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Tuscan countryside

Tuscany’s Castellos, wine and country

7-day tailor-made self-drive staying at Castello del Nero & Castello Banfi Il Borgo from £2,505 pp incl. flights

Special offer: Free car hire – Save up to £55pp

Free car hire available on this itinerary


Short description

Exquisite wine and food is showcased alongside medieval towns and luxury countryside hotels


  • Experience an ultra-scenic road trip through the beautiful vineyards and olive groves of the Tuscan countryside
  • Discover the fascinating history and architecture of the area's ancient towns and cities
  • Enjoy a complimentary 5-course dinner paired with 6 exquisite Tuscan wines
  • Explore tiny authentic Italian villages with picturesque bike rides and walks
  • Relax alongside rolling countryside in two luxury hotels, one with a Michelin star restaurant and spa

In Brief

  • 3 Nights Tavarnelle Val di Pesa
  • 3 Nights Montalcino


Recommended for:
Food & wine | Free car hire | History & culture | Self-drive

This Tuscan self-drive will see you start in iconic Pisa before driving through the spectacular vineyards of Tuscany in your included hire car. You'll reach the historic town of San Gimignano, exploring its hilltop squares and frescoes, before continuing on to the medieval fortresses and art heritage of Siena. Discover Chianti's winelands with vineyard tours and wine tasting, sample exquisite Italian gastronomy via cookery classes and 5-course dinners, and horse ride along olive groves and gently undulating valleys. You'll do it all from two luxury hotels; Castello del Nero and Castello Banfi Il Borgo set deep in the hills of the Tuscan countryside, featuring gourmet restaurants, luxury spas, with, of course, endless green vineyard surrounds. 

Day by day itinerary

Day 1
UK to Pisa

You’ll begin your trip in style with included VIP airport lounge access before flying to Pisa where you’ll collect your included hire car. Begin the ultra-scenic drive to Castello del Nero along the hills of quintessential Italian countryside, stopping off at the iconic Leaning Tower of Pisa. Then, head to the historic walled town of Volterra, located on a steep hill and founded by the Etruscans 2700 years ago – explore the ancient walls and discover the remains of temples and the Roman theatre. You’ll then reach your hotel for the next three nights, the spectacular 5-star Castello del Nero. It lies among acres of rolling green hills and features a luxury spa and Michelin star restaurant, La Torre. Here, exquisite Italian cuisine is paired with fine wines, served al fresco overlooking the forest-fringed olive groves and vineyards of the Chianti countryside.

Stay: Castello Del Nero, Tuscany

Day 2
San Gimignano

After enjoying a breakfast, you’ll visit the stunning hilltop town of San Gimignano, where endless undulating hills frame ancient squares and stone houses sheltered among medieval fresco-lined churches and towers. Here, you'll enjoy an included private guided tour, discovering a prestigious collection of frescoes and important works of art dating back to the 13th and 17th centuries, as well as the historic Piazza, town hall and several museums. Spend the afternoon climbing the town’s highest tower, Torre Grossa, taking in the endless countryside views. After returning to your hotel, perhaps enjoy sunset yoga before a pre-dinner cocktail in the bar of poolside La Taverna, the second exquisite dining option in your hotel.

Stay: Castello Del Nero, Tuscany

Meals: B

Day 3
Castello del Nero

Today may be spent at your leisure, so take full advantage of your hotel's amenities and spectacular surrounds. Perhaps go horse riding through the sprawling Tuscan hills, walk along olive grove-lined forests, or learn about the fine wines of the region in the hotel’s 12th century wine cellar. Or, take a walk into the nearby village of Tavarnelle, before enjoying a massage in the luxury spa back at the hotel. End your last evening here with another Michelin-starred dinner or a typical Tuscan dinner at La Taverna before stargazing on the nearby Astronomical Observatory of Chianti’s panoramic terrace.

Stay: Castello Del Nero, Tuscany

Meals: B

Day 4
Castello del Nero to Siena

After breakfast today, you'll speed through the countryside to Siena, a drive characterised by winding roads along bright green hills and vineyards, and, upon on arrival, you’ll meet your official guide for an included private tour of Siena. Gothic streets and squares give way to historic monuments and cathedrals in this magnificent medieval city, while local artisans and bakeries perch round every corner. Discover the medieval Duomo, the fresco-topped ceiling of the stunning Baptistery and the Piazza del Campo, known for the famous horse race held here every summer. After exploring the city you’ll drive to your hotel for the next few evenings, the hilltop-perched Castello Banfi Il Borgo. A welcome drink will greet you on arrival, whilst in your elegant suite, all exposed timber ceilings and hand-decorated Italian flourishes, you'll find a welcome gift of a half bottle of local Castello Banfi Brunello di Montalcino as well as two Banfi Sparkling wines. This hotel is a true Tuscan gem, filled with intimate garden corners overlooking the rolling fields, while historic architecure contrasts with modern comforts in bedrooms, such as walk-in rainfall showers. The stunning onsite restaurant uses fresh, local ingredients to create exquisite dishes, served al fresco with acres of green wineland as the backdrop.

Stay: Castello Banfi il Borgo, Tuscany (Deluxe)

Meals: B

Days 5-6
Castello Banfi Il Borgo

You’ve got day 5 to spend at your leisure – perhaps go on a panoramic bike tour of the charming surrounds, or enjoy a massage in the comfort of your room or in the gentle breeze of the garden. Be sure to visit L’Enoteca, the hotel’s wine bar, where a range of the region’s finest varietals are presented with artisanal foods and crafts. Unwind with a glass in the pergola gardens or by the pool, where sun loungers lie alongside spectacular views of Brunello’s vineyards. You’ll receive an included 5-course dinner tonight, complemented by a selection of 6 Castello Banfi wines as you overlook the uninterrupted views of the valley. 

You’ll receive free access to The Giovanni F. Mariani Museum of Glass the next day, a gallery showcasing glass production throughout history, including ancient Roman glassware. You'll also get an included wine-tasting of 3 Sangiovese wines as well as a tour of The Balsameria, the cellars that house the production of Balsamic Vinegar. Perhaps spend the afternoon with a ‘chef’s experience’, where you’ll spend a few hours with the hotel’s expert chef preparing a 4-course lunch. Your last evening can be spent however you wish, perhaps with a stroll through the vineyards before a dinner either under the stars or in the opulent vaulted-ceiling dining room. 

Stay: Castello Banfi il Borgo, Tuscany (Deluxe)

Meals: B D

Day 7
Castello Banfi Il Borgo to UK

After breakfast you’ll drive to Pisa airport, return your hire car and fly home to the UK. 

Meals: B



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

7-day tailor-made self-drive staying at Castello del Nero & Castello Banfi Il Borgo from £2,505 incl. flights


Special Offer

Free car hire: Save up to £55 pp.

Book by: 31 January 2019

Low Season

from £2,505 pp. incl. flights

Mid Season

from £2,770 pp. incl. flights

High Season

from £3,075 pp. incl. flights


  • Return flights from UK – Pisa
  • 7 days car hire in an Economy 4 door vehicle
  • 3nts at the Castello del Nero in a Superior Room on a B&B basis
  • Private guided tour in San Gimignano
  • Private guided tour in Siena
  • 3nts at Castello Banfi Il Borgo in Deluxe Room Reserva
  • 5 course dinner with 6 Castello Banfi wines
  • Wine tasting experience and tour of Balsamic Vinegar cellars; The Balsameria
  • Complimentary access to Mariani Museum of Glass and Bottles at Banfi

Special offer saving valid for stays 29 Mar - 26 Apr & 26 Oct - 17 Nov

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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