Days Like These

June 5–11, 2027 | 7 days / 6 nightsEstalagem da Ponta do Sol, Madeira, Portugal
Celebrating the relationships that carry us through life
Some relationships deserve the gift of time together. Days Like These is a small-group retreat for women who share an important bond: mothers and daughters, sisters, lifelong friends, or women who have simply become family to one another. Together, we'll experience Madeira through its spectacular landscapes, food and wine, culture, history, and local life, with plenty of time to explore, gather around memorable tables, and simply enjoy being here. Woven into the week will be moments for reflection, conversation, and shared experiences that celebrate the relationships and stories that connect us. There will be laughter, adventure, beautiful places, and intentional downtime to enjoy one another's company. A chance to step away from everyday life, experience something new together, and create memories you'll carry home long after the week ends. Because some trips are as much about who you share them with as where you go.
What Awaits You
Meaningful Experiences
  • Guided levada walks and cultural excursions that bring Madeira's landscapes, history, and local life to life
  • A private culinary gathering at my family home featuring Madeiran and Portuguese cuisine, fresh local ingredients, and the joy of gathering around the table
  • Wine tasting at Blandy's Wine Lodge, connected to generations of island history
  • A personal storytelling walk through Ponta do Sol, my family's village
  • Thoughtful moments of reflection, conversation, and shared activities celebrating the relationships that connect us
  • Time to relax, explore, laugh, and enjoy Madeira together
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
  • Cultural and nature-based experiences throughout the week
  • Facilitated moments of reflection and connection woven into the experience
  • Group transportation throughout the week, including scheduled airport transfers
  • A small, intentionally designed group setting with space for connection and ease
  • A welcome gift and thoughtful personal touches throughout the week
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Inside the Experience

This retreat is designed to balance movement and stillness, exploration and rest. Each day invites a spirit of ease and presence.
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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.
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Reserve Your Spot

Days Like These Pricing
Early Bird pricing (available through December 15, 2026):$3,650 USD per person (shared room)$3,950 USD (single occupancy)
Standard pricing (beginning February 22, 2027):$3,800 USD (shared room)$4,150 USD (single occupancy)

  • Your retreat includes:
  • Six nights of accommodation
  • Daily breakfast, two group lunches and four group dinners, including the culinary gathering at the founder’s family home
  • All excursions and scheduled activities
  • Group transportation, including airport pickup
  • Welcome gift and curated touches throughout
Reserve Now
A $500 deposit secures your spot.Flexible payment plans are available.
Still Deciding?
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Frequently Asked Questions

When should I arrive?
The retreat begins mid-to-late afternoon on June 5. If you’re flying from North America or elsewhere, we recommend arriving a day early. We’re happy to assist with an extra night at Estalagem or a nearby guesthouse.
What’s included?
Six nights of ocean-view accommodation, daily breakfast, two group lunches and four group dinners, including the culinary gathering at the founder’s family home, all scheduled excursions and cultural experiences, airport transfers, and retreat hosting and facilitation. You'll also receive a welcome gift and meaningful extras throughout the week.
What’s not included?
Flights, travel insurance, optional meals and activities outside the itinerary, and personal expenses.

Will I receive a full itinerary?

Yes. The full day-by-day schedule will be shared in the spring of 2027 with confirmed times, experiences, and details.

Can I extend my trip?

Absolutely. Whether you’re dreaming of extra days in Lisbon or time to unwind in Funchal, we’re happy to assist with planning before or after the retreat.

What is the cancellation policy?

A $500 deposit is required to reserve your place and is non-refundable.If you cancel before April 1, 2027, all additional payments will be refunded.After that, all payments are non-refundable.You may transfer your spot to another guest with prior approval.We strongly recommend purchasing travel insurance.