8 Day Bespoke Tuscany

8 Day Bespoke Tuscany

Tuscany embodies the romantic image of Italy. With its breathtaking rolling hills dotted with olive groves, vineyards, cypress trees and century old villas, there is a special charm that enhances its calling. Rich in history, there are endless medieval hilltop villages to discover as well as the larger cities of Florence, Siena, Pisa, and Lucca. A famous cultural destination, the area is home to some of the world's most recognizable Renaissance art and architecture as well as incredible cuisine and renowned wines. From Brunello through Chianti to the vines of Sassicaia and Ornellaia the Super Tuscans, Tuscany’s more than 10,000 years of wine history is unrivalled.

Why Into The Vineyard

Why Into The Vineyard

Commitment to Service

We believe life is most enriched when time is spent meaningfully, and the people around us are well cared for. We offer tailored travel that is effortless and designed to inspire discovery, foster connections, and build community.

Private & Customizable Journeys

Travel preferences are as unique as an individual’s fingerprint. Our expertise lies in designing bespoke journeys to the wine regions of the world. Using our global networks, we craft your trip to suit your own style.

Regional Expertise

Discover the world alongside passionate locals who bring each destination to life. Garner authentic insights and connection. Our Sales and Planning teams have explored at length the destinations they specialize in. We continuously revisit regions, inspect accommodations, and experience wineries, so we can deliver the quality and service you expect.

Extraordinary Experiences

We design immersive experiences with excellence. Whatever your request - a private Mendoza vineyard lunch, truffle hunting in Piedmont, or a First Growth in Bordeaux - you will enjoy exclusive access to unparalleled encounters.

Trusted Support

Plan and travel at ease with the support of expert travel professionals. Headquartered in Canada and with staff around the world, we ensure you are supported from initial planning discussions to full on-trip coverage.

Responsible Travel

Our aim is to provide travel that inspires both the traveler and the communities we visit. We prioritize privately-operated accommodations, locally-owned restaurants and generational wineries, and encourage low-carbon private transportation where viable.

Quick Summary

Itinerary Detail

Day 1: Arrival into Florence

Arrival into Florence
Daily Summary
  • Transfer: Florence Airport to Hotel
  • Transfer: Transfer to Chianti
  • Accommodation: Borgo San Felice

Welcome to Italy! Upon arrival into Florence Airport, you will be greeted by your private driver and transferred to your accommodations in Chianti.

After checking out of your hotel this morning, you will be transferred to your accommodation in the Chianti Region. You have arrived in the land of the Gallo Nero, one of most historic wine growing regions in Italy.

Chianti Classico

The Chianti Classico wine region is located in Tuscany, Italy, between the cities of Florence and Siena. This picturesque area covers an area of approximately 70,000 hectares, with vineyards and olive groves dotted throughout the rolling hills and valleys. The region's winemaking history dates back to the 13th century, and it is renowned for its production of Chianti Classico, one of Italy's most famous wines. The region's unique terroir, with its mineral-rich soil and a mild, temperate climate, creates ideal growing conditions for the Sangiovese grape variety, which is the main component of Chianti Classico. The region is also known for its ancient villages, medieval castles, and stunning landscapes, making it a popular destination for wine lovers and tourists alike.

Rest of Day at Leisure

Enjoy the remainder of your day at leisure. Relax and unwind at your accommodation or set out for your own discovery of the area.

Day 2: Chianti Classico

Chianti Classico
Chianti Classico
Chianti Classico
Chianti Classico
Chianti Classico
Chianti Classico
Daily Summary

Chianti Classico

En route to your hotel, enjoy an exciting day of touring in one of the most historic wine growing regions in Italy, Chianti Classico. We will spend the day exploring the heart of the area with private visits and a focus on the great vineyards and wineries here. This small wine-region produces perhaps one of the best-known and appreciated wines in Italy, Chianti Classico DOCG, comprised of 80% of Sangiovese, and 20% other various varietals such as native grapes Canaiolo and Colorino. Chianti Classico stretches between Florence and Siena and includes 14 different municipalities.

Some of the producers we will consider for todays tastings include:
• Buondonno - This farm is in the Chianti hills, surrounded by woods, vineyards and olive groves. It covers approximately 20 hectares, of which 8 are vineyards and 4 are olive groves.
• Podere La Piaggia - Located in the heart of Chianti, La Piaggia is a small family business farm and has the oldest vines in the area of Chianti Classico, dating back to around 1920!
• Caparsa - Produces an organic Chianti Classico wine called Doccio a Matteo, the wine is considered an essential food for life. The cellar of Caparsa is more than 400 years old and, pending availability, you may be able to taste the famous wines of Caparsa with Paolo Ciamferoni, owner and winemaker.
• Castello della Paneretta - Situated on the western slopes of the dominating hills of the Elsa valley, looking towards San Gimignano. Ancient records date back to wine production since 1596 and with 22 hectares of vineyards, only Sangiovese and Canaiolo Nero grape varieties are grown.
• Castello di Ama - Sitting at the end of a long, narrow road, Castello di Ama is a medieval Italian village perched on a hilltop surrounded by vines and black cypress trees. The village, which dates back to the 18th century, looks as if it's been here for all of eternity. These days, it's owned almost entirely by Lorenza Sebasti and Marco Pallanti, the couple behind Castello di Ama, one of Tuscany's most famous wineries.

Throughout the day explore one of the many beautiful Tuscan villages such Radda in Chianti or Castellina in Chianti.

There are several great restaurants along the way and your guide will discuss your lunch options today. Some of our favourites include Osteria di Fonterutoli, Osteria Rosticceria il Re Gallo, Osteria alla Piazza and Ristorante Il Vescovino.

As your charming day comes to an end, your guide will deliver you to your accommodation.

Day 3: Chianti at Leisure

Chianti at Leisure
Chianti at Leisure
Chianti at Leisure
Chianti at Leisure
Daily Summary

Chianti at Leisure

Enjoy a day at leisure. We can provide suggestions to make the most of your day or set out and explore at your own pace.

Indulge in a peaceful day today at the property exploring the surrounding vineyards and olive groves or set out to discover the nearby charming villages. If you are feeling adventurous, discover the White Roads that branch in the area and make the ideal setting for strolls by foot, horse or bicycle.

Day 4: Vino Nobile di Montepulciano

Daily Summary
  • Transfer: Hotel Transfer
  • Tour: Vino Nobile di Montepulciano
  • Accommodation: Castello di Velona
  • Meals: B

Check out of your hotel this morning and meet your driver guide who will transfer you to Val D'Orcia. En route, enjoy a day of touring.

Vino Nobile di Montepulciano

On the ridge that divides the Val D'Orcia from the Val di Chiana, Montepulciano stands on a chalky hilltop. A summer retreat for Florentine aristocrats, the town has palazzi and piazze embellished by Florence’s leading 15th century architects. Montepulciano is full of elegant Renaissance palazzos, a slew of artisan workshops, beautifully façaded churches and boasts vast panoramas of the wonderful Val d'Orcia and Val di Chiana valleys that surround it. Wine took center stage in the 1700s, when its popularity among nobles and literati earned it the moniker Vino Nobile di Montepulciano.

After meeting your guide at your hotel, drive together on the scenic roads through vineyards and olive groves towards Montepulciano. Throughout the day enjoy a visit to the hilltop town, tastings at family run vineyards and lunch at one of our favourite traditional restaurants serving fresh dishes typical of the region (to be paid directly).

We will consider at least two of the following wineries to visit during your day.:
• Boscarelli - A small, historic family winery producing Vino Nobile di Montepulciano DOCG, which represents 80% of all of their products. Vino Nobile is the most important and oldest label. Based on the age of the grapes and their selection, different typologies are produced.
• Bindella - Situated in one of the oldest areas of production, the Argiano wine region, the story of Bindella began over a hundred years ago. The Bindella property in Montepulciano, is divided into 40 hectares of vineyards, 13 ha olive groves, 30 ha grass-and farmland plus 20 ha oak forest. Today they produce 9 different wines, made with 10 different grape varieties, 2 sorts of grappas and olive oil.
• Contucci - As far back as the Renaissance the Contucci family were cultivating the grape and by 1700 this activity of theirs' was much appreciated. In fact they were one of the founding fathers of Vino Nobile, as is documented in texts from 1773 “having a major role in making it world famous a noble wine destined for the table of nobles."
• Azienda Agricola Polizian - Federico Carletti’s leading Vino Nobile estate, with 120ha of vines lies a few miles northeast of Montepulciano. The production focuses on modern, polished Nobile, planted to high-density with select Sangiovese and aged in barrique.

You will be delivered to your accommodations at the end of the day to check in

Day 5: Day at Leisure

Day at Leisure
Day at Leisure
Day at Leisure
Day at Leisure
Day at Leisure
Daily Summary

Val d'Orcia at Leisure

Enjoy a day at leisure. We can provide suggestions to make the most of your day.

Indulge in a peaceful day today at the property exploring the surrounding vineyards and olive groves or set out to discover the nearby charming villages.

Day 6: Brunello di Montalcino

Brunello di Montalcino
Brunello di Montalcino
Brunello di Montalcino
Brunello di Montalcino
Daily Summary

Brunello di Montalcino

This morning meet your guide at your accommodation and travel through scenic countryside to the area renowned for its excellent wine, Montalcino. Brunello di Montalcino was awarded the first Denominazione di Origine Controllata e Garantita (DOCG) designation and today is one of Italy's best-known wines.

You will visit at least two of the best producers of Brunello Wine. Some of our favourite producers we will consider include:
• Capanna - Owned by the Cencioni family since 1957, is situated in the Montosoli area, to the north of Montalcino. It was founded by Giuseppe Cencioni who was one of the 25 founders of the Consorzio del Vino Brunello di Montalcino. Helped by his sons Benito and Franco, they started bottling their own wines in the 1960's.
• Podere Le Ripi - a biodynamic vineyard on a sloping 55-hectare site between forest, vineyards and olive trees. Formerly inhabited by a shepherd and his sheep until 1998, Francesco Illy, heir to the famous Trieste coffee dynasty, purchased the land and planted the first vines 3 years later. The estate is divided between two opposite Montalcino mountainsides, with soils belonging to different geological eras.
• Casanova di Neri - The outcome of a process of productive and philosophical evolution, a new vision of Brunello di Montalcino that interprets tradition in a different innovative way. A profound commitment and respect for the land, a conviction that it is the lynchpin for the production of unique wines and that the care given in treating the grapes.
• Poggio di Sotto - Founder Piero Palmucci, a former shipping executive, spent several years researching the soil types and microclimates best suited to Sangiovese Grosso before choosing a property to found his own Brunello estate. His search led him the current site in 1989, just outside the town of Castelnuovo dell’Abate in the southern part of Montalcino, with parcels at three different altitudes combining to make a particularly well-balanced Brunello.
• Altesino has become a reference point for the entire territory. The introduction of the "Cru" (Montosoli) concept in 1975, the first experiments with barriques in '79, the production in '77 of the first Grappa di Fattoria under the consultancy of the master distiller Gioacchino Nannoni and the first printed for Brunello 1985 are some of the positive contributions putting Montalcino on the world map.
• Cinelli Colombini - The roots of the Colombini family in Tuscany go back to 1592, and their tradition of excellence in winemaking began in 1790 with the founding of the Fattoria dei Barbi. It was in the 1960’s that Francesca Cinelli Colombini, also known as the “Lady of Brunello” made a name for herself as the stalwart leader of Barbi’s top wines.

Stop for lunch near Montalcino in a local trattoria such as Boccon di Vino, which offers panoramic views of the region (to be paid directly).

After lunch visit the charming hilltop town of Montalcino. The town takes its name from a variety of oak tree that once covered the terrain. The very high site of the town offers stunning views over the Asso, Ombrone and Arbia valleys of Tuscany, dotted with silvery olive orchards, vineyards, fields and villages. The lower slopes of the Montalcino hill itself are dominated by highly productive vines and olive orchards.

As your day concludes, you will be returned to your hotel.

Day 7: Val D'Orcia to Florence

Val D'Orcia to Florence
Val D'Orcia to Florence
Val D'Orcia to Florence
Val DOrcia to Florence
Val D'Orcia to Florence
Val DOrcia to Florence
Daily Summary
  • Transfer: Hotel Transfer
  • Tour: Siena Walking Tour
  • Accommodation: Hotel Lungarno
  • Meals: B

Check out of your hotel this morning and meet your driver guide who will transfer you to Florence. En route, enjoy a half day of touring.

Siena Walking Tour

The Medieval town of Siena stands on three hills with an idyllic backdrop of arable fields, where the edges of this ancient city melt into a countryside. Siena was first settled in the time of the Etruscans (c. 900–400 BC) and the Roman origin accounts for the town's emblem: a she-wolf suckling infants Romulus and Remus. According to legend, Siena was founded by Senius, son of Remus.

Meet your local guide in town and together wander through the streets as you discover the highlights on offer. Begin in the beautiful Piazza del Campo with its unmistakeable seashell shape lined with travertine. The piazza is known worldwide for the famous Palio di Siena, a traditional medieval horse race run around the piazza two times every summer. Next visit the incredible Palazzo Comunale and its soaring Torre del Mangia, thought one of the oldest and tallest towers in Italy. Complete your tour with a visit to the Siena Cathedral, or Duomo, built in the 12th century and one of the great examples of Italian Romanesque-Gothic architecture.

Florence at Leisure

Check in at your accommodations in the mid afternoon and enjoy the remainder of the day exploring as you wish. We will be on hand to provide some guidance so that you can make the most of your time in the city. We strongly recommend you make some time for shopping – Florentines are well known for their leather handicrafts. Enjoy a picturesque afternoon browsing the open-air markets such as San Lorenzo and Piazza del Mercato Nuovo.

If you are looking for more history and architecture, the Medici Chapel and Santa Maria Novella are often overlooked highlights.

After working up an appetite, it time to seek out the best Bistecca alla Fiorentina in Florence, or perhaps indulge at Enoteca Pinchiorri (3-star Michelin). The choice is yours and we will be on hand to help make any necessary reservations.

Day 8: Departure

Daily Summary
  • Transfer: Hotel to Florence Airport

Your driver will meet you at your accommodation and bring you to the Florence airport for your onward flight. Buon Viaggio!

Accommodation

Borgo San Felice
Borgo San Felice
Borgo San Felice

Borgo San Felice

An old Tuscan hamlet nestled in the hills of Chianti Classico. Siena, Montalcino, and the enchanted lunar landscape of the creti senesi are all nearby. The property is surrounded by woods, olive groves, and vineyards that have been cultivated for centuries. It has been the only Mansion Relais & Chateaux in Chianti Classico since 1992. The 5-Star Relais & Chateaux Borgo San Felice are in perfect harmony with the enchanted surrounding countryside and are defined by traditional Tuscan elegance. Here, you will experience refined modernity perfectly mixed with centuries-old charm.

Castello di Velona
Castello di Velona
Castello di Velona
Castello di Velona
Castello di Velona
Castello di Velona

Castello di Velona

Castello di Velona Resort, Thermal Spa & Winery is an historical property and renovated fortress dating back to the 11th century. Located on a hilltop five miles from Montalcino, it overlooks the entire Val d'Orcia area, a landscape of olive trees and vineyards which produce the world-famous wine Brunello of Montalcino. All rooms have breath-taking views over the Val d'Orcia and half the rooms also feature a dedicated tap where natural hot thermal water is supplied directly to your private bathtub.

Hotel Lungarno
Hotel Lungarno
Hotel Lungarno

Hotel Lungarno

50 years since its first inauguration, Hotel Lungarno has been completely renewed and reopened its doors after six months of renovation. Without sacrificing its charm, the blue, white and leather found in its lobby reflect the style of an elegant boat swaying on the Arno with the Ponte Vecchio as its backdrop. Our living room suspended over the river provides space for private rendezvous only steps away from the Borgo San Jacopo 1 Star Michelin restaurant, where you can experience masterful, world class gastronomy right in the heart of Florence.  And like any elegant boat, its fascination perseveres throughout the corridors, full of stories to tell. The recently improved hotel art collection includes more than 450 art works.

Details

Details

Price Includes

Bespoke organization of the trip

Bilingual guide with expert regional knowledge

Regional restaurant recommendations

Accommodation as per the daily summary

Meals as per the daily summary

All transfers on private basis as per the daily summary

All tours on private basis as per the daily summary (unless otherwise stated)

Wine tasting fees

Price Excludes

International and domestic airfares

Any entrance tickets not mentioned in the itinerary

All meals and beverages not included in the daily summary

Dinner restaurant reservations (available for a supplement)

Gratuity (at your discretion)

Travel insurance

Items of a personal nature

Rental vehicle hire (if applicable)