From Florence: 2-Day Combo Tour to Pisa, Cinque Terre & Tuscany

Planning to squeeze Italy’s most famous sights into a short trip? This 2-day combo tour from Florence offers an efficient way to see Pisa, Cinque Terre, and Tuscany’s scenic countryside without the stress of planning every detail yourself. With a straightforward itinerary, expert guides, and comfortable transportation, it’s designed for travelers who want a balanced mix of culture, scenery, and delicious wine.

What we particularly love about this experience is how it combines iconic landmarks with authentic regional flavors: the stunning coastal villages of Cinque Terre, the medieval charms of San Gimignano, and the famous Leaning Tower of Pisa—plus the rolling hills of Chianti. The fact that all logistics are taken care of means you can focus on enjoying each moment.

One thing to consider: the schedule is quite packed, especially on day two, which involves a full-day train ride and multiple stops. If you prefer more leisurely exploration, this might feel a bit rushed. But for those wanting a taste of Italy’s top sights in just two days, this tour hits the sweet spot.

This experience is best suited for travelers who love a mix of sightseeing, culture, and wine tasting, and who appreciate having a knowledgeable guide to provide context along the way. If you’re after a practical, well-organized trip that maximizes your time, this tour could be a perfect fit.

Good To Know:

• All logistics handled — transportation, tours, and tickets included for a stress-free experience
• Visit iconic sights — Pisa’s Leaning Tower, Cinque Terre villages, and Tuscany’s San Gimignano
• Expert guides provide insight and local tips, making each stop more meaningful
• Authentic regional experiences — wine tastings, olive oil samples, and charming medieval towns
• Long travel days — expect a full schedule, including train rides and considerable driving
• Limited free time — the itinerary is busy, so plan to make the most of each stop

Exploring the Itinerary: A Day-by-Day Breakdown

Day 1: From Florence to Tuscany and San Gimignano

The tour kicks off early at Piazza della Calza, near Porta Romana, at 9:45am. Meeting there means you’re close to Florence’s heart, and the group is small, with a maximum of 20 travelers, which helps keep things intimate and manageable. The guide, who’s likely to be lively and well-informed, sets the tone for the day, sharing tidbits about the region even before you leave Florence.

Driving through Tuscany offers more than just a scenic backdrop. It’s a chance to appreciate why this area is considered the heart of Italy’s viticulture and olive oil production. Expect rolling hills, cypress-lined roads, and charming villages — a postcard-perfect setting that you’ll see from the bus.

The highlight of the day is the visits to two wineries. The first estate is in Ulignano, near San Gimignano, where a guided wine tasting introduces you to local wines and oils. The review mentions a “welcoming atmosphere” and “extra virgin olive oil tasting & snacks,” making this a delicious and authentic regional experience.

The second winery near San Gimignano offers stunning views of the landscape, perfect for snapping photos. After the tastings, you’ll spend about 1.5 hours exploring San Gimignano itself, known as the “Medieval Manhattan” thanks to its skyline of ancient towers.

Expect to walk around the town’s narrow streets, soaking in medieval architecture, boutique shops, and panoramic vistas. The guide’s advice and recommendations can elevate your visit, helping you find the best spots to enjoy gelato or buy souvenirs.

Back in Florence after about an hour, you’ll arrive with a camera full of scenic shots and plenty of stories to tell.

Day 2: Pisa, Cinque Terre, and Return to Florence

The second day starts bright and early at Santa Maria Novella station, where you meet your guide at 7:30am. This early start is necessary to fit everything into one day, but it means fewer crowds at the major sights.

Your first stop is Pisa, home of the world-famous Leaning Tower. Walking into Piazza dei Miracoli feels almost surreal—this expansive green space is dotted with the Baptistery and the cathedral, all with the tower as the centerpiece. The guide leads you to the field, where you can snap those classic photos of the Leaning Tower or choose to go inside for an extra fee.

While you get about an hour here, the real value is in the feel of standing in a place everyone recognizes, but few realize how much history and craftsmanship is involved in the architecture. As one reviewer pointed out, the guides are friendly and attentive, answering questions about the tower’s tilt and history.

Next, a train ride from Pisa to La Spezia takes about an hour, whisking you to the gateway of the Cinque Terre. Here, the real magic begins. You’ll visit three villages—Riomaggiore, Vernazza, and Manarola—each with its own unique charm.

Riomaggiore greets you with its colorful cliffside houses and scenic port, perfect for wandering winding streets and snapping colorful photos. Then, in Vernazza, a seaside town with a tiny port, you’ll get free time to explore or relax on the beach. It’s often called the most beautiful of the five villages, and from what reviewers say, the view of houses cascading down to the sea is truly breathtaking.

Finally, Manarola offers an iconic landscape—bright houses perched on rugged cliffs overlooking the Ligurian Sea. The town’s natural beauty makes it a favorite among photographers and travelers alike. After the visits, you’ll take a train back to La Spezia or Pisa and then catch your return train to Florence, concluding the trip around 8:00pm.

Logistics and Value

One of the tour’s biggest selling points is how it combines multiple regions without the hassle of independent travel planning. The full-day train travel is included, along with guided visits and wine tastings, which add immense value considering the cost of individual tickets and tours.

The tour’s pricing at $359.19 per person reflects the inclusions—guided experiences, transportation, and tastings—making it a practical choice for travelers who want to experience Italy’s highlights without overspending or organizing multiple bookings.

Authentic Experiences and Insider Tips

Several reviewers highlighted their appreciation for guides like Elisa, who provided great local tips and answered questions thoroughly. The free time in San Gimignano was especially praised for allowing genuine exploration, and the wine tastings were described as enjoyable and well-curated.

The small group size means you get personalized attention and the chance to ask questions or seek recommendations, which can make the experience more engaging and tailored.

Practical Considerations

While the itinerary is packed, it offers a comprehensive taste of Italy in just two days. Expect moderate walking—mostly through towns and around piazzas—and be prepared for weather, as the tour operates in all conditions. Comfortable shoes and weather-appropriate clothing are advised.

Since meals aren’t included, you might want to budget for lunch and snacks, especially during busy days. The tour provides plenty of opportunities for photos and to soak in the scenery, so having your camera or smartphone ready is a must.

Summary: Is This Tour Worth It?

For travelers eager to see a bit of everything—iconic Pisa, colorful Cinque Terre villages, and Tuscany’s rolling hills—this tour offers a practical, well-organized solution. The combination of expert guides, authentic experiences like wine tastings, and seamless logistics makes it a compelling choice for those short on time but longing for a rich taste of Italy.

It’s particularly suitable for first-time visitors who want a rundown, as well as those who appreciate small-group settings and guided commentary. If you’re comfortable with a busy schedule and a fair amount of movement, you’ll find this tour rewarding and full of memorable moments.

However, if you prefer slow-paced exploration or have mobility concerns, this may feel a bit rushed and you’ll want to plan for extra downtime on your own.

Frequently Asked Questions

Do I need to book in advance?
Yes, bookings are typically made around 56 days in advance. The tour operates rain or shine, and booking ahead guarantees your spot.

Are meals included?
No, meals are not part of the tour, so you’ll need to plan for lunch and snacks during the day.

Is this tour suitable for children or elderly travelers?
Most travelers can participate, but be prepared for some walking and moving between towns and train stations.

What is the group size?
The maximum group size is 20 travelers, ensuring a more personal experience.

Can I customize or extend the tour?
The itinerary is fixed, but you can contact the operator to confirm specific activities or ask about additional options.

What should I wear?
Dress comfortably for walking and in weather-appropriate clothing, as the tour operates in all conditions.

Final Thoughts

This From Florence 2-Day Combo Tour offers a well-rounded glimpse of Italy’s most cherished destinations, blending scenic beauty, cultural landmarks, and regional flavors in a manageable package. The guided approach ensures you learn and experience more than you might on your own, while the included activities—wine tastings, visits to picturesque villages, and iconic sights—are thoughtfully curated for maximum enjoyment.

While the schedule is busy, the value for money, expert guidance, and authentic experiences make it a worthwhile choice for curious travelers eager to tick off multiple top spots in just two days. Whether you’re a first-time visitor or a seasoned Italy lover, this tour will deepen your appreciation for Italy’s diverse landscapes and historic charm.

Overall, if you’re looking for a practical, engaging way to see some of Italy’s most famous regions in a short time, this tour delivers on both excitement and convenience.