How To Spend 5 Days In Italy - 6 Unique Itineraries

Welcome to enchanting Italy, where timeless beauty and rich history come together to create a truly unforgettable experience. If you only have a few days to explore this captivating country, fear not, as we have designed six unique 5-day Italy itineraries that will show you how to make the most of this short period of time.

See our itineraries below, or get inspired by duration and regions: 7 day Italy itinerary - 10 day italy itinerary - 14 day Italy itinerary - Northern Italy itinerary - Southern Italy itinerary - Amalfi coast itinerary - Tuscany itinerary

Itinerary #1: Wine and Food in Tuscany

Stay at a beautiful hotel in San Gimignano, a medieval hill town halfway between Florence and Siena. Tuscany is known for its wines and food and that's what you'll be exploring on this 5-day itinerary - several wine and food pairings await. All are hand-picked by our local travel specialist.

On day one, arrive in Tuscany and take a private transfer to your hotel near the medieval town of San Gimignano. Settle in, unwind, and soak up the Tuscan views.

Day two is for exploring San Gimignano at your own pace. Stroll through the charming town, admire the ancient towers, and take in the surrounding countryside.

On day three, enjoy a full-day winery experience, including a tasting of 15 Tuscan wines and a delicious vineyard lunch. Learn about local wine-making traditions directly from the experts.

Day four is dedicated to Tuscany’s traditional cuisine. Savor local dishes paired with Chianti wine, all with a stunning backdrop of rolling hills and vineyards.

On day five, a private driver will take you to Florence for your departure, marking the end of your Tuscan adventure. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day 1

• Transfer to San Gimignano and free time.
• Overnight in San Gimignano.

Day 2

• Free day in San Gimignano.
• Overnight in San Gimignano.

Day 3

• Romantic lunch in the vineyards.
• Overnight in San Gimignano.

Day 4

• Chianti - food and wine pairing.
• Overnight in San Gimignano.

Day 5

• Transfer and departure from Florence.

Dreaming of exploring? Turn your dreams into reality and book this trip now.

Itinerary #2: Eternal Rome for the Weekend

Experience the essence of Rome in just a few days with this simplified itinerary, perfect for a weekend getaway.

Once you arrive in Rome, spend your first day exploring at your own pace. Stroll through local neighborhoods, sample a gelato, and soak up the city's unique energy.

On day two, immerse yourself in the Vatican Museums, home to the Sistine Chapel. Afterward, visit St. Peter's Basilica to admire the Pieta and admire the view from the dome.

Day three takes you back in time to the Colosseum, where gladiators once battled. Nearby, explore the Roman Forum’s ancient ruins and imagine life in the heart of the Roman Empire.

Spend day four visiting Rome’s iconic landmarks: start at the Spanish Steps, toss a coin into the Trevi Fountain, and visit the Pantheon. End at Piazza Navona, where you’ll enjoy a taste of local Italian specialties.

On your final day, check out of your hotel and head to the airport, taking unforgettable memories of Rome’s history and charm with you. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day 1

• Arrival in Rome.
• Overnight in Rome.

Day 2

• Visit the Vatican.
• Overnight in Rome.

Day 3

• Colosseum (Flavian Amphitheatre).
• Overnight in Rome.

Day 4

• Rome Fountains & Square Wine Tasting.
• Overnight in Rome.

Day 5

• Departure from Rome.

Ready to embark on an adventure? Book your trip now.

Itinerary #3: Florence: A Trip Back In Time

Immerse yourself in Florence’s Renaissance beauty and rich cultural heritage with this focused 5-day Italy itinerary.

Arrive on day one and settle into the city. Take some time to explore Florence at your leisure, with recommendations like the Uffizi Gallery for Botticelli’s masterpieces and the Accademia to see Michelangelo's David.

Day two unveils the secret Vasari Corridor, a hidden passage linking Palazzo Pitti to Palazzo Vecchio, adorned with 15th-century self-portraits. While at Palazzo Vecchio, marvel at the grand Room of the Five Hundred, filled with works by Vasari, Leonardo, and Michelangelo.

On day three, step into the world of Dante at Casa di Dante, a museum dedicated to the famed poet. Follow this with a visit to Piazza del Duomo and admire the Baptistery’s golden Gates of Paradise.

Enjoy day four as a free day to explore Florence on your own or take a day trip to the Tuscan countryside. You might visit Siena, San Gimignano, or Pisa, and end the day with a three-course meal of Florentine specialties at a local restaurant.

On day five, say goodbye to Florence as you head to the airport, taking with you memories of this enchanting city’s art, history, and charm. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day 1

• Arrival in Florence.
• Overnight in Florence.

Day 2

• Exploring the Vasari Corridor and the Palazzo Vecchio.
• Overnight in Florence.

Day 3

• Experiencing medieval Florence.
• Overnight in Florence.

Day 4

• Free day in Florence or a day tour to the Tuscan countryside.
• Overnight in Florence.

Day 5

• Transfer to Florence Airport and departure.

Interested? Don't miss the opportunity to book this trip now.

Itinerary #4: Romantic Venice

Enjoy a romantic 5-day escape to Venice, filled with history, charm, and unforgettable experiences.

On day one, arrive at Marco Polo International Airport and transfer to your hotel. Spend the rest of the day exploring Venice’s enchanting canals and winding streets at your own pace.

Day two features a private walking tour of Saint Mark's area, where you’ll learn about Venice’s powerful maritime history. Visit landmarks like the Doge’s Palace, St. Mark's Square, and St. Mark's Basilica, each showcasing the city’s rich heritage.

On day three, start with a luxurious breakfast before enjoying a 30-minute gondola ride through Venice’s canals. The afternoon is free for you to wander, ending with a romantic three-course dinner at a local restaurant.

Day four is a full free day to explore Venice’s hidden gems, from quiet alleys to unique local shops.

On day five, check out of your hotel and take a private transfer back to the airport, bringing your Venetian getaway to a close. Read more.

Itinerary overview

Check this overview of the 5 day Italy itinerary.

Day 1

• Arrival in Venice.
• Overnight in Venice.

Day 2

• Venice walking tour.
• Overnight in Venice.

Day 3

• Exploring Venice.
• Overnight in Venice.

Day 4

• Free day in Venice.
• Overnight in Venice.

Day 5

• Departure from Venice.

Interested in the itinerary? Don't wait, book this trip now.

Itinerary #5: Trieste - a combination of hiking and culture

Discover the authentic charm of Trieste with this unique 5-day itinerary that combines hiking, history, and local experiences.

On day one, arrive at the airport or train station and transfer to your hotel. Begin exploring Trieste’s historic city center, strolling through Piazza Unità d'Italia and along the scenic seafront. Head up to San Giusto Hill for sweeping views of the city.

Day two takes you to the Karst plateau. Ride the historic Opicina tram up to the plateau, where a panoramic hike awaits. Walk through Miramare Castle Park, taking in beautiful views of the sea and city.

On day three, visit the Lipica equestrian park, famous for its Lipizzan horses. Enjoy a guided tour of the estate and take a peaceful walk to the Valley of the Blessed Virgin of Lourdes, a tranquil sanctuary from the 1800s.

Day four is dedicated to hiking in the Rosandra Valley Reserve. Follow the ancient salt road along the Rosandra stream, with stops at the valley’s waterfall and natural pools.

On day five, end your trip with a visit to Grotta Gigante, one of the world’s largest caves. After the tour, return to Trieste to collect your luggage and continue your journey or head home. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day 1

• Arrival in Trieste.
• Overnight in Trieste.

Day 2

• From the Karst to Miramare Castle.
• Overnight in Trieste.

Day 3

• Lipica Stud farm.
• Overnight in Trieste.

Day 4

• Rosandra Valley Nature Reserve.
• Overnight in Trieste.

Day 5

• Grotta Gigante.
• Departure from Trieste.

Want to explore? Turn your dreams into reality and book this trip now.

Itinerary #6: Exploring Vatican City and Assisi

Soak up sights and delights of Ancient Rome, with this 5-day itinerary, including visits to the Sistine Chapel, the Colosseum, and St. Peter's Basilica, before journeying to the home of St. Francis of Assisi, Eremo delle Carceri.

On day one, arrive in Rome and transfer to your hotel. Take the evening to settle in and prepare for the adventures ahead.

Day two is dedicated to Vatican City. Explore the Vatican Museums, marvel at Michelangelo’s Sistine Chapel, and visit St. Peter's Basilica. Skip the lines to admire masterpieces in the Tapestry Gallery, the Geographical Maps, and more.

On day three, dive into ancient Rome with visits to the Colosseum, the Roman Forum, and Palatine Hill. With priority access and a local guide, uncover the stories behind Rome’s most iconic landmarks.

On day four, leave Rome for Assisi, the birthplace of St. Francis. Visit Eremo delle Carceri, a secluded sanctuary in the hills, where St. Francis and his followers once lived. Enjoy the serene atmosphere of Assisi before returning to your hotel.

On day five, conclude your journey with a transfer to Rome airport, bringing home memories of Rome’s grandeur and Assisi’s tranquility. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day 1

• Arrival in Rome.
• Overnight in Rome.

Day 2

• Vatican Museums, Sistine Chapel and St. Peter's Basilica.
• Overnight in Rome.

Day 3

• Exploring Ancient Rome.
• Overnight in Rome.

Day 4

• A day in Assisi.
• Overnight in Assisi.

Day 5

• Transfer to Rome airport and departure.

Excited about the possibilities? Don't hesitate and book this trip now.

You might also want to browse our customizable Italy itineraries, or talk to our local Italy experts.

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