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Tuscany & Roman Holidays Art & Gourmet Small Group Tour

An insider’s gourmet tour of Tuscany and coastal Lazio to discover the rich wine and food culture through our exclusive “Master Classes” and tasting sessions. Enjoy the unique atmospheres of Florence and Siena, and relax with scenic landscapes of rolling hills dotted by picturesque villages like Montalcino and San Gimignano, a “medieval Manhattan”. A unique journey to the heart of Italian excellence and a hands‐on meeting of many signature products of Italian cuisine. This 7 night/8 day 'tiny group' tour (with up to just 6 participants) is almost all‐inclusive too, with all meals (or tastings in place of meals) except for three dinners covered, along with accommodation in atmospheric hand-picked locations and an English‐speaking guide/driver, airport pick‐ups. Dates for 2018: Sun Sept 23 - Sun Sept 30 Dates for 2019: Sat Apr 20 - Sat Apr 27 Sat Sept 21 - Sat Sept 28 Sat Nov 2 - Sat Nov 9 Other dates available upon request for private groups Package price: $3750 per person, based on two sharing a double/twin room. All departures are guaranteed once four or more people have signed up. A deposit of 50% is required at the time of booking to secure your place. The balance is due 30 days before arrival. Travel insurance is not included and participants are advised to obtain their own policy. Price includes all meals/experiences listed, and a bottle of mineral water on transfers. Tasting experiences take the place of lunches on all the days of the tour, and 4 dinners are included in the program (day 1, 2, 3, 7)
• Trequanda
• Castellina in Chianti
• Montefiascone


3 Nights in Trequanda

Day 1

Your flight should arrive in the morning at Rome Fiumicino airport where you will meet the rest of the group and your guide/driver. After a good cappuccino, we head towards Tuscany, one of the heartland of Italian wine culture. Tuscan wines are appreciated worldwide both in the typical varieties based on Sangiovese grapes, and the more recent Super Tuscans" inspired by the French chateaux. We will check in to a charming and historic 15th century brick and stone farmhouse complex run by a family of traditional winemakers in Trequanda, with the possibility to relax in the scenic pool, stroll around the lovely countryside and visit their wine cellars. In the evening we will sit down to a classic home‐style dinner and dig into a selection of starters and main courses prepared according to original recipes and accompanied by the family´s robust red wines and “vin santo" digestive.

Included : Gourmet Tour Package, transport, guiding, tasting experiences, 7 breakfasts, 7 lunches or equivalent, 4 dinners or equivalent

Day 2

Val d'Orcia & Montalcino, home of Brunello
After a sumptuous breakfast we will drive along the cypress‐lined countryside roads of the enchanting Crete Senesi (Siena clay hills) and visit the Benedictine abbey of Monte Oliveto Maggiore, set amongst forests of pine and oak and famous for the cycle of frescoes depicting the life of St Benedict by Luca Signorelli and Sodoma. “Brunello di Montalcino" is considered among the most prestigious Italian wines, and our “Master class of red wines" will take place by a local winemaker close to the imposing castle of Montalcino, a bastion of the Republic of Siena in the endless rivalry with Florence. One last afternoon stop by the beautiful Pienza, a Unesco world heritage site located on the crest of a hill overlooking the Val d'Orcia: redesigned in the 15th century by the leading humanist Enea Silvio Piccolomini (later Pope Pius II), his birthplace became the symbol of elegant renaissance town‐planning. Return to our agriturismo for relax by the swimming pool and tasting dinner.

Day 3

Truffle hunt and Cooking Class
Truffles are among the treasures of Italian gastronomy, in particular the white truffles, which can be found in autumn and winter in specific parts of Italy like Piedmont, Umbria and Tuscany. The best way to enjoy them is to take part in an exciting hunt with local hunters and their trained dogs. That way you can learn all the secrets of this elusive mushroom, and then savour it in fresh, homemade dishes like tagliolini, which you will learn to prepare in a cooking class at your accommodation.

Day 4

We will transfer to the picturesque wine region of Chianti and check‐in at the fifteenth-century Palazzo Squarcialupi, one of the most important historical symbols of this typical and characteristic medieval Tuscany village of Castellina in Chianti. This will be our home base for the next days: a nobleman's mansion converted into a winery and luxury hotel with stunning views over the rolling hills, along the way there we will make a stop to visit to a traditional cheese producer.

A little about Trequanda

Tucked away in a corner of Tuscany is an oft-overlooked area around the town of Trequanda where two of our favorite winemaker-agriturismos can be found. Idyllic places you'll never want to leave and decidedly remote so leaving is really only a possibility by car. This area is called the Colli Senesi, the Siena Hills, and it lies south-east of Siena. Here you'll find undulating terrain covered in vineyards, olive groves and wheat fields. This is great truffle-hunting country and an excursion with a truffle hunter and his dog is a must.

2 Nights in Castellina in Chianti

Day 1

After a tasting lunch in the mansion´s restaurant paired with the local Chianti wines and digestives, we will explore San Gimignano, an architecture jewel reminiscent of a “medieval Manhattan" thanks to the unique skyline of ancient tower‐houses. Dinner will be served in a family‐run restaurant offering a choice of rich dishes like “pappardelle with wild boar" and assorted venison.

Day 2

Free day: Relax poolside or explore the area or visit Florence
Today's the day to luxuriate in the surroundings of the mansion. you can enjoy some free time to soak in the magic atmosphere of the medieval town center and a refreshing aperitivo. If you're feeling adventurous, there's a Vespa rental shop in town, or should you wish to stretch your legs, there's plenty of hiking to be done from Castellina. Alternatively you could get an early start and visit Florence, a transfer can be arranged to the closest train station. For dinner this evening (not included) your guide will give you some recommendations of eateries in Castellina. Be sure to leave some room for dessert at the gelateria on the edge of the village!

Day 3

After a rich breakfast, we will drive towards the enchanting Gothic city of Siena, home to one of Italy’s most beautiful squares, the Piazza del Campo which hosts the annual horse‐riding neckbreaking competition “Palio di Siena". The local Cathedral was planned to be the largest in the world and, although interrupted by the Black Death, remains an unforgettable sight. Tasting lunch in a lively osteria in the city center to sample a selection of ham and cheese delicacies like “prosciutto di cinta senese", “Panzanella" summer bread salad, “Pappa al pomodoro" fresh tomato soup, “Lardo di Colonnata". A sweet topping is guaranteed by the famous honey and almond pastries “ricciarelli", “cavallucci" and “panforte" served in a traditional bakery. From Siena we will travel to Lake Bolsena, just over the Tuscany/Lazio border. Should the weather and your sense of adventure allow you could try visiting the limestone-enriched natural hot springs at Bagni San Filippo.
Castellina in Chianti

A little about Castellina in Chianti

We have chosen Castellina as one of our key destinations in Tuscany as this small town or large village offers all the facilities most visitors need while allowing them to enjoy the countryside location as well. Public transport is limited so you will definitely need a driver or rental car while you're here. On the edge of a village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings. Close by you'll find San Gimignano, a 'medieval Manhattan' well worthy of a day trip and the walled town of Monteriggioni is even closer.

2 Nights in Montefiascone

Day 1

First we will check in at our boutique hotel with commanding views over Lake Bolsena, a locale popular with Romans escaping the city for short breaks before making a visit to a winery in the late afternoon to sample the locally produced wines, the interestingly named Est! Est!! Est!!! from Montefiascone, accompanied by an array of snacks that will more than fill you up. Should you wish to eat more the hotel's restaurant offers a very reasonable a la carte menu. In our experience after the wine tasting an appetiser, salad or dessert is as much as you'll need!

Day 2

Cheesemaking, fisherman's lunch on the lagoon and a cheese feast
The last full day of your trip will start early with a trip to a family owned and run organic sheep and goat farm, 45 minutes away towards the Lazio coast. You'll try your hand at cheese making and get to meet the animals whose milk goes into the many delicious cheeses produced there. The day continues with a visit to the coast and the chance to try some seafood for the first time on the trip. After some further exploration of the coastal region it's time to return to the farm for the final dinner of your week long gourmet experience to taste the fruit of your labors along with the many different pecorino and caprino cheeses made using various techniques and levels of ageing, paired with wines from nearby and further afield in Italy along with many other dishes prepared by the family, a fitting final night's feast for your gourmet tour.

Day 3

After breakfast you will be transferred to Rome Fiumicino airport for your departing flight back home or to continue your exploration of Italian wonders, should you extend your stay in the land of la dolce vita.

What's Included

Below you will find all the services provided as part of your complete vacation package.

Should you wish to add any optional tours and excursions listed on the Itinerary tab, please let us know.

Please note, no particular accommodation is specified in the package. The price you see on this proposal is based on estimated costs of 3 Star accommodation, or next best available class, in each destination. The total package price will depend on the accommodation you choose.

  • 3 Nights Accommodation in Trequanda
  • Gourmet Tour Package, transport, guiding, tasting experiences, 7 breakfasts, 7 lunches or equivalent, 4 dinners or equivalent
  • 2 Nights Accommodation in Castellina in Chianti
  • 2 Nights Accommodation in Montefiascone
  • Pre-trip assistance of the JayWay Destination Manager.
  • On-trip assistance from local JayWay Representatives.
  • A pre-paid local cell phone for all destinations.
  • Excursion booking advice and assistance.
  • Access to your personalized Guest Page, containing detailed destination information and tips on the best that these cities can offer.

- Flights to and from Europe.
- Tips for Tour Guides, Drivers and Local Reps.
Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.

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