Rachael's Guide to Tuscany, Italy: Where to Stay, Eat and Shop

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Playing Where to Stay, Eat + Shop in Tuscany, According to Rach (PART 1)

Rachael is kicking off season 17 in Italy—and not only is she giving us a tour around her own property (which is absolutely stunning!), but she's also sharing some of her must-see spots in her neighborhood. So, if you didn't have a trip to Italy already planned, you're going to want to start looking up flights ASAP to see these places in person.  

To Stay:

Monteverdi Tuscany Sarteano  

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Not only is one of Rach's favorite hotels on a magical property, but there seem to be endless opportunities to explore. "Monteverdi is a boutique hotel, which is dispersed within a medieval village, so it doesn't matter where you are located, you walk through the village to the spa, to our lounge or to our restaurant, so you're actually living in the village" says Giancarla, the executive chef at Monteverdi. How unique!  

Not to mention, the food is also next-level (of course, we'd expect nothing less from a Rach pick!) AND there's a culinary academy on the premises with an amazing vegetable and herb garden.  

"What I love about having people come here is that they really get to understand and know what true food culture is in Italy," explains Giancarla. 

La Gustea 

la gustea
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If you're looking for a quaint little hotel and restaurant, La Gustea is another one of Rach's top picks.  

"The chef cooks traditional Tuscany dishes, but in a very innovative way," says Nadia, the owner. They are known for their incredible homemade pastas, but also their 36 different kinds of pizza. Yes, you read that right. Rachael loves the one with tomatoes, mozzarella, Buffalo mozzarella and artichokes—sounds delish!  

To Eat:

Porta Di Bacco  

porta di bacco
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Now, once you're settled in your hotel, Rach has no doubt that Porta Di Bacco should be on your itinerary. "Porta Di Bacco is my life," says the owner Andrea, whose grandparents first opened the restaurant in 1962. He started working first as a chef there for eight years and now is the manager.  

"Andrea and his staff are so warm, funny, and full of electric energy. The food is absolutely excellent, but it's a relaxed environment," says Rach.  

They grow their own vegetables in a massive garden—and everything is extremely fresh, so their dishes are seasonal. "We select our ingredients depending on the seasons—seasonal vegetables, seasonal pasta—and the meat comes from a small producer in the countryside," explains Andrea.  

Boccon DiVino 

boccon divino
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This spot holds a very special place in Rach's heart, as it was where she and John had their rehearsal dinner. The family business—first opened in 1992 by two sisters, Marina & Alessandra, along with their parents—not only has incredible food, but also has unbelievable views of the Italian countryside.  

"Rachael loves our cuisine. We've known her for many, many years, " says Marina. Some of Rach's favorite dishes include the onion soup and a biscotti dessert served with chocolate liquor—yum! 

Al Tocco  

al tocco
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Even though Al Tocco opened in 2021, the building holds a ton of history. "We kept everything original to keep a proper Tuscany atmosphere with innovation at the same time," explains Mattia, the head chef.  

"Our restaurant is unique because it's the only restaurant inside the Cortona walls that offers a tasting menu. We do a seasonal menu. It's very important to us to change ingredients with the seasons, which makes our jobs easier and the taste better for you," says Mattia. There's nothing we love more than a seasonal tasting menu! 

La Grotta 

la grotta
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This spot, which opened in 1966, serves incredible Tuscan cuisine and looks out on a beautiful church. Dinner with a view? Yes, please!  

"La Grotta is a local restaurant focusing on recipes of this area. Light, fresh, simple—using just three or four ingredients. The more important thing for us is the quality," says David, the owner. "90 percent of the ingredients that we use come from the local area," he explains. We're adding this one to our bucket list ASAP.  

To Shop:

Laura Laureto  

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Even though oftentimes people first set foot in this store for leather bags, the owner Laura assures us that her collection offers much more than that. "Everything I design is limited addition," Laura explains.  

"Something special that we do is we recycle leather. I like to use the leather that comes from food distribution that typically would go in the garbage. We take that and we use it for leather bags," explains Laura. This is definitely a must-visit on Rach's Italy itinerary.  

DelBrenna Jewelry  

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The DelBrennas have been making jewelry for three generations—and their store and jewelry showroom are absolutely stunning. We're in awe of the beautiful jewelry—plus, the history behind the showroom building is truly remarkable.  

"This room used to be an olive oil mill," explains Sebastian, the owner. There's even an olive press that's still there to prove it, which Sebastian thinks has been there since the 1300s. Wow! Plus, the cellar room is the oldest part of the building and has been there since between 1000 and 1100.  

Another thing that makes this place so unique? "They actually make the jewelry in shop," explains Rach. "And you can watch it all being made there, which is very special."   

Stay tuned the rest of the season for more of Rachael's favorite spots in Tuscany!

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