ANNOUNCING Madeira, Portugal IN 2027!
March 2-9, 2027
Answer the call of Madeira... where rugged trails, fresh ocean air, and unforgettable shared moments push your limits, clear your mind, and ignite your sense of adventure!
Are you a woman ready to lace up your boots, hit the trails, and get out into something real?
Join us in Madeira for a hiking retreat as we explore hidden places, take on challenging climbs, and spend our days surrounded by the beauty of nature.
Along the way, you’ll share the experience with like-minded women, push yourself in new ways, and take in the kind of scenery that stops you in your tracks.
Why You Want to Be There...
Ready to step away from the noise of everyday life and recharge in one of the most breathtaking places on earth? We’ve designed a powerful week in Madeira just for you.
Join a group of driven, like-minded women for days spent on the trails, in nature, and fully present in the moment. Between challenging hikes, stunning views, and time to reset, you’ll slow down, reconnect, and return home feeling clearer, lighter, and more grounded.
This retreat is about pushing yourself in the best way—moving your body, clearing your head, and remembering what it feels like to simply be outside, fully alive.
It’s time to do something for you. And Madeira is waiting.
Hike.Live.Explore... An Adventure Retreat
Madeira is our playground for the week—a wild Atlantic island of towering cliffs, ancient forests, and trails that wind through some of the most dramatic landscapes in Europe.
We’ll spend our days out exploring it all: hiking along cliffside paths with endless ocean views, stepping into misty mountains, and finding hidden waterfalls tucked deep in the valleys. There are quiet corners everywhere—natural salt pools carved into volcanic rock, rugged beaches, and viewpoints that make you stop mid-step.
Every route feels different. One day it’s high ridgelines above the clouds, the next it’s coastal trails where the sea crashes below you.
Back at our home near Funchal, the pace softens. Mornings are slow(maybe:), evenings are golden, and the terrace becomes our favorite place to unwind with views stretching out over the Atlantic.
Each day flows naturally between adventure and ease… after exploring the island’s trails, salt pools, and hidden beaches, we return to shared meals prepared by our private chef and time spent together, relaxed and unhurried.
It’s a week shaped by contrast: wild days outside, calm evenings in, and the kind of simple moments that stay with you long after you’ve left Madeira.
All-inclusive, with a few exceptions.
You’ll stay in a beautiful all-inclusive home near Funchal, right in the heart of Madeira.
Everything is taken care of. We’ll kick things off with a welcome dinner from our private chef, who’s with us for the whole week. Mornings start with breakfast before we head out to the trails, and we’ll pack picnic lunches to enjoy out in the mountains.
After full days exploring the island, we come back together for easy, shared dinners… good food, good company, and no rush.
Simple, relaxed, and all about enjoying Madeira.
PLUS an ah-mazing Gift Bag upon arrival loaded with Hike.Live.Explore. essentials!
Everything is planned and taken care of for you… all you have to do is show up! And Enjoy!
Hike.Live.Explore... OUR ADVENTURE
HIdden Gems
Get ready to explore the lesser-known side of Madeira—where quiet mountain paths, secret waterfalls, and dramatic coastal viewpoints reveal the island’s true magic. Off the main routes, you’ll discover raw, untouched beauty and moments that feel like they’re yours alone.
A Day Your Way
Spend a day your way in Madeira—either getting adventurous with an optional canyoneering experience through waterfalls and rugged rock pools, or slowing things down exploring the charming streets and local shops of Funchal. Whether you’re chasing adrenaline or wandering boutiques and cafés, it’s a relaxed day to enjoy the island at your own pace.
Madeira Wine Tasting
Spend an easy afternoon in Madeira tasting local wines and taking it all in. You’ll try a few different styles the island is known for, learn a bit about how it’s made, and just enjoy the moment—good wine, good views, and relaxed conversation.
Find your tribe
Be in the moment as we spend time with our tribe. Connect with new and old friends who encourage you to rise up as we take on this adventure. It's the BEST part of the journey!
As always...
Welcome our very own PRIVATE CHEF:
Chef Iain
During your retreat, you’ll be in the hands of Chef Iain McBride, a chef with over 20 years of experience in award-winning hotels and 4- and 5-star kitchens.
Now based in Madeira, Iain brings a calm, thoughtful approach to food—creating seasonal menus inspired by the island’s local ingredients and flavours from around the world. His style is refined but unfussy, focused on real food that tastes as good as it feels.
From nourishing breakfasts before we head out on the trails, to relaxed lunches and shared evening meals, everything is designed to fit the rhythm of the retreat. Good food, made with care, enjoyed together.
THE Hike.Live.Explore. Adventure IS JUST...
$3395-3695
ALL-INCLUSIVE ADVENTURE
(*airfare & car rental excluded*)
SEE WHAT OTHERS HAVE SAID ABOUT THEIR EXPERIENCE!
THE Hike.Live.Explore. Adventure IS JUST...
$3395-3695
ALL-INCLUSIVE ADVENTURE
(*airfare & car rental excluded*)
Frequently Asked Questions
A week in Madeira filled with hiking, hidden natural beauty, shared meals, and meaningful time with like-minded women in a stunning island setting.
Pretty much everything ladies! 6 Breakfasts, 5 Picnic Lunches, 6 Sisterhood Family Style dinners with a personal chef, a Welcome Night Celebration, Taxes, Chef Gratuities, Fees, Park Pass, Shuttle Bus Fees, Park and Ride Fees, Madeira Wine Tasting, Swag Bag, and tons of fun! Not to mention the personal growth… is priceless! Excluded is your optional excursion, Wine/Beer, Airfare and Rental Car.
No. The closest major airport to Madeira is Cristiano Ronaldo Airport which is an easy 20-30 minute drive to Funchal. Car Rental is additional so load a car up. Make sure it’s an automatic!
Sure do! Personal payment plans can be arranged after a non-refundable $300 deposit is made to reserve your spot. 1/3 Payment is due August 15, 2026. 2/3 payment is due October 15, 2026. Final payment is due January 15, 2027 Message me at jill@jillallencoaching.com to create a personal plan. Venmo @jill-allen-3, cash or check on.
All retreat sales will be FINAL. With your $300 deposit, you are committing to the full payment of the retreat. Refunds are not available. Tickets are transferable. Just plan to be there.
Absolutely! We actually encourage it. Message me and I can help set you up for your travel insurance options.
Reach out to me at jill@jillallencoaching.com and let’s get them answered!
I’m so glad I finally have consistency again
“This retreat was good for the soul. It wasn’t always easy but in those moments of vulnerability, I felt surrounded by love, support, and laughter. I was reminded that I could do hard things. I can’t wait until next year!”
~ Michelle
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Workout At Your Own Pace
From any device, any time at your convenience. Resume exactly where you left off. No limits on the number of times you can view video lessons.
MORE, BUT DIFFERENT
Join me for a 7-day reset—step out of the noise, slow things down, and reconnect with what actually matters. Grab your workbook and audio guide to help you move through the week with clarity, calm, and a grounded sense of rest.