The Art of Becoming with Left Sleeve:
Set in the heart of Italy, The Art of Becoming with Left Sleeve is a 5-day immersive creative and personal-growth experience with South African poet and motivational creator Left Sleeve. Through storytelling, poetry, mindset work, and a signature live improv performance, guests explore their inner voice, unlock emotional clarity, and discover new ways to express themselves. This retreat blends creativity with introspection in a warm, engaging, world-class environment — crafted to leave each participant feeling inspired, renewed, and deeply seen.
Left Sleeve – Storyteller. Believer. Recovery Poet.
Left Sleeve is a tapestry of experience – a grateful recovering addict, a believer, a storyteller, and a writer of sentimental truths. With over 2 million followers across social media, his voice has become a global resonance, soft and fierce, like a moment of stillness after chaos, where you find your strength again. His journey began in the quiet corners of an introverted childhood, where imagination was not a pastime – it was survival. Raised in a loving, valuesdriven home, he was shaped by the warmth and wisdom of his parents. But life offered its crossroads – and at one of them, he chose recovery. That choice, he says, remains his proudest achievement. Not the numbers. Not the stage. But the commitment to live as a gentleman, a virtue passed down by his father.
Today, Left Sleeve is a magnetic presence on stage and screen. His viral poetry, live shows, and emotional storytelling touch audiences across the world – not by preaching, but by sharing. His work is grounded in realness. He speaks of love, pain, beauty, addiction, grace, identity, masculinity, and transformation. And every word he shares is lived, not just written. Whether he’s hosting a retreat, performing at a sold-out show, or creating poetry admired across the world, the mission is the same: To make you feel something. To remind you that you are not alone. His philosophy? “I can only keep what I have by giving it away,” And it shows – in the comments, in the messages, in the lives changed. Currently focused on expanding his live offerings – including international retreats, theatrical storytelling, national television shows, and improv poetry – Left Sleeve is also working on his first book, and dreaming of writing for film. Every post, every poem, every show is a love letter to survival, to storytelling, and to the magic of starting again.
Tuscany is not simply the birthplace of the Italian Renaissance: from north to south, it boasts countless places worth visiting. The story of Tuscany spans more than 3000 years of art, with architectural wonders, culinary delights, and warm, welcoming hospitality.
Culture, food, art, and traditions combined with gentle hills, vineyards, and charming villages make Tuscany not only the most dreamed-of Italian destination, but an unforgettable experience that leaves you wanting to discover more and more about this fabulous region. Its timeless beauty invites every visitor to slow down, breathe deeply, and connect with a sense of harmony that can only be found here.
The Torre a Cona Wine Estate stands strikingly in the Florence hills, only 10 kilometers from the birthplace of the Renaissance. The charming eighteenth-century villa makes an immediate impression. With an unforgettable view of the countryside, the estate is surrounded by olive groves, verdant vineyards, and sturdy centuries-old walls. It is a place rich in history and beauty, preserved over time.
Each room is unique, featuring original details such as antique doors, wooden beams, and terracotta floors. The spaces are painted in soft colors that echo the hues of the Tuscan countryside.
- Check-In & Settling In Guests arrive, settle into their rooms, and explore the retreat environment at their own pace.
- Community Dinner: A relaxed shared meal that opens the space for connection and sets the tone for the days ahead.
- Breakfast
- 10:00–10:15 — Opening Ritual Welcome • Grounding breath / intention setting • Quick intro round: “What brought you here?”
- 10:15–11:00 — Left Sleeve’s Story (Interactive Format) Left Sleeve shares his journey in a motivational storytelling style. Three reflection pauses where participants respond silently or write: 1. A turning-point moment 2. Someone who shaped them 3. A time they surprised themselves
- 11:00–11:30 — Guided Reflection Exercise Writing prompt: “My life in five moments” — quiet writing time.
- 11:30–12:00 — Pair Sharing Circles Participants share one moment with a partner. Left Sleeve moves between groups, listening and engaging.
- 12:00–12:30 — Group Q&A; + Close Open floor for questions to Left Sleeve. Session closes with one of Left Sleeve’s poems.
- Free Time to Reflect & Explore
- Community Dinner
- Breakfast
- 10:00–10:10 — Warm-Up Writing 5-minute free write • Fun prompt: “Write a poem in 4 words.”
- 10:10–10:40 — Technique Demonstration Left Sleeve teaches using his own poems: emotional layering, word economy, rhythm, imagery, and a before & after poem edit.
- 10:40–11:10 — Guided Writing Round 1 Prompt: “Write about a moment that made you feel emotions differently forever.”
- 11:10–11:40 — Group Edits & Feedback Volunteers read • Left Sleeve provides live, inspirational feedback and editing suggestions.
- 11:40–12:10 — Guided Writing Round 2 Prompt: “Write a piece to someone you’ve never thanked properly.”
- 12:10–12:30 — Sharing Circle Participants read their pieces • Left Sleeve closes with a piece of his own.
- Free Time to Reflect & Explore
- Community Dinner
- Free Time to Reflect & Explore
- Community Dinner
- Breakfast
- 10:00–10:15 — Centering Ritual Gentle breathing • Calm focus.
- 10:15–10:40 — Left Sleeve’s Mindset Story Left Sleeve shares how he rebuilt his habits and emotional awareness. He discusses routine, accountability, and reflective practices.
- 10:40–11:10 — The “Daily Reset Framework” Left Sleeve teaches his practical mindset toolkit: Morning intention • Midday check-in • Evening reflection • Awareness of emotional habits • Gratitude micro-rituals.
- 11:10–11:40 — Practical Exercise: “Where am I now?” Participants complete: 1) What I want 2) What holds me back 3) One thing I’m willing to change.
- 11:40–12:10 — Partner Coaching Session Participants practice listening, reflecting, and affirming. Left Sleeve guides the structure.
- 12:10–12:30 — Visualization & Close Left Sleeve leads a simple visualization of their future self and a closing thought or poem.
- Free Time to Reflect & Explore
- Community Dinner
- Breakfast
- 10:00–10:15 — Soft Opening Light music • Warm welcome • Recap of the week’s themes.
- 10:15–10:45 — Audience Warm-Up & Story Prompts Left Sleeve asks participants: • “What surprised you this week?” • “What moment did you need most?” • “If this week were a title, what would it be?”
- 10:45–11:45 — Left Sleeve’s Signature Improv Show Improvised poetry and storytelling that incorporates the group’s stories, personalities, and shared moments — emotional, humorous, and deeply personal.
- 11:45–12:10 — Closing Circle: “I am becoming…” Each participant completes the sentence aloud • Left Sleeve shares one final piece written for the retreat.
- 12:10–12:30 — Farewell & Photos Gratitude • Casual meet-and-greet • Optional group photos
- Free Time to Reflect & Explore
- Community Dinner
- Breakfast A relaxed final meal with time for goodbyes, reflection, and closing the shared experience.
- Checkout & Departure
Disclaimer: This schedule is indicative and is subject to change as we move closer to the retreat date.
Transform
your life
Event Highlights
Storytelling & Self-Discovery: Begin by exploring the origins of your personal story and connecting with what brought you to this journey.
Creative Expression Through Poetry: Learn to transform emotions into words through guided writing, practical techniques, and supportive creative exercises.
Mindset Transformation: Gain clarity and resilience with daily practices and mindset tools designed to shift perspective and strengthen self-awareness.
Signature Live Improv Experience: Conclude with a unique, improvised storytelling + poetry performance created from the group’s own experiences—an unforgettable finale.
Immersive 5-Day Experience in Italy: A world-class environment blending creativity, introspection, and emotional connection, leaving every participant inspired and deeply seen.
- All sessions with Left Sleeve
- 5-night accommodation at Torre A Cona
- All breakfast meals & dinner meals
- Traditional Pasta Cooking Class
- Airfare to/from Italy – We strongly advise you to book flexible airfare tickets and flights with fewer carbon emissions to contribute to environmental protection, as it is our responsibility to safeguard our environment
- Arrival and departure land transfers
- Accommodation tax per person per overnight stay
- Water, tea, soft drinks, and beverages
- Whatever is not mentioned clearly in the inclusions
We strongly advise you to book flexible airfare tickets and flights with fewer carbon emissions to contribute to environmental protection, as it is our responsibility to safeguard our environment
Payment Plan: Available – contact info@travelgems.com
Language: English
Land Transfer: Available upon request – contact info@travelgems.com
Cancellation Policy: A 10% deposit secures your spot and is refundable within one week. An additional 20% payment is required within one month (non-refundable). The remaining 70% balance can be paid in flexible installments, with full payment due no later than 45 days before the retreat start date. Cancellations after this point will incur a 100% cancellation fee
Important Info: In case there are Covid-19 restrictions or any other restrictions related to any other pandemic that prevent guests from traveling, the total amount paid will be refunded.
Transport: For Left Sleeve’s retreat in Tuscany, you can fly into Florence Airport (FLR). It’s the closest airport to Torre a Cona Wine Estate (21km away). From there, you can book a transfer to the hotel. Please contact info@travelgems.com for further information or assistance.
Prices
3400 EUR / person in Double Occupancy Room
4400 EUR / person in Single Occupancy Room
Price Includes:
- All sessions with Left Sleeve
- 5-night accommodation at Torre A Cona
- All breakfast meals & dinner meals
- Traditional Pasta Cooking Class
Booking Instructions: Double Occupancy Room
If you’d like a Double Occupancy room, you can either book a single spot and be paired with a like-minded retreat participant in a TWIN room, or book 2 spots if you already know the person you’ll be sharing with. In that case, the room can be king-sized or twin, based on your preference.
Please note: if you require a twin setup, you must request it in advance so we can confirm availability.
Kindly contact us at info@travelgems.com for any further assistance.
