Self-Launched Tuscany: Chianti Walks & Wine Tastings
8 days · Tuscany, Italy
Exodus charges £2,620
No-markup version: ~£555 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Experience the very best of Tuscany independently — rolling vineyards, medieval hilltop towns, Renaissance cities and world-class Chianti wines — all without the guided group price tag. This self-launched version of Exodus's popular Tuscany Walks & Chianti Wines tour follows the same route through Pancole, San Gimignano, Castellina in Chianti, Siena and Florence, using local trains, public buses and self-booked wine tastings. Staying in a guesthouse or agriturismo near San Gimignano keeps you rooted in the Tuscan countryside, while free-booking platforms like GetYourGuide give you access to the same quality walking tours and tastings at a fraction of the cost. All cost estimates are approximate and per person.
Day-by-day
Arrive in Pancole / San Gimignano
Pancole, Tuscany
Make your way to the San Gimignano area. The easiest route from Florence is by SITA bus from Florence's Santa Maria Novella bus station to Poggibonsi, then a connecting bus to San Gimignano (total ~1.5 hrs, ~£6 return). Alternatively, take the train from Florence to Certaldo (~45 mins, ~£5) and a taxi or local bus to your accommodation. Check into a budget-friendly agriturismo or guesthouse near Pancole or San Gimignano — options include Agriturismo Ponte a Nappo or similar farmhouse B&Bs from around £40–55pp/night sharing. Settle in, grab a local Vernaccia di San Gimignano at a nearby enoteca, and plan your week ahead.
🚌SITA bus from Florence to San Gimignano via Poggibonsi (~£6), or Trenitalia train Florence–Certaldo (~£5) plus local taxi
🛏Agriturismo or guesthouse near Pancole/San Gimignano (e.g. Agriturismo Ponte a Nappo or similar), ~£45–55pp sharing
- →Travel to San Gimignano area via Florence by SITA bus or train+taxi (~£6–10)
- →Check into agriturismo or guesthouse near Pancole
- →Evening stroll into San Gimignano to explore the medieval towers and grab dinner at a local trattoria
Via Francigena Walk: Gambassi Terme to San Gimignano + Wine Tasting
Via Francigena, Tuscany
Walk the same classic stretch of the Via Francigena that the Exodus tour uses — the 9km section linking Gambassi Terme to San Gimignano. Take the local bus from San Gimignano to Gambassi Terme (check Tiemme bus timetables, ~£3), then walk through olive groves and vineyards back towards San Gimignano. The route is well waymarked with VF pilgrim signage and downloadable on Komoot or Wikiloc for free. In the afternoon, book a wine tasting at a local farmhouse winery — Azienda Agricola Pietralta (featured in the Exodus itinerary) can be booked directly. Alternatively, Fattoria Poggio Alloro and similar estates offer tastings with cheese pairings from around £20–28pp.
🚌Local Tiemme bus San Gimignano–Gambassi Terme (~£3), walk back 9km
🛏Agriturismo/guesthouse near Pancole/San Gimignano
- →Walk the Via Francigena: Gambassi Terme to San Gimignano (9km) — download route on Komoot for free
- →Bus to Gambassi Terme to start the walk (~£3 each way, Tiemme bus)
- →Afternoon wine tasting with cheese pairing at a local farmhouse winery (~£22–28pp, book direct or via GetYourGuide)
Hike from Fonterutoli to Castellina in Chianti
Chianti, Tuscany
Today's hike mirrors the Exodus route: start at Fonterutoli and walk the 8km trail through rolling vineyards and olive groves to the medieval hilltop town of Castellina in Chianti. Getting to Fonterutoli independently: take a taxi from your accommodation or arrange a pick-up (~£20–25 shared), or rent a car for the day (~£35pp if splitting). The walk follows part of the historic Via Romea and passes near Etruscan necropolis remains. Once in Castellina, explore the wine cellars built into the medieval walls (Enoteca Le Volte is free to browse), grab lunch at a local osteria, then take the afternoon bus or taxi back to your base. Download the GPX track from Wikiloc before you go.
🚌Taxi/rideshare to Fonterutoli (~£20–25 split), local bus or taxi back from Castellina
🛏Agriturismo/guesthouse near Pancole/San Gimignano
- →Hike Fonterutoli to Castellina in Chianti (8km) via the Via Romea — track downloadable on Wikiloc
- →Explore Castellina in Chianti's medieval streets and underground wine cellars
- →Lunch at a local osteria in Castellina (~£12–15)
- →Return by local bus or taxi to base
Siena City Tour + Tuscan Wine Lecture
Siena, Tuscany
Head to Certaldo station (local bus or taxi ~£8) and catch the train to Siena (~45 mins, ~£8 each way on Trenitalia). In Siena, book a self-launched walking tour through GetYourGuide or Airbnb Experiences — local guides offer 2–3 hour city tours for around £20–30pp, covering the Piazza del Campo, the cathedral and contrada history. The Museo delle Contrade (Contrada Oca, etc.) can be visited independently; entrance is typically €5–8. For the wine education experience, look for Enoteca Italiana in the Fortezza Medicea, which runs wine tastings and talks from around £18–25pp. Return by train to Certaldo in the evening.
🚌Local bus/taxi to Certaldo station (~£8), Trenitalia Certaldo–Siena return (~£16)
🛏Agriturismo/guesthouse near Pancole/San Gimignano
- →Train Certaldo to Siena (~45 mins, ~£8 each way on Trenitalia)
- →Self-booked walking tour of Siena with a local guide via GetYourGuide (~£22–28pp)
- →Visit a contrada museum independently (~£5–8 entrance)
- →Wine tasting or educational experience at Enoteca Italiana in the Fortezza Medicea (~£20pp)
- →Dinner in Siena before returning by train
Free Day: Chianti Villages, Cooking Class or Pool
Pancole / Chianti, Tuscany
A free day to recharge or explore at your own pace — exactly as the Exodus tour offers. Options include: renting an e-bike from San Gimignano (several hire shops from ~£25/day) and cycling between nearby Chianti villages; booking a Tuscan cooking class (available via GetYourGuide from ~£55–70pp, typically including a market visit, cooking session and lunch); or arranging a self-guided wine tasting at a different estate. Alternatively, relax at your agriturismo if it has a pool. Your host will be a great source of local recommendations.
🚌E-bike hire or on foot — no transport needed
🛏Agriturismo/guesthouse near Pancole/San Gimignano
- →Option A: E-bike hire and self-launched Chianti village cycling (~£25–30/day rental)
- →Option B: Tuscan cooking class via GetYourGuide (~£55–70pp, includes lunch)
- →Option C: Relax at agriturismo pool and explore local wines at leisure
- →Option D: Self-guided walk to nearby villages using Komoot or AllTrails routes
Florence: Renaissance Art & Walking Tour
Florence, Tuscany
Travel to Florence from Certaldo by Trenitalia train (~45–60 mins, ~£7 each way). Florence is one of the world's great art cities — book a self-launched walking tour via GetYourGuide or Airbnb Experiences (2–3 hrs, ~£18–25pp) covering the Duomo, Piazza della Signoria, Ponte Vecchio and beyond. For the Uffizi Gallery, pre-book tickets online at uffizi.it to skip the queues (~£22 entrance). If you'd rather self-explore, the streets themselves are free and extraordinary. Grab lunch at Mercato Centrale (~£8–12) for an authentic, affordable Florentine spread. Return by train to Certaldo in the evening.
🚌Local bus/taxi to Certaldo station, Trenitalia Certaldo–Florence return (~£14)
🛏Agriturismo/guesthouse near Pancole/San Gimignano
- →Train Certaldo to Florence (~45–60 mins, ~£7 each way on Trenitalia)
- →Self-booked Florence walking tour via GetYourGuide (~£20–25pp)
- →Uffizi Gallery entry — pre-book at uffizi.it/en/tickets (~£22)
- →Lunch at Mercato Centrale (~£8–12)
- →Explore Ponte Vecchio, Piazza della Repubblica and Oltrarno neighbourhood independently
San Gimignano Explore + Farewell Wine Tasting at Cesani Estate
San Gimignano, Tuscany
Today focuses on beautiful San Gimignano itself — a short bus ride or walk from your base. Visit the Palazzo Comunale and climb the Torre Grossa (54m, ~£8 entrance, purchase at the door) for panoramic views across Tuscany. Wander the medieval streets and piazzas freely. In the afternoon, book a tasting at the Cesani estate (mentioned in the Exodus itinerary) — Vincenzo Cesani's family winery produces excellent Vernaccia and Chianti, and tastings with bruschetta and local charcuterie can be booked directly via their website or through GetYourGuide from around £22–28pp. A perfect farewell evening to this unforgettable region.
🚌Short bus or walk into San Gimignano from accommodation
🛏Agriturismo/guesthouse near Pancole/San Gimignano
- →Visit Palazzo Comunale and climb Torre Grossa for panoramic views (~£8 entrance)
- →Free time to explore San Gimignano's medieval lanes and artisan shops
- →Afternoon wine tasting at Cesani Estate with bruschetta and Tuscan charcuterie (~£22–28pp, book direct at cesani.it or via GetYourGuide)
- →Farewell dinner at a local trattoria in San Gimignano (~£18–22)
Departure from Pancole
Pancole / Florence or Pisa, Tuscany
Check out from your agriturismo and make your way to your onward destination. For Florence airport (Peretola), take a taxi to Certaldo then train to Florence Santa Maria Novella, then the Volainbus or tram to the airport (~1.5–2 hrs total). For Pisa airport, take the train from Empoli (connect from Certaldo) to Pisa Centrale, then the dedicated Pisa Mover train to the airport (~2 hrs total). Consider booking a final night in Florence or Pisa if your flight is early.
🚌Taxi to Certaldo station, then Trenitalia to Florence (~£7) or Pisa (~£10) for onward connections
🛏None (departure day)
- →Check out and pack up
- →Travel to Florence or Pisa airport via local train connections
- →Optional: final espresso and cornetto at a local bar before departure
Self-launched vs. Exodus
| This itinerary (self-launched) | Exodus | |
|---|---|---|
| Price per person | ~£555 | £2,620 |
| Duration | 8 days | 8 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £2,065 per person (79%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more Exodus-style trips? Check them out here.~£555
estimated per person
You never pay Travel Crew for this — you pay hostels, transport, and activity providers directly, the same as if you'd booked it all yourself.
This publishes your dates so other travellers can find and join you — no tour operator needed.
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Frequently asked questions
How much does Self-Launched Tuscany: Chianti Walks & Wine Tastings cost?+
Doing it yourself with this self-launched itinerary costs an estimated £555 per person for 8 days in Tuscany, Italy. This is an AI-generated estimate based on typical budget-traveller prices — actual costs will vary by season and how you book.
Is this cheaper than booking with Exodus?+
Yes — Exodus charges around £2,620 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £555 — a saving of roughly £2,065 (79%) per person.
How long is the Tuscany, Italy trip?+
This itinerary runs 8 days, covering 8 day-by-day stops through Tuscany, Italy.
How do I join this trip?+
You can join an existing open departure using this itinerary if one is scheduled, or launch your own departure with your own dates and invite other travellers to join you — no tour operator required.
Isn't it easier to just use a tour operator?+
Well, yes, a tour operator will book all the individual parts of your travel for you and provide a guide. That's obvious, but doing this has the potential to save the group thousands, which can in turn improve your itinerary substantially or save you huge amounts of money. Also, when you launch a departure, Travel Crew has tools in place to help you book the individual sections of the trip or make it easier for you to do this as a group. Really, you do not need a middle man. If you are more comfortable paying more and using a middle man, then you should certainly do this.
Is it safer to book through a tour operator?+
Arguably, there isn't much difference. A self-launched trip runs on the same principle as a group travel crew: collective responsibility, everyone looking out for each other, the same way it would if a group of friends organised the trip themselves — because that's exactly what's happening. You should always take out travel insurance before you go, self-launched or not; that doesn't change either way. Every open departure is published publicly with real dates and a real trip organiser, so it's never an anonymous arrangement, and our support team is reachable any time you need help, including in an emergency while you're away. Longer-term, we're building direct relationships with ground DMCs in popular destinations, offered as an optional paid add-on for extra on-the-ground support. Ultimately, though, the group is responsible for its own conduct and safety on a self-launched trip, same as on any trip you plan yourself.
What kind of trip is this?+
This is a hiking, culture, foodie trip through Tuscany, Italy, self-launched rather than run by a tour operator — you organise it with a group you find or bring yourself.
Would you like to name the operator, name the trip, or have any suggestions about how to improve this itinerary?
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