Tuscany Countryside Escape
May 30 – June 6, 2027
Experience the beauty of Tuscany without the crowds on this exclusive small-group adventure.
Join Tara Turner for an unforgettable week in the heart of Southern Tuscany. Unpack once and settle into a charming Agriturismo Villa nestled in a picturesque hilltop village surrounded by vineyards, olive groves, and rolling countryside.
Wake each morning to breathtaking views, enjoy homemade organic cuisine, savour world-renowned wines, and explore Tuscany’s most enchanting towns and villages. With a maximum of just 24 guests, this immersive experience offers the perfect balance of culture, food, wine, and relaxation.
A Personal Invitation from Tara
I have travelled to Tuscany several times and absolutely love everything about this beautiful region. From the rolling hills dotted with vineyards and olive groves to the relaxed pace of life, Tuscany captures the essence of Italy.
The food and wine are truly exceptional, with every meal showcasing the region’s rich culinary traditions and locally sourced ingredients. What makes Tuscany even more special are the people—warm, welcoming, and always eager to share their culture and way of life.
I am excited to share some of my favourite towns, experiences, and hidden gems with you on this unforgettable journey through one of Italy’s most captivating regions.
Tour Highlights
Included in Your Tour
- 7 nights accommodation at a beautiful 3.5-star Agriturismo Villa in Southern Tuscany
- Hosted by Niche Travel Group’s advisor Tara Turner
- Private transfer from Rome to the villa
- Daily breakfast featuring fresh, organic local ingredients
- Six gourmet four-course dinners showcasing authentic Tuscan cuisine
- Guided tours of Pienza, Montalcino, and Siena
- Wine, cured meat, and pecorino cheese tasting for dinner at Bradi Toscani in the hilltop town of Chianciano
- Day trip to Orvieto, including admission to the famous Well of San Patrizio and round-trip private transfers
- Excursion to Montepulciano with private transfer
- Winery tour and wine tasting
- Olive oil tasting and educational experience
- Transfer to Chiusi Train Station on June 6
Extend Your Italian Adventure
Why not make the most of your time in Italy? We would be delighted to assist with optional pre- or post-tour arrangements, including:
- Rome
- Florence
- Venice
- Milan
- Lake Como
- Amalfi Coast
- Sicily
Optional Experiences
Available at an additional cost:
- Visit to the renowned Thermal Spa in Chianciano
- Hands-on Tuscan cooking class
Pricing
Double Occupancy: $2,999 CAD per person
Single Occupancy: $3,899 CAD per person
Payment Schedule
Deposit: $500 CAD per person (non-refundable)
Final Payment Due: March 1, 2027
Good to Know
- Maximum group size: 24 guests
- Small-group touring for a more personalized experience
- Perfect for travellers seeking authentic Tuscany, local culture, exceptional food and wine, and a relaxed pace
Not Included
- International airfare
- Optional excursions
- Travel insurance (strongly recommended)
- Suggested gratuities of $100 CAD per person for villa staff and local guides
Detailed Itinerary
May 30 : Day 1 – Depart for Tuscany
Transfer from a central Rome hotel to the Villa
Meet the owner, Stefano and enjoy a welcome drink on the panoramic terrace while he tells us about his organic farm and the slow-food movement.
4-course dinner with homemade organic products at 8PM
May 31 : Day 2 – The Val D’Orcia Region
Breakfast with homemade organic products starts at 8:30 AM
Depart the Villa at 10:00am for a lovely day of touring the The Val d’Orcia region with our local Italian tour guide. This region of Tuscany extends from the hills south of Siena to Monte Amiata and in 2004 the entire valley was included on the list of UNESCO’s World Cultural Landscapes.
First, we visit Pienza, known as the “touchstone of Renaissance urbanism” It is a picturesque 35-minute drive to this quaint village. Make sure to sample the well-known pecorino cheese for which the village is famous. Snap a cute photo on the ‘love’ and ‘kissing’ lanes for a great memento.
Next, we will head to Montalcino, a hill town and commune famous for its Brunello di Montalcino wine. The town is located a short drive to the West of Pienza. Enjoy a leisurely lunch, do a little shopping, or find a terrace and sip some Brunello wine while overlooking the valley.
4-course dinner with local homemade products at 8 PM
June 1: Day 3 – Siena
Breakfast with homemade organic product 8:00am- 9:00am
Private Tour of Siena with local Italian guide
The historic centre of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation’s most visited tourist attractions. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year. Our local Guide will tell you all about the 17 contrades of the city and how they have shaped its unique culture for hundreds of years.
The Stunning Cathedral of Siena is not to be missed – with art by Donatello, Bernini, Michelangelo, and Pisano (to name just a few!) It will take your breath away, inside and out.
There will be plenty of free time for strolling through the winding streets, a leisurely lunch, shopping and gelato in the Piazza del Campo. Siena is about a 75 minute drive, great time to edit your photos or catch a nap on the way home.
Take a late afternoon dip in the villa’s pool and enjoy your local wine on the terrace before dinner.
Four course dinner with homemade organic products at 8 PM
June 2 : Day 4 – Local Living
Breakfast with homemade organic products 8:30am- 9:30am
Join our Villa owner Stefano for an optional cooking class. You’ll be preparing a 4-course lunch with local products. Then sit back and enjoy the wonderful dishes you have prepared.
Spend the rest of the afternoon relaxing by the pool and enjoying your local wine on the terrace. Or choose to work off your lunch by walking to the hilltop town of Chianciano. Visit the Etruscan Museum, stroll the streets, check out the local shops and take in the beautiful views.
Early evening, we will meet at Bradi Toscani for a wine tasting and light meal with local cheeses, meats, and other delicacies.
June 3 : Day 5 – Montepulciano
Breakfast with homemade organic products 8:30am- 9:30am
Depart for a 30-minute drive to Montepulciano. This medieval and Renaissance hill town is a true gem. Wander through the winding, narrow streets on your own or hop on the mini trolley for a ride and tour.
Spend the day at your leisure trying out various gelato or shopping at the fabulous stores in town. Or visit either the Consorzio de Vino Nobile di Montepulciano or Enoliteca Vino Nobile to try more of the regional wines.
Meet at the famous Cantina De Ricci winery in the afternoon. Here, you will descend into the stone cavern where they have been making Vino Nobile for over 800 years. The vaulted-stone ceilings with the large, stacked wood barrels and dim lights create a cathedral of wine! Enjoy a brief tour of the cave and hear about what makes the wine so special, then sit and enjoy a wine tasting.
Return to the Villa by private transfer at 5 pm
Take a late afternoon dip in the villa’s pool and enjoy your local wine on the terrace before dinner.
4-course dinner with homemade organic products at 8:00pm
June 4 : Day 6 – Local Living
Breakfast with homemade organic products 8:30am- 9:30am
Spend the day by the pool or get your heart pumping with a walk into the newer town of Chianciano.
OPTIONAL excursion $$: Theia Thermal Spa in town
Afternoon Olive oil instruction and tasting with Stefano when we return.
4-course dinner with homemade organic products at 8:00pm
June 5: Day 6 – Orvieto
Private Tour of Orvieto with local Italian guide
Breakfast with homemade organic products 8:30am- 9:30am
Visit the beautiful ancient hill town of Orvieto today. Orvieto is one of the most striking, memorable, and enjoyable hill towns in central Italy. This delightful little town is perfectly preserved, and virtually traffic-free. The colorful cathedral is a great visit after a relaxing lunch with some of Italy’s best wine.
Tour the stunning Gothic cathedral, experience the famous Well of San Patrizio and the amazing underground cave system that lies beneath the city.
4-course dinner with homemade organic products at 8:00pm
June 6: Day 7 – Arrivederci!
Breakfast with homemade organic products 8:30am- 9:30am
Say goodbye to our hosts and depart at 10:00 am by private transfer to train station Chiusi – Chianciano Terme. Trains are available to Rome, Florence, Venice, or your next Italian adventure.
Why Choose This Tour?
Unlike larger escorted tours, you’ll enjoy a relaxed pace, authentic local experiences, and the opportunity to truly immerse yourself in Tuscan life. Staying in one beautiful villa for the entire week means more time enjoying Tuscany and less time packing and unpacking. From medieval hilltop towns and world-class wines to unforgettable meals and stunning countryside views, this journey has been designed to showcase the very best of Southern Tuscany.
Activity Level: 7/10 – You’ll get your steps in! 😊 Ideal for active travellers who are comfortable navigating hills, steps, and historic cobblestone streets while exploring destinations on foot.
Reserve Your Spot Today
Space is limited to just 24 guests and is expected to sell quickly.
