The Essence of Portugal
Wellness & Exploration Retreat
A Portugal Collection – Curated by Briana Masson & The Little Orange
October 20th-23rd, 2026
Serra da Arrábida
Where the rhythm of Pilates meets the soul of Portugal’s coast. Four unforgettable days of movement, wine, and coastal wonder designed to awaken and renew.
A Retreat Beyond Escape
Experience four days in Portugal’s Serra da Arrábida, where ocean air meets rolling vineyards and quiet hills. The Deepening Retreat is designed to help you slow down, strengthen, and reconnect through Pilates, nature, and simple intentional living.
Wake each morning in a restored villa on an eight-hectare winemaking estate with views of the Atlantic and surrounding mountains. Each day begins with Pilates led by Briana Masson, Classical Pilates Master Teacher. After breakfast, enjoy curated experiences including guided hikes, local wine tastings, and a private catamaran along the coast.
Evenings are for connection and rest - sharing local meals, conversation, and time to unwind. Between activities, you’ll have time to relax by the pool, explore the estate, or simply pause.
This retreat is an invitation to reset, move with purpose, and reconnect with yourself in one of Portugal’s most authentic and peaceful regions.
Daily Rhythm
October 20th
DAY 1
3 pm - Check-in with time to settle in before the first group activity
4 pm - Pilates with Briana
6 pm - Premium wine tasting led by the winemaker
7 pm - Arrival Dinner
October 21st
DAY 2
8:00 am - Pilates with Briana
9:00 am - Breakfast
10:30 am - 4x4 buggy/Tractor & Walking Tour inside the estate
1:00 pm - Rustic buffet lunch
4:00 pm - Guided visit and tile painting workshop in Azeitão
6:30 pm - Early dinner at a local restaurant in Azeitão
October 22nd
DAY 3
8:00 am - Pilates with Briana
9:00 am - Breakfast
10:30 am - Guided hike inside Serra da Arrabida (weather permitting)
1:00 pm - Lunch at a coastal restaurant
3:00 pm - Private luxury catamaran trip along the coast (weather permitting)
7:30 pm - Dinner
October 23rd
DAY 4
8:00 am - Pilates with Briana
9:00 am - Breakfast
12:00 pm - Check out
1:00 pm - Farewell barbecue lunch
Program Details
What’s included:
Three nights in a private villa nestled on an eight-hectare winemaking estate, with daily breakfast included
Daily Pilates classes guided by Briana Masson, Classical Pilates Master Teacher
All meals and beverages included, featuring fresh, seasonal cuisine and local wines
Premium wine tasting led by the estate’s winemaker
Private buggy, tractor, or walking tour through the vineyards and grounds
Hands-on tile-painting workshop with a local artisan
Guided hike through Serra da Arrábida Natural Park
Private catamaran experience along Portugal’s stunning coastline
Private Transfers During the Retreat – luxury vehicle, English-speaking driver, bottled water, A/C & Wi-Fi
On-site hosting and tour leading by Briana throughout the retreat
24/7 on-ground support from The Little Orange team
What’s not included:
International airfare
Gratuities
Transportation to and from Serra da Arrabida (airport transfers can be arranged at an additional cost).
Extra meals or beverages beyond those included in the itinerary.
Optional personal expenses, spa treatments, or additional activities outside the retreat itinerary.
Meet your Guides
Briana Masson
Briana Masson is a Certified Classical Pilates Master Teacher and Luxury Travel Advisor with more than 25 years of experience guiding clients toward strength, alignment, and renewal. She’s worked with everyone from elite athletes to new moms to those recovering from injury, always blending precision with intuitive teaching.
Having lived in Los Angeles, New York, Paris, and now Lisbon, Briana brings a global perspective and a love of discovery to her work. Hosting this retreat is her way of weaving together movement, culture, and connection—inviting guests to recharge, explore, and feel at home in their bodies.
The Little Orange
The Little Orange is a boutique DMC crafting bespoke journeys across Portugal, including the Azores and Madeira. From boutique stays and private villas to exclusive experiences, each trip is personally designed and supported 24/7 by a dedicated Travel Designer. Partnering with local experts and prioritizing sustainable, Portuguese-owned projects, they deliver authentic, seamless, and responsible luxury travel.
Daily Overview
-
3 pm - Check-in with time to settle in
4 pm - Pilates
6 pm - Premium wine tasting led by the winemaker
7 pm - Arrival Dinner
-
8:00 am - Pilates
9:00 am - Breakfast
10:30 am - 4x4 buggy/Tractor/Walking Tour inside the estate
1:00 pm - Rustic buffet lunch
4:00 pm - Guided visit and tile painting workshop in Azeitão
6:30 pm - Early dinner at a local restaurant in Azeitão
-
8:00 am - Pilates
9:00 am - Breakfast
10:30 am - Guided hike inside Serra da Arrabida (weather permitting)
1:00 pm - Lunch at a coastal restaurant
3:00 pm - Private luxury catamaran trip along the coast (weather permitting)
7:30 pm - Dinner
-
8:00 am - Pilates
9:00 am - Breakfast
12:00 pm - Check out
1:00 pm - Farewell barbecue lunch
The Setting
Where the mountains meet the sea, Serra da Arrábida reveals one of Portugal’s most captivating landscapes. Stretching along the country’s southwestern coast, this protected natural park is a sanctuary of wild beauty rolling green hills, limestone cliffs, and secluded coves where turquoise waters lap gently against the shore.
The nearby villages of Sesimbra and Azeitão carry the charm of old-world Portugal: cobblestone streets, whitewashed homes, and a rhythm of life that moves at nature’s pace. Here, time slows down. The scent of salt air mingles with that of olive trees and vineyard soil, inviting you to breathe deeply and be present.
Just 30 minutes from Lisbon, Arrábida feels like a world away, an untouched escape where you can reconnect with movement, nature, and with yourself.
Accommodation
Our retreat home is a historic winemaking estate nestled within eight hectares of vineyards and gardens inside Serra da Arrábida Natural Park. With centuries of heritage and a deep reverence for the land, the estate blends tradition and design, offering a serene backdrop for rest and renewal.
The Main House features seven thoughtfully appointed rooms - three with queen or king beds and four with twin beds while the Secondary House offers two additional twin rooms, creating space for both privacy and connection.
Inside, you’ll find elegant living rooms, a professional kitchen and pantry, and a spacious dining room perfect for shared meals and conversation. Outside, the estate opens to a swimming pool, tennis court, and quiet corners ideal for reading, journaling, or soaking in the tranquil atmosphere.
Each morning begins with a fresh breakfast prepared on-site, and daily housekeeping ensures your stay feels effortless. Every detail is designed to honor comfort, community, and the natural beauty of Arrábida.
The Investment
Single Bedroom:
4650 € per person
Shared Bedroom:
3850 € per person
Booking & Payments
Booking your spot is simple, transparent, and flexible so you can reserve with confidence.
Deposit: 30% due at booking (non-refundable)
Second Payment: 40% due by June 15th, 2026
Final Payment: 30% due by August 15th, 2026
Travel Insurance
We highly recommend travel insurance with “cancel for any reason” coverage for extra peace of mind. (Reach out for a quote.)
Cancelation Policy
Our flexible cancellation policy offers peace of mind. If you need to cancel, bookings canceled between December 15 and February 15, 2026 are eligible for a 40% refund. Cancellations made after February 15, 2026 are non-refundable and the full amount will be charged. In the unlikely event that The Renewal Retreat is canceled by the organizer, you will receive a full refund (credit card fees may apply).