Restaurants in Tuscany

Centrally located in San Gimignano’s Piazza della Cisterna, Gelateria di Piazza has won awards for its owner’s (Sergio) creations. Taste unique flavors like blackberries and lavender and gorgonzola cheese and walnuts or stick with your tried and true favorites.

Never ever go anywhere near Le Bontà when you’re hungry. It is a dessert lover’s dream and a calorie counter’s nightmare. Not only does it sell excellent gelato, but this shop is wall-to-wall with other treats (tiramisu, chocolate, mille-feuille cake, tarts, mousse, and cream puffs).

Pienza, a small hill-town of 2,000 and counting, holds more than just amazing views. It holds one fantastic gelato shop. Off one of the main roads, Gelateria Toscana is the place to go for flavors like hazelnut, lemon, unique liquor-based flavors like beer, or even cheese flavors.

Nothing tastes better on a hot Siennese afternoon then a delicious gelato. A bit off the path from the touristy haunts (but near the Bascilica di San Francesco), this gelato shop is worth the effort to find.

Marco and his wife Cinzia treat gelato as any chef would his favorite masterpiece. Using only fruits in season and limiting the sugar so as not to mask natural flavors, their gelato is authentically gourmet and revered by the locals.

If you come here after visiting the Antinori memorial, you’ll be re-living Charles Dicken’s The Prince and the Pauper. But the view is majestic—eleven layers of hills to the sea— the grounds romantic, and the family a hoot.

Hold onto your hats: architecturally, this is the most stunning winery in Italy, perhaps the world.

OK. So this may just be the most beautiful spot on earth. At the end of the bucolic Argentario peninsula, on the edge of Mediterranean scrub forest, with nothing but limestone bluffs and sea and sky, is a dramatic estate—the name means Man’s Head Cape.

On the Etruscan coast, between Livorno and Grosseto, lies the world-celebrated Bolgheri zone, home to such revered and pricey labels such as Sassicaia and Ornellaia.

With an unobstructed view of the most dramatic hill town of Tuscany, full of towers and spires, this winery, now in its 30th year, produces truly interesting wines.

It’s no easy task creating a romantic restaurant in a city, but Il Palagio manages very well. Attached to the Four Season’s Hotel comprised of an old palazzo and a small convent, all is immersed in lush botanical gardens.

You want romance? I give you romance. Oreade is a restaurant named after the mythological mountain nymphs. The setting is truly another world, another time.

Some call it “a little piece of paradise.” We stayed there this fall and I must say it’s pretty close.

My favorite small medieval hill town, among the vineyards of one of the worlds’ greatest wines Brunello, this tiny, circular, little-visited jewel has the most amazing views from east to west. Lit by sunlight or moonlight, the great volcano, the valley below, and the hills beyond must be seen.

Near the romantic fishing village of Porto Ercole, in one of the world’s most striking locations, is Il Pellicano. As only an Italian can, chef Sebestiano Lombardi has been fascinated by la cucina from childhood.