Portugal Retreat: World of Wonder

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Overview

Portugal Retreat: World of Wonder
Portugal
Nov 2 - 9, 2026
The Traveling Sisterhood image
The Traveling Sisterhood
$3,197
Deposit: $497

About this trip

Discover the Enchantment of Portugal:


Join us for an unforgettable retreat in Portugal, where history, culture, and breathtaking landscapes await. This stunning destination will excite your mind and ground your soul.

Be ready to explore charming cobblestone streets where every corner feels like a love letter from the past. We will fill our time with slow mornings and long nights, breathing in the ocean air, meandering within intimate cafes, and listening to fado music that pierces the soul. We will explore vast castles, discover secret beaches at golden hour, and reignite our curiosity through adventure.

Portugal makes you feel at home - warm, cozy, and seen - while also immersing you within the fairytale fantasy of your dreams. Come experience the magic of Portugal with us!

Your HOST: Erin Johnson

Erin is a mother of three daughters, and devoted partner whose life is rooted in curiosity, connection, and presence. With a tender yet steady spirit, she brings women together in ways that feel both playful and deeply reverent. Her leadership is not about having all the answers, but about asking the right questions—inviting each woman to be seen, heard, and honored for who she truly is.

On this journey through Portugal, Erin leads women along coastal trails, into quiet villages, and through the vibrant streets of Lisbon, where time is spent connecting with the culture, history, music, and everyday rhythms of the city. From hiking the dramatic coastline to wandering village paths and sharing moments in cafés and plazas, the experience weaves nature and culture into a rich, soulful tapestry.

Through shared meals, laughter, tears, and moments of silence, Erin creates space for genuine connection and renewal. Whether gathered in circle, moving in stillness, or sharing stories under an open sky, women are invited to come exactly as they are—and to leave more awake, aligned, and rooted in their truth. With Erin, the journey becomes more than a trip; it becomes a remembering of what it feels like to be fully alive.

What's included

All accommodations

Breakfast every morning

Airport transfers

You can fly in at any time and fly out at anytime on the arrival and departure dates

All transportation

Welcome dinner

Leather journals

All activities mentioned

What's not included

Airfare for flights

Lunch & Dinner each day

(Welcome dinner is the only dinner included)

Travel Insurance

DAY 1 - LISBON

DAY 1 - LISBON image

Arrival & Welcome Dinner

Arrive to the vibrant heart of Lisbon, discovering iconic sites and indulging in the local magic of the Alfama neighborhoods. Partake in a welcome dinner accompanied by a Fado experience.

DAY 2 - LISBON

DAY 2 - LISBON image

Tuk Tuk Tour of Lisbon & Sunset Cruise

The tuk tuk tour will take you away on a sunlit adventure through Lisbon— part fairytale ride, part secret-city safari. You hop into your little open-air chariot and suddenly the city becomes a playground of hills, hidden alleyways, and tiled wonders, unfolding faster than your mind can keep up with. While you ride, the breeze carries the scent of espresso, warm bread, and sea air drifting up from the river. You don’t just see Lisbon on this tour… you feel her: vibrant, romantic, and wildly alive.

As you step aboard the sunset cruise, the boat glides onto the Tagus River as the city shimmers behind you, glowing in warm honeyed light. As the sun begins to dip, everything turns luminous. The river becomes molten gold, rippling with light, and the pastel buildings along the shoreline blush in shades of rose and amber. Slowly, Lisbon becomes a silhouette — dreamy, ancient, and breathtakingly alive.

DAY 3 - PENICHE

DAY 3 - PENICHE image

Boat Tour & Percurso de Berlenga Hike

On the Peniche boat tour, the coastline begins to unfold in dramatic beauty — rugged cliffs carved by time, secret coves tucked between stone walls, and waves crashing below. As you drift closer to the Berlengas Islands, the world starts to feel enchanted. The water shifts into impossible shades of turquoise and emerald, so clear you can see the rocks beneath like ancient jewels.

On the Percurso de Berlenga hike, the path is simple but enchanting — a mix of dusty trails, stone steps, and wooden walkways that guide you along the island’s edges. At times you feel like you’re walking at the very rim of the world, with nothing but sky, ocean, and ancient rock surrounding you. As you reach the viewpoints, everything becomes quiet inside you. You pause, breathe, and take in the vastness — the kind that resets your nervous system and reminds you how sacred life is.

DAY 4 - SINTRA

DAY 4 - SINTRA image

Quinta de Sant'Ana Winery Tour & Explore Ericeira

As you wander through the Quinta de Sant'Ana vineyard, you begin to feel the story of the land: the rhythm of the harvest, the care in every row, the balance between tradition and artistry. Your guide shares how the wines are shaped by this unique terroir — kissed by Atlantic winds, nourished by mineral-rich soil, and crafted with patience and devotion.

The vibe of Ericeira is effortlessly cool but still deeply authentic — a place where you can shop in little boutiques, visit the beach to watch surfers ride across the rhythmic waves, sip wine at sunset, and eat grilled fish so fresh it tastes like the ocean.

DAY 5 - SINTRA

DAY 5 - SINTRA image

Pena Palace & Moorish Castle

Pena Palace and the Moorish Castle feel like two chapters of the same enchanted story — one painted in vivid color, the other etched in ancient stone.

The architecture of Pena Palace feels playful and romantic — domes inspired by the Middle East, Renaissance arches, Manueline carvings, and fairytale turrets that look lifted from a storybook. Inside, rooms are filled with ornate details, chandeliers, and velvet-covered furniture, but it’s the views that leave you breathless. From the terraces, the entire Sintra region spreads beneath you in rolling waves of green, with the Atlantic shimmering in the distance.

The walls of the Moorish Castle wind along the mountaintop, offering some of the most dramatic views in all of Portugal, clinging to the ridge like an ancient stone serpent. The energy here feels older, quieter, more primal. It carries the echoes of warriors, watchmen, and civilizations that came long before.

DAY 6 - SINTRA

DAY 6 - SINTRA image

Coastal Hike & Azenhas do Mar at Sunset

As you follow the path along the rugged coastline, the world opens wider with every step. The air is crisp and salty, the sky feels enormous, and the cliffs drop away into churning blue water far below. You can feel the power of the ocean in your chest — ancient, endless, and completely alive.

Azenhas do Mar at Sunset feels like the world has paused just to show off its most breathtaking beauty. Perched dramatically on the cliffs above the Atlantic, this tiny seaside village looks like a whitewashed dream spilling down the rocks — little houses stacked like sugar cubes, glowing softly as the sky turns to gold.

DAY 7 - SINTRA & CASCAIS

DAY 7 - SINTRA & CASCAIS image

Explore Dunes, Beaches & Caves

The dunes are rolling and golden like a desert meeting the sea. Soft sand shifts beneath your feet and every step feels like you’re walking through nature’s quiet masterpiece. The beaches are rugged, cinematic, and breathtaking. The sound of the waves becomes your soundtrack — steady, cleansing, and alive. The caves are tucked into the cliffs, carved by centuries of sea and storm — they feel like portals to another world. Inside, it’s cooler and quieter — the air damp and salty, the walls echoing with the ocean’s deep voice. Some caves reveal secret arches and tunnels, where you can watch waves surge in and retreat like breath.

DAY 8 - LISBON

DAY 8 - LISBON image

Departure

Reflect on your journey while enjoying some last-minute leisure time before heading to the airport. 

Location

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1. Portugal

Portugal

About your organizer

Since 2016, we’ve been leading women’s retreats across the globe—creating safe spaces of sisterhood, unforgettable experiences, and a ripple of positive impact that extends far beyond the journey itself. We are so glad you're here!

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