May 22 - 29, 2027
Chianti, Tuscany, Italy
Italians have made an art out of enjoying life. In Tuscany, that philosophy is woven into the everyday: long meals made with fresh, local, seasonal ingredients; meaningful conversations with people who are genuinely interested in connecting; the beauty of the landscape and architecture; and the simple pleasure of being present for it all.
This week is an invitation to step outside your everyday, slow down, and experience a different way of living.
We'll stay in a beautiful villa overlooking the rolling countryside of Chianti, one which easily invites us to see life from a fresh perspective.
The month of May brings ideal conditions for being outdoors, and we'll spend much of our time taking in the Tuscan countryside and enjoying all it has to offer.
Whether you're discovering Tuscany for the first time or returning for a deeper, more authentic Italian experience, this week is for anyone craving more than a vacation. It's an opportunity to reconnect with what makes life feel good, rediscover a sense of passion through the simple act of enjoying yourself, and experience what becomes possible when you make a little more room for living.
Come for Tuscany. Leave with a little more room to enjoy your life.
Who's it for
An itinerary designed for the curious.
Arrive in Florence before retreating to the Tuscan countryside, where life slows and beauty expands. Our home base is a private villa in wine country just outside the city - surrounded by rolling hills, vineyards, and historic towns.
From this grounding home base, you’ll explore multiple regions of Tuscany, balancing guided experiences with spaciousness. Each day includes the option for gentle wellness, meaningful cultural outings, unhurried meals, and time to rest or wander.
A taste of what's ahead:
A private chef dinner and exploration of Italy's food culture
A panoramic countryside hike and a local market experience
Restorative time at healing mineral springs and the spa
A wine sensory course led by a sommelier
Grounding yoga with horses
A joyful, hands-on cooking experience that embraces you like family
Authentic dining at some of Tuscany's most memorable tables
Nothing is rushed. Every experience is chosen to feel effortless while offering depth.
This is Italy experienced with intention - rooted, nourishing, and quietly unforgettable.
Meet your guides
Jenny
Jenny's Italian love story began at 15 when she first set foot in the country. Enchanted by the culture, landscape, and delectable cuisine, she not only learned the language but also felt a magnetic pull to return. Post-college, she made Florence her home. She spent her time uncovering genuinely authentic gems.
Jenny is now on a mission to share the depth of Italian experience that she has experienced, firmly convinced that immersing oneself in the culture is a game-changer. She aims to offer shifts in perspective through awe-inspiring journeys.
You can read more about Founder Jenny and wellTRVLD's story, here.
Enrica
Enrica is Italian-born movement teacher, retreat facilitator, and equine-assisted coach based in Costa Rica.
Before this chapter of her life, she spent 13 years as a competitive figure skater and later worked in film and commercial production. She eventually felt the pull toward a different path centered in practices that reconnect people with their bodies, emotions, and sense of aliveness!
For the past decade she’s been teaching yoga internationally and facilitating equine-assisted sessions, where horses become partners in helping human finding their joy. She’s also trained in a movement practice called 5Rhythms.
Enrica has a very calm, down-to-earth, fun presence. You’ll feel comfortable and well supported with her there.
What you can expect
The essentials of travel, but with all the extra bells & whistles.
Beautiful. Intentional Accommodations
You'll stay seven nights in the heart of Tuscany, surrounded by rolling hills, vineyards, and walkable town squares. Our accommodations are chosen for comfort, character, and calm, designed to feel like a true landing place, not just a place to sleep.
Thoughtful Food & Wine Experiences
Expect some of the most memorable meals of your life. We prioritize family-run and small local businesses, where food is personal and deeply rooted in place. Daily breakfast and one hosted group meal with wine are included. Additional meals are yours to choose so you can follow your cravings, just like the locals do.
Seamless Ground Transportation
Once you arrive in Florence, we take it from there. Airport pickup, luggage handling, and group transportation to all scheduled activities are included. No navigating, no logistics-just easy movement from one experience to the next. (Airfare not included.)
Off-the-Beaten-Path Cultural Outings
This is what we're most known for. Private, local experiences that go beyond sightseeing… meaningful interactions, and a deeper understanding of how Italians live, eat, and connect. These are the moments that subtly change how you return home.
A Curated Group & Guided Flow
You're traveling with a small group of like-minded people, guided throughout the journey so you never feel lost or overwhelmed. We handle the planning and pacing, while leaving room for spontaneity, rest, and personal choice.
Daily Wellness Opportunities
Each day includes a chance to move, breathe, or reset-whether that's a group class at the villa or a long, unhurried walk through a hillside town. Participation is never required. We encourage you to listen to your body and your intuition-something Italians do beautifully.
Trip Pricing
Claim your spot now.
Prices start at $4,000 per person and are largely inclusive.
Your specific price will be based on your room selection and occupancy.
Payment plans are available at check-out.
Snag your favorite spot in the villa before it's gone!
Have questions or just want to chat about a trip?
TEXT 813-465-8616
EMAIL explore@wellTRVLD.co
