Medieval Villages & Chianti Day Trip from Florence | Tuscany4.8(3,003 Reviews)10 hours and 30 minutes
From€250.00per person
Listing ID : 63800
4.8(3,003 Reviews)
Medieval Villages & Chianti Day Trip from Florence | Tuscany
10h 30mDuration
Max 12 peopleGroup Size
EnglishSpeaking Guide
Mobile ticketAccepted
About this experience
Duration10 hours 30 minutes
Group SizeSmall Group
Starts AtFlorence City Center
LanguagesEnglish
Small-Group Day Tour from Florence
Medieval Tuscany & Wine Experience: Certaldo, San Gimignano & Volterra
Three medieval villages, one family winery, and the timeless landscapes of Tuscany in a single unforgettable day.
This Tuscany medieval villages day tour from Florence takes you through three of central Italy's most historically layered hilltop towns, combining Etruscan archaeology, UNESCO-listed towers, and a guided wine tasting at a local family-run winery.
The route passes through the rolling scenery of Chianti and Val d'Elsa before reaching Certaldo Alto, a terracotta-hued hilltop settlement that remains largely off the radar of mass tourism. From there, the itinerary moves to San Gimignano and its famous medieval skyline, then closes in Volterra, where Etruscan walls and alabaster ateliers share the same narrow streets.
A traditional Tuscan lunch at a working vineyard anchors the day, offering five wines paired with regional produce. The pace is relaxed, the group is small, and the guide is English-speaking throughout.
Tour Highlights
Walk the tower-lined streets of San Gimignano, a UNESCO World Heritage Site known as the Manhattan of the Middle Ages.
Explore Volterra's Roman Theatre, Etruscan ruins, and centuries-old alabaster workshops in one of Tuscany's most layered towns.
Stroll the cobbled lanes of Certaldo Alto, the serene hilltop birthplace of medieval writer Giovanni Boccaccio.
Taste five local wines including Vernaccia di San Gimignano, Chianti, and Super Tuscan varieties at a family-run winery.
Enjoy a traditional light lunch paired with bruschetta, pecorino cheese, cured meats, and homemade pasta or fresh salads.
Travel through the scenic Chianti hills and Val d'Elsa valley in a comfortable air-conditioned minivan with panoramic views.
Benefit from the expertise of a dedicated English-speaking guide who brings the region's medieval history to life throughout the day.
Itinerary Overview
1
Departure from Florence
Meet your guide in the heart of Florence and board a comfortable air-conditioned minivan. The drive west reveals the quintessential Tuscan countryside of Chianti and Val d'Elsa, with vineyard-covered slopes and hilltop villages appearing at every turn.
2
Certaldo Alto
Arrive at this perfectly preserved medieval hilltop village, birthplace of the celebrated writer Giovanni Boccaccio. Wander terracotta-coloured streets lined with artisan shops and take in sweeping views of the surrounding Tuscan countryside largely untouched by mass tourism.
3
San Gimignano
Explore the iconic stone towers and medieval squares of this UNESCO World Heritage Site. Your guide shares stories of the merchants and rival families who shaped this extraordinary town, and there is time to browse local shops or sample the award-winning gelato at Dondoli Gelateria.
4
Winery Lunch & Wine Tasting
Settle into a family-run winery surrounded by vineyards and olive groves for a guided tasting of five wines, including Vernaccia di San Gimignano and Chianti. The tasting is accompanied by a traditional light lunch of bruschetta, pecorino, artisanal cured meats, and homemade pasta or fresh salads.
5
Volterra
Conclude the day in Volterra, where Etruscan walls, a well-preserved Roman Theatre, and a medieval fortress occupy the same hilltop. The town is equally known for its alabaster artisans, and the valley views from the upper streets provide a memorable close to the day.
6
Return to Florence
Board the minivan for a relaxed journey back to the city. Drop-off is in the Florence city center, typically by evening.
What Is Included
Included
Professional English-speaking guide for the full day
Air-conditioned minivan transport throughout
Guided tour of Certaldo Alto, San Gimignano, and Volterra
Guided tasting of 5 local wines at a family-run winery
Traditional Tuscan light lunch at the winery
Small-group experience
Not Included
Hotel pickup and drop-off
Entrance fees to museums or monuments
Gratuities for the guide (optional)
Personal expenses and additional food or drinks
Travel insurance
Important Information
Please read the details below carefully before booking. This tour involves walking on uneven cobbled surfaces typical of Tuscan hilltop towns.
Duration
Approximately 10 hours and 30 minutes. The exact end time may vary slightly depending on traffic and group pace.
Meeting Point
The tour departs from Florence city center. Exact meeting point coordinates are provided upon booking confirmation.
What to Bring
Comfortable walking shoes are strongly recommended, as all three towns feature cobblestone streets and inclines. Bring sunscreen, a light jacket, and a bottle of water for the journey.
Cancellation
Cancellation policies are stated at the time of booking. It is recommended to review the terms before confirming your reservation.
Accessibility
This tour is rated Easy, but the medieval villages involve uneven cobbled streets and some slopes. The tour is not suitable for wheelchair users without prior arrangement.
Age Range
This tour is suitable for all ages. Guests who intend to participate in the wine tasting must be of legal drinking age in Italy (18 years or older).
Book Your Spot Today
Places on this small-group tour fill quickly, particularly during spring and summer. Secure your seat to explore three of Tuscany's finest medieval villages alongside a knowledgeable local guide and a memorable winery lunch.
Yes. A guided tasting of five local wines, paired with a traditional Tuscan light lunch, is included as part of the tour itinerary at the family-run winery.
How many people are in the group?▼
This is a small-group tour. The exact maximum group size is confirmed at the time of booking, but the format is designed to provide a more personal experience than a large coach tour.
Is hotel pickup included?▼
Hotel pickup is not included. Guests meet the guide at a designated point in Florence city center, with the exact location provided in the booking confirmation.
Are entrance fees to monuments covered?▼
Entrance fees to museums and monuments in Certaldo, San Gimignano, and Volterra are not included. Your guide can advise on which sites are worth visiting and their current admission costs.
Is this tour suitable for people with mobility limitations?▼
The tour is rated Easy in terms of overall pace, but all three villages feature cobblestone streets and hilly terrain. Guests with significant mobility limitations are advised to contact the operator before booking.
What languages does the guide speak?▼
The tour is led by an English-speaking guide. Available languages are confirmed at the time of booking and depend on the specific departure selected.
Tuscany Day TourSan GimignanoVolterraCertaldoWine Tasting TuscanyMedieval Villages ItalyFlorence Day TripChianti Wine TourUNESCO World HeritageEtruscan TuscanySmall Group Tour ItalyTuscan Countryside
This tour operates from Florence, the capital of the Tuscany region in central Italy, and visits three distinct municipalities: Certaldo (province of Florence, Val d'Elsa valley), San Gimignano (province of Siena, a UNESCO World Heritage Site at approximately 56 km southwest of Florence), and Volterra (province of Pisa, approximately 76 km southwest of Florence). The route traverses the Chianti wine country and the Val d'Elsa corridor, two of Tuscany's most recognized scenic and viticultural zones. The winery stop takes place within the San Gimignano appellation, home to the Vernaccia di San Gimignano DOCG, Italy's first designated white wine appellation. Volterra sits on a high plateau at approximately 545 meters elevation and is one of the twelve Etruscan city-states, featuring some of the best-preserved Etruscan and Roman-era monuments in the region.
Region: Tuscany, Italy | Departure City: Florence | Key Destinations: Certaldo Alto, San Gimignano (UNESCO), Volterra | Tour Type: Small-Group Cultural and Wine Day Tour | Difficulty: Easy | Duration: 10h 30min | Themes: Medieval History, Etruscan Heritage, Tuscan Wine, Gastronomy, UNESCO Sites
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