Archway in Castiglioncello del Trinoro
Tuscany with its rolling hills, bucolic settings, ancient wineries and hilltop towns is a true gem. It is possible to have an experience akin to the one popularized by Francis Mayes best selling Under the Tuscan Sun, if you do your research. It’s a vast area and some towns are more touristy then others. Chefs are doing amazing things in some of the lesser known towns and new boutique hotels are bringing modernity to the region, while also preserving the integrity of the original stone exteriors. My husband and I didn’t make it to every village we wanted to see (you would probably need a whole week to see everything) but we enjoyed our time in Tuscany immensely, and definitely plan to go back. These were some of the highlights.
Dario Cecchini’s Solociccia and Officina Della Bistecca
One of Dario Cecchini's buildings in Panzano
This master butcher has taken over an entire street in tiny Panzano with two restaurants and a butcher shop. Solociccia and Officina Della Bistecca are true destination restaurants- delicious food served in memorable settings. At Solociccia, food is served family style and includes six different meat courses. At the more expensive Officina, it’s all about the Tuscan specialty Bistecca alla Florentina (a huge slab of bone-in rib eye grilled on the outside but rare on the inside). Cecchini’s aesthetic is modern yet whimsical and the communal atmosphere makes for a memorable evening. Menus are fixed price and include house wine, water, bread, dessert and a narly grappa. Reservations are recommended for dinner. Also a great stop for lunch if you’re on the wine tasting circuit.
Via XX Luglio, 11
Panzano in Chianti Firenze
39 0558 52020
This beautifully restored medievel castle winery specializes in delicious Chianti Classico. Castello D’Albola is owned by one of Italy’s largest producers but it actually feels more laid back and less corporate than other wineries we visited. Castello D’Albola offers a great free tour of the winery several times a day and wine tastings are laid back and generous. Castello D’Albola’s Chianti Classico is incredibly smooth and at about 10 euros, very reasonably priced.
Pian d’Albola 31 53017
Radda in Chianti
Castello Di Brolio
Considered the birthplace of Chianti Classico, Castello Di Brolio is one of the oldest wineries in the world and well worth a visit. The castle itself dates back to 1000 AD. I found the tasting room, which is located in a more modern building at the bottom of the hill, to be fairly lackluster, but the castle itself is stunning. Park in the designated parking area and climb 15 minutes up the forest path to the castle gates. Purchase a ticket and enjoy a walk through the castle gardens.
53013 Gaiole di Chianti – Siena
39 0577 730220
View from the dining room at Osteria Aquacheta
Eating at this osteria may be one of the most entertaining and delicious meals you’ll ever have. The stars of the show are Giulio Ciolfi, the owner/chef, and his meat cleaver. From the small dining room, you’ll be able to see him hacking away at a huge piece of meat in the open kitchen. A two inch thick slab is brought out to those who have ordered steak for inspection. If you approve of the size, Ciolfi will write the price down on your place mat and grill it for you with a simple preparation of olive oil, salt and pepper. The rareness of the meat might take you aback at first, but try it. My husband and I were both knawing on the bone at the end of our meal. Most steaks are big enough to share. Aquacheta offers two seatings a night at 7:30pm and 9:30pm. Tables are shared. Reservations are an absolute must. Not open Tuesday.
Via del Teatro 2,
53045 Montepulciano Siena
Osteria Del Merlo
Outside Osteria Del Merlo
We heard about this restaurant from a local and it ended up being one of our favorite meals of the trip! Osteria Del Merlo is everything you hope to find in a restaurant while you’re traveling- delicious inventive food, great ambiance and affordable prices. We were aboslutely blown away by our appetizers, grilled peach with gorgonzola cheese and a burrata and slow roasted tomato salad. Located at the end of Garibaldi square, the restaurant’s main dining room is located inside a beautifully restored medieval tower, ahh Italy. The wine list offers all the regional favorites at reasonable prices. If you decide to indulge in dessert, the chocolate cupcake, basically chocolate cake with a gooey center, is delicious.
Via Sobborgo, 1
53040 Cetona – Siena
Inside Cafe Monteverdi
Located in the tiny etruscan village of Castiglioncello del Trinoro, Cafe Monteverdi is a great place to grab lunch or a snack when you’re touring southern Tuscany. Like all the other buildings in Castiglioncello del Trinoro, the outside of the cafe has been brilliantly preserved but the inside is very modern. There’s even an ipad on the wall where you can check your email, or look at pictures of the beautiful villas that are also located in the town. Cafe Monteverdi is owned by the same person as the Villas at Mondeverdi (see below), but luckily, you don’t have to be a guest to eat there. The cafe has great salads, meats, cheeses and panini’s. It’s also the only place in the world where you can Tenuta di Trinoro by the glass-an extremely exclusive wine grown in the valley below.
Castiglioncello del Trinoro
Enoteca La Dolce Vita
This wine store and restaurant in Montepulciano offers a great wine list and delectable small bites. The restaurant is known for their bruschetta, but there are other fun things on the menu like pork shank with prunes and scallions and delicious meat and cheese plates. Go for lunch or a light dinner. Enoteca La Dolce Vita has several tables on the cobblestone street, but I also like the restaurants cellar like interior.
Via di Voltaia nel Corso 80/82
53045 Montepulciano (Siena)
39 0578 758760
Osteria Del Teatro
We did not get to eat at this restaurant in Cortona, because it’s closed Wednesday (the only day we were there). We thought dishes like filettini di maiale all mele e caffe, pork fillets with apples and coffee sounded delcious-think Tuscan food with a twist using seasonal ingredients. Hopefully we’ll be back.
Via Maffei, 2
39 0575 630556
Pool at Poggio Piglia
It took 7 years to turn this old tuscan farm house into a hotel, but the attention to detail paid off. The newly opened boutique hotel is the perfect place to pick as a base while you explore southern Tuscany. Poggio Piglia maintains the beauty of the original structure while the interior and grounds infuse it with elegance and modernity. The vanishing edge pool, which overlooks the countryside, is stunning. Imma, the hotel’s concierge, provided us with some of the best service we’ve ever had at a hotel including making restaurant reservations and printing out directions on how to get everywhere. The guestrooms are spacious and tastefully decorated with rustic, yet modern furniture. After braving small, antiquated bathrooms at most hotels in Italy you’ll scream with delight when you see Poggia Piglia’s large modern ones. Starting at 135 euros a night, the room rates are extremely reasonable for a place of this caliber.
53043 Chiusi (SI)
39 0578 274286
The Villas at Monteverdi
View from the Villas at Monteverdi
If you can afford it, and are traveling with a group of 4 or more, stay at the Villas at Monteverdi. Located in 900 year old Castiglioncello del Trinoro, the villas have been beautifully restored and retain the original facade, while the interiors offer all the comforts of a modern 5 star hotel. Owner Michael Cioffi, is behind the only privately funded archeological dig in Tuscany at Castiglioncello del Trinoro and a visit is a great opportunity to see archeologists and historians at work. Accommodations can sleep 4, 9 or 12 and a Saturday to Saturday stay is required. Dinners by a private chef under a grape arbor at your villa can also be arranged. Work has also started on a boutique hotel in town, so stay tuned.
Castiglioncello del Trinoro
Taste Brunello somewhere
Aged a minimum of four years in oak, Brunello is one of Italy’s most special wines. The grape, a rare clone of Sangiovese, is grown in the hills surrounding Montalcino. Unfortunately, the 14th century town seems to have one purpose only these days-selling Brunello. Its narrow streets are filled with wine shop, after wine shop each the same as the next. It all feels a bit touristy and inauthentic. Instead of tasting in town, I recommend going directly to one of the vineyards. Casanova di Neri is located just outside of Montalcino and grows some of the most delicious and award winning Brunello d’Montalcino. Go in for a tasting, and consider taking a bottle home. Brunello’s can be aged for decades, but beware, you’ll be hard pressed to find a bottle for under 30 euros.
53024 Montalcino SI
This blush colored Abby sitting in a field surrounded by gentle Tuscan hillsides seems to be plucked from a painting. The church was built in the 12th and 13th centuries and is considered the most important Romanesque building in southern Tuscany. Simple and anadorned, the Abbey is a refreshing departure from many of Italy’s famous and more opulent duomos and cathedrals.
From Siena take direction Buonconvento > Montalcino. Once in Montalcino follow the signs for Abbazia di Sant’ Antimo or Castelnuovo dell’ Abate. Before you reach Castelnuovo dell’Abate you will see the Abbey on your right.
Walk through the wine cellar at Redi Winery
Redi Winery makes delicious Vino Nobile but perhaps the most fun part about the winery is making your way to its tasting room deep within the hillside. After finding the entrance next to the Palazzo Ricci, you’ll travel down an ancient staircase that leeds you through cavernous ancient wine cellars. You’ll pass through rooms filled with large wooden casks of wine that look like they haven’t been moved for centuries, before ending at the wine tasting room and shop. There you can taste and purchase wine.
Via di Collazzi 5
39 0578 716092
Hike to the top of Cortona
Tuscany’s many hilltop towns will no doubt give you an appreciation for a nice flat stroll, and perhaps none more than Cortona. The town, which was made famous by the film Under the Tuscan Sun, has a web of quant cobblestone streets that snake their way up a very steep hillside. Why not embrace it and put on your hiking shoes? At the very top of Cortona is an ancient fort that offers spectacular views of the Tuscan countryside. It’s a good climb and will certainly leave your heart pumping. On your way down, treat yourself to dinner at Osteria Del Teatro. You’ve earned it.
Just start walking up. If you pass the 19th-century Chiesa di Santa Margherita, you’re on the right track.
Taste cheese in Pienza
Pienza is famous for two things, being the home of Pope Pius the II, and pecorino cheese. The town is a bit touristy for my taste, and I wouldn’t recommend staying there, but you can easily see everything in an afternoon. Park your car outside the city walls and stroll through town, taking in the well preserved Renaissance architecture and the beautiful Palazzo Piccolomini which contained the Pope’s private apartments. On your way out stop at Bottega di Naturalista and pick from a mouthwatering array of pecorino di pienza. You can choose, fresh, medium-aged or mature depending on your taste.
Pienza is on the main road to Montepulciano
Bottega di Naturalista is at Corso Rosselino 16
Facade of the Cathedral in Orvieto
See the Cathedral in Orvieto
Orvieto’s 14th century cathedral is a true masterpiece and a must do for anyone interested in Gothic architecture. When you approach the cathedral, you’ll immediately be struck by the ornate golden frontage. My favorite part is the more simple side walls made of alternating white travertine and blue-grey basalt stone. The Dr. Seuss like effect is echoed on the inside and gives the cathedral a more whimsical feel then other religious buildings in Italy. Once inside, you’ll be humbled by the sheer size of the nave, which was left uncluttered on purpose. The cathedral is famous for the Chapel of Madonna di San Brizio, or new chapel. Painted by Luca Signorelli in the 1500’s, the frescoes depict the events surrounding the Apocalypse and the Last Judgment and are said to have influenced the style Michelangelo used in the Sistine Chapel. As in all cathedrals in Italy, make sure your shoulders and knees are covered or they won’t let you in.
Orvieto is in Umbria, south of the Tuscany region right off the A-1