5 DAY TUSCANY RETREAT
23 - 27 SEPTEMBER 2026 | CORTONA, TUSCANY
SWEET DOING NOTHING MEETS LA DOLCE VITA
Five days in Tuscany where you don't have to think about a thing.
Benedetta – the Tuscan girl who's hosted thousands at Flash Festival and knows every secret corner of this region – is curating an intimate retreat for you.
Staying in a quintessential 18th century Farmhouse Resort.
VIP Spa day at ancient hot springs most tourists never find.
Wine tours with small producers she's known for years.
Pasta & cooking classes with the actual Nonne.
Exploring medieval Cortona, sip aperitivo in the Piazza like a local.
Exceptional dining experiences with paired wines and aperitivi throughout.
Daily yoga if you want it, or pure dolce far niente if you don't.
No itinerary stress. No Googling "best places in Tuscany." No tourist traps.
Just real connection, incredible food and wine, and the kind of slow living that reminds you why you traveled in the first place.
Small group. September sunshine. Everything organised.
You just bring yourself (or a plus 1 if you prefer).
Reset
Escape the ordinary and disconnect from your busy life. Everything is organised for you, so you can switch off completely. A full mind and body experience to slow down and feel grounded.
Indulge
Your sunshine recharge before autumn arrives. Tuscany at its finest - the scorching heat has passed, yet the Mediterranean glow remains, filling you in with its natural beauty and abundance of flavours.
Reconnect
Disconnect to reconnect - within yourself and with others - while embracing the qualities of Tuscan living. You will feel what 'la dolce vita' really means.
A PERFECT END-OF-SUMMER TREAT TO YOURSELF
YOUR HOST: BENEDETTA
Me, Bene, will be your host for 5 days.
Think of it as traveling with your local friend who knows where to go, what to order, which wine pairs perfectly - secrets you won't find online.
I'll be moving my hands, teaching you Tuscan slang, and showing you my favorite spots. A full discovery of what makes life in Tuscany so special.
You'll be together with a small group of like-minded travelers seeking this kind of authentic experience.
THE LOCATION
Terre dei Cavalieri - A quintessential 18th-century farmhouse resort in the Cortona countryside
Elegant rooms in a historic Tuscan property
Swimming pool surrounded by countryside views
Renowned chef preparing breakfast, 3-course lunches, and dinners
Set in the hills near Cortona - that iconic, chic hilltop village you've seen in Under the Tuscan Sun and Succession
This is Tuscany as you've imagined it.
WHAT'S INCLUDED
(This is the best part)
Accommodation
4 nights (From 23rd to 27th September 2026) at Terre dei Cavalieri with your choice of:
- Classic Room - Comfortable and authentic
- Deluxe Room - Extra space and charm
- Suite - The ultimate Tuscan experience
Each room is unique. Solo or shared options available.
VIP Spa Day
Surrender to ancient hot springs rising naturally from the earth in Rapolano village. One of Tuscany's best-kept secrets - thermal waters few travelers discover.
2 Exclusive Wine Tours
You're in one of the world's finest wine regions. Meet passionate winemakers, wander their vineyards, discover the craft. One estate hosts lunch, the other serves sunset aperitivo among the vines.
Pasta Making & Cooking with the Nonne
Learn the art of fresh pasta and traditional cooking with Nonna Ginetta and Nonna Silvia. Weekend mornings in Italy belong to the kitchen - they'll transport you there, teaching recipes passed down through generations.
Medieval Town Exploration
Discover Cortona - an hilltop town with breathtaking views at every turn. Sip aperitivo in the iconic Piazza Signorelli, then gather for our farewell feast at one of Benedetta's favorite local restaurants.
Exceptional Cuisine Throughout
Prepare to be deliciously spoiled:
- Daily breakfast at the resort
- Three-course lunches (at the resort, in vineyards, with the nonnas)
- Aperitivo moments throughout
- Elegant dinners featuring local ingredients
- Wines paired with every meal
All meals, wines, and most drinks included.
Daily Wellbeing Sessions
A blend of meditation, breathwork, and yoga each morning to restore or energise. All levels welcome. Completely optional.
The best way to regenerate and recharge for the day.
Stress-Free Travel
Airport pick-up and drop-off included - You don't have to do anything except book your flights.
We will arrange a Wednesday pick-up and Sunday drop-off from either Florence or Pisa airports (plenty of affordable flight options). Get in touch, we will suggest the best and convenient route.
Can also arrange pick-up from Cortona or Castiglion Fiorentino train stations if you prefer.
THE ITINERARY
Everything is optional - relax by the pool whenever you wish.
Day 1 - Benvenuti
Arrive at Terre dei Cavallieri and settle in
Meet & Greet + Welcome Breathwork & Meditation
Poolside Arrival Aperitivo
The First Supper
Day 2 - Spa & Wellbeing
Yoga & Meditation Session
Buongiorno Tuscan Breakfast
VIP Spa experience at the ancient hot springs of Terme di San Giovanni with lunch
Massages & treatments (additional)
Evening Melt Yoga
Dinner at Terre
Day 3 - Wine Country
Yoga & Meditation Session
Buongiorno Tuscan Breakfast
The Wine Tour - wine tastings and canteen tours of 2 wineries
Lunch at one winery
Sunset Aperitivo in the vineyard
Dinner at Terre
Day 4 - Pasta & Culture
Yoga & Meditation Session
Buongiorno! Tuscan Breakfast
Optional Activities: book massage, e-bike or mountain bike rentals, or simply walking
Pasta Making & Cooking Workshop: hosted by the actual Nonne
Saturday Pasta Lunch
Food coma free time & chill
Explore Cortona + Aperitivo in Piazza
Last Tuscan Supper Dinner in Cortona
Day 5 - Arrivederci
Yoga & Meditation Session
Farewell Brunch
Goodie bags & warm hugs
Check-out
ROOMS & PRICING
Limited rooms available. Book early to secure your preferred accommodation.
Each room is unique and different.
Options to have 1 double or 2 comfy single beds per room.
Can add an extra bed to make it triple if wish.
Payment Plans Available - Pay in 3 instalments (5% fee applies).
Classic Room
Solo: £1,795pp | Shared: £1,545pp
Large double bedrooms elegantly decorated, with a private bathroom and windows overlooking the Tuscan countryside.
Deluxe Room
Solo: £1,855pp | Shared: £1,605pp
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.
Suite
Solo: £1,915pp | Shared: £1,665pp
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.
EXTRAS
Additional treats and experiences to enhance your stay
Welcome Hamper
- Welcome Hamper - £45
For aperitivo at arrival (for 2 People): a bottle of natural wine, fresh goods from the local forno, olives, salame and pecorino cheese.
Rent A Bike
- E-Bike - £50
- Mountain Bike - £25 a day
Rent a bike for a day to cycle on your free time. Discover the Val di Chiana and ancient Medici's roads, an equipped and protected route (without much difference in height and hills) immersed in nature and the Etruscan history. Various itineraries provided.
Massages
- Deep Tissue or Ayurveda Massages - 60 Minutes - £80
- Face & Feet Massage with Facial Treatment - 40 minutes - £60
Caterina offers therapeutic Deep Tissue massage for muscle tension relief, harmonizing Ayurveda massage with medicated oils for energy rebalancing, and a Face & Feet ritual combining customized facial treatment with reflexology for complete rejuvenation.
Your next adventure is waiting.
Limited spots available for September 2026.
Questions? Email us at hello@sweetlands.live
FAQs
How many people attend?
This is intentionally intimate curated experience - a small group for genuine connections and personalised attention.
There are 12 rooms available.
Can I come solo?
Absolutely. We welcome solo travelers and can arrange shared rooms if you prefer (let us know any preferences).
What if I can't do yoga or have dietary restrictions?
Everything is optional and adaptable. We cater to vegan, vegetarian, and gluten-free diets. Just let us know.
Which airport should I fly into?
We will arrange a Wednesday pick-up and Sunday drop-off from either Florence or Pisa airport (plenty of affordable flight options).
Get in touch at hello@sweetlands.live, we will suggest the best and convenient route.
Can also arrange pick-up from Cortona or Castiglion Fiorentino train stations if you prefer.
Is this Flash Festival?
No - this is Benedetta's curated retreat experience. Quieter, more intimate, focused on authentic Tuscan living rather than music and festival energy.
What's the weather like in late September?
Perfect. Summer heat has passed but Mediterranean warmth remains. Ideal for outdoor activities and exploration.
Can I extend my stay in the region?
Yes! We can help coordinate if you want to explore Tuscany before or after the retreat.
We can also book the accommodation for extended stays.
What if I don't drink?
No problem at all. While wine is part of the Tuscan experience, drinking is completely optional. You'll still enjoy the vineyard tours, meet the producers, and savor incredible food pairings. We'll have non-alcoholic options throughout, and the retreat is just as enriching without alcohol.
What's included in the price?
Accommodations, all meals (breakfast, lunches and dinners), all organised activities, local transportation during the trip and an airport pick-up (Wednesday) and drop-off (Sunday). Wine flows freely at group dinners (this is Flash, after all).
What's not included: flights to/from destination, travel insurance, and anything you buy because you fell in love with a local ceramics shop.
Some additional activities - such Welcome Hamper, bike rentals, massages are available to be booked additionally with us before your stay.
Each trip page has the full breakdown.
What if I don't know anyone?
Even better. That's the whole point. Everyone's in the same boat - curious people choosing to travel with strangers who won't be strangers for long. We structure the first day to ease you in, and by dinner that night, you'll wonder why you were nervous. The Flash Fam takes care of its own.
What's the typical age range?
Most travelers are 25-45, but we've had everyone from 22 to 55. What matters more than age is attitude - people show up curious, open, and ready to be present. If that's you, you'll fit right in regardless of when you were born.
What's the group size?
You will be together with a very small group of like-minded humans. Can vary from 10 - 25 people.
Can I share a room with a friend?
Yes, of course. You can choose from one double bed or 2 comfy single beds in each room. You can also add an extra bed to make it triple!
If you travel solo and happy to share a room, no worries! Please email us your preferences and we can find a solution together :)
What's your cancellation policy?
Only for fully paid bookings, not in an active payment plan, we offer this refund policy:
Cancel by 1st April 2026 - 100% refund of face value
Cancel by 1st June 2026 - 70% refund of face value
Cancel by 1st July 2026 - 50% refund of face value
Cancel after 2nd July - no refund.
Questions? Email us at hello@sweetlands.live
This is Flash Holidays - Part of Flash Worldwide
Curated by Benedetta Venturini, co-founder of Flash Festival Tuscany
Follow @flashworldwide_ for more year-round Flash experiences
Con amore,
Bene x
WHAT'S INCLUDED
✓ 4 nights at Terre dei Cavalieri, a 4 stars 18th century Tuscan Farmhouse Resort
✓ All meals – breakfast, three-course lunches & dinners, aperitivi
✓ All wine & most drinks throughout your stay
✓ Daily wellbeing sessions – yoga, meditation, breathwork (all levels welcome and all optional)
✓ VIP Spa day at ancient hot springs at Terme di San Giovanni
✓ Two wine tours with tastings, vineyard lunch & aperitivo
✓ Pasta making & cooking classes with the local Nonne
✓ Cultural excursions to Cortona & more
✓ Airport pick-up and drop-off either from Florence or Pisa Airport (we will coordinate everything)
✓ All transport between experiences
Not included: Flights to Tuscany (we'll help you find the best routes), Travel Insurance
Welcome Hamper, bike rentals, massages are available to be booked additionally