Beyond the Tuscan Wine Trail
Tuscany Wine Retreat in Cortona | September 21–24, 2026
A hosted small-group retreat exploring Tuscan wine, aperitivo culture, local food, and insider experiences in Cortona. Limited to 10 guests.
Join us for an intimate four-day retreat in and around the hilltop town of Cortona, where wine, food, and aperitivo culture come together in one unforgettable experience.
Who's This Perfect For
Travelers who value depth and context over fast-paced itineraries
Wine lovers who want to understand the culture behind what they’re drinking
Those who prefer small groups and a more personal, hosted experience
Curious and independent travelers comfortable exploring beyond the typical tourist path
People who appreciate food, aperitivo culture, and the rhythm of Italian daily life
Why This Retreat Is Different
Many wine tours simply move from one tasting to another.
This retreat is designed as a curated cultural experience, combining education, hospitality, and authentic local encounters.
Throughout the program you will experience:
guided wine tastings led by an Italian wine sommelier and educator
insider access to local producers and hidden gems
aperitivo traditions at its finest
Tuscan farm culture and seasonal cuisine
small group travel designed for connection and conversation
Who You Will Be Spending Time With
Hosted by Italian wine educator Alessia Botturi, along with hospitality expert and sommelier Kristine Bocchino, this retreat offers a rare opportunity to explore Tuscany through the eyes of two professionals who have spent decades working in the global wine, spirits and hospitality industries.
Retreat highlights
During our three days together, guests will enjoy a series of curated experiences including:
Welcome aperitivo introducing the traditions of Italian social drinking
A Cortona farm visit & seasonal estate picnic
A Montalcino winery tour, tasting & lunch experience
A sunset excursion to the Sabatini Gin Estate & Gardens at Villa Ugo
An after-dinner introduction to Italian amaro and digestif
Two hosted dinners featuring regional cuisine and wine pairings
Time to explore Cortona at your own pace
These experiences are complemented by relaxed conversations, shared meals, and the opportunity to learn directly from your hosts.
September 21–24, 2026 | Cortona, Tuscany
DAY 1 - September 21st - Arrival and Welcome Dinner
Guests arrive and settle into the hotel, with time to relax and explore the surroundings.
In the early evening, we gather for a welcome aperitivo paired with a breathtaking view, exploring the traditions behind Italy’s most beloved social ritual.
A relaxed Tuscan dinner follows, where we begin our journey into the wines and culinary culture of the region, as Alessia shares some insights behind the evening Cortona and Tuscany wine pairings.
Then we’ll wrap up the night with an amari & digestivi tasting with local chocolates at Amaro Cortona Tasting Room.
DAY 2 - September 22nd - Tuscan Terroir and Wine Culture
After breakfast, we visit a local winery known for its unique approach to winemaking and strong focus on sustainability and respect for nature. Here, we explore the connection between land, agriculture, and wine, gaining a deeper understanding of how environment and philosophy shape what is in the glass.
A seasonal lunch is served at the estate.
After some free afternoon time to explore or recharge, we head just outside the city for a visit to the Sabatini Gin Garden, learning about the botanicals grown on the property, and the revival of Italian craft spirits.
Dinner is left open, allowing you to explore and enjoy the restaurants of the town at your own pace.
DAY 3 - September 23rd - Craft, Regional Pride & Hospitality
Today we’ll take a drive west, to the world class wine regional of Montalcino, where you’ll enjoy an exclusive visit and tasting session, followed by a relaxed lunch.
In the afternoon, back in Cortona you’ll have some freetime back for a bike ride, hike to Bramasole Villa, some shopping or just to casually explore the village.
The afternoon is free to rest or explore. For those interested, Alessia and Kristine can accompany guests on a wine shopping experience through selected local wine shops. Additional activities can also be arranged, such as a guided hike or a hands-on pottery class.
In the evening, to cap off the retreat in style, we’ll dine at one of Cortona’s most divine restaurants, enjoying a beautifully curated 4-course dinner with wine parings.
DAY 4 - September 24th - Departure
Breakfast at the hotel and guest departures.
Your Home in Tuscany
You will stay in a 4 stars hotel enjoying a breath-taking view from the hilltop, located in the town center of Cortona, one of Tuscany’s most beautiful medieval villages.
Perched above the Val di Chiana valley, Cortona offers breathtaking views, quiet piazzas, artisan shops, and a relaxed rhythm of life that captures the essence of Tuscany.
This intimate setting allows us to experience Tuscany not as tourists, but as temporary locals.
What is included
Three nights in a 4-star hotel Deluxe room with view of the valley
Three breakfast
Two hosted dinners with wine pairings
Two lunches
One Amaro experience
Two Aperitivo experiences
Three wine education sessions
Two Winery visits with tasting
Wine seminar and guided tastings
Winery visit with tasting
Sabatini Gin Garden experience at Villa Ugo
Local transportation for all scheduled activities
Hosted program led by Alessia and Kristine
What is NOT included
Transportation to and from Cortona (available upon request)
Parking at the hotel (available upon request)
One dinner in Cortona during free evening
Personal purchases and additional wine
PRICING
This retreat is intentionally limited to 10 guests to ensure a personal and relaxed experience.
Small groups allow for deeper conversations, flexible exploration, and meaningful connections.
Minimum 6 guests required for the retreat to operate.
DOUBLE OCCUPANCy
september 21-24, 2026
$2300 per person
SINGLE OCCUPANCy
september 21-24, 2026
$2600 per person
Disclaimer: Partners in Wine organizes wine experiences in collaboration with independent third-party providers. We are not liable for injury, loss, delays, or disruptions related to these services. Participation involves inherent risks. We strongly recommend obtaining comprehensive travel insurance.
Frequently Asked Questions
Who is this retreat for?
This experience is designed for wine lovers, hospitality professionals, and curious travelers who want more than a standard wine tour. You don’t need to be an expert, but you should have a genuine interest in wine, food, and Italian culture. The focus is on understanding how Italians live, drink, and experience hospitality—not just tasting wine.
What makes this different from a typical Tuscany wine tour?
Most Tuscany tours focus on back-to-back tastings.
This retreat is structured as a curated cultural experience, combining wine education, aperitivo traditions, food, and local lifestyle.
You are hosted directly by two international beverage professionals, with insider access, guided conversations, and context behind everything you experience—from winery visits to amaro and aperitivo culture.
What’s included in the price?
Your retreat includes:
3 nights in a 4-star hotel in Cortona
Daily breakfast, 2 lunches, and 2 dinners with wine pairings
Winery visits (Cortona + Montalcino)
Aperitivo and amaro experiences
Sabatini Gin Garden experience
Wine education sessions led by Alessia
Local transportation during scheduled activities
This is a fully hosted experience, not just a tour package
What’s not included?
Flights, transportation to Cortona, one free evening dinner, and personal expenses are not included.
Private transfers from airports or train stations can be arranged upon request
Where does the retreat take place and how do I get there?
The retreat is based in Cortona, Tuscany, a historic hilltop town.
The closest access points are:
Florence (FLR)
Rome (FCO)
From there, you can reach Cortona by train or private transfer (we can assist with planning or booking).
How physically demanding is the experience?
This is a relaxed but active experience. Activities include walking in town centers, winery visits, and some uneven terrain typical of Tuscan countryside.
You should be comfortable walking and standing for periods of time, but no intense physical activity is required.
What is the group size?
The retreat is intentionally limited to 10 guests maximum to maintain a personal, high-quality experience.
A minimum of 6 participants is required for the retreat to run.
Can I join as a solo traveler?
Yes. Many guests join solo.
You can choose:
Shared double occupancy (paired option if available)
Single occupancy upgrade (limited availability)
What are the payment and cancellation terms?
30% deposit to secure your spot
Balance due 60 days before departure
Cancellation terms:
Deposit is non-refundable
31–60 days: 50% retained
15–30 days: 75% retained
Under 14 days: no refund
Is travel insurance required?
Yes—travel insurance is required.
You must have coverage for:
Trip cancellation/interruption
Medical expenses
Emergency evacuation
This protects both you and the experience.
What if I don’t drink (or I drink very little)?
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Can dietary restrictions be accommodated?
Yes, within reason.
Please communicate any dietary requirements in advance, and we will coordinate with our partners to accommodate them where possible.
