Friendship and travel for women 50+
Guest blog post from Felicity Leo
Travel in your 50s isn’t about going alone, it’s about going deeper. Friendship-centered journeys create space for connection, reflection, and shared experiences that turn beautiful destinations into lasting memories. For women 50+, travel becomes a celebration of meaningful moments, new beginnings, and the joy of discovering the world together.
Meaningful Destinations | Legacy Journeys | Meaningful Experiences
When I think about traveling solo, I quickly realize it doesn’t mean traveling alone. Solo travel opens the door to self-discovery, genuine connection, and friendships that begin with intention and often grow into lasting bonds. Friendship enriches travel in ways nothing else can!
It shows up in restorative moments and in bursts of laughter over wine at dinner, in shared stories during scenic drives, and in conversations with local artisans at bustling outdoor marketplaces. These exchanges add emotional depth, turning a trip into a lived, magical experience.
I absolutely love being part of women’s group trips that are intentionally small and deeply personal and offer a sense of belonging, stillness, and purpose. They often align with huge life transitions like empty nesting, career shifts, retirement, or the simple realization that now is the time! Traveling alongside like-minded women honors and celebrates these milestones such as birthdays, anniversaries, healing journeys, or the courage to say yes to something new.
Friendship Travel + Luxury Travel
Personal, Purposeful, and Transformative
Today’s women travelers are redefining luxury. Long gone are rigid itineraries and checklist travel. Certain destinations naturally slow us down, awaken the senses, and create space that nourishes the soul, offering clarity, and room to breathe.
Wine, Chocolate & You
Sicily: La Dolce Vita. The "sweet life" welcomes women travelers with warmth, flavor, and soul. Days unfold through vibrant markets, hands-on cooking classes with passionate chefs, and immersive cultural experiences led by local guides. Quiet moments of reflection balance lively evenings filled with bold wines, rich chocolate, and laughter shared around long tables.
Secret Spain: Discover Andalusia
Today’s luxury lives in thoughtful welcome touches. For example, the Andalusia tour will be an unforgettable adventure through Southern Spain, exploring the Andalusian gems of Granada, Seville, Córdoba, Ronda, and Cádiz. This thoughtfully curated journey blends culture, beauty, and shared discovery in a way that feels both immersive and effortless.
You’ll walk through the Alhambra, a UNESCO World Heritage site and one of the most remarkable expressions of Moorish art in Spain. Along the way, you’ll:
Visit a working olive oil estate
Experience the passion and artistry of flamenco
Enjoy wine tasting in an old convent transformed into a winery
Take part in a sangria-making demonstration!
Each moment is designed to be savored together.
Southern Italy Foodie Adventure
With the new year, women travelers are redefining luxury through hyper-personalized experiences shaped by rhythm, mood, and intention. Puglia’s gentle pace invites you to breathe deeply and savor life. Long tables, shared meals, and the simple pleasure of fresh burrata.
You’ll explore towns like Alberobello, Matera, and Ostuni with a professional guide; each tour feels personal and rooted in place, tradition, and togetherness.
United Kingdom’s Castles & Gardens
There is a true elegance in wandering historic castles and lush gardens with fellow travelers who appreciate reflection and beauty. Mornings unfold along garden paths, afternoons are spent listening to stories etched into ancient stone, and evenings invite relaxed, thoughtful conversation over delicious dinners. This is travel that allows space for perspective, and peace.
Trips like these have a way of becoming treasured stories. Consider this your invitation to explore thoughtfully curated trips and genuine connections that often become some of your most meaningful memories.
Whether you’re curious, dreaming, or ready to take the next step, every journey begins with a conversation - the team at Olegana Travel Boutique would love to connect with you!
Excited to travel to Europe? Join a women’s small group tour with Olegana Travel Boutique: where culture, community, and comfort truly come together.
Grab a time on Anna’s calendar for a free consultation here!
Disclaimer: The information provided in this blog post is for general informational purposes only. All content is provided in good faith; however, we make no representation or warranty of any kind, express or implied, regarding the accuracy, adequacy, validity, reliability, availability, or completeness of any information. The views and opinions expressed in this post are those of the author and do not necessarily reflect the official policy or position of any other agency, organization, employer, or company.
Readers are encouraged to do their own research and consult with a qualified professional before making any decisions based on the content of this blog.