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: 7-days - 10 days - 14 days - North Italy - South Italy

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 your local travel specialist.

The first day of adventure begins with a private car transfer to a hotel in the charming San Gimignano area, offering free time to unwind and adjust to the new surroundings. The second day allows for a leisurely exploration of the region at one's own pace.

The highlight of day three is a captivating winery experience, featuring a vertical Wine Tasting of 15 Tuscan products, paired with a delectable lunch served amidst the vineyards or in the winery itself. The day encompasses everything from vineyard visits to wine-making techniques, providing a comprehensive understanding of the art behind Tuscan wines.

Day four is dedicated to indulging in the region's traditional cuisine. Guests can savour a selection of mouthwatering dishes while sipping on the finest Chianti wine, all set against the backdrop of the picturesque Tuscan landscape.

On the final day, a private driver ensures a smooth departure, bidding farewell to Tuscany as they are taken to the airport in Florence for their onward journey. The memories of this extraordinary trip, filled with extraordinary experiences, will undoubtedly linger, leaving travellers longing for a return visit to this captivating Italian region. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day one

• Transfer from Florence to San Gimignano
• Overnight in San Gimignano

Day two

• Free day in San Gimignano
• Overnight in San Gimignano 

Day three

• Romantic lunch in the vineyards
• Overnight in San Gimignano 

Day four

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

Day five

• 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

Welcome to the timeless allure of Eternal Rome, a city steeped in history, art, and culture. Embrace the essence of this enchanting destination in just a weekend with our carefully curated 5-day itinerary. From iconic landmarks to hidden gems, immerse yourself in the heart of the ancient world and experience the eternal charm that Rome has to offer.

On the first day, after a warm welcome, enjoy free time to explore the city at your own pace. Day two unveils the Vatican Museums and the awe-inspiring Sistine Chapel, offering insight into the brilliant works of Michelangelo and other renowned artists. The tour then leads to St. Peter's Basilica, where the breathtaking architecture and "La Pietà" masterpiece await.

On day three, venture to the iconic Colosseum, once the stage for gripping gladiator battles. Nearby, immerse yourself in the rich history of the Roman Forum, the political, commercial, and religious heart of ancient Rome.

Day four begins with a small-group walking tour, encompassing symbolic landmarks like the Spanish Steps, Trevi Fountain, and the magnificent Pantheon. The journey concludes at "Piazza Navona," graced by Bernini's Fountain of Four Rivers and a delightful tasting of local Italian products.

As the sun sets on your Roman adventure, day five bids farewell as you check out of your hotel and head to the airport, taking cherished memories and a newfound appreciation for Eternal Rome with you. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day one

• Arrival in Rome
• Overnight in Rome

Day two

• Vatican visiting
• Overnight in Rome

Day three

• Colosseum - Flavian Amphitheatre
• Overnight in Rome

Day four

• Rome fountains & square wine tasting
• Overnight in Rome

Day five

• Rome departure

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

Itinerary #3: Florence: A Trip Back In Time

Step into the enchanting city of Florence and experience a mesmerising journey back in time with our carefully planned 5-day Italy itinerary. This enchanting destination is a treasure trove of Renaissance art, ancient architecture and rich cultural heritage.

On day one, after a warm welcome at Florence Airport, explore the city at your leisure, with must-see recommendations like the renowned Uffizi Gallery and the Accademia, home to Michelangelo's masterpiece, David.

Day two unveils the mysterious Vasari Corridor, a secret passageway connecting Palazzo Pitti to Palazzo Vecchio. Adorned with a fascinating collection of self-portraits from the 15th century, this hidden gem offers a glimpse into Florence's rich past. Witness the grandeur of the Room of the Five Hundred in Palazzo Vecchio, adorned with artwork by Vasari, Leonardo da Vinci, and Michelangelo.

Venture off the beaten path on day three to Casa di Dante, a museum commemorating the life of the famed poet. Journey through three important stages of Dante's life, tracing his footsteps through 13th-century Florence to his exile and lasting legacy. The tour then continues to the iconic Piazza del Duomo, the Badia Fiorentina, and the awe-inspiring Baptistery with its mesmerizing Gates to Paradise.

Enjoy a free day on day four to explore Florence at your own pace or opt for a picturesque day trip into the Tuscan countryside, visiting enchanting towns like San Gimignano, Siena, or Pisa. The day concludes with a delightful 3-course meal at an authentic, local restaurant, offering a true taste of Florentine cuisine.

As your adventure draws to a close on day five, cherish the memories of this remarkable journey. Depending on your flight time, bid farewell to Florence as you are transferred to the airport, carrying with you the beauty and essence of this enchanting city forever in your heart. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day one

• Arrival in Florence
• Overnight in Florence

Day two

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

Day three

• Experiencing medieval Florence
• Overnight in Florence

Day four

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

Day five

• Transfer to Florence Airport and departure

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

Itinerary #4: Romantic Venice

Enjoy a weekend getaway in the most romantic of cities. This compact 5-day itinerary features a pleasant walking tour, which provides a unique insight into the history, art and architecture of Venice, and a gondola ride. You will also have some free time to explore this labyrinthine city.

Day one welcomes you as you arrive at Marco Polo International Airport and are transferred to your hotel, leaving the day free to explore Venice at your leisure.

On day two, embark on a private walking tour, beginning at the Saint Mark's area, where you'll delve into the historical significance of the powerful maritime empire of the Mediterranean. The tour includes iconic landmarks such as The Doges' Palace, St. Mark's Square, and the Basilica, each showcasing unparalleled beauty and historical importance.

Day three commences with a sumptuous breakfast, followed by a picturesque 30-minute gondola ride through Venice's waterways, allowing you to soak in the city's unique ambience. The afternoon is yours to explore at your own pace, culminating in a delightful three-course dinner at a centrally located restaurant (drinks not included).

Enjoy a free day on day four, allowing you to fully immerse yourself in the beauty of Venice and discover its hidden gems.

As your journey comes to an end on day five, check out of your hotel after breakfast. A private transfer will take you to Marco Polo International Airport, leaving you with cherished memories and the desire to return to this mesmerizing destination once again. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day one

• Arrival in Venice
• Overnight in Venice

Day two

• Venice walking tour
• Overnight in Venice

Day three

• Exploring Venice
• Overnight in Venice

Day four

• Free day in Venice
• Overnight in Venice

Day five

• Departure from Venice

Fascinated by the itinerary? Don't wait, book this trip now.

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

Experience an authentic adventure in Trieste with our exclusive 5-day Italy itinerary. This journey goes beyond just sightseeing; it will allow you to truly experience the city like a local. Immerse yourself in the small daily rituals and discover hidden gems tucked away off the tourist trail.

Day one welcomes you with a warm reception at the train station or airport, followed by a leisurely exploration of the city centre. Marvel at the historic streets and squares, the seafront, and the renowned Piazza Unità. Wander up to the hill of San Giusto for breathtaking views.

Day two takes you on a scenic journey to the Karst plateau. Hop on the iconic Opicina tram, dating back to 1902, to ascend to the plateau. Embark on a picturesque walk with panoramic views of the city and sea, leading you to the splendid Miramare Castle Park.

On day three, embark on a discovery of the equestrian park of Lipica, an oasis of tranquillity and home to the elegant Lipizzan horses. After a guided tour and serene strolls in the estate, visit the valley of the Blessed Virgin of Lourdes, a unique sanctuary dating back to the 1800s.

Day four begins with a trip to the Rosandra Valley Reserve. Walk along the ancient salt road, enjoying views of the Rosandra stream with its waterfall and natural pools.

Conclude your trip on day five with a visit to the awe-inspiring Grotta Gigante, the largest cave in the world. At the end of the visit, you will return to the city. From here, once you have recovered any luggage left at the deposit of your facility, you can continue your journey independently or return home. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day one

• Arrival in Trieste
• Overnight in Trieste

Day two

• From the Karst to Miramare Castle
• Overnight in Trieste

Day three

• Lupica Stud farm
• Overnight in Trieste

Day four

• Rosandra Valley Nature Reserve
• Overnight in Trieste

Day five

• Grotta Gigante
• Departure from Trieste

Dreaming of exploring? 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-long 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.

Day one will begin with your arrival in Rome, where a transfer will take you to your hotel for an overnight stay and preparation for the adventures ahead.

On day two, you'll immerse yourself in the cultural wonders of Rome as you tour the Vatican Museums, the Sistine Chapel and St Peter's Basilica. Skip the long queues and check out one of the world's most important art collections, and admire the Tapestry Gallery and the Geographical Maps. The day culminates with a visit to the famous Sistine Chapel and the awe-inspiring St Peter's Basilica.

On the third day, you will continue your exploration of Rome's iconic landmarks with visits to the Colosseum, Roman Forum and Palatine Hill. With priority entry and a qualified local guide, you'll discover the fascinating history and stories of ancient Rome.

On day four, you'll venture from the bustling streets of Rome to the serene city of Assisi, the birthplace of St Francis. Discover the Eremo delle Carceri, the first home of St Francis and his followers, as you immerse yourself in the tranquil beauty of this sacred monument. Enjoy a relaxing day of sightseeing before returning to your hotel for an overnight stay.

On the fifth day, at the conclusion of your journey, you will return to Rome airport and fly home, taking with you fond memories of the historical wonders of Rome and the peaceful serenity of Assisi. Read more.

Itinerary overview

Check this overview of the 5 days Italy itinerary.

Day one

• Arrival in Rome
• Overnight in Rome

Day two

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

Day three

• Exploring Ancient Rome
• Overnight in Rome

Day four

• a day in Assisi
• Overnight in Assisi

Day five

• Transfer and departure from Rome

Captivated by the possibilities? Don't hesitate and book this trip now.

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