Your itinerary
Day 1
Adventure starts in Pancole
Start at Hotel Le Renaie, our welcoming family-run hotel 4mi (6.5km) from San Gimignano.
Around 6pm, say ciao to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome over a group dinner.
If you have extra days at hand and wish to extend your adventure, consider booking additional nights in Pisa or Florence. Speak to your sales representative for more information.
Meals: Dinner
Day 2
Walk a section of the Via Francigena • Afternoon local wine tasting
Get ready for a day full of history and nature as we explore one of the most popular sections of the Via Francigena, which links the villages of Gambassi Terme to San Gimignano. The Via Francigena is an ancient pilgrimage route that links Canterbury in the UK to Rome; the full trip takes well over 90 days, but our section is far gentler, cutting through olive groves and vineyards.
Later in the afternoon, we head to Azienda Agricola Pietralta, a picturesque farmhouse in the heart of the countryside, where we enjoy three glasses of wine and a trio of cheeses.
Dinner this evening is back at the hotel, where we have time to relax, perhaps with a game of billiards or another glass of local wine on the garden-view terrace.
Meals: Breakfast,Dinner
Day 3
Hike from Fonterutoli • To the hilltop town of Castellina in Chianti
Start our scenic walk from Fonterutoli, surrounded by the rolling hills, vineyards and olive groves of the Chianti region. At the beginning, we enjoy beautiful views towards Siena before following part of the historic Via Romea, an ancient pilgrimage route to Rome.
Along the way, we may pass near the remains of an Etruscan necropolis, offering a fascinating glimpse into the ancient past of the area.
Finishing the hike, we transfer to Castellina in Chianti, a charming hilltop town known for its medieval atmosphere, stone streets and strong connection to the Chianti wine tradition.
Meals: Breakfast
Day 4
Explore Siena • Learn about Tuscan and Italian wines in Palazzo delle Papesse
Head to Certaldo station and catch a train to Siena (approximately 45 minutes). This medieval city is dominated by impressive gothic monuments and is divided into 17 contrade (districts), each of which goes head-to-head in the twice-annual Palio, a thunderous horse race around the central square for which the whole city turns out.
Our tour includes a visit to a contrada museum, which is typically closed to the public. You may also opt to visit the medieval Siena Cathedral. After we join a local guide on a tailor-made tour of the city, stopping at the landmarks, plus captivating sites most tourists normally pass by.
In the afternoon, learn about Tuscan wines during a one-hour lecture in the courtyard of Palazzo delle Papesse. Unlike traditional wine tastings, this expert-led experience is more educational, offering in-depth insights into Tuscany’s most important wines.
Meals: Breakfast,Dinner
Day 5
Free day to visit other Chianti villages or relax by the pool
Today is free to rest by the poolside (seasonal opening periods apply). Alternatively, your tour leader can advise on local chianti wine-tasting tours, cooking classes, e-bike hire or offer assistance for unguided walks or daytrips.
Meals: Breakfast
Day 6
Discover the magnificent city of Florence
Our destination today is Florence, the birthplace of the Italian Renaissance. We reach Florence from Certaldo by train, approximately a one-hour journey. Most of the greats from the movement lived or passed through here: Leonardo da Vinci, Michelangelo, Sandro Botticelli and more.
Your leader will walk with you into the city centre and help you get your bearings before you set off to explore independently. Guided tours in Florence must be led by a locally registered city guide, but there are several excellent walking tours available if you’d like to discover the city on foot. Your tour leader can help you organise this.
If you’re planning to visit the Uffizi Gallery, housing works by Renaissance masters, including The Birth of Venus by Botticelli and the striking Medusa by Caravaggio, we recommend booking well in advance as tickets can sell out. Tickets can be purchased at www.uffizi.it/en/tickets.
We normally arrive in central Florence at around 10am, so we recommend booking any activities from 11am onwards, giving you plenty of time to reach the meeting point or venue. With so much to see, we suggest choosing just one activity and leaving plenty of time to explore independently. Train times can vary, but we typically leave the city centre between 4pm and 4.30pm.
Meals: Breakfast,Dinner
Day 7
Hike to San Gimignano • Afternoon wine-tasting
Transfer to the hamlet of San Donato. Here, we should have time for a wine tasting before embarking on a scenic hike (6mi/10km) to San Gimignano. Our route passes through vineyards and offers glorious views of San Gimignano.
Arriving, we have free time to explore this medieval town, perhaps with a visit to the Palazzo Comunale, a 13th-century stone palace that’s home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa (you can purchase the entrance ticket locally).
Before your farewell dinner, we visit the family-run Cesani estate, which produces some of the finest wines in the region. Here, we enjoy an expertly led tasting, sampling three glasses accompanied by bruschetta, extra-virgin olive oil and a selection of Tuscan cheeses and charcuterie.
Meals: Breakfast,Dinner
Day 8
Adventure ends in Pancole
You’ve walked some of the most scenic trails in Tuscany and explored the local wine scene, but now it’s time to bid Hotel Le Renaie a fond farewell and begin your return journey home.
Alternatively, speak to your sales representative to extend your adventure and spend more time exploring the Renaissance flair of Florence.
Meals: Breakfast
What’s included
What’s not included
Additional information
Food
Breakfast is usually a continental-style buffet. The five included dinners are taken at Hotel Le Renaie. Four meals consist of three courses, dessert and a glass of wine. On Tuesday evening, when the restaurant is closed to the public, you will be treated to a special pizza feast.
All meals are homemade and prepared using locally sourced ingredients and following traditional Tuscan recipes. For this reason, the menu doesn’t include fish-based options.
Vegetarian, vegan, gluten-free and dairy-free choices are available – please advise us of dietary requirements on booking.
Tuscan Welcome Dinner at Hotel Le Renaie
Settle into village life at a convivial evening where you meet your Tour Director and fellow travelers over dinner at the family-run Hotel Le Renaie. Expect warm hospitality from the Sabatini family and a relaxed, friendly atmosphere.
Savor homemade Tuscan recipes—rustic pastas, fragrant herbs and local olive oil—paired with a glass of local wine. It’s a flavorsome welcome that introduces the rhythms and tastes of the surrounding hills.
Chianti Hills Hike: Fonterutoli to Castellina via the Via Romea
Set out to hike among rolling vineyards from Fonterutoli toward Castellina in Chianti, with open views toward Siena across quilted hills and silvery olive groves. Trails weave between low dry-stone walls and neat terraces alive with birds and wild herbs.
Trace the historic Via Romea, a medieval route once used by pilgrims and merchants. Along the way, pass near remains linked to the area’s Etruscan heritage before finishing in a hilltop town of stone streets and wine cellars.
Siena Guided City Walk & Contrada Museum
Explore Siena with a local expert as you join a guided city walk through narrow lanes, brick-red Gothic facades and the sweeping fan of Piazza del Campo. Hear how bankers, artists and saints shaped this Tuscan powerhouse.
Step inside a contrada museum—typically closed to casual visitors—to learn how neighborhoods prepare year-round for the thunder of the Palio horse race. Stories of rivalries, silk flags and solemn rituals illuminate Siena’s deep civic pride.
Tuscan Wine Masterclass at Palazzo delle Papesse
Deepen your palate in a focused seminar as you learn about Tuscan wines in the Renaissance courtyard of Palazzo delle Papesse. In this guided session, styles and regions are unpacked with clarity and verve.
An expert contrasts Chianti Classico and Super Tuscan expressions with whites like Vernaccia di San Gimignano, linking grape to landscape and producer. Expect an engaging, educational format spotlighting terroir and traditions rather than a formal tasting.
Florence Orientation Walk: Birthplace of the Renaissance
Arrive with confidence as you walk into the historic centre of Florence with your leader, passing the Cathedral of Santa Maria del Fiore (Duomo), Piazza della Signoria and the Ponte Vecchio. Landmarks come into focus so you can prioritize what matters most.
This orientation helps you get your bearings and plan independent time—where to find worthy gelato, art-filled churches and quieter viewpoints over the Arno. For in-depth guiding, licensed local guides are recommended and can be arranged.
San Donato to San Gimignano Vineyard Trail
Follow cypress-fringed tracks on a countryside ramble to walk to San Gimignano, crossing vineyard-carpeted hills and pockets of oak woodland alive with birdsong. Farm lanes and ridge paths reveal working estates and kitchen gardens.
As the route undulates, the skyline of medieval towers draws closer, recalling a merchant town enriched by wool, saffron and pilgrim traffic. Arrive ready to wander stone alleys, artisan workshops and sunlit squares between crenellated walls.
Cesani Family Estate Wine Tasting with Tuscan Bites
Visit the family-run Cesani estate for an afternoon of local flavors. You’ll sample regional wines alongside bruschetta drizzled with extra-virgin olive oil, poured in a welcoming tasting room surrounded by vines.
Learn how the family crafts crisp Vernaccia di San Gimignano and expressive Sangiovese-based reds, pairing sips with Tuscan cheeses and charcuterie. Vineyard views and friendly hosts make this a relaxed, palate-pleasing stop.
Uffizi Gallery Timed Entry (Florence)
Enter the heart of Renaissance art with timed tickets to the Uffizi Gallery, home to Botticelli’s The Birth of Venus, masterpieces by Leonardo and Michelangelo, and Caravaggio’s Medusa. Rooms unfold chronologically, revealing how ideas and technique evolved in Florence.
This visit is at additional cost and bookable on tour (subject to availability). Early reservations are recommended in peak months; your Tour Leader can advise on time slots and logistics from the station to the gallery.
Florence Licensed Walking Tour
See Florence through a local expert’s eye as you join a guided walking tour led by a licensed city guide, weaving past the Duomo, Piazza della Signoria and the Baptistery’s famed Gates of Paradise. Stories of artists, guilds and Medici power bring facades to life.
At additional cost and bookable on tour, this compact introduction layers history and orientation so you can return with confidence to explore churches, galleries and cafés at your own pace.
Siena Cathedral Entry & Piccolomini Library
Siena Cathedral rewards a closer look: a Romanesque-Gothic landmark of striped marble, sculpted pulpits and the luminous Piccolomini Library with Pinturicchio frescoes. The interplay of light and stone amplifies Siena’s artistic ambition.
Admission is at additional cost and bookable on tour. At certain times of year, sections of the inlaid marble floor are on special display; your Tour Leader can advise on timings and queue-beating options where available.
San Gimignano Palazzo Comunale & Torre Grossa Ticket
Climb Torre Grossa, the tallest of San Gimignano’s towers, then explore frescoed halls of the Palazzo Comunale before stepping out for sweeping panoramic views over tiled roofs and patchwork fields.
Tickets are at additional cost and bookable on tour or locally. The medieval stairways are sturdy and well-kept; bring a camera for late-afternoon light across the Elsa Valley and distant Apennines.
Chianti E-Bike Adventure
Trade boots for wheels and e-bike through the Chianti hills, gliding along cypress-fringed lanes between vineyards, hamlets and wayside chapels, with optional pauses at village wineries for photos or tastings.
At additional cost and bookable on tour, this guided ride suits most fitness levels thanks to pedal-assist bikes. Routes and duration are tailored to weather and ability for a relaxed, scenic outing.
Tuscan Cooking Class at a Local Agriturismo
Roll up your sleeves to learn to make fresh pasta and seasonal sauces in a hands-on class at a country farmhouse, guided by nonna-style recipes passed down through generations. The setting is warm, informal and flour-dusted.
This experience is at additional cost and bookable on tour. After class, taste what you cook alongside regional wine while hearing stories about ingredients, harvests and Tuscan culinary traditions.
Via Francigena Walk: Gambassi Terme to San Gimignano
Walk a storied pilgrimage path as you walk a section of the Via Francigena from Gambassi Terme toward San Gimignano. Follow farm tracks through olive groves and vineyards, past stone farmhouses and cypress-lined lanes, with the town’s skyline on the horizon—ideal ground for steady, scenic hiking.
Your leader evokes the pilgrims’ route from Canterbury to Rome while you tread the soft strade bianche. Expect gentle gradients, birdsong and broad views; pause to photograph the soaring medieval towers of San Gimignano as they rise from the Tuscan hills.
Azienda Agricola Pietralta Wine Tasting & Local Cheeses
Taste Tuscan terroir at Azienda Agricola Pietralta, a countryside farmhouse tucked among oak woods and vines. In this convivial session you’ll sample regional wines paired with a trio of Tuscan cheeses, while taking in views of sunlit rows and stone barns.
Discuss grape varieties, cellar traditions and how soils shape flavor, from bright Chianti to supple IGT reds. Expect approachable, Sangiovese-led blends and insight into everyday winemaking life in rural Tuscany.