Small Group Tuscany Wine Tasting Safaris with Lunch / Dinner
Depart from Florence to eat and drink your way through Chianti, famous for red wines, cuisine, and stunning landscapes. Enjoy a Tuscan lunch or dinner and wine-tasting...
Day-by-day estate-visit plans for Tuscany: weekend, first-timer and deep-cellar editions.
Day-by-day plans
Chianti Classico two-day weekend ★ 4.7
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Day 1
- Morning
- Drive south from Florence along the SR222 Chiantigiana, stopping for an early visit at Marchesi Antinori's Antinori nel Chianti Classico cellar at Bargino for the 90-minute tour and tasting.
- Afternoon
- Continue to Panzano in Chianti for a 16:00 cellar tasting at Fontodi in Conca d'Oro, focused on the certified-organic estate's Sangiovese and Flaccianello.
- Evening
- Aperitivo on Piazza Bucciarelli in Panzano followed by dinner at Officina della Bistecca with Dario Cecchini.
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Day 2
- Morning
- Drive east to Radda in Chianti for a 10:30 tasting at Castello di Volpaia inside the medieval Volpaia village, focused on high-elevation Sangiovese.
- Afternoon
- Continue south-east to Castelnuovo Berardenga for an estate visit at Felsina for the Berardenga Chianti Classico and Fontalloro IGT.
- Evening
- Return to Florence for a late aperitivo at Le Volpi e l'Uva off the Ponte Vecchio before dinner.
Brunello and Vino Nobile three-day loop ★ 4.8
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Day 1
- Morning
- Begin in Montalcino at Biondi-Santi's Il Greppo estate for a 10:00 visit, focused on the 19th-century clone selection and a Riserva tasting.
- Afternoon
- Drive south to Sant'Angelo in Colle for a 16:00 tasting at Il Poggione, the historic Franceschi family estate.
- Evening
- Dinner at Re di Macchia or Drogheria Franci in Montalcino with a Rosso di Montalcino comparison.
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Day 2
- Morning
- Visit Casanova di Neri for the Cerretalto cru tasting; cellar tour through the recent Mastrojanni acquisition.
- Afternoon
- Cross the Val d'Orcia eastward via Pienza for a 16:30 visit at Avignonesi in Valiano di Montepulciano; focus on the biodynamic-certified Vino Nobile and the Vin Santo Occhio di Pernice.
- Evening
- Drive into Montepulciano for dinner at La Grotta below the town walls.
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Day 3
- Morning
- Tour Salcheto's off-grid carbon-neutral cellar, with a no-added-sulfite Vino Nobile tasting.
- Afternoon
- Drive west to Boscarelli for a 16:00 tasting of the De Ferrari Corradi family's Riserva and IGT bottlings.
- Evening
- Return drive to Florence or Siena.
Bolgheri and Maremma coast four-day route ★ 4.8
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Day 1
- Morning
- Drive from Florence to Bolgheri along the Tyrrhenian coast. Arrive at Tenuta San Guido for a noon tasting of Sassicaia in the Bolgheri Sassicaia DOC sub-zone.
- Afternoon
- Continue to Tenuta dell'Ornellaia for a 16:00 cellar visit and Ornellaia flight.
- Evening
- Aperitivo on the cypress-lined Viale dei Cipressi, then dinner at Enoteca Tognoni in Bolgheri.
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Day 2
- Morning
- Visit Masseto's hill estate for the dedicated Merlot tasting; allocations are small but cellar visits accommodate serious enthusiasts.
- Afternoon
- Tour Le Macchiole, the Cinzia Merli estate that pioneered the Cabernet Franc-led Paleo bottling.
- Evening
- Dinner at the Castagneto Carducci hilltop trattoria scene.
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Day 3
- Morning
- Drive south into the Maremma. Visit Tua Rita at Suvereto for the Redigaffi Merlot tasting.
- Afternoon
- Continue south to Le Pupille at Istia d'Ombrone for a Morellino di Scansano DOCG tasting.
- Evening
- Aperitivo in Grosseto, then dinner at Trattoria Toscana in the centro storico.
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Day 4
- Morning
- Drive inland to Rocca di Frassinello for the Castellare-Domaines Barons de Rothschild joint-venture estate.
- Afternoon
- Return north via Massa Marittima with an optional stop at Massa Vecchia for the natural-wine cellar visit (referral only).
- Evening
- Drive back to Florence or Pisa airport.
Tuscany grand tour, seven days ★ 4.8
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Day 1
- Morning
- Arrive Florence; walk to Le Volpi e l'Uva off the Ponte Vecchio for a Tuscan by-the-glass introduction.
- Afternoon
- Drive west to Carmignano for a tasting at Tenuta di Capezzana, the historical centre of the 1716 Cosimo III appellation.
- Evening
- Return to Florence for dinner at Coquinarius.
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Day 2
- Morning
- Drive into Chianti Classico. Visit Castello di Ama at Gaiole for the contemporary-art-and-wine tour.
- Afternoon
- Continue to Isole e Olena (Barberino Val d'Elsa) for the Paolo De Marchi (Proprieta Sperino link) cellar visit and Cepparello tasting.
- Evening
- Dinner at Officina della Bistecca in Panzano with Dario Cecchini.
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Day 3
- Morning
- Visit San Felice at Castelnuovo Berardenga for the Vigorello IGT and Brunello at Campogiovanni in Sant'Angelo in Colle.
- Afternoon
- Continue south to Riecine for a high-elevation Gaiole Sangiovese tasting.
- Evening
- Drive to Montalcino. Aperitivo at Enoteca La Fortezza di Montalcino inside the fortress.
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Day 4
- Morning
- Brunello morning at Casanova di Neri or Mastrojanni.
- Afternoon
- Visit Argiano for the Sesta cru and the Solengo Super Tuscan.
- Evening
- Dinner at Re di Macchia.
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Day 5
- Morning
- Cross to Montepulciano via Pienza. Visit Poliziano for the Asinone single-vineyard Vino Nobile.
- Afternoon
- Tasting at Salcheto's off-grid carbon-neutral cellar.
- Evening
- Drive west to Bolgheri via the SS1 Aurelia coast road.
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Day 6
- Morning
- Tenuta San Guido for Sassicaia.
- Afternoon
- Tenuta dell'Ornellaia tasting.
- Evening
- Dinner at Enoteca Tognoni.
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Day 7
- Morning
- Drive north to San Gimignano for the Tuscany white-wine pause. Tasting at Panizzi or Cesani for Vernaccia di San Gimignano DOCG.
- Afternoon
- Return to Florence; final aperitivo at Procacci on Via Tornabuoni with truffle tramezzini and Antinori sparkling.
- Evening
- Departure dinner at Enoteca Pitti Gola e Cantina.
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Itineraries in Tuscany, FAQ
When is the best time to visit Tuscany for wine?
Peak wine-travel season in Tuscany is spring through autumn, with harvest the standout window.
Do I need an appointment to taste at Tuscany estates?
classified-growth and grand-cru estates require booking days to weeks ahead; smaller family domaines often take walk-ins midweek.
What hours do Tuscany cellars and tasting rooms keep?
most estates open 10:00 to 17:00 by appointment, often closed Sunday and Monday.
How does tipping work at Tuscany tastings?
tipping is not expected at tastings; buying a bottle from the cellar door is the customary thank-you.
What is the one wine to try in Tuscany?
Ask the next local you meet what they would order. Tuscany rewards trust.