Walking Tuscany'sHilltop Towns,Italy

Walks & Treks

Solos Board

From
£2655

+approx. £18.58 in tourist taxes payable locally

7 nights in Italy

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No single supplements

Your own room guaranteed

Fly from local airports

100% solo travellers

What to expect on your Tuscany walking holiday

Four Guided Walks

Walk through iconic Tuscan landscapes following sections of the Via Francigena

San Gimignano

Stay in the heart of Tuscany, surrounded by spectacular views across the Tuscan countryside

Wine Tasting

Enjoy wine tasting at Castello di Volpaia a historic wine estate in the heart of the Chianti Classico region

Medieval Hilltop Towns

Visit beautiful historic towns including Radda in Chianti, Monteriggioni and Asciano

About this trip...

Join a sociable group of solo travellers and discover the very best of Tuscany on foot, combining beautiful countryside, historic hill towns, outstanding food and world-renowned wines. Our base is the beautiful medieval town of San Gimignano, where we’ll enjoy the charm of its famous towers and historic streets. From here, scenic trails lead through the surrounding countryside, taking us to the fortified village of Monteriggioni, the vineyards and olive groves of Chianti, and the rolling landscapes of the Crete Senesi.

Along the way, we’ll experience the region’s rich history and culture, from ancient abbeys to historic estates and wineries. There are also plenty of opportunities to savour the flavours of the region, including a gelato tasting in San Gimignano and a wine tasting at the beautiful Castello di Volpaia. Perfect for solo travellers, this holiday combines rewarding guided walks with plenty of opportunities to relax, explore and enjoy Tuscany’s famous cuisine in the company of like-minded travellers.

Walking Level:

What's this?

What's included?

Return flights & transfers
One piece of checked baggage
Airport taxes & charges
Double/Twin room for sole use
Breakfast daily, 1 lunch & 2 dinners
Gelato tasting
Wine tasting
Welcome drink & information meeting
4 guided walks
Free Solos App with all your travel documents
Dedicated WhatsApp group for your trip
Accompanying Solos Tour Leader
Fully financially protected

What's Extra

Insurance see here
Tourist Tax €3.00 per night (payable locally)

Itinerary

Arrival Day
San Gimignano Loop
Radda to Volpaia
At Leisure
Strove to Monteriggioni
Asciano Loop
At Leisure
“Arrivederci”

What you'll be doing

Day One: Arrival Day

We arrive into Pisa and transfer to our hotel in San Gimignano where we can meet each other and enjoy a welcome drink and dinner at a local restaurant.

Dinner included

Day Two: San Gimignano Loop

Set out from our hotel on a scenic circular walk through the beautiful Tuscan countryside. Our route follows quiet country tracks and sections of the historic Via Francigena, winding through rolling hills, vineyards and olive groves. As we walk away from the town, enjoy wonderful views back towards San Gimignano and its distinctive medieval towers, before the route loops through the peaceful countryside around Monteliveto, Santa Lucia and Aiano.

Lunch will be enjoyed at a local restaurant, before returning to San Gimignano for a guided tour of the town, discovering its historic streets, impressive towers and fascinating heritage. We'll finish with a gelato tasting at a world-renowned, award-winning gelateria, the perfect way to round off our day.

Distance: 8km
Duration: 3-4hrs approx.
Ascent: 215m+
Terrain: A mixture of quiet country lanes, unpaved tracks and well-established trails, with some uneven and gently undulating sections. Expect a few moderate climbs and descents through vineyards, olive groves and rolling Tuscan countryside.
Breakfast & lunch included

Day Three: Radda to Volpaia

After breakfast, we depart for the charming hilltop village of Radda in Chianti. From here we'll walk through the spectacular landscapes of the Chianti Classico region towards the medieval village of Volpaia. The route follows quiet gravel tracks and country paths through rolling vineyards, olive groves and shady woodland, with beautiful panoramic views across the surrounding Tuscan hills. Along the way, pass historic farmhouses and traditional Chianti vineyards before the route climbs gently towards Volpaia, where the ancient fortified village and its castle provide a wonderful reward at the end of the walk.

Enjoy a memorable wine tasting at the historic Castello di Volpaia. Discover the fascinating history of the estate as we explore its unique cellars, hidden within the medieval walls, before sampling a selection of Volpaia's renowned wines accompanied by its extra virgin olive oil. With its beautiful setting, centuries-old winemaking heritage and exceptional Sangiovese-led wines, this is a wonderful opportunity to experience the flavours and traditions of Tuscany at their source.

Transfer Time: 1hr + 1hr
Distance: 6km
Duration: 2-3hrs approx.
Ascent: 215m+
Terrain: A mix of paved paths, quiet roads, and well-maintained woodland trails, with some uneven ground, gentle inclines, and steps.
Breakfast included

Day Four: At Leisure

Today is ours to enjoy San Gimignano at our own pace. Explore its atmospheric medieval streets and historic towers, browse the local shops and cafés, or simply relax and soak up the beautiful Tuscan surroundings.

Breakfast included

Day Five: Strove to Monteriggioni

After breakfast, we’ll travel by bus to the charming village of Strove, where we’ll begin our walk through the peaceful Tuscan countryside towards the medieval walled village of Monteriggioni. Following quiet country lanes and rural tracks, the route winds through the rolling landscapes of the Val d’Elsa, passing vineyards, olive groves and woodland along the way. We’ll also visit the atmospheric village of Abbadia a Isola, with its historic abbey, before continuing through the beautiful countryside to Monteriggioni, one of Tuscany’s best-preserved medieval fortified villages.

Transfer Time: 30mins + 35mins
Distance: 6.5km
Duration: 2-3hrs approx.
Ascent: 100m+
Terrain: A mixture of quiet country lanes, gravel tracks and rural paths, with generally gentle, rolling terrain. Expect some uneven and unpaved sections as the trail passes through vineyards, olive groves and woodland, with a few gentle climbs and descents along the way.
Breakfast included

Day Six: Asciano Loop

Today we depart for the historic town of Asciano to explore the beautiful Crete Senesi, one of Tuscany’s most distinctive landscapes, on a scenic circular walk. Our route passes through the rolling countryside, characterised by gently undulating hills, cultivated fields and classic Tuscan scenery, before visiting Asciano, a charming medieval town rich in history and character. We’ll also visit the magnificent Abbazia di Monte Oliveto Maggiore, a peaceful Benedictine monastery set amid woodland and countryside, renowned for its impressive Renaissance frescoes and beautiful setting.

Transfer Time: 1hr + 1hr
Distance: 6km
Duration: 2-3hrs approx.
Ascent: 100m+
Terrain: A mixture of quiet country lanes, gravel tracks and rural paths, with gentle undulations. Expect some uneven and unpaved sections as the trail passes through the open landscapes of the Crete Senesi, with a few gentle climbs and descents along the way.
Breakfast included

Day Seven: At Leisure

After breakfast at the hotel, enjoy another free day exploring San Gimignano. Visit the impressive Duomo and climb Torre Grossa for panoramic views across the Tuscan countryside, or simply relax over a leisurely lunch, sample the local Vernaccia wine and enjoy a gelato in one of the town’s beautiful piazzas.

Breakfast & dinner included

Day Eight: “Arrivederci”

Today we check-out of our hotel and say goodbye before transferring back to Pisa airport for our flight home.

Breakfast included

Accommodation

Relais Santa Chiara, San Gimignano

Set just outside the medieval walls of San Gimignano, Relais Santa Chiara is a charming four-star hotel offering a peaceful Tuscan retreat within easy walking distance of the historic centre. Surrounded by beautiful gardens and rolling countryside. With its combination of traditional Tuscan character, countryside views and convenient location, Relais Santa Chiara is an ideal base for exploring San Gimignano and the wider Tuscan region.

Facilities Include:

Enjoy a range of facilities designed for a relaxing stay, including an outdoor swimming pool with panoramic views of the Tuscan countryside, a beautiful Mediterranean garden and outdoor relaxation areas. The hotel also features the I Cipressi Bistrot, offering drinks, snacks and light meals, as well as breakfast service.

Room Includes:

Rooms are equipped with Wi-Fi, TV, minibar, air conditioning, safe, tea and coffee making facilities and hairdryer.

Dates & Prices

Departure	Return	Nights	Price from	Other Info	Regional flights
2 Oct 2027	9 Oct 2027	7	£2655 +approx. £18.58 local fees		Please call for regional flights

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Essential Information

Transfer Time

The transfer time from Pisa Airport to San Gimignano is approximately 1hr 10mins depending on traffic.

Walking Programme

Guided walks are included as part of this holiday. Your dedicated walking guide will brief you in resort on the daily walking programme.

The walking programme is graded by difficulty, and you can expect to walk varying distances with a range of ascents and descents. Some walks may be challenging, with uneven or rough terrain underfoot and sections at higher altitude. Please refer to the day-by-day itinerary for full details of each walk.

A good level of physical fitness is required to fully enjoy this holiday.

It is important that you consider whether your chosen holiday is suitable for your level of fitness, mobility and any medical conditions or additional needs. If you are unsure, please contact our team before booking. We will be happy to discuss the holiday requirements and your individual circumstances to help you decide whether the holiday is suitable for you.

We are committed to treating all customers fairly and will consider any reasonable adjustments where possible. Please let us know before booking if you have a disability, medical condition or any additional requirements that may affect your holiday. This allows us to assess whether we can safely and appropriately accommodate your needs and to ensure you have the best possible holiday experience.

Care should be taken at all times, particularly on uneven or wet terrain. If you normally use walking poles, we recommend bringing them with you. Sturdy walking boots or walking shoes are essential.

Please note that the route and content of the walking programme may need to change during the holiday, at the discretion of the specialist walking guide or local organiser, if local conditions require.

If you have any concerns during your trip, please speak to your specialist walking guide or Solos Tour Leader.

For further information, please refer to our website Terms and Conditions

Gratuities

We suggest a Group Collection to cover transfer drivers, and hotel staff of €25.00 per person. Your Tour Leader will collect this on your behalf and distribute it accordingly, thus relieving you of the burden of who, when and how much to tip. The tipping of housekeeping will be left to your individual discretion (a small amount left in your room on departure should cover this and would be much appreciated). As is customary, ‘the hat’ will be passed around for the driver and guide on all optional excursions. For any meals that are not included in your itinerary, or taxi fares, your Tour Leader can advise of an appropriate add on.

What to Wear - Walking Days

It is important that you have the correct footwear. It is essential to wear walking boots that are comfortable and preferably lightweight, with some ankle support and a good grip. If you already have a pair of boots that you are happy walking in (including during hot/wet weather and on hard ground), then bring these along. However, if you are bringing new footwear, do make sure they are well broken in before you arrive. The weather, even in summer, can be unpredictable. We would therefore recommend you travel with clothing suitable for all conditions, and suggest you use the following checklist as a guideline of what to take:

Walking boots with good ankle support
Waterproofs – jacket and trousers
Walking poles – recommended as they provide good support for the knees, particularly on downhill sections of walks and when conditions are wet/slippery
Lightweight trousers and shorts with pockets
Shirts or t-shirts for walking in
Walking socks – several pairs
Lightweight fleece or jumper
Hat & gloves
Daysack/rucksack for walking
Umbrella – it can be used also for protection from the sun as well as rain
Lightweight drinking bottle to carry water whilst walking
Small first aid kit – plasters, insect repellent, etc
Good, high factor sunscreen, sunhat and sunglasses – the sun’s strength is often multiplied in mountainous areas.

Passports and visas

Passport validity requirements If you are travelling to an EU country (except Ireland), or Switzerland, Norway, Iceland, Liechtenstein, Andorra, Monaco, San Marino or Vatican City, you must follow the Schengen area passport requirements.Your passport must be:

issued less than 10 years before the date you enter the country (check the ‘date of issue’)
valid for at least 3 months after the day you plan to leave (check the ‘expiry date’)

You must check if your passport meets these requirements before you travel. If your passport was issued before 1 October 2018, extra months may have been added to its expiry date. Contact the embassy of the country you are visiting if you think that your passport does not meet both these requirements. Renew your passport if you need to. Check with your transport provider or travel company that your passport and other travel documents meet their requirements. Passport stamping At Italian border control, you may need to:

show proof of your accommodation, for example, a hotel booking confirmation or proof of address if visiting your own property (for example, a second home)
show proof of insurance for your trip – check FCDO’s travel insurance guidance
show a return or onward ticket
prove that you have enough money for your stay. The minimum amount required depends on your accommodation
follow procedures if you are hosting a guest at your property in Italy

Check your passport is stamped if you enter or exit the Schengen area through Italy as a visitor. Border guards will use passport stamps to check you’re complying with the 90-day visa-free limit for short stays in the Schengen area. If relevant entry or exit stamps are not in your passport, border guards will presume that you have overstayed your visa-free limit. You can show evidence of when and where you entered or exited the Schengen area and ask the border guards to add this date and location in your passport. Examples of acceptable evidence include boarding passes and tickets. Visa requirements You can travel to countries in the Schengen areafor up to 90 days in any 180-day period without a visa. This applies if you travel:

as a tourist
to visit family or friends
to attend business meetings, cultural or sports events
for short-term studies or training

If you are travelling to Italy and other Schengen countries without a visa, make sure your whole visit is within the 90-day limit. Visits to Schengen countries within the previous 180 days before you travel count towards your 90 days.

From the 12^th October 2025 the EU is introducing a new European Entry System (EES) that will be phased in and fully operational by the 10^th April 2026. Non-EU nationals including British passport holders will now be required to complete biometric checks on arrival and exit to Schengen countries, which will include facial recognition and fingerprints. There is no cost for this, and no action needs to be taken prior to departure.

Health requirements

Compulsory vaccinations: None. At least 8 weeks before your trip: All clients are responsible for acquainting themselves with up to date health information of the countries being visited and where necessary take the required precautions.

We recommend that you check with your doctor prior to departure as this information can change. You can also visit the travel health website for more information; Italy

Altitude sickness is a risk in parts of Italy, including the Alps and the Dolomites. More information about altitude sickness is available from TravelHealthPro (from the UK’s National Travel Health Network and Centre).

Currency

Euro

Time Difference

Italy is one hour ahead of the UK.

Electrical Appliances

Voltage 230v
Travel adaptor type C (EuroPlug)

WhatsApp Group

Shortly before your holiday, you will be invited to join an optional WhatsApp group to connect with your fellow travellers and your Tour Leader.