5 Days In Italy - Six 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. PLanning to go longer? Check our 7 days, 10 days or 14 days itineraries.

Tailor-made travel itineraries for Italy, created by local experts

6 days / from 2650 USD
Wine and food in Tuscany
Stay at a beautiful hotel in San Gimignano, a medieval hill town half way between Florence and Siena. Tuscany is known for its wines and food and that's what you'll be exploring on this itinerary - several wine and food pairings await. All hand-picked by your local travel specialist.
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10 days / from 3392 USD
Piedmont Discovery
Piedmont is a culinary heaven, with world-class wines and truffle waiting to be discovered. The capital city Turin is a cultural center with a picture perfect skyline. Afterwards, continue to the countryside around Alba, with wine tastings, cooking classes and enjoying the mountains and nature.
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4 days / from 1007 USD
Eternal Rome for the Weekend
Welcome to this whirlwind tour of Rome, also known as the Eternal City. Rome is one of the most photogenic cities on earth, so make sure you pack your camera.
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10 days / from 3021 USD
Fascinating Southern Italy: Naples, Sorrento and Capri
Southern Italy is the dream of many: charming towns to explore on the Amalfi Coast, crystal clear waters around the island of Capri, a heaven for foodies in Naples and surroundings as well as historical sights such as Pompeii are at your fingertips to discover.
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10 days / from 2809 USD
Best of South Italy: Rome, Naples, Sorrento and the Amalfi Coast
Colourful villages draped over steep cliffs, cities steeped in culture and history, crystal-clear warm waters and cities frozen in time – South Italy has a lot to offer. Experience it for yourself with this exciting trip.
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8 days / from 3175 USD
Italian Cities of the Renaissance
Enjoy a week in Italy, discovering the historical landmarks that the country's top cities have to offer; from the ancient sites of Rome, to the waterways of Venice and the cobbled streets of Florence.
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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.

City of San Gimignano, a small medieval town in Tuscany, Italy © Vaflya/Shutterstock

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.

Tuscany Vineyards, Italy @ Shutterstock

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.

Night view over Fountain di Trevi in Rome © trabantos/Shutterstock

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.

Vatican at night, Italy @ Shutterstock

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.

Florence cityscape © Bob Hilscher/Shutterstock

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.

Uffizi art gallery in Florence, Tuscany, Italy @ Shutterstock

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.

Burano island canal, colourful houses and boats, Italy © StevanZZ/Shutterstock

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.

Gondolas in Venice © Shutterstock

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.

Trieste, Italy @ Shutterstock

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.

Fisherman, Trieste, Italy @ Shutterstock

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.

Piazza San Pietro in Vatican City