The Essence of Portugal A Week of Laughter, Connection & Exploration

There’s something truly special about women traveling together. It’s not just the destinations we explore, but the laughter shared over meals, the late-night talks that turn strangers into friends, and the quiet moments that remind us why we fell in love with travel in the first place.

This past October, I hosted a women’s group trip to Portugal, exploring Lisbon, Sintra, and Évora over one unforgettable week. It was a beautiful blend of meaningful conversations, perfect weather, shared curiosity, and the kind of easy laughter that fills your heart long after you return home.

Why a Women’s Group Trip

When I decided to make this an all-women’s trip, my goal was to create a space where women could simply be — comfortable, open, and themselves. That atmosphere led to the most genuine conversations about travel, family, and what it means to be a woman navigating different stages of life.

There’s something about being immersed in a new culture that sparks connection and curiosity. The mix of experiences, from tasting local food to sharing first impressions of a new city, naturally brought out thoughtful, authentic discussions.

By day two, contact info was being exchanged, inside jokes were forming, and new friendships were blossoming. The group was a wonderful mix — sisters, mother-daughter duos, a solo traveler, and longtime clients who invited friends along. Coming from a family of strong women myself, it was truly special to be surrounded by that same kind of energy throughout the trip.

Why Portugal

I chose Portugal for its accessibility, authenticity, and welcoming spirit. It’s a destination that offers incredible variety — from vibrant cities to peaceful countryside — yet feels easy to navigate and approachable for travelers.

October is one of the best times to visit Portugal: warm days, crisp evenings, and fewer crowds. Traveling during the shoulder season meant we could enjoy the country’s charm at a relaxed pace, with picture-perfect weather every single day.

On a personal note, Portugal holds a special place in my heart. I spent a month there in January 2023, when Ellie’s Travel Bug was just getting started. Coming back a year later to host a group of women through the same regions felt beautifully full-circle. To walk those familiar streets again — this time as a guide and host — was both humbling and energizing.

Lisbon: Sweet Starts & City Charm

Our journey began in Lisbon, where we stayed at a restored 16th-century palace-turned-boutique hotel in the heart of the city. Mornings started with cappuccinos in the courtyard, soft chatter about the day ahead, and that quiet excitement that only comes at the start of a great adventure.

One of my favorite moments from the entire week was our pastel de nata baking class. Watching everyone laugh, help each other, and proudly show off their imperfect pastries was pure joy. It was a moment that perfectly captured the essence of this trip — connection through shared experience (and a little sugar).

Later, we explored Lisbon by tuk-tuk, winding through its seven hills, stopping for local ginginha (cherry liqueur), and soaking up sweeping city views. We ended the day at a cozy Fado dinner, where soulful music and candlelight set the tone for an unforgettable evening.

Sintra: A Fairytale Come to Life

A highlight for everyone was our day trip to Sintra, a place that feels straight out of a storybook. We wandered through the colorful towers of Pena Palace, explored the mysterious gardens of Quinta da Regaleira, and meandered through cobblestone streets lined with pastel homes.

The weather was absolutely perfect — golden sunlight and crisp autumn air — the kind that makes every photo glow and every moment feel cinematic. It truly was one of those “pinch me” travel days.

Évora & Alentejo: Slowing Down in the Countryside

Midweek, we traded city life for the golden countryside of Alentejo. On the way, we stopped at the José Maria da Fonseca Winery for tastings of regional wine, cheese, and olive oil — the ultimate Portuguese trio.

Our home base for the next few days was Octant Évora, a peaceful retreat surrounded by rolling hills and cork trees. Life slowed down beautifully here. We spent one morning on an e-bike ride through the countryside, passing Roman ruins and open fields before stopping for a picnic lunch under the sun.

Later in the week, we visited Herdade dos Grous, one of Alentejo’s most picturesque wineries, for a long, leisurely lunch paired with their signature wines. The day felt like the perfect expression of what makes Portugal special — delicious food, warm hospitality, and a slower rhythm that invites you to savor it all.

What Made This Trip Special

What stood out most to me wasn’t just the incredible scenery or meals (though Portugal delivers plenty of both), but the energy of the group. Every conversation was filled with laughter and warmth. Every meal felt like a celebration of friendship.

By the end of the week, everyone had found connection — with each other, with Portugal, and with themselves. It was a week that reminded me what travel is really about: shared experiences that fill your heart and expand your perspective.

Until Next Time, Portugal

As we packed our bags and said our goodbyes, I couldn’t help but feel a wave of gratitude. This trip was a reminder of why I love what I do — not just crafting itineraries, but creating spaces where people can connect, slow down, and experience the world together.

It truly was a week well spent: good meals, good company, and countless moments I’ll never forget.

Cheers to travel, to connection, and to the incredible women who made this journey so special.

Feeling Inspired?

If this post has you dreaming of your own adventure, whether it’s a girls’ trip, a romantic escape, or a solo adventure, I'd love to make it happen!

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