PRIVATE Full-Day Siena, San Gimignano & Chianti (Romantic Couples) from Florence
Private 8–9 hour door-to-door tour from Florence visiting Siena, Monteriggioni, the Chianti countryside (optional winery lunch) and San Gimignano — tailored for couples with romantic moments, scenic photo stops and a relaxed pace.
In Collaboration with UNIQUETUSCANY private tours. Updated on February 13, 2026.
This itinerary was created in collaboration with UNIQUETUSCANY private tours, inspired by the tour PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence. Please check the tour information during your booking process.
Highlights
- Piazza del Campo, Siena
- Siena Cathedral (Duomo)
- Medieval walls of Monteriggioni
- Scenic Chiantigiana drive & winery lunch (optional)
- San Gimignano towers & Gelateria Dondoli
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Itinerary
Day 1
Private pickup in Florence at 09:00. Full-day private minivan tour through the Chianti hills with time to explore Siena, Monteriggioni, an optional winery lunch and San Gimignano — designed for couples with relaxed pacing and at least one special moment (vineyard toast / lunch terrace).
Pick-up: Florence city centre (meeting point) — meet driver
Meet your licensed English-speaking driver at a central Florence meeting point for a quick briefing and boarding. The driver will confirm your preferences (winery lunch or Monteriggioni stop) and phone contact.
Tips from local experts:
- Have your phone on and share the mobile number you provided at booking; drivers may message on WhatsApp if traffic alters pick-up timing.
- If you prefer a very private start, ask your driver to meet you at your hotel address — they can pick up from most central Florence hotels.
- Bring a light jacket in May — mornings can be crisp in the van before the heat of the day.
Scenic drive along the Strada del Chiantigiana (photo stop)
Begin your journey north with a scenic drive through the Chianti hills on the SS222 (Chiantigiana). Short roadside stop for photos of rolling vineyards and cypress-lined lanes.
Tips from local experts:
- Ask your driver for the best short photo angle — they know quieter overlooks away from coaches.
- For a romantic shot, request the driver to stop at a vineyard gate with rolling rows and hills in the background (perfect golden-hour framing later in spring).
- If you feel a chill on the hilltops in May, the driver can park where there’s a short walk with minimal steps — ideal for couples wanting a quick, private photo.
Piazza del Campo — Siena’s shell-shaped square (stroll & photos)
Arrive in Siena’s historic center. Enjoy an unhurried walk in Piazza del Campo — soak in medieval atmosphere and sit for a coffee if you wish. Great spot for couple photos on the curved brick surface.
Tips from local experts:
- Aim to arrive mid-morning to avoid the largest crowds and get a quieter corner of the piazza for photos.
- Sit at a café terrace facing the square for a 10–15 minute espresso together — a small, romantic pause.
- Watch your step on the sloped piazza; there are benches and shaded arcades if you want a brief sit-down between strolls.
Duomo di Siena (Cathedral of Santa Maria Assunta) — exterior & optional interior visit
Explore the magnificent Gothic Duomo (optional entrance). Admire striped marble facades and the ornate interior. Your driver can advise on skip-the-line ticketing or a licensed local guide if you want deeper art history context.
- Monday10:30 AM – 5:00 PM
- Tuesday10:30 AM – 5:00 PM
- Wednesday10:30 AM – 5:00 PM
- Thursday10:30 AM – 5:00 PM
- Friday10:30 AM – 5:00 PM
- Saturday10:30 AM – 5:00 PM
- Sunday1:30 – 5:00 PM
Tips from local experts:
- If you want to enter the Duomo, pre-booking tickets or asking the driver to arrange a timed entry saves queue time — interiors can be chilly, so bring a light wrap.
- Couples should head to the cathedral terrace (if open) for a quieter vantage point and a lovely photo backdrop of Siena rooftops.
- Wear shoes with good grip — the Duomo steps and nearby lanes are stone and can be uneven.
Drive to Monteriggioni (short scenic stop at the medieval wall)
Short drive from Siena to the small walled village of Monteriggioni. Enjoy a leisurely 25–40 minute walk along the fortress wall and narrow lanes — a romantic, storybook setting.
- Monday11:00 AM – 10:00 PM
- TuesdayClosed
- Wednesday11:00 AM – 10:00 PM
- Thursday11:00 AM – 10:00 PM
- Friday11:00 AM – 10:00 PM
- Saturday11:00 AM – 10:00 PM
- Sunday11:00 AM – 10:00 PM
Tips from local experts:
- The fortress walls make a charming quick visit; climb a short section for panoramic countryside photos (some steps involved).
- If you prefer more time at a winery instead, note that choosing the full winery lunch usually replaces the Monteriggioni stop — confirm with your driver.
- There are small cafes by the walls where you can share a light snack and a glass of prosecco if you want an impromptu toast.
Drive to a Chianti winery / farmhouse — countryside transfer
Head deeper into Chianti to a family-run organic winery (example venue: Tenuta Casanova or similar boutique estate). This short transfer brings you to the lunch/tasting location.
Tips from local experts:
- Confirm with the driver before departure whether you chose the optional full lunch (recommended for couples) — the winery meal is the day’s special moment.
- If you booked the winery lunch, let them know any dietary requests now so the estate can prepare — they often accommodate vegetarians and allergies with notice.
- Keep your camera handy for roadside olive groves and vineyard rows — the driver can pause briefly for romantic photos.
Optional Full Lunch & Wine Tasting at an organic winery (special romantic moment)
Optional multi-course Tuscan lunch at a boutique family-run winery. Enjoy typical regional dishes paired with Chianti Classico and Super Tuscans — the winery terrace provides views and a private, romantic atmosphere.
- Monday9:00 AM – 5:00 PM
- Tuesday9:00 AM – 5:00 PM
- Wednesday9:00 AM – 5:00 PM
- Thursday9:00 AM – 5:00 PM
- Friday9:00 AM – 5:00 PM
- Saturday9:00 AM – 5:00 PM
- Sunday9:00 AM – 5:00 PM
Tips from local experts:
- This is the day’s romantic 'special moment' — request a table on the terrace for vineyard views and a quiet, intimate meal.
- Wine pairings are local and often include a tasting of three wines; ask the sommelier to recommend a lighter pairing if you prefer to continue afternoon exploring.
- Plan about €60–€70 per person (payable locally) — bring cash or card; confirm any dietary restrictions at booking to ensure a tailored menu.
Drive to San Gimignano (transfer)
Short scenic transfer to the walled hill town of San Gimignano — known for its medieval towers and panoramic views. Relax in the van and enjoy countryside scenery.
Tips from local experts:
- Use the drive time to chat with your driver about the best viewpoint in San Gimignano for sunset photos and romantic shots.
- If you skipped the winery lunch, you’ll have extra time in San Gimignano — consider paying a short visit to a local wine bar for an aperitivo together.
- Keep a light layer handy: hilltop breezes can be cool in May when walking the town ramparts.
San Gimignano centre: towers, streets & Gelateria Dondoli
Wander the medieval lanes, admire the towers and enjoy gelato at the famous Gelateria Dondoli (award-winning). Free time for shopping, photos and a relaxed stroll around Piazza della Cisterna.
- 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:
- For a romantic treat, share a scoop (or two) of local saffron or Vernaccia gelato at Gelateria Dondoli — Piazza della Cisterna is a picturesque backdrop.
- Climb a short tower or head to the town walls for sunset-facing views if it’s early evening — the skyline is especially flattering for couple photos.
- San Gimignano’s boutiques sell local saffron, Vernaccia wine and ceramics — pick a small souvenir to remember the day.
Return to Florence — relaxed drive back and drop-off
After a full day, unwind on the drive back to Florence. Your driver will drop you at your hotel or agreed city centre address and can suggest dinner spots if you want an evening dinner in town.
Tips from local experts:
- If you’d like a scenic finish, ask the driver to detour briefly to Piazzale Michelangelo for a panoramic Florence view before drop-off (adds ~20 minutes).
- Confirm your preferred drop-off address with the driver after San Gimignano so timing is precise.
- Tip guideline: 10–15% of the tour price is appreciated for a private driver-guide who delivered a personalized day.
Itinerary Attributes
| Days | 1 |
| Highlights | 5 |
| Season | - |
| Month | - |
| Persona | Couples |
| Transfers | 4 |
| Restaurants | 1 |
| Total Activities | 6 |
| Total Places | 6 |
| Activities Types | Transfer, Outdoor, Attraction, Culture, Meal, Neighborhood |
Why this experience
Leave Florence behind for a day and enter Tuscan legend. You'll be chauffeured through rolling vineyards to Siena, where you'll explore the gothic Piazza del Campo and Cathedral at your own pace, then to medieval San Gimignano — a fortress of stone towers rising from the hills — before finishing in Chianti wine country. Your private driver navigates the winding roads; you sit back with your partner and watch the landscape change.
This is the escape that couples dream about: no group tour, no set schedule, no rushing between stops. Your driver can pause at a viewpoint, wait while you explore a church or shop, and know exactly where to take you for the best light and the quietest corners.
Before you go
- Best time: Spring or autumn — perfect driving weather, vineyard colors, and comfortable temperatures for exploring medieval towns
- Budget: Check the booking widget for current tour pricing. Budget extra for lunch, wine tastings, and any shopping in San Gimignano or Chianti.
- Difficulty: Easy — you're driven the entire day; walking is at your own pace in towns
- What to bring: Comfortable walking shoes, camera, light jacket, sunscreen, water bottle, cash for tastings and lunch
- Getting there: Pickup from your Florence hotel or a central meeting point; confirm details with the operator when booking
- Accessibility: The driver will assist with mobility needs; inform the operator in advance if you need step-free routes or frequent rest stops
Frequently asked questions
How long is the drive to each town, and will there be a lot of time in the car? Total drive time is roughly 2–2.5 hours spread across the day. You'll spend approximately 1.5–2 hours in Siena, 1.5–2 hours in San Gimignano, and 1–1.5 hours in Chianti. The drives are scenic — you'll pass vineyards and rolling hills, not highways.
What's included — do we need to book restaurants or tastings in advance? This varies by operator. Some include a lunch reservation and winery visit; others let you choose. Confirm what's arranged when you book, and the driver can recommend restaurants and wineries if you want flexibility.
Can we visit specific wineries or restaurants, or does the driver choose? Your driver knows the best options and can take you to your preferences. If you have a specific winery or restaurant in mind, mention it when you book, and the driver will arrange the timing.
What's included in this itinerary? This itinerary on TheNextGuide is free to read and follow at your own pace. The full-day private car service, driver, and transportation between Florence, Siena, San Gimignano, and Chianti is the bookable experience. Meals, wine tastings, and entry fees to towns are typically your own cost unless otherwise specified.
Complete your trip in Florence
Round out your romantic escape with these experiences:
- Golf cart tour through panoramic hills — Scenic hills and sunset at Piazzale Michelangelo
- Chianti wine tour with two wineries and San Gimignano — Another Chianti option focused on wine tastings
- Exclusive Cinque Terre day trip — Coastal villages and train rides for a different landscape
Browse all Florence itineraries at TheNextGuide.
Last updated: April 2026
