Chianti Wine Tour from Florence to San Gimignano with 2 Wineries (Private, Couples)
Private 7.5-hour chauffeured tour from Florence—start with panoramic views at Piazzale Michelangelo, visit medieval San Gimignano, enjoy two intimate winery visits (Sant'Appiano area + Castello di Verrazzano) with optional lunch and tastings, then return to Florence. Designed for couples seeking a relaxed, romantic day in Chianti.
In Collaboration with Limousine tour in chianti. Updated on February 13, 2026.
This itinerary was created in collaboration with Limousine tour in chianti, inspired by the tour Chianti Wine Tour from Florence to San Gimignano with 2 Wineries. Please check the tour information during your booking process.
Highlights
- Private driver in a Mercedes-Benz vehicle
- Piazzale Michelangelo panoramic viewpoint
- Walking time in medieval San Gimignano
- Two winery visits with tasting options (Sant'Appiano + Castello di Verrazzano)
- Scenic drive along the Chiantigiana (SR222) vineyards
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Itinerary
Day 1
A relaxed, romantic day: meet at Piazzale Michelangelo, visit San Gimignano, enjoy two intimate winery visits with optional lunch and tastings, then return to Florence.
Meet & Sunrise View — Piazzale Michelangelo
Meet your private driver at Piazzale Michelangelo for a sweeping morning view over Florence and the Arno. Light photoshoot opportunity to begin your romantic day.
Tips from local experts:
- Arrive a few minutes early to claim a quiet spot on the terrace for photos of the couple with the Duomo in the background.
- Bring a light scarf or shawl for September mornings—golden-hour light is lovely but there's often a breeze.
- There are limited kiosks nearby; if you want espresso before leaving, pick it up here — otherwise your driver will have bottled water on board.
Scenic Drive: Florence → San Gimignano (Private transfer)
Relax in your air-conditioned private vehicle while your driver takes the scenic route through the Tuscan hills toward San Gimignano. Use the time to plan the day's photos and ask your driver for local anecdotes.
Tips from local experts:
- Sit on the window side facing the hills for the best vineyard views—ask the driver to pause briefly for photos if a viewpoint appears.
- Download offline maps before leaving Florence if you want to follow the route or stop for spontaneous photos.
- If you prefer quieter travel, request soft music in advance — perfect for a relaxed, romantic ride.
Explore Medieval San Gimignano — Piazza della Cisterna & Towers
Wander hand-in-hand through the narrow lanes and medieval squares. Highlights include Torre Grossa (view if you wish), Piazza della Cisterna, and the charming shops—ample photo opportunities.
- MondayOpen 24 hours
- TuesdayOpen 24 hours
- WednesdayOpen 24 hours
- ThursdayOpen 24 hours
- FridayOpen 24 hours
- SaturdayOpen 24 hours
- SundayOpen 24 hours
Tips from local experts:
- Head straight to Piazza della Cisterna to secure classic tower-front photos before mid-day crowds build.
- Choose a quiet trattoria terrace for a quick gelato break — look for spots overlooking the towers for extra romance.
- Cobblestones can be uneven; wear comfortable shoes and leave high heels for dinner. Take brief rests on shaded benches for slower-paced enjoyment.
Transfer: San Gimignano → Sant'Appiano winery (Barberino Val d'Elsa)
Short drive to the first winery near Barberino Val d'Elsa for a cellar visit and optional lunch with wine tastings. The cellar here frequently offers guided tours and seating overlooking the vineyards.
Tips from local experts:
- If you want a quieter, more private lunch experience, tell the driver to request a quieter table or a terrace seat when confirming the visit.
- Carry a light sunhat for the short walk from the parking area to the vineyard terrace—September sun is warm but pleasant.
- Confirm the winery’s tasting & lunch options on arrival (tastings typically 30€; lunch + tasting 50–60€ per person as noted).
Winery Visit & Optional Lunch — Sant'Appiano (cellar tour & 7-wine tasting option)
Guided cellar tour showing winemaking processes, followed by an intimate tasting of local wines. Option to upgrade to a full lunch with multiple wine pairings (pay locally). Perfect for couples who enjoy relaxed, flavorful meals together.
Tips from local experts:
- Book the lunch/tasting on arrival (or in advance if you prefer certainty); ask for a table with vineyard views for a memorable meal.
- Ask the host to recommend one local bottle to take home as a keepsake—many wineries offer small shipping services for visitors.
- Request smaller pours if you both want to taste more varietals without feeling overly tipsy; sip slowly and pair with local cheeses for the most romantic experience.
Transfer: Sant'Appiano → Castello di Verrazzano (Greve in Chianti)
Short scenic drive deeper into Chianti toward a historic castle estate. Time to relax and enjoy rolling vineyards en route to your second tasting.
Tips from local experts:
- Ask the driver to pause briefly on the SR222 (Chiantigiana) if you want photos of the classic cypress-lined vistas.
- Carry a light cardigan—castle cellars can be cool even on warm September afternoons.
- If you’re celebrating something special, let the tour operator know in advance—many estates will arrange a small surprise (flowers, special corkage) if requested.
Castello di Verrazzano — Private Tasting & Romantic 'Special Moment'
Enjoy a castle estate tasting and a guided walk among vines. This is the day's 'special moment'—a curated tasting paired with views across Chianti and a private photo opportunity in the vineyard.
- Monday10:00 AM – 5:00 PM
- Tuesday10:00 AM – 5:00 PM
- Wednesday10:00 AM – 5:00 PM
- Thursday10:00 AM – 5:00 PM
- Friday10:00 AM – 5:00 PM
- Saturday10:00 AM – 5:00 PM
- Sunday10:00 AM – 5:00 PM
Tips from local experts:
- Request the vineyard photo spot during booking so the staff can suggest the best angle and light—perfect for a couples portrait.
- Opt for estate labels in the tasting to experience classic Chianti Classico—ask the sommelier for a recommended bottle to open later.
- Take a slow stroll around the estate terraces after tasting—the quiet paths are ideal for a private conversation and sunset-hinted views in September.
Return Drive — Chianti → Florence (Drop-off)
Relax on the final scenic leg back to Florence. Your driver will drop you off in central Florence (suggested Piazza del Duomo or your hotel).
Tips from local experts:
- If you want a central drop-off, request Piazza del Duomo; for a quieter finish, request drop-off at your hotel—confirm when booking.
- Enjoy one last taste of the countryside from the vehicle—September light is often golden and makes for romantic window-side photos.
- Keep purchases (wine bottles) strapped or boxed in the car—ask your driver for padding to prevent breakage during the return trip.
Itinerary Attributes
| Days | 1 |
| Highlights | 5 |
| Season | - |
| Month | - |
| Persona | Couples |
| Transfers | 4 |
| Restaurants | - |
| Total Activities | 4 |
| Total Places | 4 |
| Activities Types | Attraction, Transfer, Neighborhood, Experience |
Why this experience
Seven-and-a-half hours in a private Mercedes with your partner, watching Tuscany change from city to vineyard to medieval fortress. You'll start with panoramic views at Piazzale Michelangelo, then drive into Chianti wine country — rolling hills of red-soil vineyards, cypress-lined roads, and the smell of earth and oak. Two winery visits give you tastings with food pairings; lunch comes slow and local. Then San Gimignano rises ahead, its stone towers cutting the sky, and you'll walk medieval streets where artisans still work.
This is wine country as romance — not a tour bus, just you, your partner, and a driver who knows where the light hits best.
Before you go
- Best time: Spring, summer (for ripe grapes), or autumn (for harvest) — avoid winter for rain and cold
- Budget: Check the booking widget for current tour pricing. Two winery visits and tastings are typically included; budget extra for lunch and any wine you want to purchase.
- Difficulty: Easy — you're driven most of the day; walking is gentle and at your pace in San Gimignano
- What to bring: Comfortable walking shoes, camera, light jacket, sunscreen, hat, water bottle, sunglasses
- Getting there: Pickup from your Florence hotel or a central point; confirm details with the operator when booking
- Accessibility: Inform the operator of any mobility needs; the driver can arrange step-free winery routes and accessible restaurants
Frequently asked questions
Will we taste a lot of different wines, or just one type? Typically two wineries with 2–3 wines tasted at each, plus food pairings. This gives you a sense of Chianti's range without overwhelming. Confirm what's planned when you book.
Is lunch included, and what's the style? Lunch is usually a traditional Tuscan multi-course meal at a local restaurant or winery. Inform the operator of dietary restrictions when booking, and they'll arrange alternatives.
How much time do we spend actually walking in San Gimignano? Plan for 1–1.5 hours to explore San Gimignano on foot — enough to climb a tower (optional), wander the piazza, browse artisan shops, and enjoy the views. The driver waits and can recommend quiet spots.
What's included in this itinerary? This itinerary on TheNextGuide is free to read and follow at your own pace. The private car service, driver, two winery visits with tastings, and the wine education are the bookable experience. Lunch and any wine purchases are typically extra.
Complete your trip in Florence
Pair wine country with other romantic experiences:
- Golf cart tour through panoramic hills — Another scenic route with sunset at Piazzale Michelangelo
- Private full-day Siena, San Gimignano and Chianti — Similar region; includes Siena Cathedral
- Evening private wine tour — Wine tastings within Florence's neighborhoods
Browse all Florence itineraries at TheNextGuide.
Last updated: April 2026
