Most Romantic Hotels in Siena

Staying in a castle is an undoubtedly romantic experience, and the Castello Delle Quattro Torra is an affordable and familial alternative to many of the more opulent castle hotels found in the Italian countryside. A short drive from Siena, this family-run bed and breakfast has only three rooms, including an apartment and a two-story tower room, all of which can be rented by the night or -- for a discount -- by the week. There's little to do in the surrounding area, and guests really need a car, although those who love walking can hike to Siena in about 45 minutes. 

This small renovated farmhouse property within the rolling green hills of Tuscany oozes relaxation and romance. With only five classically rustic rooms and an adults-only policy, the upscale Aia Mattonata Relais' intimate vibe is ideal for couples seeking a secluded starting point to explore Siena and other nearby areas of Tuscany. The ultra-boutique B&B may be quaint, but with a wellness center with Turkish bath and body treatments, a saltwater infinity pool, and small exercise room, it is not lacking on features. Since it's a few miles outside of town, guests will either need to have their own car or rely on public transportation. The attentive owners aim to do what they can to accommodate guests.

Housed in a restored 18th-century villa just outside Siena's medieval city walls, the 22-room Hotel Santa Caterina is an intimate, welcoming, mid-range little hotel, often with budget-friendly rates. It's simple and with few amenities, and guests seem to like it that way; the historic building feels authentic and atmospheric, without being chintzy or overwrought. The hotel is typically Tuscan, with antique wooden wardrobes, terra-cotta floors, and views over the picturesque countryside. An extensive, free homemade breakfast is served in the conservatory in winter, and in the lush private garden in warmer months. While there's no full restaurant, there is a small lobby bar, and room service is available 24 hours a day. In-room massages can be arranged, as can babysitting and airport transfers, and the staff offers extensive concierge service. All of Siena's main sights are within walking distance.

The only luxury hotel in Siena's centro storico, or historic center, the Grand Hotel Continental is a lovingly restored Renaissance palazzo -- originally a wedding gift from Pope Alexander VII -- and is within a stone's throw of all the city's iconic sights. Rooms range in size and style, but all are inflected with Tuscany's signature Renaissance gilt; lower-priced rooms still have ornate chandeliers, heavy drapes, and rich upholstery, while suites have high, frescoed ceilings, antique furnishings, and panoramic views of the city. Apart from a wine cellar bar and a fine-dining restaurant serving gourmet Tuscan cuisine, there are few other common spaces or facilities (there's no fitness center, pool, or spa), although the grand ballroom would be a memorable place for events.

A 20-minute drive outside of Siena, Hotel Garden is a classic 125-room hotel surrounded by lush garden grounds with roses, pine trees, and stone paths. There’s a large outdoor pool in a grassy lawn, as well as a tennis court (but no fitness center). The restaurant serves regional cuisine on a beautiful terrace as well as in a dining room with wrap-around windows offering views of Siena. The outdoor areas of the hotel are beautiful, but the indoor spaces are in need of a revamp. The lobby feels dated and bedspreads and curtains in some rooms are in need of an upgrade.