Something is shifting. I see it every season, and it’s been building for years now.
More women over 50 are reaching out to me. Not to plan a family vacation. Not to organize an anniversary trip. To ask about traveling on their own, or with a friend, or with a group of women they haven’t met yet.
Photo: Olegana Travel Boutique’s Puglia Women-Only Group Tour: Our beautiful group is enjoying gorgeous weather and unforgettable moments in Puglia for a week
Photo©: Anna Fishman / Olegana Travel Boutique
And when I ask them what changed, the answer is almost always some version of the same thing: “I’ve been putting everyone else first for 25 years. I’m done waiting.”
I’ve watched this happen dozens of times now. A woman reaches out, a little uncertain, maybe even a little apologetic about wanting something just for herself. She joins one of our small group trips. And somewhere between the first evening together and the last morning, something shifts. She stops apologizing. She starts planning the next one.
Here’s what I’ve learned from hosting these trips, and why I think this kind of travel is one of the most important things a woman can do for herself.
It’s not really about the destination
I could tell you about Alberobello at dusk, or the lemon houses above Lake Garda, or what it feels like to walk through a Scottish castle with rain on the windows and no one else in the room. And I will, because those moments matter.
Olegana Travel Boutique’s Women-Only Puglia Group Tour: Exploring the ornate Baroque façade of the Basilica di Santa Croce in Lecce, Italy, known for its intricate limestone carvings and stunning architecture.
Photo©: Anna Fishman / Olegana Travel Boutique
But when I ask past travelers what they remember most, it’s rarely a specific landmark. It’s the dinner table. It’s the conversation that happened in the back of the van on the way to a vineyard. It’s the woman from Toronto who said something that made everyone cry, and then everyone laughed, and then they ordered more wine.
The destination provides the setting. The group provides the experience. And when both are designed with care, something happens that’s hard to describe until you’ve felt it. You feel like yourself again. Or maybe, for the first time in a while, you feel like the version of yourself you’ve been too busy to be.
What makes these trips different from a regular group tour
I need to be direct about this, because there are a lot of “women’s group tours” out there, and most of them are just regular group tours with a different label on the brochure. Here’s what I do differently.
Olegana Travel Boutique’s Spring 2024 Women-Only Puglia Group Tour: Enjoying olive harvesting and authentic local food in Puglia, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
The groups are small. Never more than sixteen women. This isn’t a marketing choice, it’s a design choice. Connection doesn’t happen in a group of 40 people following a flag. It happens when you can sit around one table and actually hear each other.
The pace is intentional. I don’t believe in cramming six cities into seven days. My trips are built around rhythm, not checklists. There’s time to wander, time to be alone, time to sit in a piazza and watch the light change. The best conversations happen in the in-between moments, and I design for those.
The experiences are curated, not cataloged. I work with local suppliers and guides I’ve known for years. A cooking class in Puglia isn’t a tourist cooking class. It’s a morning in a local woman’s kitchen, learning her grandmother’s recipe while her kids run through the garden. A wine tasting isn’t a production line. It’s a cellar visit with a family who doesn’t advertise.
Olegana Travel Boutique’s Spring 2026 Castles and Gardens UK Tour: Exploring the formal water gardens and grand façade of Blenheim Palace in Woodstock, Oxfordshire, England.
Photo©: Anna Fishman / Olegana Travel Boutique
We talk first. Every woman who applies has a one-on-one video call with me before she’s offered a place. It’s how I make sure the trip suits you, and that the group will work as a group.
I’m there, or my host is. I know every woman’s name, her story, her dietary needs, and what she’s hoping to get out of the week. On the trips a host leads for me, she sends me photos and a few lines every evening, so small things get fixed while you’re still there. I’m not an anonymous tour operator. I’m the person who planned the trip, and I care deeply about how it feels for every single person in the group.
And every woman has her own room. On every one of our 2027 trips, there’s no sharing with a stranger.
The moment that changes everything
Green alpine meadows stretch beneath the dramatic limestone peaks of Seceda, overlooking Val Gardena and the Sassolungo massif in the Dolomites, South Tyrol, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
I notice it on every trip, usually around day two or three.
Women arrive a little guarded. A little polite. Keeping a safe distance the way you do when you’re surrounded by people you don’t know yet.
And then something cracks open. Maybe it’s a conversation that goes deeper than expected. Maybe it’s laughing until you can’t breathe over something ridiculous. Maybe it’s watching a sunset from a terrace in Puglia with a glass of Primitivo and realizing you haven’t thought about your to-do list in three days.
A heart-shaped wooden planter stands against the dramatic limestone peaks of the Dolomites in Val Gardena, South Tyrol, Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
By the end of the week, these women are exchanging numbers, planning reunions, and crying at the airport. And I hear from them months later: “That trip changed something in me.”
I don’t take that lightly. It’s why I do this.
Experiences worth building a trip around
Anna Fishman, founder of Olegana Travel Boutique, enjoying ice cream with royal insignia wafers during the 2026 Castles and Gardens UK Tour, with the historic towers and battlements of Windsor Castle in the background.
Photo©: Anna Fishman / Olegana Travel Boutique
A few of the moments on our 2027 trips that a group of sixteen makes possible, and that none of us could easily arrange alone.
A morning at the Rialto Market with a Venetian chef, then a cooking class and a long lunch at his own table.
A private opening of one of Europe’s last great mosaic workshops, in Venice.
The Poison Garden at Alnwick, toured privately before the gates open to anyone else.
Afternoon tea in the walled garden at Floors Castle, in the room where Queen Victoria took tea in 1867.
A panzerotti lesson in Puglia, with traditional folk dancers filling the room.
A glass of Vino Santo by Lake Toblino, poured by one of the few families who still make it.
Curious about our women’s group trips?
Small groups, curated experiences, and the kind of travel that reminds you who you are when you’re not taking care of everyone else.
Book a call with me here.
One guest, back from her second trip with us, described how I run a week better than I could:
“The trip was well-organized and yet she adjusted to the needs of the group. We had full days with great activities, delicious dining, and luxury accommodations. All of the guides were knowledgeable and personable.”
Cindy B., two-time Olegana women’s trip guest
Where we go, and when
Every destination I choose for a women’s trip earns its place, and so does the month. I pick places that create the right conditions for the experience I’ve been describing: beauty, warmth, depth, and a pace that lets you actually feel where you are. Then I pick the weeks when they are at their best.
Puglia, Southern Italy: spring and fall
Photo: Highlights and memorable moments from Olegana Travel Boutique’s Puglia group tour, celebrating the region’s charming towns, beautiful landscapes, authentic Italian cuisine, and unforgettable cultural experiences.
Photo©: Anna Fishman / Olegana Travel Boutique
Puglia is the trip that converts the skeptics. The ones who said “I don’t know if group travel is for me” come home texting the group chat every week. The food is extraordinary (burrata that ruins all future burrata, orecchiette made by hand in the street), the towns are gorgeous (Ostuni, Alberobello, Matera), and the pace is slow enough to actually savor it all. In 2027 we go three times, April 30 to May 7, October 2 to 9 and October 14 to 21, and all three of our 2026 departures sold out.
See the dates and the full week: Puglia Trips
Venice, Asolo & the Prosecco Hills: April
Photo: Highlights and memorable moments from Olegana Travel Boutique’s women only Venice, Asolo, and Prosecco hills tour, featuring picturesque landscapes, charming Italian towns, and unforgettable cultural experiences.
Photo©: Anna Fishman / Olegana Travel Boutique
Venice is one of those cities people think they already know. They’ve seen the photos, walked the same bridge everyone photographs, done the gondola ride between the other gondola rides. This trip is built on a different premise: nine days through Venice and the Veneto with a small group of women who chose to do Italy slowly and well. Five nights in the city, three in a villa in the hilltop town of Asolo, and long lunches in the Prosecco Hills. This is not a Venice tour. This is a Venetian spring.
April 1 to 9, 2027 had been full for months, but our palazzo has just opened a penthouse, which gives us three last places until registration closes on November 15, 2026: Venice, Italy Trip
UK Castles and Gardens: May
Photo: Highlights and memorable moments from Olegana Travel Boutique’s 2026 women only Castles and Gardens UK tour, featuring beautiful gardens in bloom, historic castles, and the charming English countryside. A glimpse into the vibrant floral displays, elegant estates, and unforgettable experiences that made this spring journey through the UK so special.
Photo©: Olegana Travel Boutique & Anyafoto Photography
For women who love beauty in its quietest form. Historic castles, manicured gardens, and the kind of English countryside that makes you want to slow down permanently. Ten days from the Scottish Borders to Windsor, timed for mid-May when the gardens are at their best, and I host it myself.
See the full trip: Castles & Gardens, UK Trip
Dolomites & Lake Garda: September
Photo: Olegana Travel Boutique’s Best of Lake Garda and the Dolomites: a luuxury journey through Northern Italy’s lakes, vineyards, and mountains.
Photo©: Anna Fishman / Olegana Travel Boutique
New for 2027! Nine days from Bergamo’s walled old town to Lake Garda and up into the Dolomites: Franciacorta in a castle cellar, a boat to a private island garden, the lemon houses of Limone, a dumpling lesson in a Trentino wine village, and three nights at a wellness hotel beneath the peaks. September 10 to 18, after the summer crowds have gone home, and I host it myself.
See the full trip: Dolomites & Lake Garda Trip
Further ahead, the calendar reaches beyond Europe: Christmas in Rome and Umbria in December 2027, the Caribbean in March 2028, and Japan in November 2028.
Every trip has its own day-by-day, with what’s included and how the week flows. You’ll find them all on our women’s group trips page.
Who comes on these trips
I want to be specific about this, because it matters.
The women who join our trips are not all the same. They’re not all retired. They’re not all solo. They don’t all look the same or come from the same place. What they have in common is a willingness to say yes to something they’ve been thinking about for a while.
Photo©: Olegana Travel Boutique Client, David G.
Some are empty nesters
Who spent two decades building a life around their kids and are now standing in a quiet house wondering, “What do I want?” Travel is often the first answer that feels entirely their own.
Photo©: Olegana Travel Boutique
Some are going through a transition:
A divorce, a retirement, a loss, a career change. They’re not looking for a distraction. They’re looking for a reset. Something that reminds them they’re still curious, still adventurous, still capable of surprise.
Photo©: Olegana Travel Boutique
Some just love to travel
And got tired of waiting for someone else to be ready. Their partner isn’t interested in Europe. Their friends can’t commit. They decided to go anyway, and the group became the company they’d been looking for.
Photo©: Olegana Travel Boutique
Some come with a friend or a sister
And leave with ten more. I’ve watched women from completely different lives, different cities, different countries, find something in common over a glass of Primitivo in Puglia that turned into a friendship that lasted years.
Before or after the group
Anna Fishman, founder of Olegana Travel Boutique, enjoying the Spring 2026 Castles and Gardens UK Tour.
Photo©: Anyafoto Photography
Many women add a few days on their own before or after a trip. A night or two in Edinburgh before the castles and gardens, so you meet the group rested. More of the south after Puglia, where the trains connect to the rest of Italy. Verona on the way home from the Dolomites. I plan those days as a custom extension, around what you want to see, so the move from your own days to the group is easy. My planning fee for custom trips starts at $950, and I waive it for extensions, as a courtesy to everyone joining a group trip.
Why this kind of travel needs to be designed, not booked
Olegana Travel Boutique’s 2024 Puglia group tour: Enjoying an outdoor picnic, local food, and a toast together in a sunlit olive grove in southern Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
You could find a women’s group tour on Google. There are plenty. Most of them are 30 to 40 people following a guide with a flag through the same places every other tour goes.
What I build is different. I know the restaurants that don’t have websites. I know the guides who turn a vineyard visit into a story you’ll tell for years. I know which rooms at which properties have the view that makes you gasp. And I know how to structure a week so that the group dynamic works, so that introverts have space and extroverts have energy and everyone feels seen.
That’s the difference between a group tour and a curated journey, and it’s the same reason people work with a luxury travel advisor for their own trips. It’s also why our trips sell out.
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 say yes?
If you’ve been thinking about this for a while, consider this your sign. You don’t need to have it all figured out. You just need to be willing to go.
I’d love to talk to you about which trip might be right for you, what to expect, and how to take the first step. There’s no pressure and no obligation. Just a conversation.
Book a call with me here. Or email anna@oleganatravelboutique.com or call (917) 345-5792.
Frequently Asked Questions
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Most of our travelers arrive solo. By the second dinner, you won't feel like a stranger. The small group size is designed for exactly this: to create connection quickly and naturally. I've watched hundreds of women walk into day one not knowing a soul and leave day seven with lifelong friends.
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Most of our travelers are in their 50s and 60s, though we've had women in their 40s and 70s as well. There's no upper or lower limit. What matters is curiosity, openness, and a willingness to be present.
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Some of the most meaningful trips I've witnessed have been for women in the middle of something hard: a divorce, a loss, a life change. You don't need to perform happiness. You just need to show up. The group will meet you where you are.
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Group size (under 16, not 40), pace (intentional, not rushed), and curation (local relationships, not catalog excursions). I personally know every supplier, every guide, and every property. And I'm involved in the experience from start to finish, not handing you off to a third-party operator.
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Moderate. There's walking involved, and some days are fuller than others, but nothing is extreme. I design the itineraries so there's always an option to rest, skip, or go at your own pace. If you have specific mobility concerns, we'll talk through it before you book.
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As early as possible. Our Puglia tours sell out every year, and most 2027 tours will fill well before the travel date. If a specific destination is calling to you, reach out now. I maintain waitlists for sold-out tours and announce new dates to past travelers first.
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Many women add a few days before or after the group tour for solo exploration or a custom extension. I can design that for you too, whether it's a few days in a city, a spa retreat, or a side trip to another region.