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Discover Tuscany, Pisa, and Cinque Terre on a 2-day guided tour from Florence, featuring wine tastings, scenic villages, and iconic sights with expert guides.
A 2-day combo tour from Florence offers an efficient way to see some of Italy’s most captivating sights: Pisa, Cinque Terre, and Tuscany. Priced with the flexibility to reserve now and pay later, this experience is perfect for travelers looking for a well-organized, all-in-one adventure. With a rating of 4.5 out of 5 based on 4 reviews, it combines highlights like the Leaning Tower of Pisa, scenic coastal villages, and wine tastings at renowned wineries.
This tour is designed for those who appreciate local guides speaking only English, offering an authentic and informative experience. It’s best suited for travelers comfortable with long days and moderate walking, as the itinerary includes train travel, village walks, and some beach time. Keep in mind that the Pisa and Cinque Terre visits involve regional trains, which may be crowded during high season, and seats are not guaranteed.


The tour begins early at 07:30 am in front of the pharmacy at Florence’s main train station. This prompt start allows ample time for exploring the highlights of Pisa and Cinque Terre in one long but rewarding day. The regional train rides between villages in Cinque Terre are part of the experience, offering a chance to see the coastline from the train windows. Be prepared for crowded trains during high season, where seat availability might be limited.
In Pisa, the iconic Leaning Tower takes center stage. The Pisa Cathedral, Baptistery, and Campo Santo complete the historic square. Visitors are free to walk around and take funny photos with the tower, which is a must-see for most travelers. After Pisa, the journey continues to Cinque Terre, famous for spectacular coastline views, scenic trails, and sunny beaches.
The first stop in Cinque Terre is Riomaggiore, where travelers receive an orientation walk and can enjoy some free time for lunch. The itinerary then takes you to Manarola, ideal for photos of boats and colorful houses, before reaching Vernazza, where there’s an opportunity to relax, sunbathe, or take a swim in the Mediterranean Sea. The day wraps up around 8:00 pm with a return train ride back to Florence.
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The second day is dedicated to discovering Tuscany’s famous wine and medieval town of San Gimignano. The day starts at 09:40 am from a different Florence meeting point, Piazza della Calza in front of Porta Romana. The day includes visits to two wineries, each offering tastings of four different wines, along with truffle-infused extra virgin olive oil and 30-year-old balsamic vinegar.
The first winery emphasizes the variety of wines and the olive oil produced on-site, providing insights into traditional production methods. The second winery, located near the famous towers of San Gimignano, focuses on Vernaccia white wine, with guided tours of vineyards and cellars. The guides share secrets of wine and oil pairings, making the tastings both informative and flavorful.
In the afternoon, the trip continues to San Gimignano, often described as the most beautiful medieval town in Tuscany. Visitors enjoy wandering through narrow streets, shopping in local shops, and admiring the tower-filled skyline. A highlight is tasting gelato from a world-champion gelateria, which adds a sweet touch to the day before returning to Florence around 5:00 pm.

The tour is led by English-speaking guides, with Ned and Alessandro being praised for their knowledgeable, calm, and friendly manner. They are noted for their ability to navigate busy sites and share insightful stories, making complex information accessible and engaging. Guides also handle logistical challenges, such as train delays or crowded sites, with professionalism.
According to reviews, the guides excel in explaining the history and traditions of the places visited, enriching the experience. Guests appreciate how guides’ expertise enhances the wine tastings and provides context for the towns and landmarks. The personalized attention makes these two days feel relaxed despite a packed schedule.

Pisa’s Leaning Tower is the most recognizable landmark on this tour. Visitors have ample free time to walk around the square and take classic photos. The Duomo di Pisa and Campo Santo are also part of the visit, offering additional photo opportunities and a glimpse into the city’s religious architecture.
Since the tour involves regional trains, it’s important to be prepared for potential crowds, especially during high season. Seats are not guaranteed, so patience and flexibility are key. The free time allows for self-guided exploration and plenty of photo sessions.
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The Cinque Terre section of the tour showcases the natural beauty of five colorful fishing villages. Riomaggiore introduces visitors to the vibrant neighborhoods, while Manarola offers iconic views perfect for photos. Vernazza is the last stop, where people can relax on beaches, sunbathe, or swim in the Mediterranean Sea.
Note that during peak season, trains can be crowded and subject to delays. The villages can only be visited by train or boat, so flexibility is necessary. The scenic train rides contribute to the overall coastal experience and supply ample chances for pictures of the rugged coastline.

The wine tasting experiences are a major highlight of the Tuscany day. The first winery focuses on variety—sampling four different types of wines and tasting truffle olive oil and balsamic vinegar. The second winery emphasizes Vernaccia, a renowned white wine, with guided tours through vineyards and cellars.
Guests are invited to learn about the winemaking process and pairings from expert winemakers, making the tastings educational as well as enjoyable. The combined tastings offer a deep dive into Tuscany’s wine culture, complemented by local food.

In the afternoon, San Gimignano provides a step back into medieval times with its tower-filled skyline and narrow streets. Visitors enjoy free time to explore shops, admire architecture, and sample ice cream from a world-champion gelateria. This town’s unique skyline is one of Tuscany’s symbols.
The gelato tasting caps off the visit, giving a sweet break before the journey back to Florence. This town combines history, shopping, and culinary delights, making it a favorite for many before concluding the day.

The tour departs from different locations in Florence, including the main train station and Piazza della Calza. The schedule balances early mornings with afternoon returns, so travelers should be prepared for long days with moderate walking.
This experience not suitable for wheelchair users, pregnant women, children under 18, or those with mobility impairments. Participants should bring water shoes for beach or swimming activities.

This 2-day experience offers a compact but comprehensive view of some of Italy’s most beloved destinations. The mix of iconic sights, wine tastings, and medieval towns makes it an appealing choice for culture, nature, and culinary enthusiasts.
The guides’ expertise and organized logistics help maximize the experience, even amid crowds and train delays. The transportation by regional train adds an authentic touch but requires patience. This tour balances sightseeing with relaxation, making it a practical way to experience Italy’s highlights in a short time.
What is included in the tour price?
The tour includes guided visits, wine tastings at two wineries, visits to Pisa and Cinque Terre villages, and transportation by train.
Are meals included?
Lunch in Cinque Terre is not included but travelers have free time to choose where to eat after the orientation walk in Riomaggiore.
What should I bring?
Travelers are advised to bring water shoes for swimming activities and water for the day.
Is the tour suitable for children?
No, the tour is not suitable for children under 18 years or those with mobility impairments.
How is the pacing of the tour?
It’s a full and long 2-day experience, with early starts and late returns, making it suitable for those prepared for long days of sightseeing.
What language are guides speaking?
All guides speak English exclusively.
Are seats guaranteed on the trains?
Seats are not guaranteed during high season, as the train rides are regional trains that can be crowded.
Can I cancel this tour?
Yes, free cancellation is available up to 24 hours in advance for a full refund.
Is there an option to reserve and pay later?
Yes, the reservation allows you to reserve now and pay later, providing flexibility for travel plans.
What is the meeting point?
The primary meeting point is in front of the pharmacy at Florence’s main train station, with an alternative at Piazza della Calza near Porta Romana, depending on the option booked.
This tour from Florence offers a balanced slice of Italy’s coastal, wine, and medieval attractions in just two days. With well-organized logistics, expert guides, and a variety of scenic and cultural stops, it earns a solid 4.5-star rating and promises a memorable journey for those eager to explore beyond Florence.
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