WALKING IN TUSCANY
20 – 27 September 2025
TOUR DESCRIPTION
Join me, and a small group of Adventurous Ewes, on an enchanting journey through Tuscany’s rolling hills, cypress-lined roads, and medieval villages.
We begin our journey in Florence, for a couple of days, before we head out to the stunning countryside of Val d’Orcia. As we stroll along easy to moderate scenic trails, you’ll pass vineyards, and olive groves, all set against the backdrop of this most photographed region.
Highlights include visiting picturesque towns like Pienza and Montalcino, tasting local wines, and soaking in natural thermal springs.
The serene landscape, combined with the region’s rich history and culinary delights, makes Val d’Orcia a perfect destination for a leisurely, yet immersive walking experience in Italy.
WOMEN ONLY
20% deposit to book your place
Private room ZAR 64 000 pp
Shared room ZAR 54 000 pp- INCLUDED IN THE TOUR:
- Airport taxis to hotel
- Charming 3* hotels
- Private Transfers
- 7 breakfasts, 6 lunches, 4 dinners
- Walking food tour
- Cooking class
- Personalised accompanied service throughout
- Professional English-speaking tour guides
View Brochure
Our Tour
ITINERARY
DAY 1
Florence
Ciao Bellisimos, welcome to Florence!
Upon arrival at Florence airport, we’ll take a taxi to our hotel. Enjoy some free time to relax or explore the city at your leisure, before we meet in the afternoon for a guided tour of Florence’s iconic sights. This evening, we’ll come together for a delightful welcome dinner at a local restaurant.
Accommodation: Charming 3 star Hotel housed in a 15th-century building.
Meals: Dinner
DAY 2
Florence
After breakfast, we meet our guide for a delicious walking food tour, sampling some of the city’s best culinary delights. The rest of the day is yours to explore at your own pace—whether you choose to shop, visit museums, stroll through the beautiful Boboli Gardens, or seek out the finest gelato.”
Meals: Breakfast, lunch
DAY 3
Pienza
This morning we catch our transfer to the town of Pienza, a small Renaissance town in Tuscany, known for its charming beauty and harmonious architecture, overlooking the stunning Val d’Orcia. This will be our home for the next 5 nights.
After lunch we walk with our guide to the Vitaleta Chapel. Perched on a gentle hill, this small yet iconic chapel captivates with its simple yet elegant design, featuring a slender bell tower against the backdrop of rolling hills and cypress trees. Our transport will take us back to Pienza.
Walk: 5.6km – easy
Accommodation: 3* boutique hotel situated in the historical centre
Meals: Breakfast, lunch, dinner
DAY 4
Montalcino
Today another scenic walk, in the Montalcino area, to the Abbey of Sant’Antimo, a stunning Romanesque monastery surrounded by vineyards and olive groves, dating back to the 12th century.
On our way we stop for wine tasting at Brunello wine cellar, which offers a glimpse into the meticulous process behind one of Italy’s finest wines, renowned for its deep ruby colour, bold aromas, and exceptional aging potential. We will need that walk!
Walk: 9 km – easy to moderate
Meals: Breakfast, lunch, dinner
DAY 5
Siena
Today we visit Siena, a picturesque medieval town known for its well-preserved Gothic architecture, charming narrow streets, and vibrant culture.
We stop for lunch at a local restaurant, after which we have a special tour known as the Porta del Cielo tour at the Opera del Duomo. The Porta del Cielo (“Gate of Heaven”) tour is a special guided experience offered at Siena Cathedral (Duomo di Siena), providing visitors with exclusive access to areas usually closed to the public.
During this tour, you can explore the cathedral’s upper levels, including walkways above the nave, hidden rooms, and stunning views from the rooftop. This tour is held only at certain times of the year and we will be there!
Meals: Breakfast, lunch, dinner
DAY 6
Montepulciano
A day in Montepulciano, a charming hilltop town in Tuscany, begins with a leisurely stroll through its medieval streets, lined with Renaissance palaces and cozy cafés.
Against a backdrop of rolling vineyards, we join our local chef for a cooking class to prepare traditional Tuscan dishes using fresh, locally sourced ingredients followed by a sit-down lunch paired with Montepulciano’s famous Vino Nobile wine.
Meals: Breakfast, lunch
DAY 7
San Quirico d’Orcia
San Quirico d’Orcia is a picturesque medieval town nestled in the heart of the Val d’Orcia, a UNESCO World Heritage Site in Tuscany. Its stone-paved streets and ancient walls exude a tranquil, timeless charm. We explore the town’s beautifully preserved architecture.
From San Quirico, a scenic walking takes us through rolling hills and olive groves to the nearby village of Bagno Vignoni. This unique spa town is famed for its large central thermal pool, which dates back to Roman times and sits in the middle of the main square.
Although the pool is not for bathing, its warm, steamy waters, fed by the natural hot springs, create an enchanting sight. Nearby, modern spa facilities allow you to dip into the therapeutic thermal waters and unwind with a cocktail amidst the stunning Tuscan countryside.
Walk: 5 km – moderate
Meals: Breakfast, lunch
DAY 8
Florence Airport
Transfer to Florence airport.
As our unforgettable journey through the rolling hills and timeless villages of Tuscany comes to a close, we hope the beauty, serenity, and flavours of this region stay with you long after you leave.
Thank you for being a part of this adventure. Until we meet again, may the spirit of Tuscany continue to inspire your steps. Buon viaggio and arrivederci!”
Meals: Breakfast
WHAT IS NOT INCLUDED IN THE TOUR
- International flights
- Visas
- Some meals – see itinerary
- All personal drinks including any alcoholic beverages
- Optional activities not part of the itinerary
- Gratuities for Guide
- Meal tips
- Travel insurance
TRAVELLER'S TIPS
- A reasonable level of fitness.
- Download the App Airalo for affordable local SIM cards www.airalo.com
WEATHER
September offers ideal weather: cool evenings and bright and sunny days with temps averaging 25°C, making it one of the more pleasant times of year to visit Tuscany. You can expect some rain. At night it can drop to 15°C.
MONEY - Euros
-
The euro is the official currency of Italy.
Euro 1.00 = ZAR 19.00
WALKING ESSENTIALS
- A small backpack
- Walking boots
- Comfortable padded walking socks
- Rain jacket
- Hat
- Water bottle
- Sunscreen and sunglasses
- Swimming costume for the thermal baths
- Jumper
- Puffer jacket
OTHER ITEMS TO REMEMBER
- Forex Euro, bank card
- Pen and notebook
- Cell phone chargers and powerbank
Italy uses two types of plugs: Type C and Type F. Type C plugs are the most common and have two round pins, while Type F plugs are similar but have two grounding clips on the sides. - Universal plug converter
- Earplugs
- Medication
- Sunscreen
- Hat
- Sunglasses and/or reading glasses
- Handbag/backpack/shoulder sling bag
SHOPPING GUIDE
- Leather goods
- Florentine paper
- Leather-bound journals, sketchbooks, and photo albums.
- Art supplies
- Perfume – One of the most famous perfumes created in Florence was Acqua della Regina, which was created for Catherine de’ Medici, the queen of France. A blend of rose, jasmine, and orange blossom found at Santa Maria Novella.