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Tuscan countryside

Best of Tuscany

9-day tailor-made self-drive from £1,850 pp incl. flights

Special offer: Black Friday special savings – Save up to £175pp

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 Brief

  • 3 Nights Pisa
  • 1 Night Siena
  • 2 Nights Cortona
  • 2 Nights Florence

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: Superior Deluxe

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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Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0796 to discuss how we can tailor your holiday.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

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Let our travel specialists curate the perfect holiday:

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Every step of the way

Every step of the way

Our services are with you from start to finish:

  • Dedicated personal consultants
  • Free airport lounges on qualifying bookings
  • Care and guidance pre, post and during holiday
  • Full financial security: ATOL & ABTOT protected