A wonderful blend of idyllic countryside and ancient towns, beautiful architecture and delectable food, Tuscany makes for an unforgettable holiday destination. On this leisurely tour we’ll seek out world-renowned treasures, explore hidden gems and become culinary connoisseurs as we fall head over heels for this exquisite Italian region.
The Back-Roads Difference
Itinerary:
Day 1 - Florence
Welcome to the birthplace of the Renaissance and the romantic capital of Tuscany. After meeting the group at our hotel, we’ll get to know each other over a delicious welcome meal. Accommodation: Hotel Roma (or similar)
Day 2 - Florence – Lucca
Our journey will begin with an in-depth walking tour of Florence. A local guide will bring the city alive as we stroll by the likes of the Duomo, Piazza della Repubblica and the Ponte Vecchio. After lunch, we’ll set a course for lovely Lucca – where cobbled streets, red-roofed buildings, fascinating history and fine architecture await us. This evening we’ll be free to explore Lucca at our leisure. Accommodation: Albergo San Martino (or similar)
Day 3 - Lucca – Cinque Terre – Lucca
A rocky coastline dotted with candy-coloured villages – today, we’ll turn our attention to the awe-inspiring Italian Riviera! After winding our way along this sublime stretch of shoreline, we’ll find ourselves in Cinque Terre: a UNESCO World Heritage Site. Having spent some time getting to know the area with our expert Tour Leader, we’ll return to Lucca for an evening spent at our leisure. Accommodation: Albergo San Martino (or similar)
Day 4 - Lucca – Pisa – Volterra
Infamous and impossible to miss, the Leaning Tower of Pisa makes for a staggering first port of call today. There will be plenty of time for photographing this iconic landmark as we explore the Campo dei Miracoli at our own pace. After a leisurely lunch, our attention will turn to the magnificent medieval ramparts of Volterra. We’ll spend some time exploring this mysterious town before concluding the day’s events at our hotel. Accommodation: Hotel La Locanda (or similar)
Day 5 - Volterra – San Gimignano – Siena – Pienza
Today we’ll make tracks to San Gimignano: home to a magnificent piazza, meandering stepped streets and some beautifully preserved architecture. While we’re here, we’ll sample some exquisite creations of a local gelato maker – before we’re treated to an indulgent Tuscan wine tasting. Before the day concludes, we’ll pay a visit to medieval Siena – an open-air museum of Gothic architecture and home to the magnificent Duomo. After taking in the town’s historic sights on an orientation tour, we’ll journey onwards to Pienza – our home for the night. Accommodation: Relais Il Chiostro di Pienza (or similar)
Day 6 - Pienza
Pienza’s timeless charm and enchanting rural backdrop makes for a serene spot to spend this morning exploring at our leisure. Later, we’ll sample some handcrafted cheese and world-class wines at a delightful local farm with sweeping views over the surrounding countryside. This evening is ours to spend as we wish. Accommodation: Relais Il Chiostro di Pienza (or similar)
Day 7 - Pienza – Rural Tuscany
After breakfast, it’s all aboard the mini-coach as we press on to the delightful Chianti region. We’ll wind our way through heavenly countryside before joining a regional cookery class. After learning some local recipes from our host, we’ll have the chance to tuck into our creations for lunch. Buon appetito! The afternoon will be ours to enjoy at our leisure before we reconvene for a final dinner together. Accommodation: Fattoria degli Usignoli (or similar)
Day 8 - Rural Tuscany – Florence
Before returning to enchanting Florence, we’ll stop off at a local oil mill for a guided tour, olive oil tasting and light lunch. All in all, it’s a fitting end to a tour celebrating the natural beauty and culinary traditions of Tuscany.
Departures on selected dates in November 2025.
Florence is the capital of Italy’s Tuscany region and home to many masterpieces of Renaissance art and architecture. One of its most iconic sights is the Duomo, a cathedral with a terracotta-tiled dome engineered by Brunelleschi and a bell tower by Giotto. The Galleria dell'Accademia displays Michelangelo’s “David” sculpture. The Uffizi Gallery exhibits Botticelli’s “The Birth of Venus” and da Vinci’s “Annunciation.”