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How to Guide: The Tuscan Countryside

"Wheatgrass swaying. Rolling hills. Winding roads. Medieval villages in the distance. It's spring 2021 and I am in my car with my husband who is lightly dozing after a delicious Tuscan lunch and winery visit. I am listening to the hum of our Mercedes Sprinter van and my driver chatting away with me about the Italian village of Siena and why she loves it. It was at this moment, I realized there is a value I cannot quite put a number on for this private transfer. Maybe it is Pina, who I adore, maybe it's the fact that she told my husband, "Christopher! Sleep! Sleep! I will gossip with your wife!" Or maybe it's the setting, but something about it is so us, it's so comforting. I am relishing in the fact that CJ (my Christopher) and I didn't have to argue about where to get the rental car, or how to dial an international line for a taxi, or wait, a little tipsy from delicious Brunnello for the taxi to make it's way 40 minutes from Siena to come get us. Instead, were embracing all Tuscany has to offer and not wasting a second of our vacation."

My name is Madeline Steuber Johnson, and I am one of the owners at Steuber Travel Group. Planning Italy is where I started our business, and it has become a deep passion of mine. I love our partners in this region of the world, and truth be told, I just love Italy. There's a reason so many of you come to us with goals to travel to this part of the world. If it ain't broken, don't fix it!



But one of my favorite destinations within Italy often gets overlooked: the Tuscan countryside. Instead of gorgeous borgos, dining in hamlets, and just sitting, with a glass of wine, staring in the distance — most clients want to go to Positano.


Don't get me wrong! Amalfi Coast is special in its own right! But I often wonder, if clients knew how to approach Tuscany, would this vast, far-stretching region not feel so overwhelming?


So I'm here to share, just a tiny sliver of my secret sauce about how I approach designing in the Tuscan countryside.


Accommodation Selection: My favorite thing about this part of Italy is you do not have to spend a lot of money to have a relaxing and beautiful experience. The offerings by 4-star providers, up to the ultraluxurious players like Rosewood and Borgo Santo Pietro all hit on a key ingredient: authenticity. Here are the questions I am going to ask you to help you pick the perfect spot for you:



Are you a foodie who appreciates variety? Do you need more than 2 dining outlets on-site? If so, I am going to steer you towards an option that is located just 5 minutes by hotel car away from a hamlet where you'll find 2 Michelin restaurants, 3 family-owned operations, and a gelato shop.


What types of experiences are you looking for? Do you want to zero in on the winery and vineyard experience? If so, what types of wines? I have the perfect spot in mind, smack dab between two winery meccas: Montepulciano and Montalcino, should they match your wine preferences.


What type of guest experience do you want? Do you like meeting other guests? Does a small intimate setting, where you all gather around the dining table at the same time for meals sound wonderful? How about meeting in the library for after-dinner cocktails as the owner says in broken English and true Italian, the story of how he took this farm and turned it into a boutique hotel with his architect son — how does THAT sound? If that terrifies you because you need more privacy, well then I have the Borgo to show you. But if this sounds like you, well then let me unlock the door to this hidden boutique gem.




Is this your home or your home base? Read that question again! I want to know, do you want to stay put and enjoy all that the property has to offer (and then that in turn means the property needs to have a substantial portfolio of offerings) or is this a means to get out into the countryside to experience other activities like cheese tastings on local farms, pizza classes in Siena, truffle hunting in the hillside, exploring underground wineries that have been at work since the beginning of time (no exaggeration). Well then, off we go to another option.



Tuscany is far-stretching — we can place you close to Pisa, or we could put you just outside Siena. We could look at the border between the Tuscan countryside and Umbria. We could head further south to 1.5 hours out of Rome to a beautiful farm resort. The key is, with Steuber Travel Group, we are going to listen. We are going to ask you a lot of questions, listen, and match.


So if you are interviewing advisors to work with, and the first words out of their mouth are, "I know the best place in Tuscany", I want to say to you: red alert. There is, very rarely in this world, one single "BEST" place. To send you to the right stop for you, we need to dig into why. I promise you, our planning fee comes with our expertise and getting into the weeds (or in this case, the Tuscan wheat fields).


So my first question for you: when are we having a call? Talk soon! Ciao bella!








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