Italy Itineraries: 5 day trips

San Gimignano, a little hamlet in Tuscany, Italy
San Gimignano, a little hamlet in Tuscany, Italy

Italy stands as a renowned travel destination, and it's easy to see why. This captivating country has consistently charmed its way onto countless bucket lists, all thanks to its exquisite cuisine, rich culture, and breathtaking landscapes. Wondering how to maximize your time in Italy? Look no further, as we've expertly designed six distinct 5-day Italy itineraries to ensure you have the best trip possible.

See more of our Italy itineraries:  7 days - 10 days - 14 days - North ItalySouth Italy

Itinerary #1: Wine and Food in Tuscany

Welcome to the heart of Italy's culinary and wine traditions in enchanting Tuscany. Nestled in the medieval hill town of San Gimignano, positioned halfway between the historic cities of Florence and Siena, this 5-day journey promises to be a gastronomic delight. Curated with care by your local travel specialist, it offers a sensory adventure through Tuscany's finest flavors.

Itinerary summary

Here’s an overview of this 5-day 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.

Chianti and italian antipasti. Photo: Shutterstock

Day 1: Arrival in San Gimignano

Your exploration commences with a private car transfer from Florence to the picturesque town of San Gimignano. Upon arrival, you'll have some free time to settle into your charming hotel and soak in the atmosphere of this medieval gem.

Day 2: Leisurely San Gimignano

Day two unfolds with the freedom to explore San Gimignano at your own pace. Meander through its ancient streets, savor local delicacies, and take in the town's unique ambiance.

Day 3: The Art of Winemaking

Prepare for an extraordinary day as you delve into the artistry of winemaking. A captivating winery experience awaits, featuring a vertical Wine Tasting of 15 Tuscan wine treasures. This vinous journey is paired with a delectable lunch served amidst the rolling vineyards or within the winery's walls. From vineyard visits to the intricacies of wine production, this day offers an immersive insight into the world of Tuscan wines.

Day 4: Chianti - A Feast for the Senses

Day four is a sumptuous dedication to Tuscany's culinary traditions. Relish a medley of mouthwatering dishes, thoughtfully paired with the finest Chianti wines. All of this unfolds against the backdrop of Tuscany's scenic landscapes, a feast for both the eyes and palate

Day 5: Farewell to Tuscany

On the final day, a private driver ensures a seamless departure as you bid adieu to Tuscany. You'll be transported to Florence airport for your onward journey. The memories of this extraordinary voyage, filled with epicurean adventures and unforgettable experiences, will linger, igniting a desire for a return visit to this captivating Italian region.

Seeking a worry-free getaway? Book this journey with our support.

San Gimignano, a little hamlet in Tuscany, Italy. Photo: Shutterstock

Itinerary #2: Eternal Rome for the Weekend

Welcome to the captivating embrace of Rome, where history, art, and culture merge into an unforgettable tapestry. In just a weekend, we invite you to immerse yourself in the eternal charm of this ancient city with our expertly curated 5-day itinerary. From iconic wonders to hidden treasures, embark on a journey to the heart of the eternal city. 

Itinerary summary

Here’s an overview of this 5-day 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.

Looking for an effortless travel experience? Trust us to plan and book it.

Colosseum. Photo: Shutterstock

Day 1: Arrival in Rome

As you arrive, Rome extends a warm embrace. Day one grants you the freedom to explore this historic city at your leisure. Get lost in its enchanting streets, savor local flavors, and soak up the atmosphere.

Day 2: Vatican Voyages 

Day two ushers you into the mesmerizing world of the Vatican Museums. The tour unveils the masterpiece-laden Sistine Chapel, a testament to the genius of Michelangelo and other luminaries. Your odyssey continues to the awe-inspiring St. Peter's Basilica, a symphony of architectural brilliance crowned by Michelangelo's "La Pietà."

Day 3: The Colosseum and Beyond

Day three catapults you into the amphitheaters of old with a visit to the iconic Colosseum, where gladiator tales once unfolded. Nearby, immerse yourself in the historical treasures of the Roman Forum, the epicenter of ancient Rome's political, commercial, and spiritual life.

Day 4: Rome's Iconic Landmarks 

Day four commences with a small-group walking tour, leading you to Rome's iconic landmarks. From the iconic Spanish Steps to the enchanting Trevi Fountain, the journey culminates at the magnificent Pantheon. It ends at "Piazza Navona," graced by Bernini's Fountain of Four Rivers, offering a delightful tasting of authentic Italian products.

Day 5: A Fond Farewell

As the Roman sun sets on your adventure, day five beckons a fond farewell. Check out from your hotel, but take with you cherished memories and a profound appreciation for the eternal allure of Rome.

Ready for a weekend of enchantment? Your Roman odyssey awaits. Book your journey now!

St.Peter's square. Photo: Shutterstock

Itinerary #3: Florence: A Trip Back In Time

Welcome to Florence, a city where the echoes of the past resonate in every cobblestone. Our meticulously crafted 5-day Italian itinerary invites you to journey through time in this enchanting city. Florence is a true treasure trove of Renaissance art, ancient architecture, and a cultural legacy that spans the ages.

Itinerary summary

Here’s an overview of this 5-day 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.

Eager to embark on this adventure with ease? Choose to book with our team.

Florence's Duomo. Photo: Shutterstock

Day 1: Arrival in Florence 

Your voyage begins with a warm welcome at Florence Airport. Day one grants you the freedom to uncover the city's splendors at your own pace. Don't miss must-see gems like the renowned Uffizi Gallery and the Accademia, home to the iconic masterpiece, Michelangelo's David.

Day 2: Secrets of the Vasari Corridor

Day two unravels the mysteries of the Vasari Corridor, a clandestine passageway linking Palazzo Pitti to Palazzo Vecchio. Adorned with an enthralling collection of 15th-century self-portraits, this hidden treasure offers a glimpse into Florence's illustrious past. Behold the grandeur of the Room of the Five Hundred in Palazzo Vecchio, adorned with masterpieces by Vasari, Leonardo da Vinci, and Michelangelo.

Day 3: Dante's Footsteps

 Venture off the beaten path on day three to Casa di Dante, a museum dedicated to the life of the renowned poet. Trace Dante's journey through three pivotal stages of his life, from 13th-century Florence to his exile and enduring legacy. The odyssey continues to the iconic Piazza del Duomo, the Badia Fiorentina, and the mesmerizing Baptistery with its enchanting Gates to Paradise.

Day 4: Choose Your Adventure

 Day four invites you to craft your own Florence experience. Explore the city at your leisure, or embark on a picturesque day trip into the Tuscan countryside. Visit captivating towns like San Gimignano, Siena, or Pisa. The day culminates with a delectable 3-course meal at an authentic local restaurant, offering an authentic taste of Florentine cuisine.

Day 5: Farewell to Florence

As your remarkable journey comes to an end on day five, carry with you cherished memories of this enchanting adventure. Depending on your flight time, bid farewell to Florence as you are gracefully transferred to the airport, taking with you the enduring beauty and essence of this captivating city, forever etched in your heart.

Want to explore Florence's timeless tapestry? Book your journey now!

Uffizi Gallery. Photo: Shutterstock

Itinerary #4: Romantic Venice

Welcome to Venice, the city of romance and timeless allure. Our 5-day Italian itinerary invites you to discover the magic of Venice, with captivating walks, dreamy gondola rides, and the freedom to explore at your leisure.

Itinerary summary

Here’s an overview of this 5-day 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.

St. Mark's square in Venice. Photo: Shutterstock

Day 1: Arrival in Venice

Your journey begins as you touch down at Marco Polo International Airport. You'll be whisked away to your hotel, leaving the day free to explore Venice's winding streets, canals, and hidden corners at your own pace.

Day 2: Discover Venice

Day two unfolds with a private walking tour, commencing in the heart of Venice, the Saint Mark's area. Delve into the history of this maritime empire as you explore iconic landmarks such as The Doges' Palace, St. Mark's Square, and the awe-inspiring Basilica. Each step reveals Venice's unparalleled beauty and historical significance.

Day 3: Gondola Serenade

Day three begins with a delightful breakfast, setting the stage for a romantic 30-minute gondola ride through Venice's enchanting waterways. Immerse yourself in the city's unique atmosphere. The afternoon is yours to explore at your own pace, culminating in a delectable three-course dinner at a centrally located restaurant (drinks not included).

Day 4: Venice Unveiled

Day four gifts you a free day to fully immerse yourself in Venice's beauty. Wander the labyrinthine streets, visit charming cafes, or discover hidden gems off the beaten path.

Day 5: Farewell to Venice

As your enchanting journey draws to a close on day five, enjoy one last breakfast before checking out of your hotel. A private transfer will seamlessly take you to Marco Polo International Airport. Depart with cherished memories and the lingering desire to return to this mesmerizing destination.

Ready to get lost in Venice's enchantment? Book your adventure now!

Grand Canal gondola trip. Photo: Shutterstock

Further reading…

For detailed Italy trip itineraries that bring your dream vacation to life, explore our Insight Guides' expertly crafted plans. Download one now for unforgettable 7-day and 14-day journeys, carefully curated by our Italy guidebook authors. 

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

Welcome to Trieste, where culture and nature coalesce to create a unique adventure. Ou5-day Italy itinerary immerses you in this captivating city, taking you beyond the tourist path to experience it like a local. Get ready for an exploration that blends small daily rituals with hidden gems waiting to be uncovered.

Itinerary summary

Here’s an overview of this 5-day Italy itinerary:

  • ay 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.

Ponte Rosso square view in Trieste. Photo: Shutterstock

Day 1: Arrival in Trieste 

Your journey kicks off with a warm welcome at the train station or airport. Day one is all about getting acquainted with the city. Stroll through historic streets and squares, along the seafront, and up to the stunning hill of San Giusto, offering breathtaking panoramic views.

Day 2: Tram Ride to Karst

 On day two, embark on a scenic adventure to the Karst plateau. Hop aboard the iconic Opicina tram, a relic from 1902, ascending to the plateau. A picturesque walk awaits, featuring vistas of the city and the sea, leading you to the magnificent Miramare Castle Park.

Day 3: Lipica Equestrian Park

Day three brings you to the Lipica Equestrian Park, a serene oasis and home to the elegant Lipizzan horses. After a guided tour and leisurely strolls in the estate, explore the valley of the Blessed Virgin of Lourdes, a unique sanctuary dating back to the 1800s.

Day 4: Rosandra Valley Reserve 

Your adventure continues on day four with a visit to the Rosandra Valley Reserve. Walk along the ancient salt road, savoring views of the Rosandra stream with its picturesque waterfall and natural pools.

Day 5: Grotta Gigante

Conclude your unforgettable journey on day five with a visit to the awe-inspiring Grotta Gigante, the world's largest cave. After your underground exploration, return to the city. If you've left any luggage at your accommodation's storage, retrieve it as you prepare for your onward journey or return home.

Don't just dream of adventure; make it a reality. Book your Trieste experience now!

Rosandra Valley. Photo: Shutterstock

Itinerary #6: Exploring Vatican City and Assisi

Get ready for a 5-day voyage through the treasures of Ancient Rome, coupled with a soul-soothing visit to the hometown of St. Francis of Assisi, Eremo delle Carceri.

Itinerary summary

Here’s an overview of this 5-day 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.

Saint Feancis Basilica in Assisi. Photo: Shutterstock

Day 1: Arrival in Rome

Your journey begins with your arrival in the Eternal City of Rome. A convenient transfer whisks you away to your hotel for a relaxing overnight stay as you prepare for the adventures that await.

Day 2: Vatican Art and Majesty

Day two immerses you in the cultural wonders of Rome. Explore the Vatican Museums, Sistine Chapel, and St. Peter's Basilica. Skip the lines and dive into one of the world's most significant art collections. Marvel at the Tapestry Gallery and the Geographical Maps. The day crescendos with a visit to the iconic Sistine Chapel and the breathtaking St. Peter's Basilica.

Day 3: Ancient Rome Revealed

On the third day, your exploration of Rome's iconic landmarks continues. Visit the Colosseum, Roman Forum, and Palatine Hill with priority entry and a knowledgeable local guide. Discover the captivating history and tales of ancient Rome.

Day 4: Assisi Retreat

Day four transports you from Rome's bustling streets to the serene city of Assisi, the birthplace of St. Francis. Explore the Eremo delle Carceri, the first abode of St. Francis and his followers. Immerse yourself in the tranquil beauty of this sacred monument. Enjoy a leisurely day of sightseeing before retiring to your hotel for an overnight stay.

Day 5: Departure from Rome

As your journey reaches its conclusion on day five, you'll return to Rome airport for your flight home, carrying cherished memories of Rome's historical wonders and the serene serenity of Assisi with you.

Sistine Chapel in Vatican. Photo: Shutterstock

Skip the hassle of planning and booking

Our local experts can plan wonderful trips for you in Italy. Simply get in touch when you would like to travel. We will then create a personalized itinerary, which you can amend until you are totally happy with every detail of the booking. All of our planned itineraries can be tailored to meet your specific needs.