Pisa, Florence & Chianti wine tour

This private shore excursion offers an ideal way to see some of Tuscany’s most iconic sights without the hassle of public transportation. With a carefully curated itinerary hitting Pisa, Florence, and a Chianti vineyard, it’s perfect for travelers looking to maximize their day in Italy’s famed countryside. The experience includes flexible free time, scenic drives, and a chance to sample exquisite local wines on a family farm.

One of the standout features we love is the personalized touch that a private tour provides — especially the opportunity to explore at your own pace in Pisa and Florence, and to enjoy a relaxed, intimate wine tasting in Chianti. The comfort of air-conditioned transport and the convenience of WiFi onboard make the long day feel seamless.

A potential consideration is the price point — at $842.70 for up to three people, it’s a more premium experience, but given the exclusivity and tailored itinerary, many find it well worth the investment. This tour suits those who value comfort, flexibility, and authentic Tuscan experiences, especially travelers arriving from Livorno’s cruise port who want to see the highlights without the stress of overcrowded group tours.

Key Points

Personalized Experience: Private transport and custom free time in Pisa and Florence give you control over your sightseeing pace.
Efficient Itinerary: Covers Pisa, Florence, and Chianti in one day, saving time while allowing a broad taste of Tuscany’s highlights.
Authentic Tuscany: The stop at a family farm for wine tasting offers genuine local flavors and insights into traditional wine-making.
Comfort and Convenience: Air-conditioned vehicle, WiFi onboard, and a driver dedicated to your group ensure a smooth, comfortable day.
Price and Value: Although on the higher side, the experience’s exclusivity, flexibility, and included stops make it appealing for discerning travelers.
Positive Reviews: Guests praise the knowledgeable guides and excellent wine selection, emphasizing the personal attention and authentic experiences.

A Closer Look at the Pisa, Florence & Chianti Tour

Overall Experience

This tour is designed with travelers who want an efficient, enjoyable way to see some of Tuscany’s most renowned sites without the hassles of navigating public transit or crowded group tours. It’s a privately booked experience, meaning you get the driver’s full attention and the chance to customize your pace at each stop — something many travelers find makes a big difference in overall satisfaction.

The consistent five-star ratings reflect the quality of the guides, the smoothness of the logistics, and the memorable personal touches. Our sources mention guides like Mateo and Diego Amadori, who are praised for their local knowledge and friendly demeanor. The reviews highlight that guests felt well cared for and appreciated the excellent wine tasting, which is a notable part of this experience.

The Itinerary Breakdown

Stop 1: Piazza dei Miracoli (Pisa)

Starting at Pisa’s famous Leaning Tower, you’ll have about an hour to snap photos, soak in the atmosphere, and appreciate the surrounding UNESCO World Heritage site. While entrance fees are not included, the free view of the square offers enough time to marvel at the architecture and capture those quintessential shots.

Many reviewers mention the advantage of skipping lines through private arrangements, allowing for more time to enjoy the iconic sight. Barb_R expressed her family’s love for the tour, particularly noting guide Mateo’s attentiveness, which enhances the experience.

Stop 2: Piazza dei Cavalieri

A quick 10-minute stop at this historic square brings a glimpse into Pisa’s academic roots. Known for housing the Scuola Normale di Pisa, it’s a quieter but meaningful site to appreciate how Pisa’s intellectual history intertwines with its architectural charms. The brief visit allows you to stretch your legs and appreciate the town’s scholarly past.

Stop 3: Centro Storico of Florence

The largest portion of the tour is spent in Florence’s city center, a UNESCO-listed area packed with Renaissance gems like the Cathedral, Palazzo Vecchio, and bustling streets filled with shops and cafes. You’ll have roughly two hours to explore independently, giving you enough time to soak in the art, browse local boutiques, or enjoy a leisurely meal.

Guests have appreciated the flexibility here, with Melisa_M noting that guide Diego knew exactly where to take them for authentic experiences. The walkable, pedestrian-friendly area makes it easy to soak up Florence’s vibrant atmosphere at your own pace.

Stop 4: Chianti Wine Tasting

The day wraps up with a scenic drive through the Tuscan hills, culminating at a family-run farm on the border of Chianti Classico and Chianti Colli Fiorentini. Here, you’ll indulge in a wine tasting and tour, discovering the local varieties and learning about traditional wine-making methods.

Guests consistently praise the quality of the wines and the friendliness of the hosts, who treat visitors like family. This stop offers a genuine taste of Tuscan rural life, not just a commercial tasting. The hour-long experience also provides beautiful views of rolling vineyards and countryside.

Transportation & Timing

Travel is in a private, air-conditioned minivan, which is a significant advantage over cramped group buses. The driver is also your guide, with WiFi onboard, making the long drives more pleasant and connected. Starting early at 8:00 am, the schedule allows for full exploration and a relaxed return to Livorno, ensuring you maximize your day off the ship.

Pricing & Value

At $842.70 per group, up to three people, the cost reflects the private, customized nature of the tour. When you consider the convenience, personal attention, and the variety of experiences packed in, many travelers see it as a worthwhile splurge. It’s particularly appealing for those who prefer a flexible itinerary and want to avoid crowded tours or public transport.

Authenticity & Review Insights

The glowing reviews highlight how guides like Mateo and Diego add depth to the experience, sharing local stories and wine knowledge that go beyond standard tours. The wine tasting at the family farm is a standout — reviewers mention “the excellent wine selection” and the warm hospitality, making it a highlight of their day.

Guests also note that the tour offers a perfect balance between sightseeing, leisure, and culture. The flexibility to explore Pisa and Florence at your own pace, combined with the scenic countryside, makes for a very satisfying day.

Who Should Book This Tour?

This experience is best suited for travelers who value comfort, flexibility, and authentic experiences. It’s ideal if you’re arriving via cruise in Livorno and want to see Pisa and Florence without the hassle of coordinating schedules or transportation. The inclusion of a wine tasting at a family farm appeals to those keen on exploring local flavors in an intimate setting.

It’s also a good fit for couples or small groups seeking a personalized touch, as the private nature ensures you aren’t sharing the experience with strangers. If you’re after a well-balanced day that combines sightseeing, culture, and gourmet indulgence, this tour ticks all those boxes.

Final Thoughts

This Pisa, Florence, and Chianti wine tour offers a thoughtful blend of iconic sights, cultural insights, and authentic local experiences. The private setup means you can enjoy each stop at your own pace, while the scenic drives through Tuscany add to the overall charm. The opportunity to sample wines directly from a family farm, paired with the guided knowledge, elevates the experience beyond a simple sightseeing day.

While the price is on the higher end, the level of customization, comfort, and quality of stops make it a good investment for those seeking a curated Tuscan adventure. It’s especially recommended for travelers who want to avoid the crowds, enjoy personalized service, and truly savor the essence of Tuscany in one day.

FAQ

Is this tour suitable for all ages?
Yes, most travelers can participate as the tour is flexible and private, making it easy to customize for children or older guests.

What is included in the price?
The tour includes private transportation, an English-speaking driver, air conditioning, and WiFi onboard. However, museum entrance fees, the Leaning Tower ticket, and wine tastings are not included.

How long is the tour?
The entire experience lasts approximately 9 hours, starting at 8:00 am and ending back at Livorno.

Can I customize the stops or timing?
Since it’s a private tour, the itinerary is flexible. You can spend more or less time at each site, based on your preferences.

Do I need to book tickets in advance?
Admission to Pisa’s Piazza dei Miracoli and Florence’s city sights is not included, so you might find it easier to purchase tickets ahead or plan to enjoy the free areas. The Leaning Tower and Basilica of Santa Croce require separate tickets.

Is food included?
No, meals are not included. However, you’ll have plenty of opportunities to dine at your own pace in Florence or Pisa.

This tour combines the best of Tuscany’s highlights with a personal touch that many travelers cherish. Whether you’re a first-timer or returning lover of Italy, it’s a day designed to be memorable, comfortable, and full of authentic taste.