Between Sea and Sky
A hosted journey through Madeira from The Madeira Experience
September 10–16, 2027 | 6 nights / 7 days Estalagem da Ponta do Sol, Madeira, Portugal
Join a thoughtfully hosted journey for a small group of 10 men on the Portuguese island of Madeira - one of Europe's most spectacular destinations, yet one still often overlooked by North American travelers. With dramatic landscapes, vibrant culture, remarkable cuisine, and a year-round spring-like climate, Madeira offers an experience unlike anywhere else in Europe.
Between Sea & Sky is designed for men who are curious about the world and appreciate great food, beautiful places, local culture, outdoor adventure, and the pleasure of experiencing them in good company.
Over the course of the week, we'll discover Madeira through carefully selected accommodations, memorable meals at hand-picked restaurants, guided hikes through mountains, laurel forests and coastal landscapes, local food and wine, vineyards, villages, and cultural and historical experiences that bring greater meaning to the places we visit.
Some days will be active. Others will leave plenty of room to relax by the pool, walk into Ponta do Sol, enjoy a drink overlooking the Atlantic, explore independently, or simply settle into the island's unhurried rhythm.
This isn't a traditional group tour, and it isn't a conventional retreat. It's a relaxed, thoughtfully hosted way to experience Madeira - with enough structure to make the most of the island and enough freedom that the week still feels like a vacation.
Come on your own, with a friend, or with a partner. Space is intentionally limited to 10 guests, creating an experience that feels personal, comfortable, and easygoing.
Madeira has become a second home to me. After returning year after year, I've come to know the island in a way that goes far beyond the guidebooks. The Madeira Experience was created to share that perspective - not simply to show people Madeira, but to help them understand something about the places they're experiencing, the people who live there, and the culture and history that shaped the island.
Between Sea & Sky is an invitation to experience that Madeira - well hosted, thoughtfully paced, and in good company.
What Awaits You
- A guided hike through Madeira’s UNESCO-protected laurel forest and historic levada landscape
- Visits to villages, vineyards, and places that reveal more of Madeira’s culture, history, and everyday life
- Memorable dining experiences at thoughtfully selected restaurants, with an emphasis on fresh, local ingredients and a strong sense of place
- A private family-style culinary gathering at my home featuring Madeiran and Portuguese cuisine and the joy of gathering around the table
- Wine experiences connected to Madeira’s history, traditions, and distinctive winemaking culture
- A personal storytelling walk through Ponta do Sol, adding cultural and historical context rooted in lived experience
- Unhurried time to relax at the hotel, walk into town, enjoy the Atlantic views, explore independently, or simply enjoy having nowhere else to be
What’s Included
- Six nights at Estalagem da Ponta do Sol, a cliffside boutique hotel overlooking the Atlantic
- Daily breakfast, two group lunches, and four group dinners at thoughtfully selected settings, with an emphasis on fresh, local ingredients, including the private culinary gathering at my home
- One guided levada hike through Madeira’s UNESCO-protected laurel forest
- Cultural experiences and island excursions that offer a deeper look at Madeira’s history, traditions, landscapes, and local life
- Thoughtfully selected dining and wine experiences that reflect the character, flavors, and traditions of Madeira
- Group transportation throughout the week, including scheduled airport transfers
- An intentionally limited group of just 10 guests for a more personal, comfortable, and well-hosted experience
- A welcome gift and thoughtful personal touches throughout the week
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Inside the Experience
This retreat balances movement and stillness, exploration and rest. Each day unfolds with intention and flexibility.
Mornings
Begin with breakfast overlooking the sea, followed by daily yoga practice. On some mornings we head out for included excursions; on others, the day begins slowly, with time to journal, stretch, or take in the view.
Afternoons
Afternoons are open for optional experiences, independent exploration, or rest. Guests are free to engage deeply or move at their own pace.
Evenings
Evenings gather around shared dinners, including one hosted at the founder’s family home — creating space for warmth, conversation, and unhurried connection. On select nights, we close with gentle, restful movement and guided breathwork for deep rest.
A detailed itinerary will be shared in Spring 2026.
Between Sea and Sky
Early Bird pricing (available through June 30, 2027):$3,650 USD per person (shared room)$3,950 USD (single occupancy)
Standard pricing (beginning July 1, 2027):$3,800 USD (shared room)$4,150 USD (single occupancy)
Standard pricing (beginning July 1, 2027):$3,800 USD (shared room)$4,150 USD (single occupancy)
Accommodations include a mix of ocean-view and garden-view rooms. Ocean-view rooms are limited and allocated based on availability at the time of booking. All rooms offer comfort, natural light, and a peaceful setting overlooking the Atlantic or the hotel’s gardens.
If you’re traveling solo, roommate pairing is available upon request. Please indicate your preference at booking.
- Your retreat includes:
- Six nights of accommodation at Estalagem da Ponta do Sol
- Daily breakfast, two group lunches and four group dinners, including the culinary gathering at the founder’s family home
- All scheduled excursions and experiences
- Group transportation throughout the retreat, including airport pickup and drop-off
- Welcome gift and curated touches throughout the week
A $500 deposit secures your spot. Flexible payment plans are available.