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Tuscany is a place where time stands completely still. This magical land is known for its rich history, dramatic landscapes, exceptional wines, and the most delicious farm to table Tuscan cuisine.You could easily spend a few days, weeks, or even a lifetime exploring all that Tuscany has to offer.


The region is massive, and filled with so many charming hilltop towns and villages. We spent three lovely nights here, and quickly realized we made the mistake of not staying longer.There’s so much to see and do, and we felt so relaxed that it was sometimes hard to leave our hotel. Trust me, four days is the minimum you’ll want to stay in this beautiful region.


I highly recommend renting a car and driving out to explore the region. The scenery is absolutely breathtaking, and it’s the best way to see all the different villages and experience the true charm of Tuscany. Just be sure to rent a small car, as the parking spaces can be quite tight in Italy. On our trip, We rented a car in Rome through Europ Car Rentals. It was the most beautiful two hour drive through Tuscany’s scenic countryside. There are also some really cool options to rent vespas and vintage cars if your plan is to take the train into Tuscany.


Picnic: Spend a relaxing afternoon in the vineyards surrounded by panoramic views of the countryside. Whether you’re purchasing or creating your own picnic, this will be an unforgettable and memorable experience. There are many hotels and companies that will help you create your picture perfect picnic. Lupaia hotel, Rosewood Castiglion Hotel; and  Caseificio Cugusi Silvana are a few great options. We had our picnic at Lupaia, and it was the most romantic afternoon.

Agriturismo Baccoleno: If you have seen any postcards or movies related to Tuscany, You will definitely recognize Agriturismo Baccoleno. Agriturismo Baccoleno viewpoint is a stunning winding road lined with cypress trees. This enchanting and breathtaking landscape is the picture perfect destination to watch a sunrise or sunset. Simply put Agriturismo Baccoleno in your google maps. Once you arrive you will park on the side of the road and walk over a few meters. 

Poggio Covili: Poggio Covili is a farm house located in the Val d’ Orcia region. This popular photo destination is known as one of the most picturesque and iconic straight cypress tree line in the world. To visit this location simply put: “Poggio Covili” in your google map. You’ll know you’re close when you see a few cars parked on the side of the road. Depending on the season, and time of day don’t be surprised to find a small line of people all there to capture the beautiful Poggio Covili. 

Wine Tasting: Montepulciano is heaven on earth for wine lovers. There are all types of wine tours and tastings for every traveler’s budget. A few favorites are: Castiglion del Bosco in Montalcino. This winery estate is owned by the famous Ferragamo family, Boscarelli Estate is one of the most famous wineries in the region and has won international recognition, and lastly De’Ricci Cantine a local winery located in Montelpuciano.

Pienza: Pienza is a small charming village located in the Val d’ Orcia region in the heart of Tuscany. Pienza is famous for its pecorino cheese and stunning landscapes. This  dreamy idyllic village is a paradise for photographers, and is the perfect place to stroll, shop, grab gelato, and enjoy some of the best views of Tuscany. For the lovers, there are two small narrow streets in the village called, “Via Del Bacio (kissing street) ” and Via Dell “Amore (love street). You will find lovers from around the world embracing and capturing their love on film in these corners.

Bagni San Fillppo: Bagni San Fillppo is a natural thermal hot spring located in the woods of a small town called Bagni San Fillippo. The springs are considered to have a healing effect due to the large qualities of minerals, and is especially healthy for joints, the bones, and your skin. It is recommend to arrive early here if you want to avoid the crowds. 

Montepulicano: Montepuliciano is a medieval hilltop village famous for its Tuscan red wines. Stroll the lovely little shops, and enjoy a coffee. This is a great place to have lunch or visit a winery. The town is small so you will be able to walk through the entire village in one hour. 

More Options: There is plenty to do in Tuscany! A few other options for your next visit include: a private cooking class at Podere il Casale; a vespa tour with Vintage Tours di Dario Rossi; stroll the dreamy villages of Montalcino and Monticchiello, a spa day, & endless wine tastings. 



Lupaia is a luxurious and intimate estate hidden away in Montepulciano. Everything about this oasis is romantic, surreal, and magical. From the moment you set foot on property there is an aura of peace and beauty all around. The grounds are absolutely breathtaking, the hospitality is unparalleled, and the food is impeccable. I spent three dreamy nights here. Lupaia is a quintessential Tuscan experience in the olive groves so far and removed from reality, it seems fictional. There is plenty to do on property. You can choose from truffle hunting, wine tastings, a picnic, cooking class, yoga, spa, and more. I highly recommend Lupaia to those seeking calmness and tranquility. This is a boutique hotel best suited for adults.


Borgo Santo Pietro: If you’re looking to Splurge, Borgo Santo Pietro is a luxury boutique hotel featuring a Michelin-starred restaurant on the property.

Rosewood Castiglion del Bosco: This bucket list hotel was recently named NO.1 best hotel in the world 2022 by Travel and Leisure. Rosewood Castiglion del Bosco is one of the oldest and most preserved estates in all of Tuscany located in Montalcino.  
Castello de Casole, A Belmond Hotel: This private estate is set one hour away from Florence. The 10th century castle has been restored and refined into a boutique hotel that features a world class spa set on 4200 acres.

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One Comment

  1. These places look so wonderful. Thank you for sharing. It brought back so many memories!!