#14 in Top 20 Tuscany for An Anniversary · ★★★★★
Castello di Spaltenna
A 37-room medieval monastery-turned-castle above Gaiole in Chianti, with a Michelin-starred restaurant, an infinity pool, and views over the vineyards.
A 37-room medieval monastery-turned-castle above Gaiole in Chianti, with a Michelin-starred restaurant, an infinity pool, and views over the vineyards.
"A 37-room medieval monastery-turned-castle above Gaiole in Chianti, with a Michelin-starred kitchen and an infinity pool over the vineyards. A romantic, distinctly old-world base for two; just bring a car and don't expect contemporary slickness."
Castello di Spaltenna works for an anniversary because it delivers the storybook version of Chianti without feeling like a film set: a real medieval monastery that became a castle, perched on a ridge just above the village of Gaiole in Chianti. There are 37 rooms split between the castle keep and the restored hamlet around it, decorated in a traditional Tuscan key with canopy or wrought-iron beds and antique wood. The romance here is the setting and the food rather than gadgetry: the kitchen, Il Pievano, has held a Michelin star since 2017, and there are two pools, including an infinity pool that looks straight out over the vineyards, plus a spa with a heated indoor pool. Manage your expectations on two fronts. Many of the rooms began life as monks' cells, so some are genuinely snug and the style is old-world rather than contemporary; and the location, while gorgeous, is rural Chianti, which means you will want a car to reach the wineries and the nearby towns. For a couple who want a centuries-old castle, a serious dinner, and long slow days among the vines, it is one of the most atmospheric anniversary bases in the region.
Ask for a room or junior suite in the main castle keep, where you get the valley views and a bit more space. Be specific that you want one of the larger rooms: several of the entry-level rooms are converted monks' cells and can feel tight for a celebratory stay.
Reserve a table at Il Pievano well ahead for the anniversary dinner, since the Michelin-starred room is small. Time a swim in the infinity pool for late afternoon when the light drops over the vineyards, and rent a car so you can actually use the Chianti wine roads around Gaiole.
Castello di Spaltenna sits within our broader Top 20 Hotels in Tuscany for an Anniversary list. It scored an aggregate 9.3/10 across the three editorial criteria, competitive against the field but, on an anniversary-specific factors, the angle above is what earned its rank. For the alternatives in the same Tuscany neighbourhood, see Gaiole in Chianti (Chianti) and adjacent. For a different city entirely, see the related lists below.
If the dates are locked in, secure the room around the three-month mark. Rooms with the coveted orientation are claimed first, while popular-month availability runs out months in advance. The plunge-pool and terrace suites, the categories that justify this ranking, tend to sell out before anything else.
A ranked shortlist, a special offer worth booking, and the overpriced stay to skip. Straight from the editors.