Italy · 23 - 27 September 2026

Tuscany Retreat - September 2026

5 days of authentic Tuscan living with Benedetta. Hidden hot springs, family vineyards, and real Nonne. Everything sorted.

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Overview

After eight years of welcoming thousands to Flash Festival Tuscany, Benedetta is opening up her world beyond the festival weekend. This is 5 days of everything she loves most about her home - curated for a small group who want to experience the real Tuscany. Small intimate group. Only 12 rooms available. 20-30 people maximum. This isn't Flash Festival. There's no music, no stages. It's quieter, deeper, more intimate. Just authentic Tuscan immersion with the woman who knows it best. No itinerary stress. No tourist traps. No planning required. Benedetta has organised everything - you just bring yourself. September sunshine. Mediterranean warmth without the scorching summer heat. The perfect end-of-summer treat before autumn arrives. Solo travelers absolutely welcome. All dietary requirements catered for (vegan, vegetarian, gluten-free). Everything is optional - participate as much or as little as you like. This is Tuscany through Benedetta's eyes. The thermal spas her family visits. The winemakers she calls friends. The nonne who welcome you like famiglia. Not tourism. Immersion.

Highlights

Accommodation: 4 nights in a Tuscan Resort

Accommodation: 4 nights in a Tuscan Resort

We have upgraded the experience to 4 nights in this wonderful, quintessential 18th century Farmhouse Resort - Terre dei Cavalieri with a pool, elegant authentic rooms and an amazing chef to cook us breakfast, 3 course lunches and dinners!

Location: Cortona

Location: Cortona

What you’d picture a quaint Tuscan hilltop village, beautifully iconic and chic (set of Succession, Under the Tuscan Sun and more)

Spa Day

Spa Day

VIP experience at the thermal baths of Terme di San Giovanni in Rapolano; Tuscany is full of natural hot springs!

Wine Tours & Tastings

Wine Tours & Tastings

You are in one of the best wine regions of the world! We will do 2 Wine Tours & Tastings. Meet the winemakers, explore the vineyards and learn how they make their wines. They will prepare us lunch at one winery and an aperitivo in the vineyards at the other one.

Pasta making & Cooking classes with Nonna

Pasta making & Cooking classes with Nonna

Nonna Ginetta and Nonna Silvia will come to teach us their easy to make and authentic Tuscan recipes

Wellbeing with Jordan Mae Antoinette

Wellbeing with Jordan Mae Antoinette

Wellbeing sessions each day - curated by Jordan Mae Antoinette a blend of Meditation, Breath Work, Yoga, Tone & Flow. 90 minutes experience each morning to start the day and help your restore or energise. All levels welcomed

From 14th - 18th October

From 14th - 18th October

Experience Tuscany in autumn with sunny days but milder temperatures, beautiful nature and fewer tourists

Hosts

Run and hosted by me, Bene (Benedetta), your local Tuscan girlie who will moving her hands, teaching you the Tuscan slangs and showing you around her favourite spots and some hidden gems that not many people know. Like a friend that knows where is best to go, which food is best to order and with which wine is best to pair it! Nothing you can find in your google searches!

Benedetta Venturini

Benedetta Venturini

After co-funding and running Flash Festival, I have not lost one bit my passion of curating real, authentic experiences that connect people from around the world. My goal has always been to get people to see the Tuscany the way I see it, so retreats seem another great way to showcase it! 

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Schedule

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Florence Airport + Terre dei Cavalieri

Day 1 - Arrivals & Benvenuti

WEDNESDAY 15 OCTOBER

Florence Airport Pick up at lunchtime 

Arrive and check-in at Terre dei Cavalieri and settle in

Welcome chat & Breath-work 

Poolside Aperitivo at sunset

The First Supper 

Spa1

Terre dei Cavalieri + Terme di San Giovanni

Day 2 - Spa Day

THURSDAY 16 OCTOBER

Buongiorno Yoga & Wellbeing Session

Tuscan Breakfast

Spa Day VIP experience at the thermal baths of Terme di San Giovanni with lunch

(optional) Massages back at the hotel

Melt Yoga 

Dinner at Resort 

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Terre dei Cavalieri + Winery 1 & 2

Day 3 - The Wine Tour

FRIDAY 17 OCTOBER

Buongiorno Yoga & Wellbeing Session

Tuscan Breakfast

The Wine Tour - wine tastings and canteen tours of 2 wineries

Lunch at the winery

Sunset Aperitivo at the vineyard

Friday Dinner at Resort 

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Terre dei Cavallieri + Castiglion Fiorentino & Cortona

Day 4 - Pasta, Cooking & Local towns

SATURDAY 18 OCTOBER

Buongiorno Yoga & Wellbeing Session 

Tuscan Breakfast

Pasta Workshop: hosted by the Nonna of the region

Saturday Lunch

Chill by the pool, walk or book a massage (extra), bike ride (extra)

Visit of Castiglion Fiorentino and Cortona

Aperitivo in Cortona in the Piazza

Last Tuscan Supper at Restaurant in Cortona

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Terre dei Cavalieri + Pisa Airport

Day 5 - Arrivederci & Departures

SUNDAY 19 OCTOBER

Buongiorno Yoga & Wellbeing Session 

Arrivederci Breakfast

Goodie bags & warm hugs

Check Out *

Airport Transfer to Pisa Airport 

* Flexible Check-out - you can also choose to stay longer by the pool and arrange your own airport transfer. We can drop you off to any train stations. 

What's included

What's Included

4 Nights in 18th Century Farmhouse Resort in Cortona, with pool, elegant rooms and chef

Spa day, a VIP experience at the thermal baths of the natural hot springs of Terme di San Giovanni in Rapolano village

2 Wine Tours & Tastings. Meet the winemakers, explore the vineyards and learn how they make their wines. They will prepare us lunch at one winery and an aperitivo in the vineyards at the other one.

Pasta making & Cooking classes with Nonna Ginetta and Nonna Silvia; they will come to teach us their easy to make and authentic Tuscan recipes;

Wellbeing sessions each day - curated by Jordan Mae Antoinette a blend of Meditation, Breath Work, Yoga, Tone & Flow. 90 minutes experience each morning to start the day and help your restore or energise. All levels welcomed.

Trip around Castiglion Fiorentino and Cortona villages with last aperitivo and supper in the iconic Piazza.

All food and wines - with Poolside Aperitivo, breakfast, 3-course lunches and dinners at the Resort, a Winery lunch and another Winery Aperitivo in the vineyards, and, for the finale, an Apertivo with Last-supper in Cortona’s Piazza. Most drinks are included.

Airport Pick Up + Drop Off now included from Florence Airport (pick-up Wednesday lunchtime) and to Pisa Airport (drop-off Sunday afternoon)

Payment plans available - you can pay in 2 instalments

Your travel to Tuscany - either flights, trains or buses. We will pick you up at Florence Airport and drop off at Pisa Airports.

Great news - there are a lot of good flights that are still cheap

My recommended route: from London to Florence (11:50am, Vueling) + return from Pisa (16:55pm, Easyjet) = only £130 return with carry-on luggage!

Please get in touch, if you need different travel routes.

Accommodation

Classic Room - Solo

Classic Room - Solo

Large double bedrooms elegantly decorated, with a private bathroom and windows overlooking the Tuscan countryside.

FROM$2,494.33/pp

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Classic Room - Shared

Classic Room - Shared

Large double bedrooms elegantly decorated, with a private bathroom and windows overlooking the Tuscan countryside.

FROM$2,146.93/pp

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Deluxe Room - Solo

Deluxe Room - Solo

For those looking for a bit of extra comfort, these spacious double bedrooms are beautiful and bright with a private and airy bathroom and with windows overlooking the Tuscan countryside.

FROM$2,577.71/pp

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Deluxe Room - Shared

Deluxe Room - Shared

For those looking for a bit of extra comfort, these spacious double bedrooms are beautiful and bright with a private and airy bathroom and with windows overlooking the Tuscan countryside.

FROM$2,230.31/pp

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Suite Room - Solo

Suite Room - Solo

The suite features a gracious bedroom with a private living room and a generous private bathroom. Step out onto your balcony overlooking the Tuscan countryside.

FROM$2,661.08/pp

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Suite Room - Shared

Suite Room - Shared

The suite features a gracious bedroom with a private living room and a generous private bathroom. Step out onto your balcony overlooking the Tuscan countryside.

FROM$2,313.68/pp

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Add Ons

Deep Tissue Massage - 60 Minutes

Deep Tissue Massage - 60 Minutes

A deep and targeted treatment to release muscle tension, stiffness and contractures. Thanks to firm and precise maneuvers, this massage promotes the relaxation of tired muscles, improves blood circulation and restores a feeling of lightness and general well-being. Ideal for those suffering from back, shoulder and neck pain....
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FROM$111.17/pp

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Welcome Hamper

Welcome Hamper

Our local food & wine welcome hamper for your arrival (for 2 People): a bottle of natural wine, fresh goods from the local forno, olives, salame and pecorino cheese....
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FROM$62.53/pp

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E-Bike Rental

E-Bike Rental

Rent an e-bike for a day for a cycle in your free time. Discover the Val di Chiana cycling along the ancient road of the Canale Maestro della Chiana, an equipped and protected route (without much difference in height) immersed in nature and Etruscan history....
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FROM$69.48/pp

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Mountain Bike Rental

Mountain Bike Rental

Rent a mountain bike for a day for a cycle in your free time. Discover the surrounding Val di Chiana cycling along the ancient road of the Canale Maestro della Chiana, an equipped and protected route (without much difference in height) immersed in nature and the Etruscan history....
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FROM$34.74/pp

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Ayurveda Massage - 60 Minutes

Ayurveda Massage - 60 Minutes

An experience of rebalancing and harmony for body and mind. This massage, inspired by the Ayurvedic tradition, uses Indian medicated oils and Tuscan essential oils selected for their beneficial properties. The gentle and enveloping movements stimulate the flow of energy, improve lymphatic circulation and promote deep relaxation, regenerating body and spirit....
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FROM$111.17/pp

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Face & Feet Massage with Facial Treatment - 40 Minutes

Face & Feet Massage with Facial Treatment - 40 Minutes

A wellness ritual that combines facial massage with foot care for a relaxing and regenerating effect. The treatment helps to relax the facial muscles and improve the brightness of the skin, thanks to movements together with a face mask selected based on the skin type. During the application time, the relaxation continues with a foot massage, which through relaxing manoeuvres and targeted pressure gives a feeling of lightness and deep well-being....
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FROM$83.38/pp

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You'll Be Staying Here

Terre dei Cavalieri

Terre dei Cavalieri

FAQs

I love and respect everyone’s needs 

So you don’t need to do everything. 

You don’t need to participate at the morning yoga/wellbeing sessions if you don’t want to 

You don’t need to drink if you don’t want to

You don’t need to get your hands with flour and make pasta 

You can also just relax by the pool whenever you want. 

  • Food - there will be an abundance of food throughout the day at breakfast, aperitivo, lunches and dinners. It can be catered also for vegan, vegetarian and gluten free diets - Italy loves to feed you all! 
  • Wine lover - this is a plus but drinking is not compulsory 
  • To travel and meet new people - solo travellers welcome!
  • No logistical stresses or travel plans - all is organised for you!
  • Discover places off the beaten track (stop googling it!) 
  • Real and authentic experiences! 

All levels welcomed - you don't need to know about food, wine or wellbeing to be part of this experience. Just the interest to appreciate them!


Airport Pick Up + Drop Off now included - here is the best part: you don’t have to do anything apart from booking your flights.

There are a lot of good flights routes to/from Florence and Pisa that are still cheap (see below suggested cheap route):

  • We will pick up from Florence Airport on Wednesday lunchtime 
  • We will drop you off at Pisa Airport on Sunday afternoon

We can also pick you up from Cortona or Castiglion Fiorentino train stations. 

My recommended route: from London to Florence (11:50am, Vueling) + return from Pisa (16:55pm, Easyjet) = only £130 return with carry-on luggage! 

All food and wines are included - with Poolside Aperitivo, breakfast, 3-course lunches and dinners at the Resort, a Winery lunch and another Winery Aperitivo in the vineyards, and, for the finale, an Aperitivo with Last-supper in Cortona’s Piazza. Most drinks are included.

Dates

Classic Room - Solo

23 - 27 September 2026

$2,494.33 / person
BOOK NOW

Classic Room - Shared

23 - 27 September 2026

$2,146.93 / person
BOOK NOW

Deluxe Room - Solo

23 - 27 September 2026

$2,577.71 / person
BOOK NOW

Deluxe Room - Shared

23 - 27 September 2026

$2,230.31 / person
BOOK NOW

Suite Room - Solo

23 - 27 September 2026

$2,661.08 / person
BOOK NOW

Suite Room - Shared

23 - 27 September 2026

$2,313.68 / person
BOOK NOW
Tuscany Retreat - September 2026

Italy · 23 - 27 September 2026 · 4 nights

FROM$2,494.33/pp

BOOK NOW