Friendship and travel for women 50+
Olegana Travel Boutique women-only group trip to Sicily, Italy, in 2025, featuring a scenic vineyard surrounded by rolling hills with Mount Etna rising in the background.
Photo©: Anna Fishman / Olegana Travel Boutique
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.
Olegana Travel Boutique women-only group trip to Sicily, Italy, in 2025, featuring Chiesa di Santa Lucia alla Badia in Piazza Duomo on Ortigia Island in Syracuse, known for its striking Baroque façade.
Photo©: Anna Fishman / Olegana Travel Boutique
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.
Olegana Travel Boutique women-only group trip to Sicily, Italy, in 2025, featuring Sicily’s stunning Mediterranean coastline, surrounding islands, crystal-clear turquoise waters, sea caves, and dramatic volcanic landscapes.
Photo©: Anna Fishman / Olegana Travel Boutique
Some of the trips below are ones Olegana women have already taken together, and some are still ahead.
Wine, Chocolate & You
Sicily: La Dolce Vita. On our Sicily trip, the “sweet life” welcomed the group with warmth, flavor, and soul. Days unfolded through vibrant markets, hands-on cooking classes with passionate chefs, and cultural experiences led by local guides. Quiet moments of reflection balanced lively evenings filled with bold wines, rich chocolate, and laughter shared around long tables. We return to Sicily in May 2028.
Sunrise at the old baroque town of Ragusa Ibla in Sicily. Historic center called Ibla builded in late Baroque Style. Ragusa, Sicily, Italy, Europe.
Photo©: Pilat666 / iStock
Secret Spain: Discover Andalusia
Today’s luxury lives in thoughtful welcome touches. Our Andalusia trip was an unforgettable adventure through Southern Spain, exploring the Andalusian gems of Granada, Seville, Córdoba, Ronda, and Cádiz. The journey blended culture, beauty, and shared discovery in a way that felt both immersive and effortless.
Olegana Travel Boutique women only group trip 2024, a group picture at Plaza de España, Southern Spain Europe.
Photo©: Anna Fishman / Olegana Travel Boutique
The group walked through the Alhambra, a UNESCO World Heritage site and one of the most remarkable expressions of Moorish art in Spain. Along the way, they:
Visited a working olive oil estate
Experienced the passion and artistry of flamenco
Enjoyed wine tasting in an old convent transformed into a winery
Took part in a sangria-making demonstration
Every moment was savored together.
The Dolomites & Lake Garda
Seceda Ridge in the Dolomites of northern Italy features dramatic jagged cliffs, lush alpine meadows, and stunning views of the Sassolungo mountain group.
Photo©: Anna Fishman / Olegana Travel Boutique
Next September, Anna takes a small group of women to the Dolomites and Lake Garda, from Bergamo’s walled old town to the shores of the lake and up into the mountains of South Tyrol. Think Franciacorta in a castle courtyard, a boat crossing Lake Garda to an island garden, and the evening hour when the pale Dolomite rock turns pink and the whole terrace goes quiet.
It is a slow trip: nine days through wine country, lemon houses and Alpine villages, ending with three nights of rest in the mountains. By the time the group reaches the peaks, the women around you won’t feel like strangers anymore. It runs September 10 to 18, 2027, with sixteen women at most.
Southern Italy Foodie Adventure
A fresh burrata, sun-dried tomatoes, basil, serrano ham, pine nuts, and balsamic vinegar with olive oil for seasoning.
Photo©: ClarkandCompany / iStock
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.
Highlights from the 2024 Puglia, Italy group tour with Olegana Travel Boutique: A pasta making and cooking session.
Photo©: Anna Fishman / Olegana Travel Boutique
You’ll explore towns like Alberobello, Matera, and Ostuni with a professional guide; each tour feels personal and rooted in place, tradition, and togetherness.
Ostuni at sunset, the beautiful white town in the Puglia region of southern Italy.
Photo©: Olga Tarasyuk / iStock
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.
Olegana Travel Boutique group picture at Edinburgh Castle, Scotland
Photo©: Anna Fishman/Olegana Travel Boutique
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.
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet the unwavering focus on authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Ready to travel with women who get it?
Our small-group women’s tours to Italy, the UK and beyond are designed for connection, not crowds. Intimate groups, curated experiences, and friendships that last long after the trip.
Book a call with Anna here!
Frequently Asked Questions
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Both. Many of our travelers arrive solo and leave with new friendships. Others come with a friend or a sister. The groups are intentionally small, so everyone feels included and no one feels like an outsider.
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Our women’s tours are kept small, sixteen travelers at most. This is by design. It allows for deeper conversations, more personal attention, and the kind of connection that doesn’t happen in a group of 40.
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More than OK. Many of our travelers are taking their first trip on their own, and they often say it's the most rewarding thing they've done in years. These tours are designed to feel safe, supportive, and full of the kind of joy that comes from doing something just for you.
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It means thoughtful, not flashy. Beautiful accommodations, curated experiences with local guides, meals that reflect the destination, and a pace that gives you room to breathe. No rushing, no rigid schedules, no checking boxes.
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Our tours sell out, some of them months in advance. All three of our 2026 Puglia departures sold out. If a specific destination is calling to you, it’s worth reaching out early, and past travelers hear about new dates before they go public.
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In 2027 our women’s group trips go to Puglia, Venice and the Prosecco Hills, the castles and gardens of Britain, and the Dolomites and Lake Garda. In 2028 the calendar reaches further, to the Caribbean and Japan. Visit our Women’s Trips page for the current lineup and availability.