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  • Stay in two of Italy’s finest hotels – a castle and Michelangelo monastery
  • Bring Florence and Tuscany to life with private tours
  • Indulge with Italy’s wining and dining favourites
  • Explore with transfers included throughout
  • Take in the medieval beauty of Siena and San Gimignano

Florence’s Renaissance beauty and Tuscany’s rural splendour – it’s a pairing as perfect as chianti and fresh tomato pasta. And, on this curated itinerary, you’ll see it all in style, with stays in the region’s two finest properties: a thousand-year-old castle and a 15th-century monastery that once housed Napoleon himself. Expect indulgent spa treatments, historically elegant rooms and fine dining served up to sunset views over Florence and vineyards alike. You’ll also explore with included transfers and private tours throughout, showcasing Florence’s artistry alongside the Gothic grandeur of Siena and the medieval severity of San Gimignano.

Days 1 – 2

Depart UK to a welcome from Michelangelo in Florence

After enjoying your complimentary chauffeur transfer to the airport, you’ll be treated to VIP lounge access before your flight to Florence. Here, you’ll be met and brought to your luxurious 15th-century accommodation to be greeted by a façade designed by Michelangelo himself.

What’s more, its majestic hillside views over Florence are taken in by everything from yoga classes and a fine-dining restaurant and opulent rooms housed in the historic monks’ cloisters. There’s even a library once used by Napoleon, and the hillside where da Vinci tested his famous flying machine.

Villa San Michele

Villa San Michele

Accommodation, Belmond Villa San Michele

Accommodation, Belmond Villa San Michele

Days 3 – 4

Florence walking tour & leisure

Don’t worry, although you’ll be delightfully secluded away from the city bustle, a complimentary shuttle is always on hand to bring you into town. However, so that you can get your bearings, we’ve also included a private walking tour, including entrance to the Uffizi Gallery’s collection of Renaissance masterpieces.

Your expert guide will also bring you among the city’s medieval maze to showcase everything from the Duomo’s iconic brickwork to the Ponte Vecchio – a multi-storey bridge of immense charm. You’ll also have plenty of time to explore at your leisure, enjoying the fashionable boutiques and sampling the Florentine steaks, best paired with a local red.

Breakfast included

Cattedrale di Santa Maria del Fiore, Florence, Italy

Cattedrale di Santa Maria del Fiore, Florence

The Ponte Vecchio and River Arno, Florence

The Ponte Vecchio and River Arno, Florence

La Loggia Restaurant, Belmond Villa San Michele

La Loggia Restaurant, Belmond Villa San Michele

Days 5 – 6

A Tuscan castle

Today, you’ll be brought out into the Tuscan countryside, your driver bringing you through rolling hills and honey-stone villages to arrive at your next accommodation – a 10th-century castle. It’s an impressive sight, wrapped in vineyards and olive groves.

Rooms are all wooden beams and intricate stonework, carpaccio is served up to sunset views and the spa treatments are superb. You’ll also want to spend some time unwinding on the gorgeous pool terrace. 

Breakfast included

Belmond Castello di Casole

Belmond Castello di Casole

Belmond Castello di Casole

Infinity pool, Belmond Castello di Casole

Days 7 – 8

The Tuscan countryside

Again, to get your bearings, we’ve included an exclusive excursion, your private driver bringing you out to two Tuscan icons – Siena and San Gimignano. You’ll have plenty of time to explore each at your own pace, taking in the former’s great Gothic architecture and extraordinary art collections before admiring the famous towers of the latter. It’s a 13th-century walled town that retains all of its medieval charm and hilltop severity.

You’ll also have plenty of leisure time, perhaps to relax with a vineyard tasting or watercolour class back at the castle. Otherwise, let the resident gamekeeper take you out on a truffle hunt and wildlife walk, or choose to explore one of the region’s many charming villages.

Breakfast included

San Gimignano, Tuscany, Italy

San Gimignano

Siena, Italy


Cip's Club by Cipriani, Castello di Casole

Cip's Club by Cipriani, Castello di Casole

Day 9

Depart for UK

After a final indulgent breakfast, a private driver will see you back to Florence for your flight. On arrival back in the UK, a chauffeur will once again be waiting to see you home.

Breakfast included

About the itinerary

"Tuscany demands style. And, I've put this twin-centre itinerary together to do the region justice, including private transfers, exclusive tours and stays in two of Italy's greatest hotels. Take it from me, there's nothing more evocative than a night in a luxurious Tuscan castle or a private tour of the Uffizi Gallery."

Andy Austen

Destination Specialist

Pricing information

Guide price from £3,945 pp incl. flights

27 Sep - 31 Oct 2021 from: £3,945 pp
01 Aug - 26 Sep 2021 from: £4,830 pp


  • Complimentary UK airport departure lounge access
  • Return flights to Florence
  • Private return airport transfers
  • 4 nts accommodation at Belmond Villa San Michelle on a BB basis
  • Complimentary transfer between Belmond San Michelle and Belmond Castello di Casole
  • 4 nts accommodation at Belmond Castello di Casole on a BB basis
  • Full day private guided excursion to Siena and San Gimignano