Soggiorno in Tuscany

Soggiorno in Tuscany

14 Days

If the idea of a prolonged stay in Tuscany for no less than 2 weeks appeals to you, then this is the tour that you’ve been looking for. Referred to as a Soggiorno in Italian, our 14 day tour is as exciting as it is authentic. You’ll have the option to visit local landmarks, explore stunning surroundings, immerse yourself in the Tuscan lifestyle – and that’s just after a few days of being here. Our guests often comment on just how incredibly diverse this tour is – and for good reason. It can be ideal for couples looking for a romantic retreat, as well as small families and groups of friends that want nothing more than to experience the local cuisine, engage with artisans and interact with locals first-hand.

You’ll get to explore iconic scenery, traverse vineyards, partake in wine tasting, learn how to prepare and cook an authentic 4 course meal and much, much more in between. With a variety of towns, including Cortona, just a short journey from your accommodation; you’ll have plenty to see and do. Every day, you’ll have the opportunity to eat freshly produced food, drink locally made wine, listen to traditional music, learn about the unique way of life and even meet with local crafts-people that have been plying their trade for decades. Tours are available between the 28th of March through to October the 24th and you’ll be pleased to hear that they commence every other Saturday, allowing you 2 weeks of our traditional villa apartments, options to explore the medieval villages, and capture memorable moments on camera and in person.

Departure Days 2024
4th May 2024
Sold Out
8th June 2024
4 Places Available
29th June 2024
Limited Availability
6th July 2024
Limited Availability
7th September 2024
Sold Out
14th September 2024
Sold Out
Contact Us for Private Group Bookings
Departure Days 2025
10th May
Limited Availability
7th June
Limited Availability
5th July
Limited Availability
6th Sept
Sold Out
Contact Us for Private Group Bookings

Tour Itinerary

14 Days - Soggiorno in Tuscany

Whether you’re here for 3:30 or 5:30pm pick up , we’ll arrive at the station to collect you and your possessions ready to be taken to your accommodation. You’ll undoubtedly want to explore the villa and its surroundings – and once you arrive, you’ll be able to do exactly this whilst settling in and unpacking. With your appetite likely stimulated, we’ll take you into the stunning town of Cortona for dinner.

“To get the first full day of your tour off to an exciting start, we’ll head into the nearby town of Cortona; where we have plenty of things for you to see and do! Our enthusiastic tour guide will take you on an enjoyable walk of the town, with coffee included. To integrate you with the Tuscan lifestyle, you’ll experience lunch at a local trattoria. With your stomach full, you’ll have the opportunity to sit and relax to your heart’s content or explore the town in greater detail.
Mid-afternoon If you feel ready to return to your apartment, we’ll give you the option to be collected and transported at this time. If you chose to stay in Cortona or travel back home to the villa – we’ll meet back up and take you into town in preparation for your evening meal. What better way to savour the flavours of Cortona than with a traditional aperitivo in the Piazza, followed by dinner!”

“San Gimignano is a town so iconic that you have to see it to truly believe it – and this is where we’ll be headed at 9am. Upon arrival we’ll have a brief coffee break and you will be given an overview of the town and its rich history. Shortly after your introduction, you’ll have free time to explore, ingratiate yourself with the locals and partake in activities at your own leisure. We’ll then travel to Siena, where you’ll meet your tour guide who will fill you with knowledge, expose you to the traditional lifestyle and allow you to get to grips with the town first-hand.
To allow you to take in as much as possible, you’ll have a little more free time before your evening meal. For dinner, you’ll be taken to one of the local restaurants in Siena, where you’ll get to taste the mesmerising flavours that the region.”

With so much to see and do, you’ll undoubtedly appreciate the option to spend the day exploring the area, taking up one of our additional activities, sitting by the pool or relaxing in your own way! Dinner will be around 7pm and you’ll be ingratiated further into the idyllic lifestyle of the Tuscan people, with a dining experience guaranteed to satisfy your taste buds, as well as wine to savour.

At 7:45am, we’ll take you to the local station where we’ll cover the cost of your train tickets and you will begin your exciting journey to the fabled City of Florence. You’ll get to explore at your leisure, shop to your heart’s content and choose from any number of the local establishments until you travel back to your villa. Don’t forgot to pick something up on your travels for dinner as you’ll have the evening to relaxing at the villa.

This morning we have an exciting tour of Chianti on the cards. We’ll be stopping in Castellina for a coffee and the exhilirating opportunity to explore the town and all it has to offer. We then have an extended lunch and tasting session planed at an exquisite organic winery, where there will be the opportunity to meet the winemakers.

To truly ingratiate you with the Tuscan lifestyle, this day will be dedicated to one of two options: The first is cheese-making. You’ll have the opportunity to learn how it’s done, as well as trying your hand at making some of your own. The second is a wellness day – where you can enjoy a host of holistic activities. With your appetite undoubtedly whetted, we’ll take you into Cortona for dinner and the opportunity to relax in the traditional surroundings

To get this day off to a flying start, we’ll take you to the local station ready for your next adventure independently. The town of Arezzo is on the agenda today, complete with an introduction to the area and information on what can be found here. You’ll then have free time to shop, have a snack, enjoy a walk, or engage with the locals. We’ll be returning to the villa in the mid-afternoon, allowing you the option to take a dip in the pool, interact with others on the tour, or partake in anything that might come to mind.
Around 7pm we will make our way into Cortona for another delightful meal.

With a full day ahead, we’ll depart to the town of Pienza, the birth place of Pope Pius II; a small township famous for Pecorino cheese and beautiful boutiques, first, allowing you to savour the stunning sights on the journey. In between Pienza and Montepulciano, we’ll make a stop for lunch at an organic farm and to allow you time to really get to grips with the iconic architecture and sights in this captivating area.
After lunch we visit Montepulciano, also located in the Val d’Orcia. This township is a true gem, great shopping, wonderful trattorias, cantinas and sulumerie for wine and cheese tastings. We’ll then transport you comfortably back to your accommodation in the late afternoon, where the rest of your evening will be yours to enjoy as you wish.

To celebrate the start of the week, you’ll have the option to take part in an additional activity, or alternatively you might choose to explore the local area at your own pace. We’ll be taking you to dinner around 7pm in one of the local trattorias – where you can enjoy fine dining and a taste of locally produced wines

If the idea of preparing your own Tuscan meal appeals to you, then this is the day that you’ve been waiting for You’ll have the option to create a 4 course meal with an expert chef, whom you’ll then get to enjoy the company of as you sit down to eat each course.

This morning we drive through Umbria to Orvieto. On arrival we enjoy a Caffè after which there is ample opportunity to visit Il Duomo, Saint Patricks Well – 1537 which is 62 metres deep with double spiral staircase or tour the underground city/caves. Orvieto has a great selection of stores, ranging from leatherware to ceramics and boutiques. Regroup for lunch at a local trattoria. Return to villa late afternoon. Dinner in Cortona.

We’ll head out to the idyllic town of Lucignano in the morning to allow you plenty of time to see the authentic sights and sounds of this ancient town. You’ll be provided with a traditional lunch and given plenty of time to traverse the scenery, walk the paved streets and photograph the breathtaking architecture For dinner, we’ll be travelling into Cortona for authentically made pizzas to satisfy your appetite!

If you’d like to take part in a memorable activity, relax by the pool, or spend the day adventuring; you’ll have hours to do so. We’ll be taking you out for dinner to a local restaurant, with more complementary wine and opportunities to submerse yourself even further into Tuscan life before you head home

We’ll take you directly to the station, so that you can begin your journey home; hopefully with a huge collection of photos, memories and even new friends.

What is Included

7 Days - Cycling in Tuscany


  • Enjoy your very own Soggiorno (14 night) stay in our luxury Tuscan villa
  • Our bilingual hosts & tour leaders will be on hand throughout the tour to assist you
  • We’ve scheduled a variety of day tours for your enjoyment
  • Your apartment will be supplied with provisions and breakfast ingredients
  • This tour includes no less than 7 lunches for your enjoyment
  • Wine is included with each of the 10 dinners at local eateries
  • You’ll get to enjoy exciting, leisurely tours of the stunning regions of Cortona, Siena & Arezzo
  • Walk away with a new set of Italian culinary skills with your very own cooking lesson with a world-class chef
  • A choice between cheese-making and a wellness day; ideal for couples, friends and small groups
  • You’ll get to explore on the back of your own Vespa, complete with guidance and safety equipment
  • We’ll cover the cost of your train tickers into Florence, where you can explore to your hearts content
  • You’ll receive a complementary bottle of wine and beer for your trip
  • All wine tasting events are held at local establishments to truly submerse you in the Tuscan way of life
  • We’ll assist with all travel as detailed on your itinerary, including special requirements
  • If you’d like to spend your tour-free day/s exploring the local regions, we’ll transport you to the station without fuss
  • We’ll also collect you from the station when you arrive for your trip, and then drop you back when it’s time for you to go home with your memories
  • If you’d like to visit Cortona on a day without a tour, we’ll be happy to assist with this as well


  • Your airfares will be your responsibility to manage and you may want to get in touch with your local carrier to assist with bookings
  • We recommend taking out travel insurance, as it’s better to be safe than sorry
  • If you wish to visit any public galleries, landmarks, or museums; you may need to book or pay for tickets on the day
  • We cover all costs of meals that are included in your itinerary – anything outside of this will be your obligation to pay for
  • You’ll have plenty of opportunities to buy from local stores or enjoy leisure activities and you’ll need to cover your personal expenditures in these instances.

Il Mandorlo, Fratticciola

Il Mandorlo is a rural house dating back to the 17th Century which has been restored in keeping with its original shape and materials. It is located in the valley ‘Val di Chiana’ nearby the historical centre of Cortona.

The house is divided into five apartments with all modern facilities including air conditioning and WI-FI. The grounds are beautifully maintained and the infinity swimming pool provides a panoramic view of the historical centre of Cortona and surrounding valley.

Set in a quiet location but close enough to the main roads which connect to all the well-known historical cities and villages.

It is an image of rolling hills, vineyards, age-old trees, golden wheat in Spring, Sunflowers in Summer and the constantly changing shades of the earth.

Accommodation is subject to availability at time of booking.

Getting there

7 Days - Cycling in Tuscany

The tour begins near the historical centre of Cortona. Upon arrival we will meet you at our local train station Camucia-Cortona and will transfer you, via vehicle to the villa, which is a short drive into the countryside.

Cortona is located 2.5 hours by regional train from the main train station in Rome (Roma Termini) and 1.5 hours by regional train from the main train station in Florence (Santa Maria Novella).

Train Travel to the Villa

If you are already in Italy connection to either Roma Termini or Firenze Santa Maria Novella train stations is easily accessible via other train stations.

Either of these two major cities are a good option for your arrival into Italy and then travel to our location. We will meet you at our local train station Camucia-Cortona and will transfer you, via vehicle to the villa, which is a short drive into the countryside.

Arrival from Rome Airport:

  1. Take the Leonardo Express Train from Rome Airport to Roma Termini Train Station (This is a 30min journey and will cost approximately 15 Euro)
  2. From there take a regional train to Camucia-Cortona (This is a 2.5hr journey and will cost approximately 15 Euro)

Arrival from Florence Airport:

  1. Take the bus that goes to Firenze Santa Maria Novella Train Station (This takes approximately 30mins and will cost approximately 15 Euro)
  2. From there take a regional train to Camucia-Cortona (This is a 1.5hr journey and will cost approximately 13 Euro)


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14 Days – Soggiorno in Tuscany

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