with each day dedicated to a different area for minimal travel and maximum enjoyment.

Day 20: Duomo and Surroundings

  • Visit Milan Cathedral (Duomo) and its rooftop for stunning views.
  • Explore the Galleria Vittorio Emanuele II for luxury shopping.
  • See Leonardo da Vinci’s “The Last Supper” (book in advance).
  • Stroll through the Sforza Castle and its museums.
  • Enjoy a Milanese lunch, perhaps trying risotto alla Milanese.

Day 21: Brera District

  • Visit the Pinacoteca di Brera for fine art collections.
  • Stroll through the charming streets of Brera.
  • Explore the Brera Botanical Garden for a peaceful break.
  • Dine in a Brera restaurant, trying dishes like ossobuco.

Day 22: Navigli and Porta Genova

  • Walk along the Navigli canals, especially beautiful at sunset.
  • Visit the Navigli District for its vibrant atmosphere and art studios.
  • Enjoy an aperitivo in one of the many bars along the canal.
  • Have dinner in the area, with options ranging from traditional to contemporary cuisine.

Day 23: Porta Nuova and Isola

  • Explore the modern skyscrapers in Porta Nuova, like the Bosco Verticale.
  • Stroll through the Corso Como for shopping and dining.
  • Visit the Isola neighborhood for its hip vibe and street art.
  • Enjoy contemporary Italian cuisine in a local Isola restaurant.

In Milan, accommodations range from budget-friendly to luxurious. Backpackers can opt for Ostello Bello, popular for its lively vibe and location close to major attractions. For a mid-priced option, Hotel Berna offers excellent service and a central location, perfect for city exploration. Luxurious travelers can indulge in the sophistication of the Armani Hotel Milano, known for its designer elegance and exceptional service.

The Unforgettable Journey of 3 Weeks in Italy

Reflecting on my 3 weeks in Italy, it’s clear this journey was more than just a holiday; it was a deep dive into a culture that celebrates life with every bite of pasta and sip of wine. This itinerary for 3 weeks in Italy is not just a travel plan; it’s a route to experiencing the essence of Italian joy. From the grandeur of Rome’s Colosseum to the serene beauty of the Cinque Terre, each destination offered a unique story. As I bid “arrivederci” to Italy, I carry with me not just souvenirs but memories that will last a lifetime. Whether you’re a history buff, a food enthusiast, or simply in love with beauty, 3 weeks in Italy offers an unparalleled journey into the heart of one of the world’s most enchanting countries.


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