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Occasion
Setting
Price
5 Hotels
Castello di Casole
$$$$Casole d'Elsa, Tuscany
A 10th-century Tuscan castle with 4,200 acres of vineyards and olive groves.
9.5
Forbes Five-Star
Rosewood Castiglion del Bosco
$$$$Tuscany, Italy
A timeless Tuscan sanctuary, steeped in history and surrounded by Brunello vineyards.
9.2
Forbes Five-Star 2025
Castiglion del Bosco, A Rosewood Hotel
$$$$Tuscany, Italy
This place is a big deal.
8.5
MICHELIN 3-Key
Hotel Il Pellicano
$$$$Porto Ercole, Tuscany
The original Italian dolce vita — a clifftop hideaway on the Tyrrhenian Sea.
9.5
#26 World's 50 Best Hotels 2025
Borgo Santo Pietro
$$$$Chiusdino, Tuscany, Italy
A 13th-century Tuscan hamlet transformed into one of Italy's most intimate luxury retreats.
9.4
MICHELIN 3-Key