Tuscany’s Hidden Gems: Exquisite Hotels, Wineries & Restaurants

Unearthing the Hidden Gems of Tuscany

In many ways, everything is hidden in Tuscany. A small, organic winery. A family-run agriturismo. A luxury hotel tucked inside a medieval village. Or even a mind-blowing, hole-in-the-wall restaurant that you would drive right past if you didn’t know you should stop.

Arguably the best part of traveling within Tuscany is that everything feels like it is waiting to be unearthed by an eager oenophile or food lover. Because of exactly this, special experiences are abundant in this beloved part of Italy, no matter a traveler’s budget.

Beautiful Luxury Hotels To Stay at in Tuscany: Il Borro
An aerial glimpse of what was once a medieval village in Tuscany, Il Borro is now dedicated to hospitality and farm-to-table catering. Image courtesy Il Borro.

Hidden Upscale Hotels & Agriturismos in Tuscany

One of Italy’s famed families, the Ferragamos, have been operating Il Borro for 30 years. Many travelers seeking a high-end experience will find it within the walls of this illustrious hotel tucked inside a medieval town surrounded by hectares upon hectares of an organic vineyard.

The estate was opened by Ferruccio Ferragamo in 1993, and today is run by his son and daughter, Salvatore and Vittoria Ferragamo. Their commitment to sustainability is clear by observing everything from the organic produce they grow to the meat they produce. They have many other initiatives, such as partnering with Bird, a scooter business in an attempt to reduce emissions throughout their property.

Villa Merlo in Tuscany, Private Villa
One of the many private villa configurations set amongst the Tuscan hills at Viesca. Image courtesy Il Borro Toscana.
Private villa in Tuscany - Hidden Gems in Tuscany
Imagine waking up in your own private villa at Viesca, in Tuscany. Image courtesy Francesca Pagliai.

Taking it a step further to expand their brand and offer travelers more options in an uncertain time, the Ferragamos launched Viesca in 2019. This suite and villa concept in the countryside covers an area of 170 acres in Reggello with different configurations of villas and suites, complete with private swimming pools and concierge services. For those looking for a family vacation, a reunion, or simply want to have a more secluded experience, Viesca hits all of the right notes. 

Horseback Riding and Wine Picnics at Il Borro in Tuscany
Amongst the numerous perks and activities at Il Borro, horseback riding and picnicking are one of our favorites. Image courtesy Il Borro.
Horseback Riding in Tuscany between the Cyprus Trees
This horseback riding experience is waiting for you when you stay at Il Borro. Image courtesy Il Borro.


RELATED: A Table for Two: Romantic Tuscany Itinerary for Couples & Honeymooners


Tuscany is continuing to be a draw for sustainability seekers. Another property that shares the love of all things natural and organic is the Oasyhotel, comprised of luxury eco-lodges situated on the Dynamo Oasis Nature Reserve.

Interior at Oasyhotel in Tuscany
The streamlined, upscale interior of one of the lodges at Oasyhotel in Tuscany. Image courtesy Oasyhotel.

The hotel has partnered with the WWF, an environmental conversation organization, and features two farm-to-table restaurants, including La Felci. At the helm of the restaurant is chef Barnaba Ciuti who showcases locally foraged berries and homemade cheeses with dishes that integrate his Italian heritage with a classic French twist.

WWF Tuscany Preserve
The WWF is an environmental conversation organization that helps to preserve these remarkable landscapes. Image courtesy Oasyhotel.

If adventure is what you seek, the hotel also offers different nature walk experiences in the wild, horseback riding, and an “Into the Night” tour that encourages guests to fully immerse themselves in nature by spending a night in a suspended tent. Guests can also opt to relax in one of the hotel’s three spa cabins that offer yoga and massage therapy with a focus on the elements of earth, water, sun, and air.

Horseback Riding at the Oasyhotel in Tuscany
One of our favorite ways to explore the Tuscan wine region is on horseback. Image courtesy Oasyhotel.

Still, part of Tuscany’s romantic charm is the smaller, family-run agriturismos like Agriturismo La Fontaccia in Val de Sieve in the Chianti Rufina area of Tuscany. This property, run by husband and wife Elisabetta and Samuele Bianchi, is where guests can see first-hand how the products grown on their farm wind up on their plates for dinner at night.

The quaint farmhouse, consisting of two apartments and three rooms, is situated between woods and olive groves. It also boasts an orchard, a vegetable garden, and a group of chickens that provide guests with their fresh, seasonal ingredients. The family’s food philosophy is based on their family’s traditional Tuscan recipes reinforced by the concept of the Slow Food movement. The menus change daily, showcasing the freshest of ingredients and can be tailored for any food preference a guest may have.


RELATED: Chianti Itinerary: How To Spend 5 Days in Italy’s Chianti Region


Unique Winery Gems in Tuscany to Explore

No trip to Tuscany would be complete without visiting some of the region’s most compelling wineries—some well-known and others that fly under the radar. One boutique winery that is not to be missed is Podere Le Ripi in Montalcino. Winemaker Sebastian Nasello offers unique wine tasting tours for small groups who are interested in delving deeper into the biodynamic farming process. Given that the wines are sourced from a single vineyard in very small quantities, those who have the most access to the vineyard are its wine club members. If you join, you’ll have the option of indulging in curated luncheons and wine pairings.

A name that may not be so hidden in Montalcino is Castello Banfi. And while a tasting there may top the list for most tourists visiting the region, some may be intrigued to learn of its Jazz and Wine event which is in its 25th year. A true blend of culture and passion. While the festival is known to locals, the outside traveler may be unaware of the musical experience that celebrates Italy’s great love of jazz that takes place every summer in mid-July, naturally paired with Banfi’s illustrious wine collection.

Must-Try Restaurants in Tuscany

With all of the exploring, wine tasting, and experiencing a traveler may have, be sure to spend time seeking out those hidden culinary gems that lie outside of the hotels, villas and agriturismos, in an attempt to get a true sense of what the Tuscan dining experience is all about. Two such eateries to keep on the list include Dolce e Forte in Montespertoli and La Pergola di Radicondoli, a pizzeria located in the province of Siena.

Dolce e Forte is a restaurant that can easily be overlooked if you aren’t sure of your destination. Once you’ve made it inside this quaint family-run restaurant, you will be taken care of by the two brothers—one the chef, the other front of house—and their beloved mother who happens to pull double duty as the pastry chef. The menu changes seasonally with dishes that are local to the region, and while you may be expecting a home-cooked type of food experience, you will be blown away by the culinary artistry that is showcased in each dish that comes out of the kitchen.

La Pergola is another family affair, where patrons can try a variety of pizzas, some that are more traditional in nature and others called “tasting pizzas” that allow guests to try a multitude of toppings making it easy for groups to taste, share and compare notes. While the cuisine alone makes this restaurant a must-try, be sure to stay for sunset on the pergola. The restaurant has sweeping views of the towers of San Gimignano, Volterra, the Berignone forest, the Chianti hills and the valley of the Cecina River.

Regardless of one’s destination within Tuscany, there will be hidden gems along the way to uncover. The best way to approach it is to slow down, put your phone on silent, grab a glass of the finest local wine and be open to any experience that may lie ahead.

If you’re still looking for more things to do and see in Tuscany, take a look at more recommendations for things to do and see in Tuscany here.

If you haven’t yet had your fill of recommendations, take a look at this itinerary for more things to do and see in Tuscany. It’s also worth perusing these other charming Italian towns to expand on your next trip to Italy.

Featured image courtesy Il Borro.


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    ABOUT THE AUTHOR

    Kristen is a New York native who received her BA in journalism from Northeastern University in Boston. She is a lover of ballroom dancing, traveling the world and cooking at home. She has worked as a freelance travel, food, wine, entertainment, finance and nutrition writer throughout her career. Follow her latest adventures on her lifestyle blog www.outerborobroad.com and on Instagram @krisoliveri and @outerborobroad.