Departures 22nd June, and 1st March, 3rd May, 21st June, 13 September, 11th October 2026
Velvety hills woven with cypress-lined avenues, grand villas and medieval hill towns – Tuscany is a vision of beauty. Yet beneath its gentle scenery and medieval treasures lies a richer, deeper Tuscany – one of rustic produce, aromatic wines, and towns and villages overlooked by typical touring itineraries.
We balance this hidden Tuscany with must-sees like Siena and Montepulciano on this 6-night tour. Staying in the quiet town of Castel del Piano, we discover Renaissance-era Pienza, ancient Orvieto, and seaside Castiglione della Pescaia, intertwining them with enriching local culinary experiences. Dine at humble trattorias, sample fragrant truffles, taste wines and cheeses at artisanal estates, and more – and leave having experienced the true taste of Tuscany.
Stay throughout in the 4-star Grand Hotel Impero, without the need to change hotels during the tour.
We fly to Pisa airport where we meet our tour manager and travel to the delightful walled city of Lucca to glimpse its charming piazzas, elegant lanes, and exquisite churches. We continue to the small town of Castel del Piano, where we check in to our hotel, the Grand Hotel Impero, for the next six nights. A welcome prosecco or spritz accompanied by local delicacies precedes a rich Tuscan buffet dinner at our hotel, where we enjoy the chance to get to know our fellow travellers.
Meals included: Dinner
We travel to the Renaissance hill town of Montepulciano, soaking up the ‘can’t–miss’ landscapes of southern Tuscany’s Val d’Orcia en route. There is free time to admire Montepulciano’s handsome piazzas, palaces and churches before we leave for the nearby authentic Bindella Wine estate for a tour and taste of some delicious wines of Montepulciano region. Finally, we visit the pink–walled Renaissance town of Pienza, where you have time free for lunch at a restaurant of your choice. As we journey back to our hotel, we pause to sample some exquisite olive oil in a picturesque and authentic setting. This evening we enjoy dinner in the hotel restaurant.
Meals included: Breakfast, Dinner
Today we can take a leisurely and level stroll into the centre of Castel del Piano about 10 minutes’ away on foot. We enjoy free time to explore here and maybe sample some local delicacies on our wanders. Afterwards, we drive to the spa resort of Chianciano Terme for a tour and wine-tasting experience at a traditional local artisan winery where the family has lived for the past 7 generations!
Meals included: Breakfast, Dinner
After breakfast we head toward Tuscany’s Tyrrhenian coast for a day of sightseeing. Winding through undulating landscapes dotted with cypresses, we visit a fantastic local cheese farm owned by Francesca and Giorgio, who produce exceptional cheese. In a typically rural setting with sheep grazing against a panoramic backdrop of rolling hills, it’s certain to provide a truly authentic experience. We then continue to Grosseto, the capital of the Maremma region, and a pretty place to explore. You may want to use free time here to visit the city’s medieval-style square, relax over frothy cappuccinos or browse the shops. Our tour continues to the castle-topped seaside town of Castiglione della Pescaia there is further free time to relax and stroll the picturesque seafront before savouring a succulent local seafood lunch. After returning to Castel del Piano this afternoon, enjoy time to unwind or stroll into the town before dinner at our hotel.
Meals included: Breakfast, Lunch, Dinner
Today we venture into neighbouring Umbria to experience the history-steeped hill town of Orvieto. Perched on a volcanic rock, this striking place once controlled the trade route between Rome and Florence, and boasts a majestic Gothic Duomo, fresco-painted churches, medieval palaces and subterranean Etruscan-era caves and tunnels. The unmissable sight here is the golden Duomo façade, which shimmers in the sun and boasts 14th century reliefs of biblical scenes. After absorbing this and other sights, we enjoy lunch at a wonderfully authentic restaurant burrowed into the volcanic rock. While the homemade fare here is terrific, the highlight is descending the restaurant’s stairway into the Etruscan catacombs below – unforgettable! This evening we enjoy a light dinner in the hotel restaurant.Â
Meals included: Breakfast, Lunch, Dinner
Nowhere exemplifies a classic Tuscan town better than Siena and this morning we immerse ourselves in this UNESCO-protected gem. During a half-day walking tour introducing its treasures and storied past, we visit its ethereally beautiful, oval-shaped Piazza del Campo, (the backdrop for the twice-yearly Palio horse race), the Gothic–Romanesque Duomo and other sights. Following our guided tour, you have time spare to meander the cobbled streets and have lunch at a restaurant by yourself. Our last stop is the classically Tuscan, family-run Azienda Agricola Trottolo winery, nestled near the celebrated Montalcino wine region, where a tasting of excellent local reds awaits us. This evening we enjoy dinner in the hotel restaurant.Â
Meals included: Breakfast, Dinner
On our transfer to Pisa airport, we stop in the historic walled town of Volterra for a farewell lunch of classic Tuscan fare – a special finale before we catch our flight back to the UK.
Meals included: Breakfast, Lunch
Occupying a former manor house standing in its own gardens on the edges of Castel del Piano, the 4-star Grand Hotel Impero combines aristocratic looks with high standards of accommodation and warm local hospitality. The owners are passionate about delivering exemplary service and top-notch cuisine – the well-regarded restaurant here uses locally sourced ingredients to serve food and wines as good as or better than those at typical local trattorias.Â
The lovely salmon-pink façade of the hotel opens to a swish, whitewashed interior with a smart lobby lounge, two stylish restaurant rooms and a lounge bar. The contemporary guest rooms are in keeping with everywhere else, each decorated in understated modern style and offering garden or mountain views, a flatscreen TV, safe, minibar and private bathroom with shower. After a day’s sightseeing, guests can also visit the peaceful spa (additional cost) to enjoy its inviting sauna, steam room and wellbeing treatments.Â
Return flights London Heathrow/Gatwick to Pisa
(Call us for flight times)
6 nights in the 4 star Grand Hotel Impero
6 breakfasts, 3 lunches, 6 dinners
Itinerary and handpicked highlights as stated aboveÂ
Services of a local, experienced English speaking Tour Manager
All coach transportation as stated in itinerary aboveÂ
Extras
Departing 22 June 2025
Twin from £2085 per person
Single Supplement £300
Departing 1 March 2026
Twin from £1995 per person
Single Supplement £300
Departing 21 June 2026
Twin from £2149 per person
Single Supplement £350
Departing 13 September 2026
Twin from £2199 per person
Single Supplement £350
Departing 11 October 2026
Twin from £2069 per person
Single Supplement £300
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