Premium wine tour of Florence and the surrounding Countryside

This tour features vineyard walks at superb wineries in Chianti, Montalcino and Super Tuscan wine country. Visits to Florence and Siena, two of the most spectacular cities in Italy, are also included. You'll have a private chauffeur and wine guide for the duration of this Luxury Tour, along with excellent local guides. The accommodation chosen for this tour is extremely luxurious, three of the most beautiful hotels in Europe and certainly in Italy. All are magnificently located in Tuscany's unspoiled countryside. Your hotel in Florence is a 500-year-old Medici Villa, now a tiny luxury hotel where movie stars and musicians flock to. You're likely to run into somebody famous at the pool or the bar here. Your hotel in Siena is a castle dating back to the 14th century. Originally a monastery (complete with cloister, gardens and adjoining villas), now it has been completely renovated to its former glory as a hotel and gained Relais Chateaux status.

Finally, your historic hotel in the Maremma wine region (Southern Tuscany) is a chic 5* luxury Villa hotel. Centuries ago it used to be the hunting lodge for the Dukes of Tuscany and the property has been refurbished to its luxuriant and decadent past. This Maremma wine hotel is considered to be one of the most exclusive properties in Italy. It also boasts a restaurant run by famed French chef Alain Ducasse. Apart from sleeping in utter luxury, you'll visit the exquisite cities of Florence and Siena, whose combined artistic heritage is more than most countries! Local art historians will lead you though the best galleries and museums (including the Uffizzi Gallery) and you'll have the chance to explore some lesser known jewels such as the Boboli Gardens and picturesque medieval villages.

The cuisine featured on this tour is, as usual, a highlight. Dine in flawless Michelin Starred locales along with rustic, mom and pop trattorias. The restaurants are hand selected to show you the best Tuscany has to offer. The wines and specialties of Toscana are revered as being some of the finest. On this tour, you'll taste vintage Brunello di Montalcino, "Super Tuscan" wines such as Petra and classic Chiantis from Radda. Delicious local dishes may include "Pappardelle a la Lepre" (pappardelle pasta cooked with hare) and wild boar cured sausage ("Prosciutto di Cinghiale"). The most famous Tuscan dish is the "Bistecca a la Fiorentina", a huge T-Bone Tuscan steak usually big enough for two. And, to finish off any proper Tuscan meal, perhaps while you are dining al fresco at one of the gorgeous hotels included in this tour, you must try the "Cantucci with Vin Santo" (Macaroons and "holy wine"). Divine! If you are looking for a luxurious food and wine orientated tour of Tuscany, with the "Best of" highlights of the region's art treasures, then this tour is for you.

Tours Highlights:

  • Private Chauffeured Wine Tours in Tuscany
  • VIP Winery Visits in Chianti, Montalcino and Maremma Super Tuscans
  • Bilingual Wine Guide
  • Excellent Gourmet Dining Wine Country
  • Ultra Luxurious Villa style historic hotels
  • Walking Tours of Florence and Siena
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Below is a suggested Day By Day Itinerary for your private Wine Tour in Florence

Day One - Privately Guided Walking Tour of Florence & Lunch

 Your exclusive 5* Villa Hotel just outside of Florence

Your exclusive 5* Villa Hotel just outside of Florence

AM: Arrive to Pisa/Florence airport

Your personal guide (specialized in wine) and English speaking driver for the tour will meet you at the airport, and you will transfer by comfortable Mercedes to your exclusive hotel, tucked away in a chic neighborhood, just south of Florence.

Arrive to your amazing hotel, a 16th century Villa which once belonged to the powerful Medici family. Numerous personalities have stayed here through the years including Winston Churchill, Elizabeth Taylor and Clark Gable. You'll be greeted with a welcome glass of champagne upon arrival.

Florence awaits! After check in, your personal chauffeur will take into the historic center of Florence, one of the most beautiful cities in the world. You will receive a private guided walking tour of Florence's "Centro Storico" to include the Mercato Centrale (the mind boggling food market), the Piazza della Signoria (the gorgeous square where the Uffizi gallery, Neptune's fountain and the Palazzo Vecchio are all located), and plenty of hidden gourmet gems enroute. Lunch will be at a lively Enotecta (chic wine bar), where you will experience your first velvety wines of the tour. Evening transfer back to the luxury hotel and dinner on your own.


5* Luxury Villa Hotel, member of "Leading Small Hotels of the World"

Meals Included in Price:

Welcome aperitif, Welcome basket & Keepsake Book of Wine Tour & Special Present. Full lunch with wine.

Day Two - Tour of the Uffizi Gallery & Gourmet Lunch

BotticelliĀ“s Birth of Venus at the Uffizi Gallery

BotticelliĀ“s Birth of Venus at the Uffizi Gallery

Breakfast: Elegant spread at the Villa

Morning free to enjoy this splendid hotel. Late morning transfer to historic Florence. Visit to the marvellous Uffizi gallery, one of the most famous art museums in the world, boasting Botticellis, Michelangelos and Da Vincis, unforgettable.

For lunch, a gourmet lunch will be waiting for you at Pinchiorri in Florence, the crème de la crème venue to begin a Tuscan gastronomic journey (3 Michelin Starred venue, wine not included). Set in a magnificent Renaissance palace, there are over 150,000 wines in the cellar, stocked with French, Italian and Californian labels. In the kitchen, French chef Annie Féolde is known for her innovative flair and this is one of Italy's most famed restaurants.

After lunch, your local Florence guide will collect you from the restaurant and lead you on a unique walking tour (about 3 hours), taking in unusual corners, hidden squares and interesting anecdotes. Guide is a young charming historian.

Dinner on your own at the luxury hotel or taxi into Florence, with our dinner recommendations.

Overnight: 5* Luxury Villa Hotel, member of "Leading Small Hotels of the World"

Meals Included in Price: Full Breakfast, 3 Michelin starred lunch (wine not included)

Day Three - VIP Wine Tastings in Chianti Classico & Montalcino

Private visits at Boutique Wine Estates

Private visits at Boutique Wine Estates

Breakfast: Enjoy a luxurious Tuscan breakfast outside on the terrace overlooking the mighty Arno River and views of elegant villas lining the riverfront.

Today will be a wine tasting extravaganza! Transfer from Florence towards Siena, via the most beautiful villages of the Chianti Classico region. Stop for a VIP winery visit to the most exclusive winery in the area. You'll enjoy a professional tasting of the full range of wines with personalized tasting sheets and even a gift, signed by the winemaker. Lunch will be at a fun, local trattoria in a medieval village. Don't miss a walk around the tiny walled village of Radda before continuing on your wine journey.

After a scenic drive passing vineyards and tiny wine villages, the next stop is a visit to the perfectly manicured, hill topped village of Montalcino. This ancient village is best known for its elixir red Brunello di Montalcino wines, made with the Sangiovese Grosso grape varietal. A VIP private visit to an artisan Brunello producer will be organized for you (normally closed to the public), followed by a fantastic vertical tasting. After the tasting, you can take in an invigorating walk around the pretty village of Montalcino, do some gourmet shopping or pop into the ancient "Chiesa" (church) before heading to your spectacular hotel for the evening, a restored monastery, now a Relais Chateaux.

Relax at the pool, in the historic library, or take a walk on the immense grounds full of olive groves and vines. Dinner on your own at the excellent restaurant of the hotel.

Overnight: 4* Ultra Luxurious and Historic Relais Chateaux

Meals Included in Price: Full breakfast, Lunch with wine, Wine Gift

Day Four - Olive Oil Tasting, Traditional Trattoria Lunch

Romantic Dining in Siena at Divo

Romantic Dining in Siena at Divo

Full Breakfast at the Relais Chateaux, served in a historic patio, surrounded by ancient trees.

Morning visit to a prestigious Olive Oil and wine producing estate Fattorie di Felsina, a half hour beautiful drive from the hotel. You'll see how the olive oil making process takes place, which is truly fascinating. An olive oil tasting will be given for you and each guest will receive a gift bottle of this famed olive oil (one of the best in Italy).

Transfer from olive groves to the historic center of Siena, one of the noblest cities in Italy. The gorgeous 14th cent. main square, called the "Campo", is where the historic "Palio" races are held. You'll receive a walking tour of the old town and have free time for shopping, or gallery hopping. A delicious 3-course lunch will be arranged for you in a fantastic local trattoria and served with lovely Vino Nobile di Montepulciano wine. Full afternoon in Siena, highlights include the 12th cent. Gothic Cathedral (one of the most exceptional in Italy, with dazzling black and white marble) and the Pinacoteca Nazionale, Siena's best art museum, housed in a 15th century palace.

Evening transfer to Relais Chateaux hotel and dinner to enjoy on your own.

Overnight: 4* Ultra Luxurious and Historic Relais Chateaux

Meals Included in Price: Full breakfast, Lunch with wine, Olive Oil gift

Day Five - Super Tuscan Wine Tasting in Maremma

Super Tuscan Vineyards

Super Tuscan Vineyards

Full Breakfast at the Relais Chateaux, served in a historic patio, surrounded by ancient gnarled trees.

Today, you'll travel southwest, from Siena to Grosseto to the mythical Maremma Wine Region. The 1 ½ hour drive leaves the cypress-covered hills of Siena and the landscape becomes more rugged but very pretty. Maremma is the land of sunflowers and in season, they seem to cover entire hills. Your first stop will be to your beautiful hotel for the next 2 nights, a historic villa just outside of the charming fishing village of Castiglione della Pescaia

Welcome aperitif in the lovely sitting room or outside by the pool, while the porters take up your luggage. After check in, you'll travel north on a country road to the tiny wine village of Suvereto. Two extra special winery visits will be planned for you at 2 of the most famous Super Tuscan estates. One is a super slick Napa-esque operation designed by well-known Swiss architect Mario Botta; the second is a family owned winery most famous for receiving 100/100 points from Robert Parker for the 2000 vintage. You'll have a tasty light lunch at one of the cellars (Pecorino Cheese, homemade pasta, bruschette, etc) served with wine of course.

After wine tasting, you'll visit the perfectly preserved fortified hamlet of Massa Marittima. Dating back to the 8th century, this picturesque village is an entirely pleasant place to enjoy a café or a bicchieri di vino. Evening transfer to your luxurious country villa. Dinner on your own at the hotel (founded by famed chef Alain Ducasse) or nearby in Castiglione della Pescaia.

Overnight: 5* Leading Small Hotel of The World

Meals Included in Price: Full breakfast, Informal lunch at a wine cellar, w/ wine

Day Six - Excursion to Bolgheri and VIP Wine Tastings

Your gorgeous wine country hotel

Your gorgeous wine country hotel

Full breakfast at elegant hotel

Morning visit to the famed wine village of Bolgheri to visit one of the most famous wineries in the world, very exclusive and difficult to get into (virtually impossible for the general public). You'll indulge in your special VIP visit and superb wine tasting. After the tasting, you'll have your driver and guide on hand to take you wherever you like. We recommend the villages of Pitigliano or Castiglione della Pescaia for sightseeing, the beaches of Monte Argentario for swimming and sailing.

Late afternoon transfer to your beautiful hotel, to truly enjoy it. The 500 hectare estate has an elegant swimming pool, fields of sunflowers, a vineyard and even olive tree groves. Wine and olive oil are produced on-site. Enjoy an afternoon of Tuscan bliss in this beautiful property.

Tonight, you have a treat in store! An amazing Farewell dinner with keepsake menus (signed by the chef) will be arranged for you, with top quality wines. This will be a gastronomic highlight on the tour!

Overnight: 5* Leading Small Hotel of The World

Meals Included in Price: Full Breakfast, Farewell dinner (with various courses) and 3 different wines to pair with the dinner.

Day Seven - End of Tour

Vineyards outside of Florence

Vineyards outside of Florence

Full breakfast at elegant hotel.

Your chauffeur will take you to where your next port of call is.

This concludes your ultra luxury wine tour of Tuscany, with wine tasting in Chianti, Montalcino and the Maremma. You will leave with many gourmet goodies and gifts, and above all with a deeper appreciation of Tuscan wines, art and architecture.

We can arrange for extra days in Rome or Venice, contact us for details.

End of Services.

Meals Included in Price:Full Breakfast

Customer Testimonial:

“You were such a pleasure to deal with so understanding of all our issues - I can't thank you enough for your caring and flexibility. The hotels were outstanding. The service aspect of each of the hotels was exemplary with exquisite care being given to every detail. Simone was also a delight. I was blown away by his knowledge of Florence and the Uffizzi. I felt like I was walking with the encyclopaedia Britannica. The restaurants...what can I possibly say? Pinchiorri is an experience one is not likely to forget. The food, the wine, the service - world class.”

Maria and Umberto Contestabile, Virginia Beach, USA

What's Included:

  • All Transportation and transfers for 6 days by luxury Mercedes (for 4 or less) or luxury coach for 5 or more (with 2 seats each)
  • Bilingual expert guide (English speaker) for duration of 7 day tour
  • Local art guides in Florence and Siena
  • All accommodation (4 nights, in ultra luxurious & charming 5* hotels, 2 nights in 4* luxury Relais Chateaux)
  • 6 Full Breakfasts with fresh squeezed juices, fresh baked bread, etc
  • 5 Lunches with wine, mineral water, other beverages (including 1 lunch at 3 Michelin starred venue)
  • 1 spectacular Farewell Dinner, Menu du Gourmand with extra special wines selected
  • Welcome aperitif cocktails (Champagne/Campari Fizz/Negroni, etc)
  • Professional Wine Tasting Presentations with Winemakers/Owners/top staff
  • All VIP Winery Visits and Wine Tastings: minimum 5 Boutique and Premium wineries incl. Super Tuscans, Brunello di Montalcino and Chianti Classico.
  • Olive Oil estate visit
  • Olive Oil gift
  • Various Wine Gifts with bottles signed by the winemakers
  • All Entrance Fees to Cultural Sites (Art museums, etc)
  • Detailed Itinerary of Tour- Keepsake Book
  • Keepsake personalized menus
  • Welcome basket with wonderful gifts (big basket per couple, and smaller basket each for the 2 singles)
  • Bottled water, juice, soft drinks and snacks available during the drives
  • All local taxes

What's Not Included:

  • Flights
  • Meals and Drinks not Specified
  • Personal Expenses such as Telephone, Minibar, etc
  • Tips and Gratuities (Guides, Restaurants, etc)
  • Travel Insurance (Strongly recommended)
  • Cancellation Insurance


This is a SAMPLE TOUR ITINERARY. Please note that our private chauffeured luxury tours are totally customized to your needs and price varies according to the number of people in your group (please note tours require minimum 2 guests), specific suppliers included, number of services included,specific dates, transport type etc. Contact us today for more information and we would be delighted to get started on a tailor made detailed itinerary with pricing for you.

  • Final price depends on chosen style of accommodation and dining. Please contact us with your group size (minimum 2 guests, no maximum group size), travel dates and preferences and we will send you custom pricing.
  • Discounts available for larger groups
  • Please note that our tours are available upon demand for PRIVATE GROUPS and are not scheduled tours for mixed groups.

More Information:

All of our tours are available year round upon request for your private group of minimum 2 people. We organize unforgettable packages in Italy that include wine and adventure touring. If you would like us to customize a private high-end tour of Italy for you

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