Florence in 1 Day for Couples - Guided walking tour of Siena (Piazza del Campo & Siena Cathedral)
In Collaboration with Ranieri Tour Operator - Montecatini Terme. Updated on February 3, 2026.
Full-day, coach-led discovery of Siena, a family-run Chianti wine estate for a three-course lunch with wine pairing, scenic San Gimignano, and the Piazza dei Miracoli in Pisa — designed for couples who want culture, rolling-hill views and intimate wine moments.
This itinerary was created in collaboration with Ranieri Tour Operator - Montecatini Terme, inspired by the tour A special day in Tuscany: Pisa, Siena and San Gimignano from Florence. Please check the tour information during your booking process.
Highlights
- Guided walking tour of Siena (Piazza del Campo & Siena Cathedral)
- Three-course Tuscan lunch with wine tasting at a countryside estate
- Panoramic viewpoint and romantic stroll in San Gimignano
- Photo stop and free time at Piazza dei Miracoli — Leaning Tower of Pisa
- Sunset return drive across the Chianti hills
Itinerary
Day 1
One-day curated route using the Bokun agenda: meet in Florence, guided Siena visit, wine estate lunch & tasting, San Gimignano viewpoint and stroll, Piazza dei Miracoli in Pisa, return to Florence at sunset.
Meet at Piazzale Montelungo (Tours & News kiosk) — check-in
Arrive early to check in at the Tours & News kiosk. This is the official meeting point — a short walk from Santa Maria Novella train station. The guide will confirm names and hand out any printed materials before boarding.
Tips from local experts:
- Aim to arrive at least 20 minutes early — it’s the busiest morning meeting point; a quick coffee at the kiosk helps set the mood.
- Ask for a coach seat on the left when boarding for the most scenic Chianti views later in the day.
- Keep shoulders and knees covered if you plan to enter Siena Cathedral later — bring a light scarf for quick cover-up.
Drive Florence → Siena (scenic Chianti route)
Relax on the fully-fitted coach while your escort introduces highlights of the region and the history of Siena.
Tips from local experts:
- Sit on the left side of the coach for rolling-vineyard views and early photo ops of the Chianti hills.
- Use this quieter transfer time for a short nap — it keeps you fresh for the walking tour and romantic lunchtime.
- Carry a small pack with water, sunglasses and light layers — mornings can be cool in September, afternoons warm.
Guided walking tour — Piazza del Campo & highlights of Siena
Local guide-led walk from Piazza del Campo through historic streets, finishing at Siena Cathedral. Learn the stories behind the Palio, Gothic architecture and secret corners ideal for couples.
Tips from local experts:
- Stand together on the lower edge of Piazza del Campo for a classic wide-angle photo — best with morning light.
- If you want to enter the Duomo, plan to wear modest clothing; cathedral entry is optional and may have a separate fee.
- Ask your guide for a quiet café recommendation near the Campo for a post-tour espresso or shared pastry.
Transfer Siena → Chianti wine estate (countryside drive)
Short coach transfer through vine-draped hills to a family-run Chianti estate where your lunch and tasting await.
Tips from local experts:
- Keep your camera ready for hillside vistas — small unplanned stops sometimes appear and make for romantic photos.
- If you prefer a quieter table at the estate, mention it to the guide on the coach (they can request seating together).
- Use the time to change into light layers; estate dining often uses outdoor or semi-covered settings in pleasant September weather.
Three-course Tuscan lunch + wine tasting at Tenuta Torciano (wine estate)
Relax at a charming family-run estate: three-course Tuscan lunch paired with a tasting of local Chianti wines — a true romantic highlight and the special moment of the day.
Tips from local experts:
- Ask to taste the estate's riserva or a dessert wine as a toast — the sommelier can suggest a pairing for the dessert course.
- Request a window or terrace seat when you arrive for valley views and a more intimate experience.
- If you have dietary needs, notify the guide before arrival — family estates are usually flexible with advance notice.
Short transfer to San Gimignano — scenic approach
A brief 15-minute drive brings you to the medieval hilltop village; enjoy the first panorama as you approach the ramparts.
Tips from local experts:
- If the group is split, move together off the coach at the viewpoint for a private photo moment.
- Hold hands while walking the ramparts — cobbles can be uneven; comfortable footwear is recommended.
- Save a small souvenir budget for an artisan shop — a locally made alabaster or honey jar is a sweet keepsake.
San Gimignano viewpoint & free stroll — Rocca & Piazza della Cisterna
Visit the panoramic viewpoint (Rocca di Montestaffoli) for sweeping Tuscan vistas, then enter through the gates to wander Piazza della Cisterna and the maze of artisan streets — free time to explore and shop.
Tips from local experts:
- Plan a shared gelato from a local gelateria in Piazza della Cisterna and enjoy it together on a bench.
- For a quieter photo, climb slightly up from the main square toward the Rocca ruins where views are less crowded.
- If you want a romantic memento, look for a small balsamic or saffron shop — local producers often give tasting tips.
Transfer San Gimignano → Pisa (coastal-bound drive)
Coach ride toward Pisa; enjoy continued commentary from your escort about regional history and upcoming photo opportunities.
Tips from local experts:
- Sit on the right side of the coach for the best late-afternoon light as you cross the countryside toward Pisa.
- Use this quieter portion to coordinate evening plans back in Florence (dinner suggestions, taxis).
- Charge your phone now — the Piazza dei Miracoli is a prime moment for couples’ photography.
Pisa — Piazza dei Miracoli, photos & optional Leaning Tower climb
Arrive at the iconic Square of Miracles. Time to admire the Cathedral, Baptistery and Monumental Cemetery — and, if lines permit, ascend the Leaning Tower for panoramic views.
Tips from local experts:
- For the best couple photo with fewer people, walk a short distance around the Campo to frame the tower against the Arno-side rooftops.
- If you both wish to climb the tower, ask the guide to check availability early — tickets and slots can sell out.
- Keep an eye on opening times and dress modestly if you plan to enter the cathedral; a wrapped shawl works well and is romantic too.
Return transfer Pisa → Florence — golden-hour drive
Relax on the coach and enjoy the sunset over the Tuscan hills. This final leg is a perfect time to reflect on the day and toast with a small bottle from the estate if you purchased one.
Tips from local experts:
- Ask the coach driver to pull slightly to the scenic side if conditions allow — golden-hour light often appears on the left when returning to Florence.
- Play a short playlist together — simple music turns the coach into a private closing moment.
- If you bought wine at the estate, store it carefully in your luggage or ask the guide for safe-transport advice for the coach ride home.
Arrive back at Piazzale Montelungo, Florence — tour ends
End of service at the original meeting point. The guide will say farewell and provide any last-minute tips for dinner or a romantic evening in Florence.
Tips from local experts:
- If you want to continue the romance, walk 10 minutes to a rooftop bar in Florence (ask the guide) for a nightcap.
- Arrange a late dinner reservation in advance for a seamless evening — many small Florence restaurants book quickly in September.
- Collect any purchases or wine from the coach before leaving; the guide will usually assist with larger items.
Itinerary Attributes
| Days | 1 |
| Highlights | 5 |
| Season | - |
| Month | - |
| Persona | Couples |
| Transfers | 5 |
| Restaurants | 1 |
| Total Activities | 6 |
| Total Places | 6 |
| Activities Types | Neighborhood, Transfer, Culture, Meal, Attraction |
