Italy symbolises a unique rhythm, soul-warming flavours and timeless beauty! From a stroll through Tuscany’s sun-drenched vineyards to a walk on Rome’s vibrant piazzas and a mouthwatering traditional meal in Bologna, this European destination promises to take you on a memorable journey brimming with authenticity and awe-inspiring vistas.
On this 21-day tour, we invite you to follow the best of Italy travel itinerary to go beyond sightseeing and experience this country’s charm to the fullest. You will wander off into storied cobbled lanes, find the most picturesque hidden gems and witness daily life in the most enchanting corners. This carefully designed adventure will offer you a balance of off-the-beaten-track experiences mixed with historically rich top attractions and coveted summer gems!
Ready to embark on this immersive Italy tour and create memories for a lifetime?
Days 1 To 3: Get To Know Rome’s Ancient Charm
Any trip to Italy always starts better in one place – Rome! Also known as the “Eternal City”, this historical gem oozes charm from every corner, with each cobbled lane and stone building reminding one that time promises to stand still.
With three days to explore, you are in for a treat brimming with popular attractions and hidden gems. Let a guided walking tour help you get to know this city’s most breathtaking marvels. Surely, this activity brings Rome’s ancient soul to life by taking you on a voyage through time in sites like the majestic Trevi Fountain, the divine Pantheon and the imperious Colosseum – a legendary edifice where the echoes of gladiators share tales of bravery.
Days 4 To 6: Say Ciao To Naples & The Amalfi Coast!
Hop on the train and journey south to find the next destination on your full Italy travel experience! Naples is a gateway to the emblematic Pizza, UNESCO World Heritage Sites, and picturesque towns planted by the Mediterranean Sea. Take your first impressions on a tranquil stroll, following your own pace, while walking past faded façades, buzzing “Vespas” and tucked-away trattorias. Via dei Tribunali can be part of your itinerary. This lane shows you the way into Naples’ religious heart with centuries-old churches.
As day 5 rolls by, dive deeper into Naples’ charm in a guided walking tour that will capture the destination’s bustling energy and striking contrasts. The Sansevero Chapel will be one of the unforgettable stops along the way. Here, you will get to see the “Veiled Christ” sculpture – always a highlight that leaves a lasting impression! On day 6, prepare for a tour of the ultimate Italy highlights for first-time visitors. A full-day guided tour will take you from the well-preserved Pompeii Ruins to the winding roads of the Amalfi Coast and the postcard-perfect towns of Sorrento and Positano. Keep an eye out – each turn offers sea-swept views to take your breath away!
Days 7, 8 & 9: Bask In Florence’s Renaissance Flair!
On to Florence, one of Italy’s top cities to visit, and a remarkable jewel of the Renaissance! From terracotta rooftops to romantic piazzas and riveting art galleries, this destination invites you to make history, art, and culture part of your immersive tour. Over three days, you will discover the top things to do in Florence, like uncovering the legacy of the Medici family and crossing the iconic Ponte Vecchio. Picture yourself walking along the streets where Michelangelo and Dante found the inspiration for their masterpieces. Explore the city’s rich past in a guided walking tour and make use of the Ghiberti Pass to access the Duomo. Gaze up at Brunelleschi’s majestic dome and let yourself be swarmed by its ethereal beauty.
As the ninth day of your tour arrives, what better way to wrap up your time in Florence than with a hands-on pasta cooking class? Learn how to cook fresh pasta from scratch and savour a delectable farewell meal that will leave this city in your heart forever!
Days 10, 11 & 12: Discover Tuscany’s Highlights
Your time in Tuscany is only complete when you explore the gems lying beyond Florence! In a region where golden hills roll into vineyards and every view feels like a real-life painting, memorable experiences are sure to abound. Your first stops include San Gimignano and Siena. The latter is a city of medieval splendour that you will get to uncover on a walking tour. From winding lanes to the famed Piazza del Campo, no stone will be left unturned!
Then it's off for Montalcino, Pienza and Montepulciano. Here, a winery tour will invite you to sip into Italy’s world of wine-making. Surrounded by quiet beauty and the Tuscan countryside, each glass of Brunello wine will offer a true taste of authentic Italian experiences. On your final day in this region, let the roads lead you to the charm of Pisa and Lucca, two historic cities brimming with iconic landmarks. Take a picture with the Leaning Tower of Pisa and explore Piazza dei Miracoli’s alluring beauty.
Days 13 & 14: Uncover Italy’s Culinary Paradise!
As your Italy art, food, and history tour continues north, the rich heart of the Emilia-Romagna region awaits. Welcome to Bologna, Italy’s culinary paradise, where medieval towers rise above elegant porticoes and traditional trattorias are complemented with the smell of freshly cooked “Tagliatelle al Ragù”. Let a local expert guide help you unveil this city’s gems, walking you through the stories hiding in sites like Piazza Maggiore and the grand San Petronio Basilica.
As a new day arrives, your Italian adventure will take yet another delicious turn with a gastronomic day trip to Modena and Parma. These towns will introduce you to two of the region’s most treasured edible products – “Parmigiano Reggiano” and “Prosciutto di Parma.” Prepare your taste buds – you are in for a mouthwatering experience defined by the taste of delicacies produced right at the source. To make your complete Italy tour package feel even more complete, you must pair these gems with locally produced wines!
Day 15: Explore Milan’s Iconic Landmarks!
Today, continue your journey in Milan. Imagine a city of timeless elegance with a modern edge – unique and mesmerizing! As one of Italy’s top cities to visit, this gem boasts a collection of dazzling art, incredible architecture, and refined urban charm.
Start your exploration in the Duomo. A guided walking tour will help you learn more about this Gothic masterpiece sitting just steps away from the Galleria Vittorio Emanuele II. The latter is perfect for a luxury shopping rendezvous graced by marble floors and domed glass ceilings! Nonetheless, Milan’s magic goes even further than its fashion and façades. Santa Maria delle Grazie is a must-visit that houses Leonardo da Vinci’s “The Last Supper.” As the day nears its end, reminisce on the memories you have created and all the Italy highlights for first-time visitors you have had the opportunity to admire!
Days 16 & 17: Find Shakespeare’s Love In Verona
It is that time of your Italian odyssey to step into the pages of a timeless love story in Verona! This city has been garnering attention worldwide for having inspired the acclaimed “Romeo and Juliet” story. Surely, this jewel must be included on your best of Italy travel itinerary.
Verona beckons your mind to travel into cobbled streets, sun-dappled piazzas and medieval façades – rightly so! This city is home to awe-inspiring, well-preserved historical sites, namely a Roman Arena, still to this day hosting live opera performances. The Piazza delle Erbe will enchant you with its colourful market stalls and lively ambience that remind you of the magic of the Italian way of life! Fear not, your walking tour in Verona must include a visit to the legendary Juliet’s House. As the sun starts setting, Verona will appear to you to be more than a legend. This city is a visual symphony of pastel-coloured buildings and scenic riverside walks!
Days 18 To 21: Arrivederci From Venice, The City Of Romance!
As you wind your way to Venice, embrace the magic of your final days in Venice, where the shimmering canals and storied buildings provide the ideal background for a romantic finale. This is undoubtedly one of Italy’s top cities to visit and one of the country’s most coveted destinations.
A guided walking tour will illuminate some of this city’s most emblematic sights, such as the elegant grandeur of St. Mark’s Basilica and the Doge’s Palace Gothic allure. Cross the charming Rialto Bridge and continue your quest with views of the Grand Canal. With your free time, dare to wander off into a quieter moment away from the tourist crowds. Find authenticity in the hidden piazzas and tucked restaurants, and allow yourself to fall even more in love with Italy’s most traditional character. This final stop offers a fitting close to your full Italy travel experience—romantic, unforgettable, and steeped in centuries of art, history, and beauty.
Ready for your customised Italian adventure?
As we travelled through this European gem, we ascertained that the best way to explore Italy from north to south is through a 21-day adventure that can feel uniquely yours! In a thoughtfully crafted itinerary, we have crossed paths with the iconic Rome and its imperious Colosseum, we have marvelled at the Amalfi Coast's natural beauty, we have found comfort in Emilia-Romagna’s praised gastronomy, and we have fallen in love with Venice’s dreamy canals.
Want more time in Tuscany? Or perhaps Milan or Verona? Your journey is yours to make. As for TourTailors, here to help you make it as seamless, effortless and as unforgettable as possible. The first step is to reach out to us. From there, our team of local experts is ready to help bring your dream Italian escapade to life!
