Food and Wine Travel
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Italy — Tuscany
A Week in Tuscany
Seven nights in a Cortona villa — cooking, wine, Siena and the very best of Tuscany
Duration
8 Days / 7 Nights
Travel Style
Small Group
Starting In
Cortona
Ending In
Cortona
Departures
April to October — Saturday to Saturday
Reference
ITFLRTAFW
Italy — Tuscany
A Week in Tuscany
Seven nights in a Cortona villa — cooking, wine, Siena and the very best of Tuscany
Duration
8 Days / 7 Nights
Travel Style
Small Group
Starting In
Cortona
Ending In
Cortona
Departures
April to October — Saturday to Saturday
A Week in Tuscany — 8 Days / 7 Nights
Overview
Our Taste of Tuscany tour is one of the most popular we offer — a first-hand look at some of the most vibrant and traditional locations in the region, from Cortona to Siena, with the finest wines, authentic local cuisine, and a four-course cooking class where you'll prepare a full Italian meal with fresh, locally sourced ingredients.
Based in a beautifully restored farmhouse near Cortona — just ten kilometres from the historic centre — this seven-night small group journey covers everything Tuscany does best: a morning exploring the tower town of San Gimignano, a guided afternoon in Siena, a day through the breathtaking Val d'Orcia to Pienza and Montepulciano, and an afternoon in the Chianti vineyards with a wine tasting lunch.
Bilingual hosts take care of every detail throughout the week. Wine is included with all dinners, three lunches are included on tour days, and a free day is built in — to relax at the villa, explore Cortona independently, or try a Vespa tour through the valley.
Trip Highlights
- —Seven nights in a restored Tuscan farmhouse near Cortona — pool, valley views, bilingual hosts
- —Cortona: Bramasole drive-by, Chiesa di Santa Margherita, caffè and free time in the historic centre
- —San Gimignano and Siena: medieval towers, ceramics, the Piazza del Campo and the Gothic Duomo
- —Hands-on four-course Tuscan cooking class — lunch with the chef included
- —Val d'Orcia: Pienza (pecorino and boutiques) and Montepulciano underground cellar lunch with Vino Nobile tasting
- —Chianti Classico: Castellina, vineyard visit, wine tasting and lunch at the estate
- —One tour-free day — Vespa or cycling tours available, or simply relax at the villa
- —Six wine-inclusive dinners at local trattorias or the villa
Day by Day
Arrival — Cortona
Arrive at Camucia–Cortona station where your hosts meet you for the short transfer to the villa. The afternoon is yours to settle in, explore the property and take in the first views across the valley. This evening, a welcome dinner at a favourite local trattoria in Cortona sets the tone for the week ahead.
Station transfer
Met at Camucia–Cortona station (accessible by train from Rome Termini or Florence Santa Maria Novella) and transferred to the farmhouse — approximately 10 km from the station.
Arrival at the villa
Check in from 3:30pm. Settled into your apartment, walk the grounds, and discover the pool and surrounding olive groves.
Welcome dinner, Cortona (included)
Dinner at a local trattoria in Cortona — a warm introduction to the town, the food, and your fellow travellers over Tuscan wine and classic dishes.
Cortona
A morning centred on Cortona — one of Tuscany's most beautiful hilltop towns. Drive past Bramasole (the farmhouse made famous by Frances Mayes in Under the Tuscan Sun), visit the basilica of Santa Margherita with its sweeping valley views, then into the historic centre for caffè and brioche. The rest of the morning is free — boutiques, art galleries, ceramics. Lunch together at a typical trattoria, afternoon free, dinner in Cortona.
Bramasole drive-by
A short drive past the villa made world-famous by Frances Mayes — the enduring symbol of the Tuscan dream.
Chiesa di Santa Margherita
Visit the basilica perched above the town, with panoramic views across the Chiana valley.
Cortona historic centre — caffè and free time
Caffè and brioche at a local bar, then free time to explore Cortona's boutiques, art galleries, and the many delights the town has to offer.
Lunch at a trattoria (included)
Lunch together at a typical Cortona trattoria.
Afternoon free
Return to the villa to relax, or continue exploring Cortona independently.
Dinner in Cortona (included)
Dinner at a local trattoria with wine included.
San Gimignano & Siena
A full day exploring two of Tuscany's most celebrated medieval towns. The morning in San Gimignano — the extraordinary tower city of the Val d'Elsa, famous for its painted ceramics, leatherware, and Vernaccia white wine. At 1pm the group moves to Siena for a guided afternoon: the magnificent Piazza del Campo, Il Duomo, the Mangia Tower, and the contrade streets. Dinner in Cortona or at the villa.
San Gimignano
A morning in the medieval tower town — two wonderful piazzas, a museum, a tower climb for breathtaking views over the Val d'Elsa, ceramics, leatherware, alabaster, and a gelato.
Travel to Siena
Depart at approximately 1pm for the drive south to Siena.
Siena — guided walk
An afternoon in Siena: the spectacular Piazza del Campo, Il Duomo, the Mangia Tower, and a stroll through the streets and boutiques of this magnificent Gothic city.
Dinner in Cortona or at the villa (included)
Return to Cortona for dinner at a trattoria or a home-cooked Tuscan feast at the villa.
Lazy Morning & Cooking Experience
A relaxed morning before one of the highlights of the week — a hands-on Tuscan cooking class where you'll prepare a four-course Italian meal with fresh, locally sourced ingredients: pasta, a main course, side dishes, and dessert. Sit down to enjoy the meal together with the chef afterwards.
Leisurely morning
A free morning to sleep in, stroll to Cortona, or simply enjoy the villa before the afternoon's programme.
Hands-on Tuscan cooking class (included)
Prepare a complete four-course Italian meal with fresh, locally sourced ingredients — pasta, a main course, side dishes, and dessert — guided by a local cook.
Lunch with the chef (included)
Sit down together to enjoy the meal you've just prepared, accompanied by local wine.
Dinner in Cortona or at the villa (included)
Evening dinner with wine included.
Val d'Orcia — Pienza & Montepulciano
A day through the Val d'Orcia — a UNESCO World Heritage landscape of extraordinary beauty. Morning in Pienza, the birthplace of Pope Pius II and home of the region's finest pecorino. At midday, travel to Montepulciano for a lunch and wine tasting in a local underground cellar in the historic centre, followed by free time to explore the city.
Val d'Orcia — Pienza
Morning in Pienza — the ideal Renaissance hilltop town, famous for pecorino cheese, beautiful boutiques, and the Piazza Pio II.
Caffè in Pienza and free time
A shared caffè followed by free time to explore the town and its food shops independently.
Montepulciano — underground cellar lunch and wine tasting (included)
At midday, travel to Montepulciano for lunch and a tasting of Vino Nobile in a local underground cellar within the historic centre.
Montepulciano free time
Explore the city at your own pace during the afternoon before returning to Cortona.
Dinner in Cortona (included)
Return for dinner at a local trattoria.
Chianti
A leisurely day through the Chianti Classico wine country — the rolling hills of Sangiovese between Florence and Siena. Morning in Castellina in Chianti followed by a visit to a nearby vineyard, interaction with the winemakers, and a wine tasting lunch with spectacular views over the vines and olive groves. Return to the villa late afternoon.
Castellina in Chianti
A Caffè together and free time to explore this atmospheric Chianti town — varied stores, the medieval Via delle Volte, and the surrounding wine landscape.
Vineyard visit (included)
A visit to a quality Chianti estate — meeting the winemakers and tasting the wines amid spectacular vineyard views.
Wine tasting lunch at the estate (included)
A relaxed lunch at the vineyard — local food paired with estate Chianti, with panoramic views over the vines and olive groves.
Return to villa late afternoon
Time to relax by the pool or take a final walk through Cortona.
Dinner in Cortona or at the villa (included)
Evening dinner with wine included.
Tour-Free Day
A free day to spend as you please — stay at the villa and enjoy the grounds, visit Cortona or another local township, or choose from the optional activities: Vespa tour or cycling tour through the valley. Dinner in Cortona or at the villa.
Free day
No programme — relax at the villa, browse Cortona's boutiques and ceramics shops, or head to a nearby township.
Optional: Vespa or cycling tour
Choose from a range of additional activities including Vespa tours, cycling tours, horse riding, and more. Booking prior to the tour is recommended.
Dinner in Cortona or at the villa (included)
A final dinner to savour the last Tuscan evening — wine included.
Departure
After breakfast at the villa, your hosts transfer you to Camucia–Cortona station for your onward journey — with plenty of Tuscan memories to savour for a lifetime. Station transfers depart at 8:00am and 9:00am.
Breakfast at the villa
A final leisurely breakfast before the journey home.
Transfer to Camucia–Cortona station
Station transfers at 8:00am and 9:00am — direct trains to Florence Santa Maria Novella (approx. 1h30) and Rome Termini (approx. 2h30).
What's Included
Included
- ✓7 nights in a traditional Tuscan farmhouse apartment near Cortona (pool, living area, kitchen, bathroom, laundry, air-conditioning, Wi‑Fi)
- ✓Bilingual hosts and tour leaders throughout
- ✓3 lunches: Day 2 trattoria lunch in Cortona, Day 4 cooking class lunch with the chef, Day 5 Montepulciano underground cellar lunch
- ✓6 dinners at local trattorias or home-cooked Tuscan feasts at the villa (wine included with all dinners)
- ✓Hands-on four-course Tuscan cooking class with fresh, locally sourced ingredients
- ✓Guided walks through Cortona and Siena
- ✓Wine tasting events at local vineyards and establishments
- ✓All transport to and from accommodation on tour days
- ✓Transport to local station or Cortona on tour-free day
- ✓Station transfers on arrival and departure
Not Included
- ✕International or domestic flights to Italy
- ✕Travel insurance (strongly recommended — proof of cover required)
- ✕Entry fees to museums, galleries, or public premises not listed in the itinerary
- ✕Meals outside those listed in the itinerary
- ✕Personal expenses and extras
- ✕Optional activities (Vespa tour, cycling tour, horse riding — available to book separately)
- ✕Private airport or hotel transfers (available on request)
Gallery
Ready to start planning?
This itinerary can be tailored to suit different travel dates, group sizes, and preferences. Book a free chat to start the conversation.
Trip at a Glance
Accommodation
Restored Tuscan farmhouse villa apartments, near Cortona
7 nights
Cortona, Tuscany, Italy (approx. 10 km from historic centre)
A beautifully restored Tuscan farmhouse complex with panoramic valley views, approximately 10 km from Cortona's historic centre. Private villa apartments of one to three bedrooms, each with a fully equipped kitchen, living area, bathroom, laundry, air-conditioning, and Wi‑Fi. Shared pool and grounds. Bilingual hosts on the property.
Good to Know
iArrive by train to Camucia–Cortona station — direct services from Florence Santa Maria Novella and Rome Termini. Private transfers from airports or hotels are available on request.
iTours operate Saturday to Saturday. Check-in from 3:30pm on arrival day; check-out by 9:00am on departure day (station transfers at 8:00am and 9:00am).
iGroup size is small and personalised. The touring day generally commences at 9:00am.
iWalking on cobblestone streets is part of the daily experience — comfortable, flat walking shoes are essential.
iAll lunches and dinners are from à la carte menus with varied selection. Vegetarians and specific dietary requirements are well catered for.
iDress code: comfortable clothing and walking shoes for tours; smart casual for dinners.
iBest time to travel: May, June, and September/early October for milder weather. July–September is peak season. Sunflowers bloom late June through July.
iPricing is based on availability and travel dates. Contact us for a personalised quote.