Journey Through the Chianti Region

50026 San Casciano In Val di Pesa, Metropolitan City of Florence, Italy

Ti
Together in Tuscany
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9 reviews
Apr 25 - May 2, 2026
Group size: 8 - 14
Journey Through the Chianti Region
50026 San Casciano In Val di Pesa, Metropolitan City of Florence, Italy

Together in Tuscany
  • Email address verified
9 reviews

Apr 25 - May 2, 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 be adventurous and hop on an e-bike for an awe-inspiring guided tour of the Chianti region with a very special local couples. You will create and eat a four-course Italian meal in a historic kitchen on a winery, alongside an Italian chef, paired with the winery’s wine. 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: San Casciano

This 7-bedroom villa is a show-stopper with it’s unbelievable location on the Villa Le Corti Estate, owned and still resided by the historical and esteemed Corsini family.  When you stay here you are immersed within the olive groves and vineyards of Principe Corsini. Their wine and olive oil are delicious and plentiful within the villa. With the estate so close, it’s only a short walk down the driveway to enjoy the fine dining at their Osteria, partake in a winery tour and tasting or get your hands messy in the chef-led cooking class.  


Why we love this villa: Its charm, its history, its proximity to Florence, the ability to walk into the town of San Casciano, the staff, the expansive areas to gather, the food, the on-site winery, the comfortable beds, and of course, the amazing views!  This beautifully restored 400-year-old farmhouse comes with a private swimming pool and stocked with Principe Corsini wine. Some mornings you may even catch a glimpse of the hot air balloons in flight!   

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 the villa
  • Personal chef dinners
    4 dinners in the villa
  • Breakfasts
    6 breakfasts in the villa
  • Restaurant dinners
    2 restaurant dinners
  • Pre-arranged activities
    private group activities
  • Transportation
    to and from the activities and the designated train/airport
  • Cooking class
  • Wine at the villa
    1/2 bottle of wine pp per day included
  • Local tourist tax
    1-4 euros pp per day
  • Tips and gratuities
    for the tour guides, chef, housekeeping, drivers, etc.
  • On-site group leader

What’s not included

  • Airfare
  • Travel Insurance
  • Personal expenses
    Anything not specified in the travel package
  • Wine and alcohol
    wine and alcohol outside of what's included in the itinerary

Available Packages

Shared Twin Room/Private Bath
Deposit: €500
4 left

There are two twin rooms, each with two twin beds and their own private ensuite bathroom with combo bathtub/shower. Each room is tastefully decorated with antique furniture.


One room is on the lower level ground floor with five steps leading down to the room and three steps within the room leading up the bathroom which has two wash basins and a combo bathtub/shower.


The second twin room is on the first floor off the living room and is reached by taking eight steps up from the main level kitchen then two steps down into the room. This room has an ensuite bathroom with one wash basin and a combo bathtub/shower.

€4,299
Deposit: €500
Shared Standard King Room/Private Bath
Deposit: €500
Only 2 left

This room is tastefully decorated with antique furniture. It is located on the first floor off the living room. The room is reached by taking eight steps up from the main level kitchen then four steps down into the bedroom. This room has one wash basin and toilet separate from its combo bathtub/shower.  Both are located within the bedroom.


This room can be reserved as a single, private room for an additional $600. 


Select "Upgrade to private room" at checkout.

€4,299
Deposit: €500
Shared Deluxe Double Room/Private Bath
Deposit: €500
Only 2 left

This is a larger shared room with two four-poster double beds.  This room is tastefully decorated with antique furniture. It is located on the first floor main area off the living room. The room is reached by taking eight steps up from the main level kitchen then three steps up into the bedroom. This room has an ensuite bathroom with one wash basin and a combo bathtub/shower.  

€4,399
Deposit: €500
Shared King Suite/Private Bath
Deposit: €500
Only 2 left

This room has one king bed and a sitting area. It is tastefully decorated with antique furnishings.  It is located on the lower level ground floor with five steps leading down to the room from the main level kitchen and three steps down into the bedroom.  This room has an ensuite bathroom with one wash basin and a combo bathtub/shower.   


This room also has a bonus door leading outside to the shaded pergola for dining and relaxing. 


This room can be reserved as a single, private room for an additional $600. Select "Upgrade to private room" at checkout.


€4,399
Deposit: €500
Shared King Superior Suite/Private Bath
Deposit: €500
Only 2 left

This is the largest bedroom in the villa. It is tastefully decorated with antique furniture and has incredible views of the countryside from its bedroom and bathroom windows.  It is located on the first floor off the living room. The room is reached by taking eight steps up from the main level kitchen then three steps down into the bedroom.  It has one king bed, a sitting area within the room, a luxurious ensuite bathroom with two wash basins, large free-standing bathtub and stall shower. This room also has a private living room with access to an outdoor balcony. 


 

This room can be reserved as a single, private room for an additional $600. Select "Upgrade to private room" at checkout.

€4,499
Deposit: €500
Shared King Suite Exterior Entrance
Deposit: €0
Only 2 left

This room is connected to the villa but has a private, separate exterior entrance to a breathtaking view and the outdoor pergola area. It has one king bed, an ensuite bathroom and a sitting area. It is tastefully decorated with antique furnishings.  


This room can be reserved as a single, private room for an additional $600. Select "Upgrade to private room" at checkout.

€4,399
Deposit: €0

Available Add-Ons

Upgrade private king room
€600
4 left
Deposit: €500

 Upgrade to have your own private room



Itinerary

Saturday
Welcome to Tuscany!

4:00 Villa check-in

Welcome reception with wine and apperitivi


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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