In the Heart of the Divine Country: 9-Day Italian Food, Wine and Culture Tour
From Rome to Venice, through medieval villages, rolling hills, and legendary wineries — a journey crafted for curious travellers who travel to taste.
This 9-day self-drive tour of Italy traces a curated arc from Rome through Umbria, Tuscany, Bologna, and Venice, pairing iconic UNESCO-listed cities with hands-on food and wine experiences at family-run farms and celebrated estates. Accommodations are 4-star hotels throughout, and daily breakfasts set a high bar that the rest of each day is designed to match. The pace is easy, the stops are purposeful, and every destination earns its place on the itinerary.
The route crosses some of Italy's most storied wine appellations — Brunello di Montalcino, Vino Nobile di Montepulciano, Chianti Classico, and Vernaccia di San Gimignano — with guided winery visits, cellar tours, and structured tastings at each. Alongside the wine, the tour builds in dedicated moments for regional food culture: handmade pasta in Bologna, cicheti in a Venetian bacaro, Roman suppli, and the singular chocolate tradition of Perugina in Perugia. These are not add-ons; they are central to the experience.
City sightseeing is led by local professional guides in Rome, Siena, Florence, and Venice, ensuring depth rather than surface-level commentary. Ancient monuments, baroque piazzas, medieval towers, and Renaissance basilicas are woven into the same days as vineyard walks and cheese platters. The result is a trip that rewards travellers who want cultural substance alongside sensory pleasure.
The self-drive format gives each day a rhythm of its own — scenic road transitions between destinations, freedom at lunch stops, and time to linger in hilltop villages without a strict group clock. The difficulty rating is easy, making this suitable for a wide range of travellers, including those new to driving in central Italy.
Tour Highlights
Guided tours of Rome, Siena, Florence, and Venice with local professional guides covering ancient, medieval, and Renaissance landmarks.
Wine tastings at estates producing Brunello di Montalcino, Vino Nobile di Montepulciano, Chianti Classico, and Vernaccia di San Gimignano.
Visit to the Perugina Chocolate House and Historical Museum in Perugia, including a factory tour and tasting session.
Exploration of UNESCO World Heritage hilltop towns: San Gimignano, Montepulciano, Montalcino, and Pienza in the Val d'Orcia.
Lunch in a traditional Bolognese restaurant sampling the dishes that define one of Italy's most celebrated regional cuisines.
Evening in a Venetian bacaro, tasting cicheti and local wines in an authentic neighbourhood setting away from the main tourist circuit.
Dinner with live music in Rome's Trastevere neighbourhood on the first evening, with a menu of classic Roman dishes.
Itinerary Overview
Check in to your 4-star hotel in Rome and take free time to begin exploring the city independently. In the evening, transfer to Trastevere for a dinner of traditional Roman dishes accompanied by live music.
A guided tour covers the Colosseum exterior, Imperial Forums, the Capitol, Altare della Patria, Trevi Fountain, the Pantheon, and Piazza Navona, with a stop for typical Roman sweet pastries. Lunch at a local trattoria is followed by free time for shopping.
Drive to Perugia and check in, then join a guided walking tour from the Etruscan Arch through the historic centre to Fontana Maggiore and Palazzo dei Priori. The afternoon visit to the Perugina Chocolate House includes the Historical Museum and a structured tasting.
The day moves through three emblematic Tuscan towns: a winery visit in Montepulciano for Vino Nobile DOCG, free time in the Renaissance jewel of Pienza, and a cellar visit with tasting in Montalcino for Brunello. Arrive in Siena for check-in and dinner.
A guided morning tour of Siena covers Piazza del Campo, Palazzo Pubblico, Torre del Mangia, and a walk through the city's historic contrade districts. The afternoon heads into the Sienese hills for a Chianti Classico DOCG winery visit in Castellina in Chianti and Monteriggioni, with a tasting platter of meats and cheeses.
Morning visit to the UNESCO-listed historic centre of San Gimignano, followed by a winery tour producing Vernaccia di San Gimignano with tasting of typical local products. Continue to Florence for a guided tour of Piazza del Duomo, Santa Maria del Fiore, the Baptistery, Piazza della Signoria, and Palazzo Vecchio.
What Is Included
Included
- 8 nights accommodation in 4-star hotels
- Daily breakfast at the hotel
- Professional local guides in Rome, Perugia, Siena, Florence, and Venice
- Guided winery visits with tastings in Montepulciano, Montalcino, Chianti Classico, and San Gimignano
- Visit to Perugina Chocolate House including Historical Museum and tasting
- Dinner with live music in Trastevere, Rome (Day 1)
- Lunch in a traditional Bolognese restaurant (Day 8)
- Evening cicheti and wine tasting in a Venetian bacaro (Day 9)
- Wine tasting with platter of meats and cheeses in Castellina in Chianti
Not Included
- Flights and international transfers
- Car rental and fuel costs
- Lunches not explicitly listed as included
- Dinners marked as not included (ni) in the itinerary
- Personal travel insurance
- Entrance fees to monuments and museums unless specified
- Tips and gratuities
- Any items of a personal nature
Important Information
Reserve Your Place on This Italian Journey
Nine days, five regions, four wine appellations, and a lifetime of memories — this itinerary is designed for travellers who want Italy at its most authentic. Spaces are limited; secure your dates now.
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