Where to stay: Siena & Chianti

Palazzo Borghesi is in Siena; Certosa di Maggiano is outside its walls. Guardastelle is near San Gimignano, Castelfalfi is in Montaione, and Vitigliano is near Greve in Chianti.

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Fyno editorial · Updated November 5, 2026

Regional choices · Compare local stays

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Choose the actual locality

Palazzo Borghesi is in Siena; Certosa di Maggiano is outside its walls. Guardastelle is near San Gimignano, Castelfalfi is in Montaione, and Vitigliano is near Greve in Chianti. [13][8]

Plan the arrival

Use a countryside base with a car for Chianti and hill towns. Park outside historic restricted areas and walk in; arrange winery appointments without relying on an unplanned late return. [13][8]

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Find your base

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Location7 stays

01 · Castelnuovo Berardenga countryside
A resort setting east of Siena for time in the countryside.
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02 · Maggiano, outside Siena’s walls
A former monastery setting just outside the city.
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03 · Historic centre, Siena
A historic residence for Siena evenings and city walks.
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04 · Near San Gimignano, Tuscany
A wine-estate stay near San Gimignano, selected in Tuscan Adventure.
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05 · Castelfalfi, Montaione, Tuscany
A countryside resort in the municipality of Montaione.
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06 · Near Poggibonsi, Tuscany
A countryside base near Poggibonsi for a western hill-town trip.
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07 · Near Greve in Chianti, Tuscany
A countryside relais in Chianti for time away from the city.
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Curated stays are planning choices, subject to availability. Use current road and site guidance for access; pins are not a driving route.

Overnights in the saved Tuscan Adventure

Eight selected overnights, followed by a departure allowance toward Florence. The route extends into Liguria. These are source choices, not available rooms.

Day 1 · Historic centre, FlorenceHotel Milù ↗
Day 2 · Historic centre, FlorenceHotel Milù ↗
Day 3 · Riomaggiore, LiguriaThe Sunset Line ↗
Day 4 · Monterosso al Mare, LiguriaBellambra ↗
Day 5 · Near San Gimignano, TuscanyTenuta Guardastelle ↗
Day 6 · Near Montalcino, TuscanyLe Ragnaie ↗
Day 7 · Near Montalcino, TuscanyLe Ragnaie ↗
Day 8 · Near Greve in Chianti, TuscanyVilla Bordoni ↗

Read the complete saved plan →

Put the choices into a route

Compare the routes and choose the plan that fits your time.

Cinque Terre Escape3-5 days ↗Florence Escape2-4 days ↗Tuscan Adventure6-10 days ↗

Questions before you go

Are all these stays in the named town?

Palazzo Borghesi is in Siena; Certosa di Maggiano is outside its walls. Guardastelle is near San Gimignano, Castelfalfi is in Montaione, and Vitigliano is near Greve in Chianti.

Are rooms currently available?

This list compares locations. Choose dates and occupancy in each hotel guide, then confirm the final total, inclusions and terms with the booking provider.

Sources & planning notes

Fyno’s saved curation and editorial planning notes. Official planning sources checked November 5, 2026 where cited. Recheck admission, transport, seasonal operation and room terms for your dates. Map pins show locations, not a driving route.