Overview
September holds a special kind of magic here, where every moment invites a deep breath or a spark of adventure, and you're free to follow whichever you need most. This isn’t a retreat about disconnecting from life; it’s about stepping into a wilder rhythm, moving your body through Pilates and hikes, savoring slow moments by the pool, and soaking up the island’s breathtaking beauty. With cobblestone villages, crater lakes, and Atlantic breezes all around, São Miguel invites you to pause, play, and feel fully awake. Here we find 'encanto'- a deep sense of wonder, and a magical atmosphere that stays with you.
Itinerary
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A Typical Day
AM
6:00 - Journaling Workshop and Mindfulness Session
6:30 - 7:15 - Morning Movement Session (some days)
7:15 - 8:15 Breakfast
8:30 - 9:00 - Morning Activity
- Friday- Coastal Walk, Visit to Ponta Formosa town, Hot Springs
- Saturday - Whale Watching (will try again on Tuesday if we don't see whales)
- Sunday - Canyoning & Visit to Furnas (full day activity)
- Monday - Sete Cidades (full day activity)
- Tuesday - Free morning or 2nd attempt to see whales.
PM
12:30 - Lunch
1:30 - Afternoon Free Time (perfect for relaxing by the pool or reading a book). On Tuesday, we'll visit breathtaking tea fields! There will be 2 days with afternoon chill time.
5:30: Early Evening Movement Class
7:00 - Group Dinner
All classes are accessible to all levels.
The itinerary allows for time to relax for a few hours at a time, at our casas.
A couple of days allow for an entire afternoon or morning to enjoy the views and do as you wish!
We remember to go with the flow and enjoy a slower pace of life in this part of Portugal. Activities may be switched from morning to afternoon depending on weather and other factors.
Our casas are in a peaceful area that is meant for relaxing. We will drive to each activity, each day.
An Artistic Oasis
Eco-Friendly Luxury
Our home for this week is a 20-hectare soulful retreat tucked into the hills of São Miguel’s North coast, part of which has been designated as an ecological reserve, protecting native flora and fauna.
The thoughtful touches and personalized service create a stay that feels both welcoming and deeply restorative. Get ready to breathe!
You'll Be Staying Here
The Common Lounge
The casas still hold that sense of history with stone walls, vaulted ceilings, and quiet corners that invite you to slow down.
Gathering Outside
The gardens are wide and peaceful, the pool is perfect for a midday float, and the views stretch all the way to the hills.
A Bit of History
Over the centuries, it has served as a military garrison, an orange and tea farm, and even housed the Ataíde tea factory, traces of which still remain on the grounds.
The Experience
Balance
Our carefully curated itineary leaves space for adventure, connection, relaxation and exploring. Get ready for untouched landscapes and unhurried moments.
Off-the-beaten Path
São Miguel may be the largest of the Azores, yet still feels like a well-kept secret. It's lush, quiet, and far from the usual tourist trail.
Movement Sessions
Each day begins or winds down with a movement session in the serene courtyard of of our venue, a peaceful atmostphere with stunning views. Whether it's an energizing Pilates flow or a grounding stretch, these sessions are designed to connect you to your body, your breath, and the natural rhythm of São Miguel. These classes are appropriate for first-timers and advanced students alike.
Meals
Our chef-prepared dinners at the house will be served family-style, creating a warm, communal atmosphere to unwind and connect after each day’s adventure. Expect vibrant, nourishing meals crafted from fresh local produce and world-famous Portuguese seafood and local sharp cheddar. Dietary needs and preferences will be happily accommodated. Lunches will be enjoyed out and about, giving us the chance to explore the island’s cafés and hidden gems along the way.
Digital Detox
This is your chance to recharge! Give yourself a mental refresh through connection to yourself, others and the environment around you. Research has shown us over and over again that disconnecting from our devices more often: - benefits our sleep cycles - increases positive self talk - promotes healthier eating habits - decreases anxiety & depression - leads to more productive days at work There are no rules. You choose what amount of detox works best for where you are, in your life, at this time.
Praia dos Moinhos Coastal Walk
We’ll stroll through the charming village of Porto Formoso, known for its whitewashed houses, vibrant gardens, and historic tea plantations, before reaching the black sand beach of Praia dos Moinhos, a peaceful cove perfect for dipping your toes in the ocean and soaking in the island’s natural beauty. It’s the perfect blend of gentle movement, local charm, and coastal magic.
Caldeira Velha Thermal Pools
Caldeira Velha is a natural sanctuary where geothermal warmth meets tropical greenery. Here we'll unwind in its iron-rich thermal pools, fed by a gentle waterfall.
Whale Watching
September offers calm seas, warm weather, and a chance to see resident sperm whales and dolphins. We keep an eye out for migratory species like sei and fin whales making their way from the North Atlantic to Southern waters. Expert marine biologists, provide insight while we adventure beyond São Miguel’s shores. Our departure point for whale watching on the island is a marina about 25 minutes from our Casas.
Canyoning
Canyoning is an unforgettable way to experience São Miguel’s wilder side! This beginner-friendly canyon invites you to rappel down waterfalls, slide along smooth rock chutes, and plunge into crystal-clear pools, all surrounded by lush forest and volcanic cliffs. Led by certified guides, it’s a safe and exhilarating way to connect with the island’s untamed landscape.
Cozido das Furnas
Cozido das Furnas is a traditional boiled stew of meat and vegetables, slow-cooked underground by volcanic heat. We experience this after our canyoning adventure, in the town of Furnas itself, getting a true taste of Azorean culture as the pots are pulled from the steaming earth; each one tagged with its owner's name, honoring a longstanding local tradition. It’s a special way to connect with the island’s history and savor its one-of-a-kind flavor.
Sete Cidades
No trip to São Miguel would be complete without a visit to Sete Cidades. Legend tells of two star-crossed lovers whose tears formed the twin lakes (one blue, one green). They're cradled within a massive volcanic caldera and is nothing short of awe-inspiring.
Gorreana Tea Factory
Surrounded by rolling green tea fields and ocean views, you’ll walk through the factory to see how tea leaves are harvested and processed, then enjoy a fresh cup of their signature green or black tea. It’s a peaceful, sensory experience that connects you to the rhythms of the land and the legacy of the island.
We Give Back
5% of profit goes straight to a non-profit on Sao Miguel that works to support local community initiatives.
Getting Around
São Miguel is the perfect island for day trips, and we’ll hit the road in two vans, giving us the flexibility to navigate winding roads and the freedom to explore at our own pace.
Accommodation
Quadruple Occupancy (twin beds)
Enjoy one of the larger casas, with 2 single beds (separated) on the first floor and 2 additional single beds in the loft. All guests share a living room, common area and bathroom.
FROM$3,920.00/pp
Double Occupancy Casa
Once the home of the former caretaker, who still visits daily to feed the goats, this house features a cozy fireplace, a bathroom with a bathtub, and a charming (though no longer active) bread oven where fresh cornbread was once baked each week. Two single beds can also be arranged in a couple-friendly setup.
FROM$4,520.00/pp
Single Occupancy in Cozy Casa
Perfect for a solo traveler or couple, this space includes a cozy fireplace, a well-equipped kitchenette, and a bathroom with a bathtub. A large arched window offers beautiful views of the garden and pool.
FROM$4,920.00/pp
Single Occupancy 1 Bedroom Casa
Enjoy a private apartment with a kitchenette, fireplace, bathroom and bathtub. You will not need the kitchen; it's an added convenience!
FROM$5,420.00/pp
Additional Person (Plan to share the Cozy Casa)
Book this along with a 'Single Occupancy Cozy Casa' booking and plan to share bed and apartment.
FROM$3,420.00/pp
What's included
What's Included
Pre-trip & Logistics Support
All breakfasts (6)
Transportation to and from Ponta Delgada Airport (PDL)
Access to your room as soon as you arrive (even if it's 6:30am)!
Brunch on arrival day
5 chef-prepared dinners
1 dinner (out) during sunset
4 lunches out, after morning activities
Transportation during retreat
Daily Pilates Class
Morning Mindfulness and Journaling Sessions
Whale-watching
Canyoning
Visit to Tea Plantation
Adventure in Sete Cidades
Beach Visits
Hot Springs Experience
What's Not Included
Roundtrip Airfare to Ponta Delgada (PDL)
Travel insurance (we require you purchase and have recommendations)
1 lunch (exploring is part of the fun here! We will help you.)
Any meals during traveling that take place before or after you meet the group
Private or Semi-Private Pilates Sessions with Anna
Specialty drinks (smoothies or alcoholic beverages)
Additional Activities or Spa Services
Hosts
We will utilize mats, props, and massage balls for sessions. Although we try not to take ourselves too seriously, we are experienced instructors and classes are for all levels!
Anna Hall
Anna’s journey with Pilates began in 2010, when she turned to the practice in search of relief from chronic back pain.
What started as a personal remedy quickly evolved into a deep passion, as she experienced firsthand the way Pilates can transform strength, alignment, and overall well-being.
Anna brings a wealth of knowledge about the body, a love for functional movement, and a deep commitment to helping others feel strong and supported.
Her classes are equal parts uplifting, challenging, and fun; always grounded in care, curiosity, and a good sense of humor.
She’s here to meet you where you are and guide you toward greater balance, strength, and ease.
Anna is comprehensively certified through the Pilates Training Institute.
Lindsay Eldridge
Lindsay has been leading groups since 2003. Her passion for adventure and travel is apparent in her pure joy with planning and implementing these activities.
In 2014, Lindsay began teaching Pilates and went on to get her comprehensive certification (500+ hours training).
Pilates turned out to be the answer to her herniated discs, degenerative disc disease, hip pain, sciatica, diastasis and more.
Lindsay's primary focus is making sure all of the logistics run smoothly during the retreat!
Gallery
Reflections
Reflections
How would it feel to be taken care of, to be understood and to have a top quality experience? We want you to find out. Once you arrive to Sao Miguel island, you don't need to worry about meals and logistics. Simply enjoy!
Reviews
Away retreats in Costa Rica exceeded all expectations, I’ve never felt so taken care of and felt so close to people I just met. Lindsay is a special soul whose joyful and playful energy is contagious, she provided a sense of love and connection that I felt deep in my soul. Everything was taken care of from air transport to beautiful accommodations, meals, movement classes and incredible excursions. I am hooked on away retreats and I can’t wait for the next one!
Karen T., Costa Rica 2025
FAQs
What is the cancellation policy?
Deposits are refundable for 10 days.
If cancellation occurs more than 120 days prior to the retreat start date, you will receive a 50% refund, less the deposit.
Cancel 75-120 days prior to the retreat start date and receive a 25% refund, less the deposit.
Unfortunately, we cannot offer refunds for cancellations that occur 75 or fewer days before the retreat start date.
However, we CAN apply any amount paid toward a future AWAY retreat!
We do require that you purchase travel insurance and have recommendations!
What is the payment policy?
A 15% deposit is required to reserve your spot on the retreat.
The remaining balance is due 120 days before the retreat start date.
Please reach out if you'd like to chat about a payment plan that might work better for you.
Is it okay to opt out of an activity?
It's so okay that we don't even call it "opting out". Your retreat vacation is a menu of choices and you know you, best.
Your choice may be to join a scheduled activity, to sleep in, to take a movement class or to lounge by the pool.
We applaud you for doing what feels right for you, each day.
Can my dietary needs be accommodated?
Yes! There are options for vegetarians, pescatarians, omnivores and carnivores alike.
Gluten-free diets can be accommodated as well. Dinner may include things like:
Citrus Avocado Salad
Beet & Goat Cheese Salad
Tuna Tataki
Grilled Calamari with Herb Oil
Fish Soup Azorean-Style
Vegetable Risotto
Stuffed Bell Peppers
Slow-Cooked Beef Cheeks
Duck Breast with Berry Reduction
Azorean Pork with Sweet Potato Mash
Crème Brûlée with Lime Sorbet
Dark Chocolate Brownie with Red Fruit Coulis
Are vaccinations recommended or required?
You may read about the current CDC recommendations and guidelines here.
Is there WIFI?
Yes. While it’s nice to unplug from the outside world, many of us have lives at home that require some communication.
We understand. There is WIFI in each Casa.
Do you recommend travel insurance?
As experienced travelers who’ve learned to expect the unexpected, we now require travel insurance.
You'll receive our recommendations after signing up (or ask in advance!).
What will the weather be like?
The weather in Sao Miguel, Azores in September is lovely!
Temperatures will likely range from 17°C (63°F) to 24°C (75°F).
Although the weather in September is relatively stable compared to other months, the Azores are known for rapidly changing weather conditions amongst each microclimate.
If we get rain, it will likely be brief.
What is on the packing list?
You'll receive a packing list 60 days before the retreat which will include items that cover all 4 traditional seasons. Layers will work best here! Some examples are:
✔ Thin cotton
✔ Lightweight wool shirts
✔ Waterproof Rain Jacket
✔ Sun hat
✔ Hiking shoes
✔ Water shoes/hiking sandals
✔ Flip flops (to wear around our retreat area or the beach)
✔ Lightweight down jacket (for cool nights)
✔ Lightweight fleece
✔ Quick dry pants
✔ Swimsuit
✔ Day pack
I'm new to Pilates and/or hiking. Can I go on this retreat vacation?
Yes! Movement classes will challenge all levels appropriately.
In Sete Cidades, we will split into two groups; a gentle hiking group and a challenging hiking group.
There is also a gentle hike option if canyoning is not your thing.
This will give participants the opportunity to explore at their desired speed. In summary, we will figure out what works best, each day!