Tuscany Hiking Adventure - Explore the Scenic Tuscan Countryside
Italy - Mon 13th October 2025

Max Participants:
15
Location:
Italy  
Date:
Mon 13th October 2025
Start Time:
12:00pm
End Time:
2:00pm approx
Duration:
6 Days
Meals:
2 Lunches 4 Dinners 5 Breakfasts
Hike Rating:
Grade 3
Non-Member Cost:
$5890.00 per person
Member Cost:
$5690.00 per person
Deposit Required:
$500.00
Single Supplement:
From $915.00 per person
Tagged:
hiking international
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The Val d’Orcia region, famous for its rolling hills, winding cypress-lined roads, charming farmhouses, and hilltop villages, is the backdrop for this exciting journey. You'll hike scenic, accessible trails that are perfect for travellers new to walking adventures, making it an ideal choice for those wanting to dip their toes into international hiking.

Each day, you’ll explore quaint medieval towns, enjoy authentic Tuscan cuisine, and immerse yourself in local culture. From visiting the iconic village of Montalcino to soaking in the rejuvenating thermal springs of Bagno Vignoni, this trip has it all - stunning landscapes, cultural insights, and plenty of moments to bond with your fellow adventurous women.

Whether you’re ticking Tuscany off your bucket list or simply looking for a friendly, supportive environment to try something new, this tour is designed to inspire confidence and create lasting friendships.

Key Details

  • Tour Dates: 13 - 18 October 2025
  • Start Location: Florence, Italy
  • End Location: Florence, Italy
  • Airport: Fly into and out of Florence Airport (FLR)
  • Arrival: Arrive by late morning on Day 1 to meet your guide and fellow travellers at Florence Airport for a group transfer.
  • Departure: The tour concludes in Florence, with a group transfer back to the airport on Day 6. You can book a return flight after 2 pm on the final day.

Gallery

Val d’Orcia
Cypress tree-lined roads
Rolling hills of Tuscany
Bagno Vignoni thermal pools
Enjoy Tuscan cuisine
Artisan cheese
Winding cypress tree-lined roads
Medieval Tuscan village
Tuscan winery
World War II memorial

Location

Please note map locations and route are approximate only

Highlights

● Explore Pienza - Discover this charming hilltop town with stunning views and historic sites.

● Hike Through Montepulciano & Monticchiello - Visit these picturesque Tuscan villages and enjoy a local winery lunch.

● San Quirico d'Orcia - Walk through scenic countryside to a lesser-known, authentic Tuscan village for a relaxing picnic.

● Relax in Bagno Vignoni’s Thermal Springs - Unwind in ancient thermal waters known for their therapeutic benefits.

● Visit Sant'Antimo Abbey - Hike through the Brunello wine region and explore this beautiful Romanesque abbey.

● Brunello Wine Tasting - Enjoy wine tasting at a local vineyard, sampling the famous Brunello di Montalcino.

● Walk with Like-Minded Women - Share this adventure with a group of welcoming, supportive women, making new friendships and memories along the way.

● Engage with Locals - With your expert local guide, you will gain insider knowledge of the region and have the opportunity to interact with the people who call this beautiful area home.

Itinerary

We’ll kick off the adventure by meeting at Florence Airport for a late morning transfer to the charming hilltop town of Pienza. With its stunning views and rich history, it’s the perfect place to start our journey. Once we’ve settled into our cosy hotel, we’ll enjoy a leisurely lunch filled with local specialties before stretching our legs on a relaxed hike to Petroio and Sant’Anna in Camprena. Afterwards, feel free to explore the village at your own pace. As the day winds down, we’ll gather for a tour overview accompanied by an aperitivo, followed by our first group dinner – the perfect time to get to know one another and share our excitement for the days ahead.

Meals: Lunch, Dinner

Accommodation: Hotel in Pienza

Today, we’ll hike through the breathtaking Tuscan countryside, stopping by the postcard-perfect villages of Montepulciano and Monticchiello. Along the way, we’ll enjoy lunch at a local winery – because what’s a trip to Tuscany without a bit of wine tasting? After returning to Pienza, you’ll have time to explore the historic Papal Palace and cathedral. We will meet for dinner and the evening will be spent together, reminiscing about the day’s adventures.

Meals: Breakfast, Lunch, Dinner

We’ll start our day hiking through the open countryside to the medieval village of San Quirico d'Orcia, where you can shop for local treats at the deli and enjoy a laid-back picnic in a beautiful rose garden - why not top off lunch with a well-deserved gelato? Later, it’s all about relaxing by the pool and watching the Tuscan sunset. Tonight, we’ll get together for a presentation on the Via Francigena, giving us a deeper connection to the history of the paths we’ve been walking, followed by dinner at the hotel restaurant.

Meals: Breakfast, Dinner

Accommodation: Hotel Palazzuolo

Today’s hike takes us to the quaint village of Bagno Vignoni, where the famous thermal springs have been soothing visitors for centuries. After stopping for lunch in the lovely hamlet of Vignoni Alto, we’ll wind our way through vineyards and oak forests until we reach Bagno Vignoni. Spend the afternoon soaking in the thermal pools or treating yourself to a massage - it’s all about relaxation today! We’ll head back to San Quirico in the evening, where you can enjoy dinner on your own and chat about the day with your new friends.

Meals: Breakfast

Accommodation: Hotel Palazzuolo

On our last full day, we’ll embark on one of the most rewarding hikes of the trip, walking through lush woodlands and iconic Brunello vineyards to the historic Sant’Antimo Abbey. After a picnic lunch in the peaceful surroundings, we’ll visit a Brunello winery to learn about the art of winemaking and indulge in a tasting. In the evening, we’ll wrap up our adventure with a celebratory dinner in Montalcino - the perfect chance to toast new friendships and reflect on the incredible journey we’ve shared.

Meals: Breakfast, Dinner

Accommodation: Hotel Palazzuolo

It’s time to say goodbye - but not before one last breakfast together. Afterward, we’ll transfer back to Florence Airport for your departure. Book your flight for after 2 pm to ensure a smooth, relaxed end to this adventure. Take with you new friendships, unforgettable experiences, and the empowerment of having explored this incredible region alongside other adventurous women.

Meals: Breakfast

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Includes

Adventurous Women Tour Leader

Local Guide

5 nights at 3-star hotels w/breakfasts (one with pool)

4 dinners

2 lunches

2 wine tastings

All transportation and entrances during the trip

Bagno Vignoni thermal pools entrance

One city tour with guide (Montalcino)

Use of walking poles

2 Lunches

4 Dinners

5 Breakfasts

Excludes

Flights to/from Florence

Travel Insurance (recommended)

Accommodation

We'll be staying in two hotels in Pienza and San Quirico d'Orcia.

What To Bring/Wear

- - Detailed Trip Notes will be provided well in advance of your departure, to help you plan & prepare.

Cancellation & Refunds

Notice of cancellation must be in writing, with an email as an acceptable form of communication, directly to Adventurous Women with the following conditions:

  • Cancellation 75 days or more prior to departure - Loss of deposit
  • Cancellation 74 days or less prior to departure - Loss of all payments

No refund is available after departure of a tour has commenced.
We highly recommend taking trip cancellation cover through your travel insurer to cover you for unforeseen circumstances that may lead you to have to cancel your participation in the tour.