Self-Launched Renaissance Tuscany: Florence, Arezzo, Siena & Beyond
8 days · Tuscany, Italy
Exodus charges £7,400
No-markup version: ~£785 per person
Estimate only, not a guaranteed price. Always verify costs independently before booking.
This self-launched version of Exodus's premium Tuscany tour takes you through the same Renaissance cities, Chianti vineyards, truffle forests, and medieval hilltowns — without the premium price tag. You'll base yourself in the Arezzo/Gargonza area using a characterful agriturismo or budget guesthouse, travel by local bus and train, and book signature experiences (olive oil tastings, truffle hunts, Chianti winery visits, Florence Cathedral terraces) independently via GetYourGuide or direct booking. Meals are a mix of self-catering, local trattorias, and the occasional splurge. Estimated costs are approximate and based on 2024/25 backpacker and independent traveller rates.
Day-by-day
Arrive in Florence & transfer to your Arezzo base
Florence → Arezzo area
Fly into Florence (FLR) or Pisa (PSA) and take the Trenitalia regional train to Arezzo (~£8–12, 1–1.5 hrs from Florence, 1.5 hrs from Pisa). Check into your agriturismo or guesthouse in or near Arezzo. In the evening, settle in with a glass of local Chianti from a nearby enoteca and enjoy a simple dinner at a neighbourhood trattoria. Arezzo's medieval centre is walkable — take an evening stroll to the Piazza Grande to get your bearings.
🚌Trenitalia regional train: Florence SMN → Arezzo, approx. £8–12 one-way. Book at trenitalia.com or on the day at the station.
🛏Agriturismo or guesthouse near Arezzo — e.g. Agriturismo Torre Santa Flora or similar B&B in the Val di Chiana. Budget ~£35–55/night.
- →Trenitalia regional train from Florence SMN or Pisa Centrale to Arezzo (~£8–12)
- →Evening stroll around Arezzo's Piazza Grande and medieval lanes
- →Dinner at a local trattoria (expect to pay ~£12–18 for a pasta and glass of wine)
Olive oil tasting at a family estate & explore Arezzo
Arezzo & surroundings
In the morning, visit Buccia Nera or a similar family-run olive oil estate in the Arezzo hills — book a guided tasting directly via their website or through GetYourGuide (~£15–25pp). Enjoy a self-arranged lunch at Osteria Cuprena or a comparable farm-to-table trattoria using seasonal local produce. In the afternoon, wander Arezzo's historic centre: the Romanesque Pieve di Santa Maria, the Piazza Grande, and the lawns of Il Prato are all free to explore. Pick up pecorino and local charcuterie from the market for a light evening spread, or dine at a neighbourhood osteria.
🚌Local taxi or hired car/scooter to the estate (~£10–15 return). Alternatively, some estates offer shuttle pick-up — check when booking.
🛏Same agriturismo/guesthouse near Arezzo (~£35–55/night)
- →Guided olive oil tasting at Buccia Nera or similar estate (~£15–25pp, book direct or via GetYourGuide)
- →Lunch at Osteria Cuprena or local farm trattoria (~£14–20pp)
- →Free self-guided walk: Pieve di Santa Maria, Piazza Grande, Il Prato
- →Evening dinner at a local osteria (~£14–18pp)
Day trip to Florence: Cathedral terraces & Renaissance streets
Florence
Take an early Trenitalia train to Florence (~£8–12, 1–1.5 hrs). Book the Florence Cathedral complex ticket in advance — this includes access to Brunelleschi's Dome and, on some ticket tiers, the lesser-visited exterior terraces and roof walkways (~£20–25pp via the Opera del Duomo website or GetYourGuide). Spend the afternoon exploring the Renaissance core: the Uffizi Gallery (book online, ~£20–25pp), Piazza della Signoria, and the narrow streets of Oltrarno. For lunch, grab a schiacciata sandwich from a local forno (~£4–6) and eat with a view. In the early evening, enjoy aperitivo at a bar near Santa Croce before catching the train back to Arezzo.
🚌Trenitalia: Arezzo → Florence SMN (~£8–12 each way). Florence is walkable from the station.
🛏Same agriturismo/guesthouse near Arezzo (~£35–55/night)
- →Trenitalia train Arezzo → Florence SMN (~£8–12 return)
- →Florence Cathedral complex ticket including Dome climb and terraces (~£20–25pp, book at operaduomo.firenze.it)
- →Self-guided Renaissance walk: Piazza della Signoria, Palazzo Vecchio, Oltrarno
- →Optional: Uffizi Gallery (~£20–25pp, book online in advance)
- →Aperitivo at a bar near Santa Croce (~£8–10)
- →Schiacciata sandwich lunch from a local forno (~£4–6)
Your Signature Day: Chianti tasting, e-biking, or a cooking class
Chianti wine region / Arezzo area
Today is your free-choice day — pick the experience that calls to you most. Option 1: Join a half-day Chianti winery tour and tasting, bookable via GetYourGuide or Klook from Arezzo (~£35–55pp including transport). Option 2: Rent an e-bike locally (~£25–40/day) and cycle the quiet lanes around the Val di Chiana, stopping at an olive grove or a hilltop village café. Option 3: Book a hands-on Tuscan pasta-making cooking class in Arezzo or a nearby agriturismo (~£50–70pp including lunch, available on GetYourGuide). Option 4: Take a day trip to Cortona (~20 min by regional train, ~£4) and explore its Etruscan museum, medieval streets, and panoramic terraces. In the evening, dine at your accommodation or a local restaurant at leisure.
🚌Varies by option. Regional trains from Arezzo to Cortona-Camucia ~£4 return. Chianti tour transport usually included in tour price.
🛏Same agriturismo/guesthouse near Arezzo (~£35–55/night)
- →Option A: Chianti winery tour and tasting via GetYourGuide (~£35–55pp)
- →Option B: E-bike hire for a self-guided rural ride (~£25–40/day)
- →Option C: Tuscan pasta-making cooking class with lunch (~£50–70pp, book via GetYourGuide)
- →Option D: Day trip to Cortona by regional train (~£4 return) — Etruscan museum (~£8), free medieval streets
- →Relaxed dinner at leisure (~£15–20pp)
Truffle hunting & the Etruscan hilltop city of Volterra
Volterra & surroundings
Book a morning truffle hunting experience with a local family and their dog — these are widely available through GetYourGuide or direct operators in the San Miniato or Volterra area (~£50–75pp including a truffle-based lunch). In the afternoon, head to Volterra, one of Tuscany's most striking Etruscan hilltowns. The Roman Theatre (free to view from outside, or ~£5 to enter), medieval piazzas, alabaster workshops, and panoramic views over the Tuscan hills are all here. Watch a live alabaster carving demonstration at one of the artisan studios on Via dei Sarti (free to enter). Return to your base by early evening for a relaxed dinner.
🚌Volterra is best reached by car or a combination of bus from Pontedera or Colle Val d'Elsa (~£8–15 by bus/regional train + bus). Consider hiring a car for the day (~£30–45) for flexibility with the truffle hunt location.
🛏Same agriturismo/guesthouse near Arezzo (~£35–55/night)
- →Morning truffle hunt with a local family and their dog, including truffle lunch (~£50–75pp, book via GetYourGuide or direct)
- →Self-guided afternoon in Volterra: Roman Theatre (~£5), medieval piazzas, panoramic viewpoints
- →Free alabaster carving demonstration at a local artisan studio on Via dei Sarti
- →Return to Arezzo base for dinner (~£12–16pp at a local trattoria)
Farm visit at Podere Il Casale, Renaissance Pienza & Montepulciano
Pienza, Montepulciano & Val d'Orcia
Drive or take a morning bus towards Pienza in the stunning Val d'Orcia. First, visit Podere Il Casale, a working organic farm offering guided cheese and wine tastings — book direct on their website (~£20–30pp including tasting and farm tour). Enjoy a leisurely lunch at the farm or a nearby trattoria. In the afternoon, stroll through Pienza, the UNESCO-listed 'ideal Renaissance city': the Piazza Pio II, the Cathedral, and the view over the Val d'Orcia are unmissable and largely free. Continue to Montepulciano for a late afternoon walk through its steep historic lanes and end at a local cantina for a Vino Nobile tasting (~£10–15pp) paired with a light aperitivo board.
🚌Hire a car for the day (~£30–45) is recommended for this route as bus connections between these villages are limited. Alternatively, join a guided day tour from Arezzo or Siena via GetYourGuide (~£35–55pp including transport).
🛏Same agriturismo/guesthouse near Arezzo (~£35–55/night)
- →Guided farm tour, cheese-making demonstration and wine tasting at Podere Il Casale (~£20–30pp, book at poderilcasale.it)
- →Lunch at the farm or nearby trattoria (~£14–18pp)
- →Self-guided walk through Pienza: Piazza Pio II, Cathedral (~£3), Val d'Orcia viewpoints
- →Walk through Montepulciano's historic centre
- →Vino Nobile cantina tasting in Montepulciano (~£10–15pp)
Siena: Piazza del Campo, the Cathedral & a farewell dinner
Siena
Take a morning bus or train to Siena (~1 hr from Arezzo, ~£6–10). Spend the morning on a self-guided walk of one of Italy's most beautiful medieval cities: the shell-shaped Piazza del Campo, the stunning striped Duomo di Siena (~£8 or £13 for the OPA SI combo pass with terraces), and the Museo Civico inside the Palazzo Pubblico (~£10). Climb the Torre del Mangia for sweeping city views (~£10). Book a table at a well-reviewed local osteria for a long, celebratory Sienese lunch — try ribollita, pici cacio e pepe, and a glass of Chianti Classico (~£20–28pp). Spend the afternoon wandering Siena's contrade (neighbourhood) lanes before catching a late bus back to Arezzo. Enjoy a final dinner at your accommodation or a local restaurant.
🚌Direct bus (Tiemme/Flixbus) or Trenitalia train from Arezzo to Siena, ~£6–10 return. Siena's historic centre is entirely walkable.
🛏Same agriturismo/guesthouse near Arezzo (~£35–55/night)
- →Bus or train Arezzo → Siena (~£6–10 return)
- →Self-guided walk: Piazza del Campo, Fonte Gaia, medieval contrade lanes
- →Duomo di Siena and OPA SI combo pass (~£13, includes terraces and baptistery)
- →Torre del Mangia climb for panoramic views (~£10)
- →Long celebratory lunch at a local Sienese osteria (~£20–28pp)
- →Farewell dinner back in Arezzo (~£15–20pp)
Farewell to Tuscany & transfer to Florence
Arezzo → Florence
After a final breakfast at your accommodation, take a slow last morning walk through the Arezzo countryside or the estate gardens. Check out and take the Trenitalia regional train back to Florence (~£8–12, 1–1.5 hrs) in time for your flight home from Florence (FLR) or onward journey. If your flight is later in the day, Florence's city centre is just a 10-minute walk from Santa Maria Novella station — pop into the Mercato Centrale for a final espresso and pastry, or browse the San Lorenzo leather market.
🚌Trenitalia: Arezzo → Florence SMN (~£8–12). Tram or taxi from Florence SMN to Florence Airport (~£5–10 by tram T2).
🛏N/A — departure day
- →Final breakfast and slow morning walk through the local countryside
- →Check out of accommodation
- →Trenitalia regional train: Arezzo → Florence SMN (~£8–12)
- →Optional: Final espresso and pastry at Mercato Centrale, Florence (~£3–5)
- →Depart from Florence Airport (FLR) or continue onward
Self-launched vs. Exodus
| This itinerary (self-launched) | Exodus | |
|---|---|---|
| Price per person | ~£785 | £7,400 |
| Duration | 8 days | 8 days |
| Who books it | You and your group, direct | Tour operator, guided group |
| Savings | £6,615 per person (89%) | |
Estimate only, not a guaranteed price. Always verify costs independently before booking.
Want to see more Exodus-style trips? Check them out here.~£785
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 Renaissance Tuscany: Florence, Arezzo, Siena & Beyond cost?+
Doing it yourself with this self-launched itinerary costs an estimated £785 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 £7,400 per person for a similar tour. Doing the same route independently, using the same standard of accommodation and activities, costs an estimated £785 — a saving of roughly £6,615 (89%) 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 culture, foodie, slow-travel 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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