Secluded Tuscany

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. 

Stay throughout in the 4-star Grand Hotel Impero, without the need to change hotels during the tour.

Departure dates available: 29 September 2024
(WAIT LIST – please email

Handpicked Highlights

  • Enjoy six nights in the authentic small town of Castel del Piano, located in one of south Tuscany’s most secluded areas 
  • Visit gorgeous Tuscan towns away from the tourist trail, such as Grossetto and Pienza
  • Enjoy a guided tour of magnificent Siena, one of the Italy’s finest medieval cities and known for its Palio horse-race
  • Savour classic Tuscan cuisine during experiential inclusions such as wine and cheese tastings at artisanal local farms and producers 
  • Indulge in an exclusive truffle, olive oil and honey tasting experience at your hotel
  • Eat at authentic trattorias and enjoy the superb Grand Hotel Impero restaurant, renowned for its fantastic Tuscan dishes and wines   

Tour Itinerary

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 moreand leave having experienced the true taste of Tuscany.

Day 1 Arrive in Tuscany

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

Day 2 Montepulciano, Pienza & Wine and Cheese-Tastings

We travel to the Renaissance hill town of Montepulciano, soaking up the ‘can’tmiss’ 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 pinkwalled 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 local cheeses at the Il Seggiano cheese factory. This evening we enjoy dinner in the hotel restaurant.

Meals included: Breakfast, Dinner

Aerial summer day view of Montepulciano town

Day 3 Castel del Piano & Chianciano Terme Wine-Tasting

Today we can take a leisurely and level stroll into the centre of Castel del Piano about 10 minutes’ away on foot. We enjoy time free to explore here and maybe sample some local delicacies on our wanders. Afterwards, we drive to the spa resort of Chianciano Terme for a wine-tasting at a traditional winery. This afternoon brings a fabulous tasting of typical Tuscan olive oil, honey and flavourful truffles at our hotel before we sit down to dinner in the hotel restaurant. 

Meals included: Breakfast, Dinner

Day 4 Grossetto & Castiglione della Pescaia

After breakfast we head toward Tuscany’s Tyrrhenian coast for a day of sightseeing. Winding through undulating landscapes dotted with cypresses, we arrive at tucked-away 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

street in Castiglione della Pescaia in Tuscany Italy on a hillside, cobbled street

Day 5 Orvieto

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. 

Meals included: Breakfast, Lunch, Dinner

Day 6 Siena & Azienda Trottolo Wine-Tasting

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 GothicRomanesque 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. 

Meals included: Breakfast, Dinner

Day 7 Departure

On our transfer to Pisa airport, we stop in the historic walled town of Volterra for a farewell lunch of classic Tuscan farea special finale before we catch our flight back to the UK.

Meals included: Breakfast, Lunch

Grand Hotel Impero

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. 

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. 

What's included

  • Flights

    Return flights London Heathrow to Pisa
    LHR-PSA Dep 07:55 Arr 11:10
    PSA-LHR Dep 19:55 Arr 21:10

  • Accommodation

    6 nights in the 4 star Grand Hotel Impero

  • Meals

    6 breakfasts, 3 lunches, 6 dinners

  • Handpicked Highlights

    Itinerary and handpicked highlights as stated above 

  • Tour Manager

    Services of a local, experienced English speaking Tour Manager

  • Coach Transport

    All coach transportation as stated in itinerary above 


  • Travel insurance 
  • Local tourist and city taxes  
  • Gratuities for tour manager and coach driver 

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