Guardastelle

This family-owned property is a genuine working farm producing olive oil and wine, and guests can take in the views of olive groves and vineyards from the breakfast terrace and lovely gardens. Guardastelle means "star-watcher" in Italian, and the dark-night sky here fills with stars. There's a definite romance to a stay here, and the cream-colored and stone buildings throughout the property have a quintessential Tuscan charm. This is a compact property, and the main gathering place is an elegant living room space with a flat-screen TV, beige antiqued walls, floral curtains, and classical furniture. Right off of this space is a simple breakfast terrace, which is a covered area with wrought-iron furniture and white tablecloths. Guests are mainly couples and families exploring the area's vineyards, small cities, and towns. The owners, a married couple, give guests their space, though are quick to offer local guidance when needed. 

The Guardastelle is a five-minute drive outside of San Gimignano, a medieval walled town that's known for its UNESCO-designated historic center that's filled with Romanesque and Gothic architecture. Located in the province of Siena, San Gimignano is home to restaurants, wine bars, shops, and a few museums. While a walk into town may be too much for many guests, plenty of those staying here make the leisurely 30-minute stroll. The city of Siena is about 40 minutes away by car, and Florence will take 50 minutes to reach. Volterra, with its Etruscan musuem, is a 40-minute drive from the hotel, while the hill town of Montalcino -- famous for Brunello wine -- is about an 80-minute drive away. The closest major airport is Florence-Peretola, which will take 50 minutes to reach. 

Design features like exposed beams, terra cotta floors, wooden lofts, and antiqued walls lend charm to the cozy guest rooms and apartments, which are named for the owners' family members and constellations, respectively. The property's traditional rooms feel classic without being stuffy or overdone, with accents like wrought iron bed frames, sparingly used floral prints, and furniture with antique lines. They are done in soft hues like blue, salmon, and gray. Rooms are air-conditioned and have double beds -- many also include sofa beds, and some have an additional lofted bed (like the lofted Francesca Room that we visited). None of the rooms or apartments have TVs. Bathrooms are modern and clean, with bidets, gilt-framed mirrors, baskets filled with toiletries, and narrow stall showers (one has a tub). Apartments vary in terms of layout and size; some can accommodate two guests, others up to four or more. The Antilla, for example, has living and dining rooms, a large terrace with a pergola, and can connect with the Renato Room to accommodate six guests. The Orione Apartment has a sleeping loft, though only has air-conditioning in the bedroom. The Virgo Apartment has a private garden. All apartments have full kitchens with ovens, refrigerators, toasters, coffee- and tea-making facilities, and dishware. Apartment bathrooms also vary; some have tubs, others showers. Guests suggest being specific when requesting rooms and apartments, as owners can accommodate a variety of needs. Guests should keep in mind that apartments are not cleaned daily. Wi-Fi is available in most rooms and apartments.

A homemade breakfast is included for guests of the property's traditional rooms (not the apartments). It includes fresh fruit, yogurt, juice, cooked-to-order eggs, cold cuts, pastries, and pancetta. The owners offer cooking classes on-site as well as wine tastings -- the vineyards are within 100 meters (328 feet) of the main buildings. Guests can eat on the terrace while taking in views of the medieval towers of San Gimignano, or gaze out from the garden. There's a good-size outdoor pool with a hedge-lined stone deck, loungers, and umbrellas, and views of the Tuscan countryside. Cribs are available for families traveling with children. Free Wi-Fi is offered in apartments, common areas, and most guest rooms.