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Italy — Tuscany
Tuscan Immersion
Fourteen nights near Cortona — the complete Tuscan experience, lived slowly
Duration
15 Days / 14 Nights
Travel Style
Small Group
Starting In
Cortona
Ending In
Cortona
Departures
April to October — Saturday to Saturday
Reference
ITFLRTAFW2
Italy — Tuscany
Tuscan Immersion
Fourteen nights near Cortona — the complete Tuscan experience, lived slowly
Duration
15 Days / 14 Nights
Travel Style
Small Group
Starting In
Cortona
Ending In
Cortona
Departures
April to October — Saturday to Saturday
Tuscan Immersion — 15 Days / 14 Nights
Overview
The Tuscan Immersion is the complete experience — fourteen nights based in a restored farmhouse near Cortona, moving at the rhythm of the Tuscan countryside rather than a tour bus schedule. Two full weeks is what Tuscany deserves: time to linger over a long lunch at a hilltop vineyard, time for a morning market and a long afternoon by the pool, time to truly understand a region that has been drawing people back for centuries.
The programme covers the full breadth of Tuscany: Cortona, Siena, San Gimignano, Florence, the Chianti Classico zone, Val d'Orcia (Pienza and Montepulciano underground cellars), Orvieto, and the quiet medieval gem of Lucignano. A traditional cheese-making day, a hands-on cooking class, wine tastings in Chianti and Montepulciano, and an independent Arezzo day round out the fortnight.
With bilingual hosts on hand throughout, seven lunches and ten wine-inclusive dinners included, and generous free days woven through the programme, this is Tuscany as it should be experienced — without rush, without compromise.
Trip Highlights
- —Fourteen nights in a restored Tuscan farmhouse near Cortona — pool, views, bilingual hosts
- —Cortona: walking tour, Bramasole drive-by, local trattoria dinners
- —San Gimignano and Siena: medieval towers, Vernaccia wine, the Piazza del Campo
- —Independent Florence: train tickets included, full day to explore
- —Chianti Classico: Castellina, vineyard visit, wine tasting lunch
- —Pecorino cheese-making at a traditional Tuscan farm
- —Independent Arezzo: train tickets included
- —Val d'Orcia: Pienza and Montepulciano underground cellar lunch and tasting
- —Orvieto: the Duomo, St Patrick's Well, underground caves and tunnels, lunch
- —Lucignano: a morning market and lunch in a medieval village
- —Hands-on cooking class with a local chef — lunch with wine included
- —Seven lunches and ten wine-inclusive dinners over the fortnight
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, discover the property, and take in the first views across the valley. This evening, a welcome dinner at a favourite local trattoria in Cortona.
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.
Arrival at the villa
Check in from 3:30pm. Explore the grounds, discover the pool, and settle into the rhythm of Tuscan life.
Welcome dinner, Cortona (included)
A first dinner at a local trattoria — the beginning of fourteen evenings of excellent Tuscan food and wine.
Cortona — La Dolce Vita
A morning in Cortona — caffè and brioche at a local bar, then a guided walk through the medieval centre: the Piazza della Repubblica, the Etruscan museum, and the basilica of Santa Margherita with sweeping valley views. A gentle drive past Bramasole rounds off the morning.
Morning caffè and brioche
Start the day the Italian way — an espresso at the bar and a fresh cornetto.
Cortona walking tour
A guided walk through Cortona's streets, piazza, Etruscan museum, and the views from Santa Margherita.
Bramasole drive-by
A short drive past the villa made famous by Frances Mayes — an iconic part of the Cortona story.
Lunch at a local trattoria (included)
A relaxed Tuscan lunch.
Afternoon free
Explore at leisure or relax at the villa.
Dinner, Cortona or villa (included)
Dinner with wine included.
San Gimignano & Siena
A full day taking in two of Tuscany's most celebrated medieval towns — the tower city of San Gimignano in the morning and the magnificent Siena in the afternoon, with a guided walk through the Piazza del Campo and the Gothic Duomo.
San Gimignano
Morning in the town of towers — medieval streets, Vernaccia wine shops, and sweeping Val d'Elsa views.
Lunch en route (included)
Lunch between San Gimignano and Siena.
Siena guided walk
Afternoon in Siena with a local guide — the Piazza del Campo, the Duomo, the Baptistery.
Dinner, Cortona (included)
Return for dinner at a Cortona trattoria.
Tour-Free Day
A free day — no plans, no schedule. Cortona is on foot, the valley is on bike, and the pool is always there. Hosts can suggest cycling routes, nearby markets, or simple day trips for those who want them. Dinner in Cortona this evening.
Free day
Explore independently — Cortona's ceramics and food shops, the weekly market (if scheduled), cycling the valley roads, or simply reading by the pool.
Dinner, Cortona or villa (included)
Evening meal at leisure.
Florence — La Capitale del Rinascimento
An independent day in Florence — train tickets included, departing at 8:12am and arriving at Santa Maria Novella at approximately 9:30am. A full day to explore the city at your own pace before returning by train in the late afternoon.
Train to Florence (included)
Depart Camucia–Cortona 8:12am, arrive Florence Santa Maria Novella approximately 9:30am. Tickets arranged by your hosts.
Florence — full day at leisure
The Uffizi, the Accademia, the Duomo, the Ponte Vecchio, the Oltrarno — an entire day in one of the world's greatest cities.
Return train
Return services throughout the afternoon and early evening.
Dinner, Cortona or villa (included)
Dinner on return.
Chianti Classico
An afternoon devoted to the Chianti Classico wine country — Castellina in Chianti, a private vineyard visit and tutored tasting, and a wine lunch at the estate.
Castellina in Chianti
Time in one of the zone's most atmospheric towns — medieval walls, underground Etruscan road, outstanding wine shops.
Vineyard visit and tasting (included)
A private visit to a quality Chianti Classico estate — cellar tour and tasting of current releases.
Wine lunch at the estate (included)
A relaxed lunch at the vineyard — Tuscan food paired with estate Chianti.
Dinner, Cortona or villa (included)
Return for dinner.
Cheese-Making at the Farm
A hands-on pecorino cheese-making experience at a traditional Tuscan farm, followed by a generous farm lunch with wine. The afternoon is free.
Pecorino cheese-making (included)
A morning at a local farm learning traditional pecorino-making, guided by the farmer.
Farm lunch with wine (included)
A celebratory lunch at the farm featuring the morning's cheese, cured meats, bread, and local wine.
Afternoon free
Time at the villa or in Cortona.
Dinner, Cortona (included)
Dinner in town.
Arezzo — Independent Day
A free day in Arezzo — train tickets are included. Arezzo is one of Tuscany's most underrated cities: the Piazza Grande, the Church of San Francesco with Piero della Francesca's famous frescoes, the antiques district, and a thriving café culture. The train departs at 9:15am.
Train to Arezzo (included)
Depart Camucia–Cortona 9:15am. Tickets arranged by your hosts.
Arezzo — at leisure
Explore Arezzo's piazza, the Piero della Francesca frescoes in San Francesco, the antiques market (first Sunday of every month), and the excellent local restaurants.
Return by train
Return services throughout the day.
Dinner, Cortona (included)
Dinner at a local trattoria on return.
Val d'Orcia — Pienza & Montepulciano
A full day in the Val d'Orcia — one of the most beautiful landscapes in the world and a UNESCO World Heritage Site. Morning in Pienza, the ideal Renaissance town, then south to Montepulciano for an underground cellar lunch and a tasting of the celebrated Vino Nobile.
Pienza
Morning in the perfectly proportioned Renaissance hilltop town — the Piazza Pio II, the cathedral, and the finest pecorino and pici pasta shops in Tuscany.
Montepulciano — underground cellar lunch and tasting (included)
Descend into the extraordinary underground cellars beneath Montepulciano for a wine lunch featuring the town's celebrated Vino Nobile di Montepulciano.
Dinner, Cortona (included)
Return for dinner.
Tour-Free Day
A second free day — rest, reflect, and absorb. The pool, the gardens, or a final wander through Cortona. Hosts can suggest cycling routes or nearby markets if you prefer to stay active.
Free day
Unscheduled time — enjoy the villa, explore Cortona independently, or take a gentle cycling route through the valley.
Dinner, Cortona or villa (included)
Evening meal at leisure.
Cooking Class — The Art of Tuscan Cooking
A hands-on Tuscan cooking class at a farmhouse kitchen — fresh pasta, a classic ragu, perhaps a dolce — with lunch at the table afterwards, paired with local wine and Vin Santo with cantucci to finish.
Tuscan cooking class (included)
A morning in the farmhouse kitchen with a local cook — fresh pasta, traditional sauces, and the fundamental techniques of the Tuscan table.
Lunch with the chef (included)
Sit down to the meal you've prepared — paired with local wine, finished with Vin Santo and cantucci.
Afternoon free
Return to the villa for a final free afternoon.
Dinner, Cortona (included)
Evening dinner at a favourite Cortona restaurant.
Orvieto
A day trip to Orvieto — one of Italy's most spectacular hill towns, rising dramatically from volcanic tufa above the Umbrian plains. Morning in the town centre: the striped Gothic Duomo, St Patrick's Well (a double-helix Renaissance masterpiece), and the extraordinary underground cave network beneath the old city. Lunch included.
Orvieto Duomo
The stunning black-and-white striped Gothic cathedral — one of Italy's finest medieval façades, covered in mosaics and bas-reliefs.
St Patrick's Well
The extraordinary Renaissance double-helix well commissioned by Pope Clement VII — 248 steps descending 53 metres, with two separate spiral staircases that never meet.
Underground Orvieto
A guided tour of the tunnels, caves, and Etruscan passages carved into the volcanic tufa beneath the old city.
Lunch, Orvieto (included)
Lunch at a local Orvieto restaurant.
Dinner, Cortona (included)
Return to Cortona for dinner.
Lucignano & the Market
A morning in Lucignano — one of Tuscany's most perfectly preserved medieval villages, built in four concentric elliptical rings around a hilltop. A local market, lunch, and a gentle final afternoon.
Lucignano
A morning exploring one of Tuscany's hidden gems — the concentric elliptical medieval town, the Museo Comunale with its famous gilded tree of life, and a slow walk around the ramparts.
Market and lunch, Lucignano (included)
Browse the local market and lunch at a traditional restaurant in the town.
Afternoon free
A gentle final afternoon at the villa or in Cortona.
Dinner, Cortona or villa (included)
Evening meal.
Tour-Free Day — Last Hours in Tuscany
A final free day before tomorrow's departure — a last swim, a long breakfast, a final passeggiata through Cortona, and the task of fitting the memories of two weeks into the luggage.
Free day
Spend the last hours at the villa, in Cortona, or taking a final drive through the landscape.
Farewell dinner, Cortona (included)
The fortnight's final dinner — a long table, old friends, and the best Tuscan wine to close the journey.
Departure
After a final breakfast at the villa, your hosts transfer you to Camucia–Cortona station. Station transfers depart at 8:00am and 9:00am, connecting with trains to Florence and Rome.
Breakfast at the villa
A final 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
- ✓14 nights in a restored Tuscan farmhouse apartment near Cortona (pool, living area, kitchen, laundry, air-conditioning, Wi‑Fi)
- ✓Bilingual hosts on hand throughout
- ✓7 lunches (days 2, 3, 6, 7, 9, 12, 13 — as specified in the itinerary)
- ✓10 dinners with wine (arrival evening through to farewell dinner, excluding Florence free day)
- ✓Florence train tickets (included, 2nd class, return)
- ✓Arezzo train tickets (included, 2nd class, return)
- ✓Chianti vineyard visit and tutored tasting
- ✓Montepulciano underground cellar lunch and Vino Nobile tasting
- ✓Pecorino cheese-making experience at a local Tuscan farm
- ✓Hands-on Tuscan cooking class with a local chef
- ✓Cortona guided walking tour
- ✓Orvieto guided underground caves tour
- ✓All wine at included dinners and tastings
- ✓Station transfers on arrival and departure; all transport on scheduled tour days
Not Included
- ✕International or domestic flights to Italy
- ✕Travel insurance (strongly recommended)
- ✕Entry fees to museums and monuments not specified in inclusions
- ✕Meals outside the included programme
- ✕Personal expenses and extras
- ✕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
14 nights
Cortona, Tuscany, Italy (approx. 10 km from historic centre)
A beautifully restored Tuscan farmhouse complex set among olive groves with panoramic valley views approximately 10 km from Cortona. 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 sun terrace. Bilingual hosts live on the property.
Good to Know
iArrive by train to Camucia–Cortona station (direct services from Florence Santa Maria Novella and Rome Termini). Private airport or hotel transfers available on request.
iTours operate Saturday to Saturday. Check-in from 3:30pm on arrival day; check-out by 9:00am on departure day.
iThe group is small — typically 8 to 14 guests — ensuring a personal, unhurried pace throughout the fortnight.
iThree free days are built into the programme — genuinely free. Hosts provide curated suggestions for independent exploration.
iMost excursions involve walking on uneven cobblestone streets — comfortable flat shoes are strongly recommended.
iA hire car can be useful for exploring beyond the programme, but is not required — all excursions depart from the villa.
iPricing is in Australian dollars and based on twin-share occupancy. Single supplement applies. Contact us for availability and a personalised quote.