Trip highlights
- 1Full-day Chianti Classico estate tour — two to three wineries, barrel cellars, and structured comparative tastings
- 2WSET Level 2 theory session covering Italian grape varieties, regions, and the systematic tasting approach
- 3Day trip to Montepulciano for Vino Nobile tasting and a medieval hill town lunch
- 4Final blind tasting session — Barolo, Brunello, and Super Tuscan in comparison
- 5Five-course wine-paired dinner on the final evening — a summation of the week's learning
Daily spend
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Wine tasting course or WSET Level 2 Award in Wines
WSET Level 2 (formal qualification, requires exam) or estate tasting certificates (informal)
Typical cost
Guided vineyard tastings: $50-100 per session. WSET Level 2 courses at Florence wine schools: $400-600 for weekend intensive. Luxury wine tour programmes: $1,500-3,000 for 5 days
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Language preparation
15 min/day for 8 weeks ≈ 672 useful words and phrases
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Day-by-day plan
Arrive Florence — First Chianti Introduction
Sunday, October 3
Est. spend
$147
per person
🌅 Morning
Arrive Florence (FLR or by train)
Florence Airport (FLR), Via del Termine 11, 50127 Florence
Florence Peretola Airport has limited international connections — many visitors fly into Pisa (PSA) or Bologna (BLQ) and connect by train. Santa Maria Novella station is 15 minutes from the historic centre on foot. The city is compact and best navigated without a car — save driving for the Chianti days.
Book a hotel in the historic centre — the Oltrarno (south of the Arno), San Marco, or the area around Santa Croce are best for access to both wine bars and transport to Chianti.
Check in and walk to the Duomo and Piazza della Repubblica
Piazza del Duomo, 50122 Florence
Settle in and take a first orientation walk. Florence's historic centre is 800 years of architecture at pedestrian scale — the Duomo, the baptistery, Piazza della Signoria, and Ponte Vecchio are all within 15 minutes of each other.
Book Uffizi and Duomo dome climb tickets in advance (operaduomo.firenze.it and uffizi.it) — October is high season and popular sites sell out days ahead.
☀️ Afternoon
Ponte Vecchio and Oltrarno neighbourhood exploration
Ponte Vecchio and Oltrarno, 50125 Florence
Cross Florence's medieval jewellers' bridge into the Oltrarno — the working-class neighbourhood that contains some of the city's best independent restaurants, wine bars, and artisan workshops. Get a feel for the neighbourhood where most of this week's serious wine drinking will happen.
Note the wine bars (enoteche) you pass in the Oltrarno — Il Santino, Enoteca Pitti Gola e Cantina, and Buca Mario's wine bar are all worth revisiting later in the week.
Self-guided introduction: browse the Mercato Centrale wine section
Piazza del Mercato Centrale, Via dell'Ariento, 50123 Florence
The upper floor of Mercato Centrale has a wine shop with a good cross-section of Tuscan producers at fair prices. Before the structured education begins, browse the labels — Chianti Classico DOCG, Brunello di Montalcino DOCG, Vino Nobile di Montepulciano DOCG, and the various Super Tuscans. A useful orientation to the producers you will encounter.
Ask the wine seller about the difference between Chianti and Chianti Classico — the geography and quality distinction between the two appellations is a fundamental lesson for the week.
🌙 Evening
Enoteca Pitti Gola e Cantina — Structured First Chianti Tasting
Piazza de' Pitti 16, 50125 Florence
This Oltrarno enoteca has a particularly well-curated Chianti Classico list with experienced staff. Tonight's goal: a structured first encounter with Chianti — ask for a guided flight of three Chianti Classico wines across the annata, riserva, and Gran Selezione quality levels. An expert sommelier introduction to the week's primary appellation.
Tell the sommelier at the outset that you are spending the week on wine education in Chianti — they will adjust the tasting notes and recommendations accordingly.
🍽️ Meals
Airport or train station espresso and cornetto
Italian · $5 · The standard Italian bar breakfast — stand at the counter for the local price.
Lampredotto sandwich or light lunch near the Duomo
Florentine · $12 · The lampredotto (tripe) sandwich from a trippaio street vendor is quintessentially Florentine — the intestine braised in tomato broth, served in a roll dipped in the cooking liquid. A cultural necessity.
Enoteca tasting and dinner at Pitti Gola e Cantina
Tuscan · $50 · Order the wine flight plus crostini, affettati, pecorino, and bruschetta. The food is secondary to the wine education tonight.
Full-Day Chianti Classico Estate Tour
Monday, October 4
Est. spend
$310
per person
🌅 Morning
Drive or tour to Chianti Classico zone
Chianti Classico zone, between Florence and Siena, Tuscany
The Chianti Classico DOCG zone occupies the hill country between Florence and Siena — the Black Rooster (Gallo Nero) is its emblem. A guided tour from Florence visiting 2-3 estates is the most efficient approach; a rental car provides more flexibility but requires a designated driver.
Book a guided wine tour with a sommelier guide rather than a generic bus tour — the educational depth is substantially different. Operators like Chianti Classico Tours and Winedering offer small-group expert-led visits.
First Estate: Tank Room and Barrel Cellar
Chianti Classico estate — confirmed at booking
A visit to the vinification facility: stainless steel tanks for temperature-controlled fermentation and the barrel cellar for ageing. The guides at premium estates explain malolactic fermentation, the oak regime (French vs Slavonian oak, new vs second-fill barrels), and the decision points in producing annata versus riserva wines.
In the cellar, smell the bung hole of a newly filled barrel, then one from a second-year barrel, then one from a third — the evolution of toasty, vanilla, and fruit integration is a sensory lesson no classroom can replicate.
☀️ Afternoon
Structured Tasting: Current Releases vs Library Wines
Chianti Classico estate tasting room
The formal tasting session at the estate: a vertical comparison of their Chianti Classico annata (current release), riserva (aged 24+ months), and Gran Selezione (single vineyard, 30+ months). Some estates also include a library tasting of an older vintage — seeing how Sangiovese evolves over 10-15 years is the most instructive single tasting of the week.
Use the WSET Systematic Approach to Tasting (SAT) framework even informally: appearance, nose (aromas), palate (acidity, tannin, fruit, body, finish), and conclusion. Writing notes on each wine builds the vocabulary you will use for the rest of the week.
Second Estate: Vineyard Walk and Organic / Biodynamic Production
Second Chianti Classico estate
Many Chianti Classico estates have converted to organic or biodynamic viticulture. A second estate visit focusing on the vineyard rather than the cellar — understanding clone selection, training systems (Guyot vs alberello), and the decisions that determine wine character before a grape is picked.
In October, if harvest is underway, ask if you can observe the sorting table — where grape bunches are inspected and destemmed before fermentation. The difference between a quality-focused selection and a volume-focused operation is visible here.
🌙 Evening
Vineyard lunch (late afternoon) or return to Florence for dinner
Florence — Buca dell'Orafo or Trattoria Sostanza
Many estate tours conclude with a lunch at the winery (included or optional supplement). If visiting in the afternoon, return to Florence for dinner at a restaurant chosen for its Chianti Classico list — tonight you can read the label intelligently.
Order a Chianti Classico riserva from a producer you tasted today — comparing the winery tasting version with the restaurant-poured version (different temperature, different context) is a useful educational note.
🍽️ Meals
Early breakfast before estate tour departure
Italian · $5 · Tours typically depart 8:30-9am from Florence. Eat before departure.
Estate lunch or packed picnic in the vineyards
Tuscan · $30 · Many tours include lunch at the estate. If not, a picnic of local cheeses, salume, and bread eaten in the vineyards is the obvious alternative.
Florence trattoria dinner
Tuscan · $45 · A full Tuscan dinner — pappardelle al cinghiale, bistecca or a secondo di carne, and a riserva from a producer you visited today.
WSET Theory Session and Florence Galleries
Tuesday, October 5
Est. spend
$291
per person
🌅 Morning
WSET Level 2 Theory Session at Florence Wine School
Florence wine school — confirmed at booking (search WSET approved providers at wsetglobal.com/find-a-course)
A structured half-day (3-4 hour) wine theory session at a Florence-based WSET approved programme provider. WSET Level 2 covers: understanding and describing wine, grape varieties and wine styles, main wine regions of the world, and the WSET Systematic Approach to Tasting. Italian wines receive particular emphasis given the location.
If you intend to complete the full WSET Level 2 award, the written exam is typically sat at the end of a full course — check whether the school offers a stand-alone theory and tasting session without examination, which is appropriate for educational tourism purposes.
Practical tasting component of the session
At the wine school
The WSET theory session includes a structured tasting using the SAT framework: 8-12 wines across styles and origins. For an Italian wine focus, this typically covers a Pinot Grigio, a Soave, a Chianti Classico, a Barolo or Barbaresco, a Brunello or Rosso di Montalcino, a Prosecco, and a Vin Santo — a structured tour of Italian wine.
Use the SAT format for every wine you taste this week — appearance, nose, palate, conclusion. The discipline of systematic note-taking produces far more retained learning than informal tasting.
☀️ Afternoon
Uffizi Gallery
Piazzale degli Uffizi 6, 50122 Florence
Florence's greatest museum: Botticelli's Birth of Venus and Primavera, Raphael's Madonna of the Goldfinch, Leonardo's Annunciation. Pre-book timed entry — October queues are 2-3 hours without booking.
The Botticelli rooms (10-14) are the destination. Spend 30 minutes in front of the Primavera — the composition repays close attention. The same patience that characterises good wine tasting applies to Renaissance paintings.
Boboli Gardens
Piazza de' Pitti 1, 50125 Florence
The formal Medici garden behind the Palazzo Pitti — a terraced hillside with long avenues, grottos, fountains, and views across Florence to the north. An hour of walking through formal Italianate garden design provides a visual rest after the museums.
The Boboli ticket also covers the Palazzo Pitti state apartments and the Costume Gallery — useful if weather deteriorates.
🌙 Evening
Frescobaldi Wine Bar — Tuscan producer flagship bar
Piazza della Signoria 5 (or check current address), Florence
The Frescobaldi family has produced wine in Tuscany for 700 years. Their Florence wine bar on Via dei Magazzini offers by-the-glass access to their full range: Mormoreto (Super Tuscan), Nipozzano riserva (Chianti Rufina), Luce della Vite (Montalcino), and Castelgiocondo Brunello. An evening of producer-focused structured tasting.
Order a 3-wine flight comparing the Nipozzano riserva (Chianti Rufina), Mormoreto (IGT), and Castelgiocondo Brunello — three price and quality points from the same producer family demonstrates how winemaking decisions differ across a portfolio.
🍽️ Meals
Breakfast before wine school
Italian · $5 · Do not eat a large breakfast before a morning wine tasting — it diminishes your palate sensitivity. Espresso and a light pastry is appropriate.
Light lunch after wine school
Italian · $18 · After a morning of tasting, a lighter lunch is appropriate before the afternoon galleries. Bruschetta, a salad, a bowl of pasta.
Frescobaldi wine bar dinner
Tuscan · $55 · A wine-led dinner at a producer flagship bar — food plays a supporting role tonight.
Day Trip to Montepulciano and San Gimignano
Wednesday, October 6
Est. spend
$275
per person
🌅 Morning
Drive to Montepulciano (1.5 hours from Florence)
Montepulciano, Province of Siena, Tuscany, Italy
Montepulciano sits on a ridge at 605 metres in the Val di Chiana — one of the most dramatically situated hill towns in Tuscany, and the home of Vino Nobile di Montepulciano DOCG. Arrive early to avoid the tour bus peak that hits the town from 11am.
Rent a car for this day trip — public transport to Montepulciano requires a train to Chiusi then a connecting bus, and the day trip becomes logistically complex. A rental car gives freedom to stop at a Brunello estate on the way through Montalcino territory.
Vino Nobile di Montepulciano Tasting and Cantina Tour
Cantina Contucci: Palazzo Contucci, Piazza Grande, Montepulciano | Avignonesi: Via Colonica 1, Valiano
Vino Nobile is made from Sangiovese (locally called Prugnolo Gentile) — a close relative of the Chianti Sangiovese clones, aged a minimum 2 years in oak and bottle. The style is typically more structured and earthy than Chianti Classico. A cantina tour at one of the town's established producers: Avignonesi, Poliziano, or Contucci (cellars beneath the main piazza).
Contucci's cantina is directly beneath Piazza Grande — their cellars have been continuously producing wine since the 16th century. The combination of medieval cellar architecture and vertical tasting makes this one of the most impressive winery visits in Tuscany.
☀️ Afternoon
Lunch in Montepulciano's medieval centre
Piazza Grande area, Montepulciano, 53045
Lunch in one of the restaurants on or near Piazza Grande — at altitude, with views across the Val di Chiana. The local cuisine pairs naturally with Vino Nobile: pici with wild boar, grilled Chianina beef, hand-made pasta with pecorino.
Order the local Vino Nobile by the glass with lunch — the comparison between the winery tasting version and the restaurant version (served slightly warmer, in a different glass) is an instructive exercise.
San Gimignano — Medieval Towers and Vernaccia di San Gimignano
San Gimignano, Province of Siena, Tuscany, 53037
A 45-minute drive west from Montepulciano, San Gimignano's 14 medieval towers (once 72) make one of the most recognisable skylines in Tuscany. The town is also home to Vernaccia di San Gimignano DOCG — Italy's first DOC appellation (1966), a textural white wine very different from the reds you've been studying.
Taste a Vernaccia di San Gimignano at one of the town's wine shops — the contrast with Chianti and Vino Nobile illustrates how dramatically different wines from the same regional Italian climate can be.
🌙 Evening
Return to Florence and wine dinner at a Chianti-focused restaurant
Florence historic centre
Return to Florence in the late afternoon. Dinner at a restaurant with a serious Chianti Classico and Super Tuscan list — a Sassicaia or Ornellaia evening if budget permits, or a deep dive into smaller-producer Chianti Classico Gran Selezione bottles.
Super Tuscans (Sassicaia, Ornellaia, Tignanello, Masseto) are Bordeaux-variety blends that sit outside the DOCG appellation system as IGT Toscana — their quality and prices challenge Burgundy and Bordeaux. Understanding why they exist outside the appellation system is one of the most interesting Italian wine regulatory stories.
🍽️ Meals
Early breakfast before departure
Italian · $5 · Depart Florence early — aim to be at Montepulciano by 10am.
Lunch in Montepulciano near Piazza Grande
Tuscan · $35 · A sit-down lunch with Vino Nobile by the glass. Allow 90 minutes — the view and the wine deserve time.
Florence wine dinner
Tuscan · $65 · A longer dinner focused on Super Tuscan exploration. Ask the sommelier to recommend a Super Tuscan at two price points — the entry level and the prestige offering.
Blind Tasting, Free Afternoon, and Farewell Dinner
Thursday, October 7
Est. spend
$575
per person
🌅 Morning
Comparative Blind Tasting Session — Barolo, Brunello, and Super Tuscan
At the wine school or at a specialist enoteca willing to run a structured tasting
The week's most demanding tasting session: three premium Italian reds presented blind. Barolo (Nebbiolo from Piedmont), Brunello di Montalcino (Sangiovese Grosso from Montalcino), and a Super Tuscan (Cabernet Sauvignon/Merlot blend). The exercise tests accumulated sensory knowledge: identifying grape variety, structure (tannin levels, acidity), and origin from the glass alone.
Approach the blind tasting with methodical SAT note-taking rather than trying to identify wines immediately. Work through appearance, nose, and palate systematically before drawing any conclusions. The structure of Italian tannins (Nebbiolo's grip, Sangiovese's dryness, Cabernet's density) is the most reliable differentiator.
Tasting debrief and note comparison
At the wine school or enoteca
After the reveals, a structured debrief comparing your notes to the sommelier's: what you identified correctly, what you confused, and why. The post-tasting analysis is as educationally valuable as the tasting itself.
Do not be discouraged if you misidentify wines in blind tasting — experienced sommeliers with decades of training make mistakes. The value is in developing the systematic vocabulary, not in the score.
☀️ Afternoon
Free afternoon in Florence — personal choice
Florence historic centre
A deliberately unscheduled afternoon before the farewell dinner. Options: Accademia Gallery (Michelangelo's David), the Bargello National Museum (Renaissance sculpture), the Brancacci Chapel (Masaccio frescoes), or simply walking through the city at a slower pace than the rest of the week has allowed.
The Bargello is frequently overlooked in favour of the Uffizi — its collection of Donatello's bronzes and Michelangelo's Bacchus is extraordinary and queues are far shorter.
Last wine shop visit — final wine purchases for home
Enoteca Murgia (Via Ghibellina) or Buca Mario wine shop, Florence
A final visit to a specialist wine shop for bottles to take home: a Chianti Classico Gran Selezione from an estate visited this week, a Brunello di Montalcino from a good producer, and possibly a Vin Santo with cantuccini. These are wines you now understand — the education contextualises the purchase.
Wines travel well in checked luggage if padded properly — a wine travel bag (available in wine shops) holds 6 bottles safely. Check your airline's alcohol allowance in checked baggage.
🌙 Evening
Five-Course Wine-Paired Farewell Dinner
Ristorante Buca Mario (Piazza Ottaviani 16) or Enoteca Pinchiorri (Via Ghibellina 87), Florence
The week's summation: a five-course dinner at a Florence restaurant with a sommelier-curated Italian wine pairing. Each course paired to a different wine — Prosecco with antipasto, Vernaccia with seafood primo, Chianti Classico riserva with pappardelle al cinghiale, Brunello with bistecca, Vin Santo with cantucci. A structured final application of everything learned this week.
Enoteca Pinchiorri is Florence's only three-Michelin-star restaurant — a fitting finale for a wine-education week if budget allows. Request a sommelier pairing menu at booking. For a more intimate option, several smaller Oltrarno restaurants offer excellent sommelier pairing dinners without the ceremony.
🍽️ Meals
Light breakfast before tasting session
Italian · $5 · Minimal food before the blind tasting — a clear palate is important. Espresso and water only, no milk or strong-flavoured foods in the 60 minutes before the session.
Post-tasting recovery lunch — something simple
Italian · $15 · After 2+ hours of tasting, something neutral and grounding. Plain pasta, bread, mineral water. Preserve your appetite for the evening's five-course dinner.
Five-course wine-paired farewell dinner
Tuscan · $180 · The week's centrepiece dinner. Budget generously — this is the evening that makes sense of every tasting note you took this week.
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