Small Group Tour in the Val D'Orcia

Ti
Together in Tuscany
  • Email address verified
9 reviews
May 2 - 9, 2026
Group size: 8 - 14
Small Group Tour in the Val D'Orcia
Tuscany

Together in Tuscany
  • Email address verified
9 reviews

May 2 - 9, 2026
Group size: 8 - 14

About this trip

Explore, savor and connect with the landscape, food, wine, people and culture of Italy.  Join us for an authentic, immersive, slower-paced, villa-based tour in the Italian countryside. This trip is perfect for solo travelers, couples, friend groups and families.


This tour is limited to 14 guests seeking a respite from their daily life and an opportunity to connect with each other and other like-minded travelers. You will leave your to do lists behind and immerse yourself in an area of Italy known for it's beauty and rich history. 

Expect to be pampered and live in the moment.


You will enjoy chef-prepared meals in your villa. You will be driven to and from all of your activities by a private driver. Your tours will be private for your group only. You will explore medieval villages and learn about what makes them unique.  You will create and eat a four-course Italian meal alongside an Italian chef . You will explore hidden gems like the local market and organic family-run cheese farms, olive groves and wineries. You will feel like a local and your senses will come alive as you see, smell, taste and touch your experiences and hear the stories told by your local tour guides.

Here's Where You'll Stay: Sarteano

The villa is located in the very pretty and tranquil town of Sarteano, a town that is rich in archaeological history with some of the most important Etruscan tombs surrounding its village. There are many shops, restaurants and bars in Sarteano, from boutique groceries to larger supermarkets, as well as an outdoor market every Friday morning.  


The villa has 7 bedrooms, each with their own en-suite bathrooms.  Two bedrooms are on the ground floor and a third is also on ground level but is separate from the villa and has its own private entrance (this one is usually reserved for the tour leader).  Four bedrooms are on the second floor, accessible via a staircase.  The villa has many indoor and outdoor gathering areas including private sitting areas between the second floor bedrooms. 


Why we love this villa:  its charm and close proximity to the beautiful medieval hamlet of Sarteano and the historical villages of Pienza and Montepulciano. The villa has incredible views of the Val d’Orcia, modern updates, lots of spaces to gather, indoor well-equipped chef’s kitchen, outdoor kitchen with grill, and gorgeous pool. This villa has all the charm of a 1700s home with all the modern amenities due to the careful restoration by its current owners.    

Terms and conditions

Cancellation Policy

A non-refundable deposit of $500 is required within 3 days of booking your Together in Tuscany trip.  Half of your trip balance is due 150 days prior to the trip start date.  The remaining balance is due 120 days prior to the trip start date.  All bookings made within 120 days of the trip start date require full payment. 


Should  an installment payment not be received seven (7) days of its due date, we will consider your space on the trip as cancelled and no refunds will be provided for any payments received. 


You understand the unique services Together in Tuscany provides.  Deposits and payments are applied to third party vendors providing itinerary activities very shortly after payments are received. As such, once payments are made to Together in Tuscany, we cannot issue any refunds.


Travel Insurance

We HIGHLY recommend that you obtain travel insurance. If you must cancel your participation in a Together in Tuscany trip for any reason whatsoever, including health conditions, death of a family member, travel difficulties, personal reasons, or any other reason whatsoever, the travel insurance can cover some or all of these expenses. 


Service Agreement

All guests are required to review and accept the terms and conditions outlined in the Service Agreement which will be provided upon booking your room. The Service Agreement addresses risks and liabilities for the Provider (Together in Tuscany) and the Purchaser (Guest).

What’s included

  • Villa accommodations
    7 nights in a luxury villa
  • Personal chef dinners
    5 dinners in the villa
  • Breakfasts
    6 breakfasts in the villa
  • Restaurant dinners
    1 restaurant dinner
  • Wine
    with dinners
  • Tips and gratuities
  • Pre-arranged activities
    private group activities
  • Transportation
    to and from the activities and the designated train/airport
  • Tour leader
    on-site tour leader to coordinate activities and ensure your trip runs smoothly

What’s not included

  • Airfare
  • Travel Insurance
  • Personal expenses
    Anything not specified in the travel package
  • Wine and alcohol
    *outside of dinners
  • Local tourist tax
    1-4 euros pp per day
  • Trip add-ons
    extra excursions outside of the itinerary or pre or post-trip planning

Available Packages

King Room Ground Floor Double Occupancy
Deposit: €500
4 left

There are 2 ground floor king bedrooms. These rooms are heated/air-conditioned and each have their own private bathroom and a shared sitting area.


These rooms can be upgraded to single occupancy for an additional fee of $600. Select "upgrade to private single room" at checkout. 

€4,399
Deposit: €500
King Room 2nd Floor Double Occupancy
Deposit: €500
8 left

There are a total of four bedrooms on the second floor, two bedrooms on either side of the house, both with a shared sitting area.  The rooms are accessed by a set of 16 terracotta stairs.


Each bedroom is heated/air-conditioned with a king bed and private ensuite bathroom. Each bedroom shares a sitting area with another king bedroom. 


These rooms can be upgraded to single occupancy for an additional fee of $600. Select "upgrade to private single room" at checkout.  

€4,399
Deposit: €500
King Ground Floor Exterior Room
Deposit: €500
Only 2 left

This room has a private entrance outside of the house. The room is equipped with a king bed, ensuite bathroom with shower and heating/air conditioning.


This room can be upgraded to single occupancy for an additional fee of $600. Select "upgrade to private single room" at checkout.   

€4,299
Deposit: €500

Available Add-Ons

Upgrade to single private room
€600
7 left


Itinerary

Saturday
Welcome to Tuscany!

4:00 Villa Check-In

You will be picked up from the nearby train station and driven to the villa.  You will meet the others in your group and enjoy the region’s wine and cheese during a welcome reception at the villa, followed by a tour of the villa and dinner in the villa.  

Your Organizer


Ti
Together in Tuscany
9 reviews
Ciao! I’m Janine! It’s my mission to curate unforgettable villa vacations for travelers seeking la dolce vita. I do this by finding the best villas, cooks, drivers, wineries and tour guides. My tours and retreats are all-inclusive packages, limited to 8-12 guests, and provide you with hands-on, immersive and off-the-beaten path experiences. I remove the stress of planning a vacation by taking care of all the details so you can relax and enjoy the journey. You can feel comfortable knowing I am with you every step of the way.

Reviews

The trip to Portugal was beyond amazing! I have always planned my own trips but this time Janine took care of everything and did an exceptional job. Janine is extremely organized and does everything with a smile. She arranged lovely hotel accommodations, amazing excursions, all our transportation around Portugal and it was all done seamlessly. We had so much fun at the wineries, open air jeeps thru the countryside, a tuk tuk tour, boat rides, a cooking class at an intimate restaurant and so much more. The hotels we stayed in were very nice with comfortable beds, pretty gardens and one even had a pool! Janine's thoughtful planning made this trip a very memorable one.
By Karen R for Portugal Girls Trip on Jul 13, 2025
This trip to Portugal was an amazing cultural experience! Our trip was full of fun, informative activities while we visited several different towns and cities. Walking tours, food tours, winery tours, boat rides, tuk tuk rides, and open air jeep rides, this guided vacation with Janine did not disappoint! I was so very impressed with the accommodations and the activities… I had a worry free travel excursion!
By Kim W for Portugal Girls Trip on Jun 30, 2025
A year ago, Janine and I sat down to discuss planning a Portugal Trip. To celebrate my 60th birthday. On June 14, 2025 we arrived in Porto and had 8 fun filled days with daily excursions, wine and food tours, beautiful hotel accommodation, three boat tours and so much more. Eight fun filled days with eight wonderful ladies. Best trip ever. Thanks Janine. The ultimate trip planner!!
By Holly B for Portugal Girls Trip on Jun 29, 2025
This was a trip that was truly a special experience. Every day brought unique discoveries that unrolled in fun, new, and different ways. From a cooking class in a small restaurant that we had all to ourselves to crawling inside a genuine wine barrel to touring the countryside in open-air jeeps… Janine put so much care into crafting memorable experiences, taking care of every single detail so that we could focus on nothing but having the time of our lives!
By Noelle L for Portugal Girls Trip on Jun 29, 2025
Janine our travel guide is easy going and caring. She was highly organized setting up our mini excursions, yet with a smile, could change direction on a whim! She has great connections with the local people in and around Porto and Lisbon. I would use Janine again in a heartbeat! Jody Ps Portugal is a great country to visit, easy to get around.
By Jody J for Portugal Girls Trip on Jun 26, 2025
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