An Immersive Italian Experience for families and Friends
Milan, Lake Como, Florence and Tuscany in 10 days
Discover Italy’s Classical Beauty with Family & Friends
Italy’s northern regions unfold like pages of a living storybook. From the vineyard-lined hills of Tuscany to the art-filled canals of Venice, from Milan’s style and sophistication to the serene elegance of Lake Como — this 10-day self-drive itinerary is an invitation to explore at your own pace with those you love.
Crafted for families and friends seeking a mix of authentic experiences, relaxed elegance, and shared adventure, this journey includes charming villa stays, curated local encounters, and seamless driving routes connecting each unforgettable stop.
Highlights:
- Expertly guided tours of Milan, Florence, and Venice
- Family-friendly cooking class in Tuscany
- Private gondola ride in Venice
- Exclusive wine and olive oil tasting in the Tuscan countryside
- Stay in handpicked boutique hotels and elegant historic villas
- Personalized travel experiences tailored to your interests
Days 1-2: Lake Como – Peaceful Waters & Alpine Views
Begin your journey in style , once landed a private transfer will bring you to the Grand Hotel in Maneggio, set on the shores of Lake Como. Explore the town and enjoy the sunset.
Explore Bellagio, known as the pearl of the lake, and relax with an espresso in the lakeside piazza. Toast your trip with a farewell dinner at a romantic lakeside restaurant, soaking in the view of twinkling villages across the water.
Day 3-4: Milan – Art, Fashion & Aperitivo Culture
Continue your journey to Milan, Italy’s cosmopolitan heart. Stay at Hotel Manzoni, a luxury hotel in the heart of Milan. Begin with a private visit to the Duomo, followed by a walk through the Galleria Vittorio Emanuele II, La Scala, and the rooftop.
Visit the last Supper and the Brera museum and walk through the world famous Fashion District. In the evening, join locals for an aperitivo crawl, sampling signature cocktails and Milanese small plates in chic neighborhood spots.
Day 5-6: Florence: Renaissance and culinary delights
Travel to Florence via high-speed train and enjoy the city’s culinary delights at the lively Mercato Centrale. Spend the afternoon exploring Florence’s medieval streets, the iconic Duomo, the Palazzo Vecchio, dive into Renaissance masterpieces on a private tour of the Uffizi and Accademia, and climb Brunelleschi’s dome for panoramic views.
Stay at Grand Hotel Cavour, a charming hotel in an unbeatable location set in a historic building dating back to 1300.
For sunset, head to Piazzale Michelangelo or San Miniato for unparalleled views of the city. Stay at Grand Hotel Cavour, located in the heart of Florence near its most celebrated landmarks.
Day 7-10: Tuscany Countryside Adventure
Pick up your rental car and head into the Chianti countryside, starting with a wine-tasting experience at Castello di Verrazzano in the Chianti region.
Stay at a restored stone farmhouse surrounded by olive groves. Join a cooking class to master Tuscan dishes, followed by a wine tasting in a historic vineyard. Spend evenings dining al fresco under the stars.
The next day visit the fortified village of Monteriggioni, a gem of medieval architecture, conclude your day with a self-guided tour of Siena.
Finally visit the stunning Val’Orcia and Pienza, Bagno Vignoni and Montalcino where you can stay at Relais Mastrojanni and spend the last day in an unforgettable cooking and wine tasting experience
A Seamless & Personalized Journey
From scenic self-drives to handpicked accommodations and immersive city experiences, this itinerary is designed to bring loved ones together through the best of Italy. Explore iconic cities and enjoy the freedom of the open road with the luxury of curated stops, insider recommendations, and local flair.
Why This Trip?
✅ Family & Friends Focus – Experiences built for connection, joy, and shared discovery.
✅ Elegantly Balanced – Iconic landmarks, hidden gems, and time to breathe.
✅ Scenic Self-Drive Adventure – Explore Italy at your own pace with picturesque routes and smart logistics.
✅ Local Connections – Meet artisans, vintners, and chefs who bring Italy’s culture to life.
✅ Boutique Comfort – Stay in unique, welcoming properties that feel like home.
Ready to explore Italy’s northern gems your way? Let’s plan your perfect road trip through elegance and history.. Contact us today!
This is just an example of what your trip to Italy could look like.
We will tailor this trip for you according to your interest, tastes and needs.
You can change anything, from duration to excursions, and from accommodation to places visited.
You can even combine this destination with other places you wish to visit in Italy.
Our Italy travel designers are here to craft the perfect Italy bespoke trip for you.