Between Sea and Sky
A Men's Retreat
September 23–29, 2026 | 6 nights / 7 days of presence, clarity, and quiet renewal.Estalagem da Ponta do Sol, Madeira, Portugal
Suspended between the Atlantic and the open sky, this retreat invites you into a slower rhythm - one shaped by reflection, beauty, and the rare luxury of time. Madeira’s dramatic cliffs, ancient levada paths, and warm coastal light create the perfect backdrop for stepping out of your routine and back into yourself. Designed for a small circle of up to twelve men who appreciate meaningful conversation, shared experience, and the unique comfort of chosen community, this retreat offers a space where you can show up fully - no explanations needed. It’s a chance to reconnect with what matters, surrounded by men who value depth, intention, and living with a bit more purpose. Across the week, you’ll move through landscapes that open your perspective, moments of stillness that soften your edges, and simple pleasures that remind you what it feels like to be truly present. Think unhurried meals overlooking the ocean, coastal walks that clear your mind, and spacious days that offer room to rest, explore, or simply breathe.
You’ll return home lighter, clearer, and more grounded - the kind of shift that stays with you long after you leave the island.
What Awaits You
Meaningful Experiences
- Curated excursions that highlight Madeira’s natural beauty and culture
- Guided levada hike
- A hands-on Madeiran cooking experience
- A sunset boat tour to enjoy the coast, with the chance to spot dolphins in their natural habitat
- A visit to Blandy’s Wine Lodge for a tasting rooted in tradition
- A personal storytelling walk through Ponta do Sol — my family’s village
- Time for exploration, connection, and spontaneous joy
What’s Included
- Six nights at Estalagem da Ponta do Sol, a stunning oceanfront boutique hotel
- Daily breakfast and five thoughtfully prepared group dinners
- Group transportation throughout the retreat, including airport transfers
- Small group setting for meaningful conversation and ease
- Thoughtful surprises and personal touches woven throughout the week
Inside the Experience
This retreat is designed to balance movement and stillness, exploration and rest. Each day invites a spirit of ease and presence.
Mornings
Begin with a relaxed breakfast by the sea. Some days lead into guided levada walks or nature outings; others begin slowly-with time to journal, stretch, or enjoy the view.
Afternoons
Afternoons are for connection and discovery. This may include visits to hidden corners of the island, creative workshops, or a full-day cultural excursion across Madeira’s volcanic landscape.
Evenings
Five of the six evenings include shared group dinners, including one interactive cooking night. These moments are designed for warmth, laughter, and lingering connection beneath the stars.
A detailed itinerary will be shared in early 2026.
Reserve Your Spot
Between Sea and Sky Pricing (available through March 20, 2026)$3,950 USD per personBased on double occupancy in ocean-view rooms.
Single occupancy available at $3,900 USD
Standard pricing begins March 21, 2026:$4,150 shared / $4,500 single
Single occupancy available at $3,900 USD
Standard pricing begins March 21, 2026:$4,150 shared / $4,500 single
Please indicate your preference at booking.All rooms are ocean view. Roommate pairing is available upon request if traveling solo.
- Your retreat includes:
- Six nights of accommodation
- Daily breakfast and five group dinners
- All excursions and scheduled activities
- Group transportation, including airport pickup
- Welcome gift and curated touches throughout
A $500 deposit secures your spot.Flexible payment plans are available.