Stepan Borovec’s Guide to Tuscany

EliteVoyage’s Chief Travel Consultant guides us through all the things you need to know about Tuscany

Stepan created EliteVoyage’s popular weekend trip to Tuscany by private jet. He was there twice last month, once with clients and then with his family.

Tuscany is well known around the world, for the Renaissance, Florence, food, wine, art, picturesque landscape and so many things. How much do you know about Tuscany?

Stepan, what’s your most important consideration when starting to create a Tuscany holiday for a client?

Selecting the right hotel is key. This depends on the tastes of the client.

Tuscany is a big region where the roads are windy and slow, so 40 kilometres on a map can take one hour by car. You want to travel a maximum of 30 – 45 minutes to go somewhere, not two hours.

Belmond Castello di Casole

I map out the area around the hotel, so the client knows the different places to see and things to do. For our recent private jet trip I selected Belmond Castello di Casole. It’s a medieval castle and hamlet, surrounded by vineyards, forest and cypress-lined roads.

Suite at Belmond Castello di Casole

Very importantly, it is only one hour from Florence Airport and is close to the village of San Gimignano, where we had the weekend’s main experience. Siena, Monteriggioni and Volterra are also within a 40-minute drive.

What are the best hotels you recommend in Tuscany?

Villa San Michele

Florence has good hotels, like Portrait Firenze and Villa San Michele. Other towns and cities don’t, because they simply don’t have enough space in the old historical centres.

Instead, they converted rural castles, farmhouses and hamlets into outstanding hotels. Part of the region’s charm is staying in a 5,000-acre property in fairytale Tuscan nature.

For couples I often recommend staying two to three nights at different hotels, so you can visit different regions and cities.

Borgo Santo Pietro

Hotel Lupaia near Montepulciano is a small boutique option, a luxurious farmhouse made for couples. Relais Borgo Santo Pietro is another little gem that is less known.

Location is so important. For example, there is a millenia-old castle transformed into a boutique luxury hotel called Castello di Reschio, which is quite popular but a long way from Tuscany’s most beautiful towns and famous rolling hills.

Hotel Castello di Reschio

What is your favourite Tuscany hotel for families?

I really recommend Rosewood Castiglon del Bosco for families. Their multi bedroom villas offer as much space and privacy as any family needs.

It’s a huge estate with different areas, including 3-6 bedroom villas. As a family you have privacy, private pool, your own tennis court (some villas only), an outdoor barbecue area with a pizza oven so a chef can prepare dinner in your villa. You can get spa treatment in your villa too.

Multibedroom villa at Rosewood Castiglion del Bosco

There’s a lot for everyone to do. Like golf, visiting a working farm, biking around the estate, truffle hunting, a kids club with cooking classes, treasure hunts, pizza making and movie nights. Their estate Brunello is superb and wine tasting is an essential experience too.

The Castiglion del Bosco estate creates superb Brunello

The hotel was founded by the Ferragamo family and is now managed by Rosewood. Chiara Ferragamo remains the ultimate decision maker in terms of hotel style and design. For example, room interiors use earth colours and materials representing Tuscany, like leather and stone.

Rosewood Castiglion del Bosco

How long do you need for a Tuscany holiday?

How you travel helps to answer this question. I like to drive. It’s a 12-hour journey from Prague with many possible overnight stops, like Innsbruck, Dolomites, Lake Garda, or Modena and visit the Ferrari factory in Maranello.

With a private jet you can land in Florence or Grosseto in the south. There’s also Siena Airport, where we can land on the short runway with very light jets.

Private jets depart at the time you want and fly direct. You save a lot of time so a long weekend in Florence is possible.

Flying private jet to Tuscany from Terminal 3 of Václav Havel Airport

There are no direct flights from Prague to Tuscany. It’s usually a two-leg flight, or flying to Rome and then travelling north. You can fly from Vienna to Florence with Austrian.

With commercial flights I think one week is good in Tuscany, if you want to stay in one place. For my last trip we drove to Tuscany and spent one week in a private farmhouse villa, doing day trips to beautiful towns like Sienna.

If you have time then ten days is also good, especially for staying in different regions.

What are your favourite Tuscan towns?


Siena is a small city where time has stopped. The Duomo (cathedral) is incredible and every year they have the famous Palio di Siena horse race. The 2023 dates are July 2nd and August 16th.

For our clients we have arranged seats to see the Palio in one of the private apartments on Piazza del Campo (Siena’s square). What an experience it was for them!

Siena’s iconic horse race. Note the apartment windows with the best view for the Palio di Siena.

Tuscany is really hilly. On almost every hill there is an old castle, private villa, converted farmhouse, historic village or important town, with a cobbled square and cathedral. Towns like Montalcino, which is of course world famous for Brunello wine.

Pienza is a little gem with only 2,000 inhabitants. It’s super small and actually cute. The best thing about visiting it? Incredible views to the UNESCO site of Val d’Orcia.

Val d’Orcia

I’ve ever been to a more heart catching area than Val d’Orcia. I am sure you will fall in love too!

Florence is very touristic but I wouldn’t miss it. When you fly to Florence it makes sense to spend time exploring the city.

How can you avoid the tourist crowds in Florence?

There are many good options, depending if the client is interested in art, history, shopping or local crafts. We can privatise one of the museums, even the Uffizi Gallery if they wish.

We can’t privatise the Duomo but I do recommend visiting the cupola (you will be fascinated by what Brunelleschi created in the 15th century) and Giotto’s belltower next to it. Both need booking in advance and the daily numbers are limited. The views are unbeatable.

Duomo Santa Maria del Fiore in Florence

Florence is big for fashion and has many hidden gems. Sure, you can visit the Gucci garden, the Ferragamo museum, but we can also arrange an artisan workshop in one of the famous leather stores, where you make your own piece and learn about the traditional craftsmanship. I know different factories and workshops for clients who want this artisanal experience.

Experiencing an artisan workshop at the Precious Stone Factory

You must expect crowds in Florence. It’s so important to have a good guide, a local with tons of stories. A guide will tell you the history and show you the secrets of the city.

What’s your favourite place and experience in Tuscany?

San Gimignano.

It’s located on an ancient road Via Francigena and was very rich and powerful during medieval times. Every family who wanted to be important built a tower in the village, so it was like a medieval Manhattan.

Enjoying a private experience on top of one of San Gimignano’s towers

When you explore San Gimignano you are alongside many tourists. There were 72 towers, now there are only 14. One of them is owned by our friends, the Torciano family.

On our recent private jet trip we spent around two hours in the city. Then we entered this private tower.

We had a private dinner accompanied by a harpist, with wine on the tower’s terrace, complete exclusivity in an amazing and popular destination.

Our interactive experience with the chefs and Giachi family

From the calm rooftop we could see hundreds of people queuing for an ice cream. Inside the tower we were interacting with the chef and conversing with one of the Giachi family, who have been making wine in San Gimignano for the last 300 years.

What about the food in Tuscany? Which restaurants do you recommend?

You don’t need a Michelin star restaurant in Italy. You just can’t fall for tourist traps.

During the private jet trip we actually tried the Gucci Osteria da Massimo Bottura, which has one star. It’s Gucci and it’s one of the world’s most famous chefs. But the wine and food was average. Looking back, I would have spent more time exploring Florence instead. I had to remind myself that local and less known places are usually better here!

Couples should have a great dinner reservation for every night. Sunset views in the Tuscan countryside accompanied with a nice aperitivo and some prosciutto are hard to beat. 

Tuscans cook incredibly well and it’s difficult to have a bad dish there. Starred restaurants are not better than the good local restaurants. Local guides, friends and concierges help me make these reservations as part of clients’ itineraries.

Truflle hunting in the forest at Belmond Castello di Casole.

Experiences with food are special too. We went truffle hunting at Castello di Casole, found a few, then enjoyed a special truffle menu connected to the afternoon experience.

Many wineries are open for tasting and lunch. We recently visited Torciano Winery, where you tour the vineyard with the family and hear the stories. For wine connoisseurs I know more exclusive, smaller places. Or you have stunning large estates like Antinori Winery.

Wine tasting at Torciano Winery

When is the best time to visit Tuscany?

The best time to visit Tuscany is April to June and September to October. July and August are very hot and crowded.

Finally Stepan, what’s most important for you when doing creative travel design?

Finding the right people is crucial. My job is about making sure we have great local people on the ground, people who deliver great service, people who are from Tuscany and not Rome or Milan.

Tuscany is about the people you meet, the people who guide you, the people who help you understand and appreciate this beautiful place.

This is a relaxed region. Many people want to decide on the spot what to do, whether a day by the pool, some hiking, biking or city sightseeing. In this case I need to be confident in the concierge service at the hotel.

I also always prepare a few ideas for the client before they travel, like ten things that are really worth their time, such as a thermo bath from ancient Roman times.

Planning Your Holiday in Tuscany

Enjoying the view over Florence from Piazza Michelangelo

I create trips individually to every client, based on their interests, time and travel style.

There’s a lot more I can tell you about Tuscany, when we have a private travel consultation.

At EliteVoyage, we take the time that’s necessary to create a perfect, personalised trip. So our clients can maximise every moment of their holiday.

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