Italy in a Wine Key: Rome, Umbria & Chianti
A nine-day journey through Rome, Umbria, and Tuscany centred on wine-country rhythm, historic hill towns, vineyard tables and the Chianti Classico Wine Festival, designed for travellers who value flavour, continuity, and unhurried days over fast sightseeing.
Trip Overview
Description:
The Experience
This journey is shaped around wine-country rhythm rather than distance. It moves from the layered intensity of Rome into the quieter hill towns of Assisi and Cortona, before settling deeply into the vineyards and medieval streets of Tuscany and closing in Florence.
Days unfold through golden-hour walks, long lunches, and shared tables rather than packed schedules. The heart of the journey is time spent in Chianti during the annual Chianti Classico Wine Festival in Greve in Chianti, where producers, townspeople, and travellers meet on equal ground. Food, wine, and conversation take precedence, allowing Italy to reveal itself slowly through flavour, stone, and story.
Who This Trip Is For
This itinerary is designed for well-travelled adults who enjoy wine, food culture, and places with a strong sense of continuity. It suits travellers who prefer walking historic towns, tasting with producers, and lingering over meals rather than covering maximum ground.
It may not suit those looking for fast-paced sightseeing, luxury shopping-focused travel, or extensive downtime at a single resort. A comfort with shared group experiences, walking on uneven streets, and curiosity about regional culture will make this journey especially rewarding
Highlights
Day 1 | Arrival in Rome
Arrive in Rome and settle into a boutique hotel near one of the city’s oldest piazzas. In the evening, walk past the Colosseum as it begins to glow, before dinner at a neighbourhood trattoria.
Overnight: Rome
Day 2 | Rome — Streets, Wishes & Food
Begin at Spanish Steps, continuing to the Trevi Fountain. Later, explore Rome’s historic market district on a curated food walk, tasting seasonal Roman specialities.
Overnight: Rome
Day 3 | Rome → Assisi — Umbrian Stillness
Travel north into Umbria, arriving in Assisi. Spend the afternoon wandering stone alleys and quiet piazzas as the light softens over the valley.
Overnight: Assisi
Day 4 | Assisi & Cortona — Sacred Stone and Vineyards
Visit the Basilica of St. Francis, then continue to Cortona for a private vineyard lunch and tasting overlooking olive groves and rolling hills.
Overnight: Assisi / Cortona region
Day 5 | San Gimignano — Towers and Vernaccia
Enter San Gimignano, known for its surviving medieval towers. Walk the historic centre with local insight, then visit a family-run winery focused on Vernaccia and local traditions.
Overnight: San Gimignano
Day 6 | Colle di Val d’Elsa & Vineyard Cooking
Explore Colle di Val d’Elsa, Italy’s centre of crystal craftsmanship. Continue to a vineyard estate for a hands-on cooking class and long-table lunch paired with estate wines.
Overnight: San Gimignano
Day 7 | Chianti Classico Wine Festival — Greve
Spend the day at the Chianti Classico Wine Festival in Greve. Taste wines from over 50 producers, learn to read the Gallo Nero seal, and experience Chianti at its most communal and expressive.
Overnight: San Gimignano
Day 8 | San Gimignano → Florence — Renaissance Close
Transfer to Florence and step into the Renaissance heart of the city. Visit the Uffizi Gallery, stroll Via Tornabuoni, and gather for a farewell dinner.
Overnight: Florence
Day 9 | Departure from Florence
After breakfast, travel onward by train to Rome for airport connections, concluding the journey. Private transfers can be arranged on request.
Inclusions
- Group airport transfer on arrival in Rome
- All scheduled private transfers between cities and experiences
- Accommodation for 8 nights as outlined
- Daily breakfasts
- Guided walking tours in Rome, Assisi, and San Gimignano
- Basilica of St. Francis guided visit
- Vineyard lunches and wine tastings as specified
- Private cooking class at a vineyard estate
- Entry, tastings, and food at the Chianti Classico Wine Festival
- Farewell dinner in Florence
Exclusions
- International flights
- Individual airport pick-up or drop-offs
- Meals not specified in the itinerary
- Personal expenses, tips, and optional activities
- Medical, emergency, or loss-related expenses
Request Add On Services
Extend Your Stay
Add nights, add cities, slow the pace, linger longer.
Milestone Moments
Birthdays, anniversaries, celebrations, planned to your brief.
Private Experiences
Art, culture, cuisine, and special access, arranged for you.
Tailored Requests
Dietary needs, accessibility, preferences, and thoughtful touches.
Subscribe to stay inspired.
Stories, ideas, and slow journeys - from hidden villages to distant valleys, straight to your inbox.
.avif)