Tuscany with Umbria by Steam Train

Embark on a journey through the hills of Southern Tuscany, exploring some of its many unique and charming towns. The vintage steam train ride will not only transport you through stunning landscapes but also unveils the hidden treasures of the region.

This 5-night escorted holiday blends Assisi, Perugia, Montepulciano, Pienza and Bagno Vignoni with a vintage steam-train day into the Val d’Orcia. Your Tour Manager handles the plans—easy coach transfers and guided strolls—so you can relax and enjoy the scenery, history and local flavors. Because the steam train and village festivals run on specific dates, we rotate the order of days by departure to put you in the right place at the right time. The inclusions stay the same every week, and the day after the steam-train is a rest day.

Sample Itinerary

The experiences are the same on every departure. The order of days may rotate to align with the vintage steam train and local events.

Day1 Arrival in Arezzo

Fly from Dublin to Pisa where you will be met at the airport by your Topflight Tour Manager. You will be transferred comfortably by coach to the Hotel Minerva in the enchanting city of Arezzo, where you will stay for five nights.

The hotel is a lovely 4 star featuring modern decor, with a classical twist, mirroring the enchanting city of Arezzo itself. You can walk to the city’s centre in around 15 minutes to explore the many monuments, museums, churches, shops and boutiques.

Day2Perugia & Assisi

On the first excursion of your Escorted Tour Holiday, we will set off on a coach following breakfast in the hotel. We will journey to the city of Perugia, which is the capital of the Umbria region. It’s known for its defensive walls around the historic center. Here you will take a guided tour to ensure you take in the historic sites along the way. The medieval history is palpable in this city which is considered to be one of the most beautiful and beloved cities in Italy.

Aside from charming streets and stunning views, churches are the main draw of the town of Assisi, the most popular tourist attraction of course being, the Basilica of Saint Francis. We will venture on a walking tour of the area, taking in the history and incredible sites before entering the Basilica. This architectural wonder is considered a masterpiece, as well as an outstanding example of a religious building that influenced the development of art and architecture of the entire city. The famed frescos on the Basiclica's ceiling were painted by Giotta and are sure to leave you feeling well and truly inspired.
Following on from the Basillica visit, we will once again board the coach, to return back to the hotel.

Day3Montepulciano, Pienza & Bagno Vignoni

Today, after breakfast at the hotel, we will take off on an exploration of the towns and villages of the Val d’Orcia. This stunning region is characterised by rolling hills and cypress trees and the quaint towns and villages seem to have been frozen in time.
First, we will visit Montepulciano, a medieval village that is awash with rich history and in particular is known for its churches and the Medici fortress of Sangallo. Notably, this area acted as the set for the film New Moon, from the Twilight saga.
Our second stop for the day will be Pienza, the jewel of the Val d’Orcia. A beautiful, atmospheric city, it is loved for its fifteenth century architecture among its enviable location atop the rolling hills that Tuscany is so famous for. We will then make our way to a local cheese producer, just outside the city, where we will be invited to taste some produce. The area is famed for it’s pecorino cheese and this is your chance to find out why.
Our last stop of the day will be Bagno Vignoni. This is a beautiful thermal town and has been used as the set of many films in its time. In the main square you’ll find a thermal water pool which has been used as a healing facility since as far back as Roman times.
Following on from this, we will board the coach once again to return back to the hotel.

Day4Steam Train Journey

We leave early by coach for Siena and board a restored vintage steam train into the Val d’Orcia. The journey rolls through classic Tuscan scenery to a local event — a wine festival, olive-oil celebration or village market depending on your departure (see “Events & festivals by departure”). You’ll have free time to wander the stalls, enjoy tastings and explore the town before rejoining our coach for the return to Arezzo.

Events & festivals by departure

Departure	Event	What it’s about
09 Oct 25 08 Oct 26	Autumn Festival — Abbadia San Salvatore Seasonal village festival	Chestnuts, mushrooms, local dishes; music and market stalls.
16 Oct 25	Festival of Olive Oil — Trequanda Food festival	New-season olive oil tastings and producers’ stands.
23 Apr 26	Orcia Wine Festival — San Quirico d’Orcia Wine festival	Orcia DOC tastings with local producers in a scenic hill town.
30 Apr 26	La Maggiorata — Sant’Angelo Scalo (Montalcino) Local festival	Village day with food stands, music and community fun.
14 May 26	Train Festival — Torrenieri (Montalcino) Rail heritage	Heritage trains, exhibits and market stalls along the line.
24 Sep 26	Wine & Grape Festival — Chiusi Harvest festival	Harvest parades, tastings and artisan stands.
22 Oct 26	Thrush Festival — Montalcino Historic festival	Medieval pageantry, archery traditions and local dishes.

Day5Day at Leisure

After a whirlwind few days of exploration of the stunning region of Tuscany and Umbria, today you have a day to spend entirely at your leisure. Stay by the hotel and make use of its fantastic facilities and relax and unwind before returning home. Or alternatively, if you are still craving some exploration and sightseeing, we highly recommend visiting the beautiful city of Arezzo - a magnificent destination that's been featured in famous films including Roberto Benigni's 'Life is Beautiful'. Speak to our Tour Manager who can suggest this and other additional day trips and sites to see.

Day6Departure

You will check out of the hotel after your final breakfast of the stay. Your coach will pick you up at your designated time and transfer you to Pisa airport for your return flight back to Dublin.

Daily Order by Departure

Departure	Day 2	Day 3	Day 4	Day 5
9 Oct 25	Perugia & Assisi	Vintage Steam Train	Day at Leisure	Montepulciano, Pienza & Bagno Vignoni
16 Oct 25	Perugia & Assisi	Montepulciano, Pienza & Bagno Vignoni	Vintage Steam Train	Day at Leisure
23 Apr 26	Perugia & Assisi	Montepulciano, Pienza & Bagno Vignoni	Vintage Steam Train	Day at Leisure
30 Apr 26	Vintage Steam Train	Day at Leisure	Perugia & Assisi	Montepulciano, Pienza & Bagno Vignoni
14 May 26	Perugia & Assisi	Montepulciano, Pienza & Bagno Vignoni	Vintage Steam Train	Day at Leisure
24 Sep 26	Perugia & Assisi	Montepulciano, Pienza & Bagno Vignoni	Vintage Steam Train	Day at Leisure
8 Oct 26	Perugia & Assisi	Vintage Steam Train	Day at Leisure	Montepulciano, Pienza & Bagno Vignoni
22 Oct 26	Perugia & Assisi	Montepulciano, Pienza & Bagno Vignoni	Vintage Steam Train	Day at Leisure

Day 1: Arrival in Arezzo · Day 6: Departure. Inclusions stay the same; we align the Steam Train with local events and keep the next day free to relax.