Villa Cicolina

Tucked away in the rolling hills of Tuscany, Villa Cicolina has evolved from its medieval origins into a delightful boutique hotel. With sweeping views over the countryside, it offers attentive, tailor-made service that promises a memorable escape.

Just a stone’s throw from Montepulciano, this former noble family’s hideaway still exudes old-world charm through its period furnishings, original artwork, and ornately painted ceilings. Wander through the expansive private grounds, which meander down to a quaint chapel, while the garden’s pool-with-a-jacuzzi sits nestled among olive groves.

The property is full of airy, open corners ideal for unwinding with a good book. Be sure to explore the cellar, where an impressive array of wines and olive oil awaits, then treat yourself to a four-course dinner featuring authentic Tuscan dishes at the on-site restaurant.

Guest accommodations span the ground, first, and second floors, with additional rooms housed in standalone cottages that come with their own private gardens. Complimentary Wi-Fi and a free internet station are available in the lobby.

What stands out for couples is the setting—they’ve given it a glowing 9.7 rating for two-person stays.