Summary
Short description
Between heritage towns, rural romance and culinary delights, experience Tuscany at its authentic best
Highlights
- Showcase such Tuscan highlights as Florence and Siena
- Head off the beaten track to the region’s medieval hilltop towns
- Indulge with Tuscany's world-leading food and wine
- Enjoy a stay in a Tuscan castle
- Explore at your own pace with car hire included throughout
In pictures
About
Recommended for:
Best of holidays | Food & wine | History & culture | June holidays | October holidays | Self-drive
This comprehensive fly-drive holiday showcases both Tuscany’s famed centrepieces and its lesser-known gems. Indeed, while you’ll take in Renaissance Florence, and Pisa’s iconic leaning tower, you’ll also be treated to the region’s abundant rural charm, showcased in sprawling vineyards, olive groves and hilltop medieval towns. And, with car hire included, you’ll enjoy life on the open road alongside stays in boutique properties and the chance to tuck in to the region's famed food and wine.
Day by day itinerary
Day
1
UK to Pisa
Begin your trip with complimentary airport lounge access before flying to Pisa. Collect your hire car and head to your accommodation, is a beautifully restored 14th-century estate nestled in the Monte Pisano hills near Pisa. Surrounded by lush gardens and historic parkland, it offers elegant suites, frescoed halls, and serene courtyards. Guests enjoy authentic Tuscan charm combined with modern comforts, making it an ideal retreat for relaxation or a refined base to explore Pisa and the enchanting landscapes of Tuscany.
Stay: Villa Scorzi (Superior)
Meals: B
Days
2-3
Pisa and Lucca
Spend two days at leisure, exploring the highlights of Pisa and its neighbour, Lucca. Make the short drive into Pisa to see its most iconic monument, the Leaning Tower, set within the exquisite Piazza dei Miracoli, which also houses the impressive Duomo Cathedral and Baptistery. Then take the scenic drive to leafy Lucca. Once a republic capital, its 16th-century wealth survives today in gilded churches and terracotta-capped residences, all watched over by dramatic Renaissance walls and even garden-topped towers.
Stay: Villa Scorzi (Superior)
Meals: B
Day
4
San Gimignano and Siena
Drive south and enjoy a walk through San Gimignano, home to a prestigious collection of frescoes and important works of art dating back to the 13th and 17th centuries. Then continue to one of Tuscany’s most beautiful cities, Siena. Leave your car and head into the city’s historic centre on foot, where stepped streets trace hilltop contours, leading you between grand piazzas and the spectacular Italian Gothic cathedral. At the heart of Siena lies its central piazza, Il Campo, world-famous for the Palio horse race held here twice every summer.
Stay: Villa Ermellina (Superior)
Meals: B
Day
5
Montalcino and Pienza
This morning, head south with recommended stops in Montalcino, nestled in the hills of the Val d’Orcia and renowned for its world-famous Brunello di Montalcino wine. Continue to Pienza, birthplace of Pope Pius II. A legacy of Pius, the small village was transformed into a Renaissance city of palaces, houses and squares. Then proceed to your accommodation – a country house dating back to the 1700s, wrapped in vineyards and olive groves and within easy reach of Cortona. Rooms feature wooden beams and intricate stonework, carpaccio is served against sunset views, and the spa treatments are superb. You’ll also want to unwind on the gorgeous pool terrace.
Stay: Relais La Corte Dei Papi, Tuscany (Deluxe)
Meals: B
Day
6
Montepulciano
After breakfast, make the short drive to Montepulciano, standing high atop a hill in southern Tuscany. This medieval town of rare beauty is full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners, boasting panoramas over the Val d’Orcia and Val di Chiana valleys. We recommend sampling one of Tuscany’s most renowned red wines, Nobile di Montepulciano, while exploring the region.
Stay: Relais La Corte Dei Papi, Tuscany (Deluxe)
Meals: B
Days
7-8
Florence
Drive north to Florence, drop off your hire car and make your way to your hotel. You’ll be perfectly placed to explore Florence, with highlights including the Duomo and its stunning polychromatic façade, the Ponte Vecchio – a multi-storey bridge recalling the city’s medieval bustle – and the Uffizi Gallery, home to masterpieces of the Renaissance
Stay: Gallery Art Hotel, Florence (Superior)
Meals: B
Day
9
Return to UK
Today make the drive back to Pisa to return your car and make take your flight back to the UK
Map
Pricing
Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.
Accommodation rating:
9-day tailor-made self-drive
from £1,850 pp incl. flights
Superior / Deluxe 2026
Special Offer
Black Friday special savings: Save up to £175 pp.
Book by: 5 December 2025
Apr / Jul
from £1,885 pp. incl. flights
Oct
from £1,850 pp. incl. flights
May / Jun / Aug / Sep
from £2,430 pp. incl. flights
Valid for travel: April to October
Includes:
- Complimentary UK departure airport lounge access
- Return flights from UK to Pisa / returning from Florence
- 8 nights accommodation on a BB basis
- 7 days car hire in a Compact vehicle
Itinerary not valid during Siena Il Palio 29 Jun - 02 Jul / 13 Aug - 16 Aug)
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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