Pisa, Cinque Terre & Tuscany: A Two-Day Italian Journey
Coast, countryside, and medieval towers — Italy's finest highlights in two unforgettable days.
This 2-day combo tour from Florence brings together two of Italy's most celebrated regions, pairing the dramatic Ligurian coastline of Cinque Terre and the iconic Leaning Tower of Pisa with the vine-covered hills, wine estates, and medieval towers of Tuscany. All logistics are handled so you can focus entirely on the experience.
On the first day, you travel by train from Florence to Pisa, spend free time at the Piazza dei Miracoli, then continue to the colorful cliffside villages of Cinque Terre, exploring Riomaggiore, Vernazza, and Manarola at your own pace. The second day shifts inland to Tuscany, visiting two family-run wineries near San Gimignano before wandering the cobblestone streets of the medieval town itself.
Expert tour leaders guide each day, comfortable train travel connects every destination, and curated stops ensure you experience authentic local culture rather than surface-level sightseeing. This itinerary suits travelers who want to cover significant ground without sacrificing depth or comfort.
Tour Highlights
Stand before the Leaning Tower of Pisa at the Piazza dei Miracoli, one of Italy's most recognized architectural landmarks.
Explore three of the five Cinque Terre villages — Riomaggiore, Vernazza, and Manarola — set along a rugged stretch of the Ligurian coastline.
Taste Chianti, Super Tuscans, Vernaccia di San Gimignano, and a Rosé at two family-run Tuscan wine estates, each with its own character.
Discover the medieval skyline of San Gimignano, the so-called Medieval Manhattan, with its ancient towers and Piazza del Duomo.
Travel entirely by train between destinations, a scenic and practical way to move through northern and central Italy.
Photograph Manarola's cascade of colorful houses above the Ligurian Sea, one of the most iconic images in all of Italy.
Enjoy sweeping views of the Tuscan landscape from vineyard estates located just a short drive from San Gimignano.
Itinerary Overview
The group meets at Santa Maria Novella train station and boards a train to Pisa. On arrival, the tour leader walks the group to the Piazza dei Miracoli, where free time allows for independent exploration of the Leaning Tower, the Baptistery, and the Duomo. Entry to individual monuments is at your own expense.
After Pisa, the group travels by train to La Spezia, the gateway to the Cinque Terre National Park, where local regional trains connect the five villages. Riomaggiore (subject to seasonal availability), Vernazza, and Manarola each offer an hour of free exploration, from swimming and dining to photography and wandering narrow alleyways.
The group takes the train back from Manarola or La Spezia to Florence, concluding the first day after approximately two and a half hours of travel. Rest, chat with fellow travelers, or simply enjoy the passing scenery on the return journey.
Meeting in Piazza della Calza near Porta Romana, the group departs for the first winery in Ulignano, a family estate offering guided tastings of Chianti, Super Tuscans, and Vernaccia di San Gimignano paired with local food. The second winery, just five kilometers from San Gimignano, adds Chianti Colli Senesi and a Rosé to the tasting experience, along with panoramic Tuscan views.
Free time in San Gimignano allows visitors to explore the Piazza del Duomo, browse artisan shops, and sample local saffron specialties. The Torre Grossa offers panoramic views across the Tuscan hills for those wishing to climb. The group returns to Florence by late afternoon.
What Is Included
Included
- Professional English-speaking tour leader on both days
- Train tickets from Florence to Pisa (Day 1)
- Local regional train passes within Cinque Terre National Park (Day 1)
- Train return from Cinque Terre to Florence (Day 1)
- Private transportation to wineries and San Gimignano (Day 2)
- Guided wine tasting at two Tuscan wineries with food pairings (Day 2)
Not Included
- Entry tickets to the Leaning Tower of Pisa, Duomo, or Baptistery
- Personal meals and beverages beyond included wine tastings
- Travel insurance
- Gratuities for tour leaders
- Any optional activities not listed in the itinerary
Important Information
Ready to Experience the Best of Italy?
Two days, two iconic regions, and a lifetime of memories — this combo tour from Florence is one of the most complete ways to discover the Italian coast and countryside without the planning stress.
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