Inspiration for your own tailor-made trip
Tuscany - Florence - Siena - San Gimignano - Lucca - Pisa
100% customisable for you
Your journey begins with a two-and-a-bit hour flight from London to Florence, Tuscany's fascinating capital city and UNESCO World Heritage site, noted for its artistic and architectural heritage. After touching down in Florence airport, you’ll be met by your driver and transferred to your hotel.
Often called 'The Cradle of the Renaissance', Florence is essentially an open-air museum, all elegant piazzas, terracotta domes and narrow Medieval streets. After checking in to your centrally located boutique hotel, spend the afternoon unwinding before your first Tuscan dinner. Whether you stay in the comfort of your hotel or venture out, our well-connected Concierge can point you towards the city’s best trattorie (and save you from the tourist traps).
This morning your guide will collect you from your hotel and take you on a private two-hour walking tour of the Uffizi Gallery – a concentrated deep dive into Florence’s artistic DNA. Stand before Botticelli’s Birth of Venus, admire Caravaggio’s dramatic chiaroscuro and weave through galleries brimming with Renaissance treasures.
Afterwards, spend a relaxed afternoon wandering Florence’s historic streets, lingering over gelato or browsing small boutiques. Come evening, sip an aperitivo in a tucked-away wine bar before choosing from our Concierge’s shortlist of Florentine favourites for dinner.
Cross the River Arno today via the oldest bridge in Florence, the Ponte Vecchio, which was rebuilt in 1345 after the wooden structure was destroyed in a flood. Then, tour Florence’s hip left bank – the Oltrarno (literally ‘beyond the Arno’) – with a knowledgeable local guide, visiting its bohemian botteghe (workshops), independent boutiques and authentic restaurants.
The rest of your day is yours to explore Florence at your own pace. Climb to the top of Giotto’s Bell Tower for views of the Florentine skyline or stroll around one of the city’s top gardens – the Rose or the Iris are the perfect place to take a break from the stone buildings of the city centre and enjoy a picnic on the soft grass.
Dinner tonight could be a low-key neighbourhood trattoria – we know some charming and resolutely non-touristy places and can reserve a table for you in advance.
Get up nice and early because today you'll be driving from Florence to the Tuscan countryside. Collect your hire car and set off on the hour-long drive to the Medieval town of Siena.
En route, enjoy a vineyard tour, wine tasting and long, lazy lunch surrounded by Chianti’s rolling hills and patchwork vineyards. Afterwards, continue to your hotel and spend the rest of the day getting acquainted with Siena. This evening promises another Italian feast, accompanied by some of Tuscany’s world-renowned wines.
Meet your private guide this morning for a walking tour of Siena, the Medieval jewel famous for its striped cathedral and the annual Palio horse race. Wander narrow streets lined with splendid palaces, visit the Duomo and pause in the vast shell-shaped Piazza del Campo, of which the Palazzo Pubblico (town hall) is the focal point. Here, you can stop for lunch in the beautiful square and people watch to your heart’s content.
The afternoon is left free for you to spend as you please. Return to your countryside hotel, explore small nearby villages or simply enjoy the quiet pleasure of doing very little in very beautiful surroundings.
Today is yours to enjoy rural Tuscany at your own pace. Borrow bikes, book a spa treatment, wander through sleepy hamlets such as Castellina or Radda, or take a scenic drive through vineyard-studded hills. If you’d like a restaurant booking, a winery visit or a guided walk arranged, your Concierge is only ever a WhatsApp away.
We can also arrange horse riding, mountain biking and yoga classes in the region if you’re looking for something more active.
Check out of your hotel this morning and drive to San Gimignano, the hilltop town famed for its sky-piercing Medieval towers. With your private guide, explore fresco-filled churches, quiet side streets and artisan workshops that still follow centuries-old traditions. After lunch, continue north to Lucca. This elegant, easy-going city – enclosed entirely by Renaissance walls – is your final overnight stop. Drop your bags at your hotel, then wander into town for dinner in one of Lucca’s atmospheric piazzas.
Start the day with a private cycling tour of Lucca, pedalling along its tree-lined walls and dipping into the historic centre to admire Romanesque churches, shady squares and handsome palazzi. With legs sufficiently stretched, it’s time to make your way towards Pisa.
Return your hire car at the airport, then if you have time and fancy one last Tuscan moment, swing by the leaning tower for a final photo. Board your afternoon or evening flight home and land back in London later that day.
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
ENQUIRE NOW
Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
