6-Day Cinque Terre, Florence & the Flavours of Tuscany Tour from Milan to Rome

A six-day journey through Italy’s most iconic spots, from the colorful Cinque Terre to the historic streets of Florence and the rolling hills of Tuscany, offers a fantastic way to see a lot without feeling rushed. Priced at $2,747.20 per person, this guided tour covers La Spezia, Pisa, Lucca, Florence, Siena, Montepulciano, Pienza, Montalcino, Bagno Vignoni, Sovana, and Capodimonte. It’s designed for those who want an in-depth taste of Italy’s art, food, and landscapes, all wrapped in a well-organized, small-group experience.

What we love most about this tour is its balance: it combines stunning scenery with cultural highlights and authentic local flavors, like a wine tasting in Tuscany. Plus, traveling comfortably in a private vehicle with a small group (max 16 travelers) means there’s enough room to relax and soak in the views. The included accommodation in 3-4 star hotels with breakfast offers good value, and the train trip to Cinque Terre helps keep the pace manageable.

One thing to consider is that the itinerary is packed—if you’re looking for a leisurely, unhurried trip, this might feel busy. Also, the tour is non-refundable, so flexibility is limited. But if you’re eager to see Italy’s top sights with knowledgeable guides who enrich the experience with stories and insights, this tour suits travelers who want a rundown, especially for first-timers or those short on time.

This experience made our article of Our 15 Favorite Lombardy Tours.

Key Points

• Diverse Destinations: From seaside villages to Renaissance cities, there’s something for all.
• Small Group: Intimate travel experience with a maximum of 16 travelers.
• Authentic Experiences: Includes wine tastings and visits to historical towns.
• Comfort and Convenience: Private mini-coach, hotel stays, and train rides.
• Rich Cultural Highlights: Art in Florence, architecture in Pisa and Lucca, and Tuscan landscapes.
• Full But Manageable: Well-organized, packed itinerary for efficient sightseeing.

Exploring the Itinerary in Detail: What You Can Expect

Day 1: The Charm of Cinque Terre

Your adventure begins in La Spezia, the gateway to the Cinque Terre. After leaving Milan, you’ll head south in a comfortable private vehicle, arriving in La Spezia for a quick check-in. Then, your guide takes you on a train to the first of the five villages—Monterosso. Here, expect to stroll along beaches or enjoy the lively promenade, soaking in the colorful seaside scenery.

Later, you’ll visit Manarola, renowned for its vineyards and wine tasting opportunities. The chance to savor local wines while overlooking the sea makes this a memorable start. The villages each have their own character—Riomaggiore, Vernazza, Corniglia—so you can choose your favorite vibe. The day ends with a train ride back to La Spezia, your base for the night.

This day is a highlight for those who love scenic coastal views and charming towns. It’s worth noting the train ride adds flexibility and efficiency, helping you cover multiple locations in one afternoon.

Day 2: From Marble to Medieval Marvels

The morning kicks off with a visit to Pietrasanta, where Michelangelo sourced marble, setting the tone for Italy’s artistic heritage. Then, you’re off to Pisa. Here, the Leaning Tower isn’t just a quirky photo prop; it’s a testament to Romanesque architecture and centuries of history. You’ll have a couple of hours to explore the Field of Miracles, admiring the cathedral, baptistery, and monument.

Next, you’ll head to Lucca, famous for its intact city walls. Walking along the ramparts offers a unique perspective on a city that thrived on the silk trade. The streets are lined with graceful buildings, and you’ll have a couple of hours to wander at your own pace—perfect for soaking up the authentic Italian charm.

This day is about appreciating Italy’s architectural diversity, from Romanesque to Gothic. The walking is moderate, and the small group size makes for engaging conversations with your guide.

Day 3: Florence—The Renaissance Heart

The day is yours in Florence, Italy’s birthplace of the Renaissance. You might spend your time marveling at Michelangelo’s David, exploring the Uffizi Gallery to gaze at masterpieces like Botticelli’s The Birth of Venus, or simply wandering through Piazza della Signoria with its lively atmosphere.

The Duomo, with its striking dome designed by Brunelleschi, dominates the skyline and is a must-see. For art lovers, the Galleria dell’Accademia offers the chance to see Michelangelo’s iconic sculpture up close.

Food lovers will appreciate the chance to try handmade pasta, pizzas, pastries, and gelato—Italy’s culinary treasures. In the afternoon, you could explore Palazzo Pitti and the Boboli Gardens for a taste of Medici opulence.

This day is perfect for those eager to experience the artistic and culinary soul of Italy. It offers flexibility for different interests, whether art, history, or food.

Day 4: The Towering Towns and Stunning Landscapes

Travel through the Chianti region to San Gimignano, with its medieval towers. The story of noble families racing to build the tallest tower adds a touch of fun and history. You can walk through the well-preserved old town, enjoy panoramic views, and taste local delicacies.

Next, you’ll visit Siena, famous for its Gothic architecture and the Piazza del Campo—a perfect setting for the Palio di Siena, the famous horse race held twice a year. The city’s atmosphere is lively, and your guide will share stories that bring its history alive.

Finally, you’ll arrive in Montepulciano, a hilltop town known for its Vino Nobile wine. You’ll stay here for two nights, giving you time to appreciate its medieval streets and spectacular views.

This day highlights Italy’s medieval architecture and culinary traditions, especially the wine culture that’s woven into Tuscany’s fabric.

Day 5: Discovering Pienza, Montalcino, and Hot Springs

Your morning starts in Montepulciano, exploring at your own pace before heading to Pienza. A UNESCO World Heritage site, Pienza is a perfectly planned Renaissance town, recognized for its harmonious layout and stunning views.

You then visit Montalcino, home to world-renowned Brunello di Montalcino wine. The included wine tasting offers a chance to sample some of Italy’s best reds. The guide will select from local wineries, ensuring quality and authenticity.

The afternoon features a visit to Bagno Vignoni, famous for its hot sulphurous waters. Historically popular with Romans, this small village’s thermal springs remain a fascinating sight—an ancient spa amid beautiful surroundings.

This day combines culinary delights with historic sites and natural beauty, ideal for those wanting a taste of rural Tuscany’s slow pace and flavor.

Day 6: The Etruscans and Farewell to Italy

The tour concludes in the Maremma region with visits to Sovana, home to Etruscan necropolises and Vie Cave—impressive Bronze Age roads carved from tuff. Then, a final stop at Capodimonte on the shores of Bolsena Lake, Italy’s largest volcanic lake, offers a peaceful ending before heading to Rome.

This day provides a glimpse into Italy’s ancient Etruscan civilization and natural beauty, rounding out a comprehensive experience of Italy’s diverse heritage.

Authentic Experiences and Traveler Insights

From the reviews, travelers praise the knowledgeable guides who enrich the journey with captivating stories, making the history come alive. One reviewer appreciated a guide named Sebastian, highlighting the flexibility and personal touch they enjoyed, especially when the group was small enough for customization.

The wine tastings in Tuscany receive high marks, with reviewers noting that they offered a perfect way to enjoy local products and learn about regional varieties. The landscapes—rolling hills, medieval towers, and seaside villages—are consistently described as stunning and picturesque.

Several travelers mention the well-organized itinerary, which packs a lot of sights into a short time without overwhelming. The accommodations are generally well-reviewed, providing a comfortable base after busy days of sightseeing.

A common praise point is the small group size, which fosters a more intimate and engaging environment, and the transportation, which is smooth and unobtrusive, allowing more focus on the scenery and conversations.

Practical Considerations and Who This Tour Fits

The price point reflects the value of included accommodation, transportation, train tickets, and wine tasting, which would otherwise be costly and time-consuming to organize independently. The tour’s timing is ideal for those who want a structured yet flexible overview of Italy’s highlights, especially first-time visitors eager to see a lot in a short span.

However, the packed schedule means this isn’t a trip for those seeking total leisure or slow travel. The non-refundable policy also requires confidence in your plans. Travelers should be comfortable with moderate walking and being part of a guided group.

This tour is best suited for history and art enthusiasts, food and wine lovers, and curious travelers who enjoy a cohesive narrative through Italy’s diverse regions. It’s particularly appealing to those who want a comprehensive, guided experience that balances sightseeing with some authentic local flavors.

Frequently Asked Questions

What is included in the tour price?
The price covers transportation in a luxury mini-coach, 5 nights in 3-4 star hotels with breakfast, train tickets to Cinque Terre, small-group experience, and wine tastings at a local winery.

Are meals included?
No, meals and refreshments outside the included breakfast are not covered, but travelers will have time to enjoy local dining in each town.

What is the maximum group size?
The tour is limited to 16 travelers, creating an intimate atmosphere and better interaction with guides.

Can I customize the itinerary?
While the itinerary is fixed, some reviews mention the guide’s flexibility, especially when the group is small, allowing for minor adjustments.

What should I bring?
Comfortable walking shoes, a camera, and some cash for souvenirs or extra snacks. The tour starts early, so pack light but be prepared for varied weather.

Is this tour suitable for children?
No, travelers under 18 are generally not permitted, owing to the nature of activities and logistics.

How much luggage can I bring?
You’re allowed a medium-sized suitcase (about 55cm x 45cm x 25cm) plus a small personal bag, with a 20kg weight limit.

When does the tour start and end?
It begins at 8:30am in Milan and concludes in Rome. Exact times can vary slightly for operational reasons.

Final Thoughts

This 6-Day Cinque Terre, Florence & the Flavours of Tuscany tour offers a finely balanced mix of scenic beauty, cultural richness, and authentic tastes. It’s well-suited for travelers eager to see Italy’s highlights with a knowledgeable guide, all while enjoying comfortable accommodations and local wine. While the busy schedule might not suit those craving a slow pace, the shared experience and expertly curated stops make it an excellent choice for first-time visitors or those with limited time.

If you love stunning landscapes, art-rich cities, and delicious food and wine, this tour delivers on all fronts. It’s a smart way to get a comprehensive taste of Italy with the convenience of expert guidance and small-group intimacy. Just be prepared for the fast pace and a no-refund policy—this is a trip designed to give you a rich, well-organized overview of Italy’s most loved regions.