Small Group Wine and Wanderlust Tour in Chianti

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 for up to 14 guests seeking a respite from their daily life.

You will have 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 known for it's beauty and rich history.

Expect to be pampered and live in the moment.

  • Culture

    Imagine the townspeople gathered in these ancient villages centuries ago. Step back in time as you wander through hidden hamlets. Explore iconic landmarks and soak in the rich cultural heritage.

  • Cuisine

    Use your hands to create delicious Italian dishes in cooking classes with experienced chefs. Savor the meals prepared by other culinary artisans, including your very own in-villa chef.

  • Tastings

    Sample select wines, cheeses, and olive oil from both world-famous, as well as small, organic, family-run venues. Learn how to pair the wine, cheese, and olive oil with each other and with local cuisine.

  • Experiences

    Take an adventurous e-bike tour and observe the beauty that surrounds you. Visit the village markets as if you were a local. Watch how olive oil, cheese, and wine are made. Appreciate a local artisan’s creative talents.

Here’s Where You’ll Stay

Gugliaie in San Casciano Val di Pesa

Why we love this villa: Its charm, its history, its proximity to Florence, the ability to walk into town, 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!

This 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.

The villa boasts many comfortable areas for gathering and lounging, both indoors and outdoors, 7 well-appointed bedrooms, modern en-suite bathrooms, heating and air-conditioning. The villa has a well-equipped farmhouse kitchen, large dining room, and shaded outdoor courtyard which includes a large dining area for al fresco meals.

Note: Due to the old, historic nature of the villa, it contains many sets of uneven stairs. Guests must be comfortable walking up and down uneven stairs and carrying their own luggage to their rooms.

Here’s Where You’ll Sleep

Shared Room with Two Twin Beds - 2 rooms

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 and one is on the first floor off the living room.

$4,125 per person based on double occupancy

Shared Deluxe Twin with Two Double Beds - 1 room

This is a larger twin 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. This room has an ensuite bathroom with one wash basin and a combo bathtub/shower.

$4,225 per person based on double occupancy

Standard King - 1 room

This is the smallest of the king rooms. This room is tastefully decorated with antique furniture and is located on the first floor off the living room. This room has one wash basin and toilet separate from its combo bathtub/shower. Both are located within the bedroom.

$4,625 per person private room

$4,025 per person shared room

King Suite - 1 room

This room has one king bed and a sitting area. It is tastefully decorated with antique furnishings and is located on the lower level ground floor. This room has an ensuite bathroom with one wash basin and a combo bathtub/shower plus a bonus exit to the outdoor shaded pergola.

$4,725 per person private room

$4,125 per person shared room

King Superior Suite - 1 room

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 and 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 plus a private living room with balcony. 

$4,825 per person private room

$4,225 per person shared room

*Note: the actual rooms may look slightly different from what is pictured.

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).