How a girl from Ukraine, a career in tech and one trip to Scotland became a luxury travel company.
I want to tell you something true about myself before I tell you about Olegana.
Travel has never been a line item in my life. It isn’t a reward for a hard quarter or a list I’m working through. It’s what I reach for when I want to feel most like myself.
Anna Fishman, the founder of Olegana Travel Boutique
Photo©: Anna Fishman / Olegana Travel Boutique
I travel to celebrate. I travel to process. I travel when I’m happy, when I need perspective, and when I just need to be somewhere other than where I’ve been all week.
“Travel. It’s always been travel. I travel to forget, I travel to celebrate. I just travel.”
— Anna Fishman
Lake Orta in Piedmont, Italy, with scenic views of San Giulio Island across the tranquil lake.
Photo©: Anna Fishman / Olegana Travel Boutique
I said that in a podcast conversation about giving yourself permission to travel, and it’s still the truest thing I know about myself. It’s also the most honest answer to why Olegana exists.
Where the story starts: from Ukraine to New Jersey
Anna Fishman, the founder of Olegana Travel Boutique
Photo©: Dania Sander / Unique Focus Photography
I came to the United States from Ukraine as a child, with my parents and my grandparents. I’ve talked about that move on my podcast, and what I keep coming back to is how much it shaped the way I see the world.
Starting over in a country that didn’t know you yet gives you a particular relationship with place. You learn what it feels like to land somewhere unfamiliar and find your footing. You learn that a city can become yours even when it wasn’t yours to begin with.
That’s probably why foreign places never intimidated me. Not knowing the language, the customs or the right neighborhood was always something to lean into, not around.
Leaving a career in tech to build something of my own
Anna Fishman, the founder of Olegana Travel Boutique
Photo©: Dania Sander / Unique Focus Photography
I grew up, earned my MBA, and built a career in tech advertising and compliance at a fast-moving company that had just gone public. I got married and became a mother. For years, travel was what I did between everything else.
Slowly it became clear that travel was the thing I wanted to build everything else around.
It all came together in 2015, the year my baby was born and the year I started Olegana. I had an MBA and a strong record at work I didn’t love as much as I loved travel. I wanted something of my own, with real stakes and real expertise. And I wanted to be there for my baby, which a fast-paced tech job didn’t leave much time for.
Park Güell in Barcelona, Spain, with Antoni Gaudí’s iconic mosaic-covered pavilions and colorful architectural details in the background.
Photo©: Anna Fishman / Olegana Travel Boutique
I’ll admit how it actually started: I typed “how to start a travel company” into Google. But building something from the ground up, without a playbook or a team or anyone to tell you what step three is, takes a particular kind of stubbornness.
Oleg and Anna
Oleg and Anna
Photo©: Anna Fishman / Olegana Travel Boutique
My husband, Oleg, believed in it before it had a name. That matters more than I can say.
The name came from him, too. Olegana: Oleg and Anna. It’s a small thing, and also not a small thing at all.
The trip that started the women’s trips
Olegana Travel Boutique’s 2022 women only Scotland group tour: Exploring Scotland’s historic landmarks, scenic landscapes, and charming towns.
Photo©: Anna Fishman / Olegana Travel Boutique
The women’s trips began with my best friend and a story we both loved. We planned a trip to Scotland to see it for ourselves. Word spread, more women asked to come along, and by the time we left there were eighteen of us.
That trip changed what I thought Olegana could be. I came home wanting to do it again, with groups small enough that every woman could sit at the same table. Today our women’s trips are sixteen at most.
The friendships last. Two women who met as strangers on one of my Scotland trips are now joining me for their fourth trip together.
What Olegana Travel Boutique became
What I built is a boutique luxury travel company with two sides that come from the same place.
Custom trips for couples and families
Anna and family.
Photo©: Anna Fishman / Olegana Travel Boutique
The first is custom travel for couples and families who want a trip that reflects who they actually are. Not famous stops checked off in order, but a trip built from a real conversation, with the right hotels, the right guides and the right pace.
Someone is looking after every detail from the moment you leave home to the moment you’re back. I specialize in Europe and the Caribbean. I’ve traveled to 34 countries, and I know the places I plan firsthand.
Small group trips for women
Olegana Travel Boutique’s spring 2026 women only Castles and Gardens UK tour
Photo©: Anna Fishman / Olegana Travel Boutique
The second is our women’s group trips: small, carefully planned journeys to places I know and love. In 2027 that means Puglia, Venice and the Prosecco Hills, the castles and gardens of Britain, and the Dolomites and Lake Garda. In 2028 we go further, to the Caribbean and Japan.
The women who come are curious, accomplished and ready to step out of their everyday roles for a week or two. Many of them travel solo. Most of them leave as friends.
A team for the rest of the world
Jennifer Day and Tracy Schatz
Photo©: Olegana Travel Boutique
For the places outside my own specialty, I work with two advisors I trust completely. Jennifer Day plans Asia and Africa, from private safaris to Japan, and Tracy Schatz plans river and ocean cruises. Both bring the same firsthand depth I bring to Europe and the Caribbean.
If any of this sounds like you
Tell me where you want to go and how you like to travel. I’ll show you what it looks like when a trip is designed around you.
Email: anna@oleganatravelboutique.com or call: (917) 345-5792. For the women’s trips, book a call with me.
One client put it better than I could:
“Before working with Anna, I spent HOURS properly researching vacation destinations. Her firsthand experience and knowledge were priceless.”
- Marina D.
What more than ten years of this work has taught me
Photo©: Dania Sander / Unique Focus Photography
I’ve planned hundreds of trips. I’ve walked the properties, tasted the menus, and sat across the table from the hoteliers, guides and local families who make the difference between a good trip and an extraordinary one.
I’ve rerouted clients stranded at midnight. I’ve secured rooms that weren’t listed as available. That’s the part of the work nobody sees, and it’s the part my clients remember.
The most important thing I bring isn’t a contact list, though that matters. It’s judgment: understanding what someone actually wants, which is sometimes different from what they first describe, and building a trip that fits them so well it feels made for them. Because it was.
The details I never skip
Photo©: Dania Sander / Unique Focus Photography
I plan around jet lag. Nothing is scheduled early on a first morning. When an overnight flight lands at dawn, I book the room from the night before, so it’s ready when you arrive instead of in the afternoon.
I talk to every woman before a group trip. Each one has a one-on-one video call with me before she joins, so I know the group will work and she knows exactly what she’s coming to.
I stay close while you travel. When I’m not hosting a trip myself, my host sends me photos and a short note every evening, so small things get adjusted while the group is still there.
I go first. I see the places I recommend with my own eyes, and I keep going back, because hotels change and so do the people who run them.
Who I do this for
My clients’ trips look completely different from each other, but the people share a few things.
Olegana Travel Boutique’s spring 2026 women only Castles and Gardens UK tour farewell dinner
Photo©: Anna Fishman / Olegana Travel Boutique
Couples who care more about how a trip feels than how many places it covers.
Families who want everyone, from the grandparents to the youngest, to come home happy.
Women traveling solo or with a friend who want company, a host and a plan, without giving up their independence.
Experienced travelers who know the difference between a trip that looked good on paper and one that actually felt right.
Olegana Travel Boutique’s Honeymoon Clients in Santorini, Greece: Celebrating their romantic getaway amid the island’s iconic whitewashed buildings, blue-domed churches, and stunning Aegean Sea views.
Photo©: Anna Fishman / Olegana Travel Boutique
What they have in common is that they want someone they can trust completely, so they can be present for the trip instead of managing it. They believe, as I do, that the best travel isn’t an escape. It’s a way back to yourself.
Why it still matters to me
People sometimes ask whether planning other people’s trips has changed my own relationship with travel. Honestly, it’s done the opposite.
Every client who calls to say a trip was more than she imagined reminds me what this is about. So does every woman who boards a plane to a place she never thought she’d go without her family, and comes home a little different.
Travel did that for me, and it still does. If you’re wondering whether you need someone like me at all, I’ve written about why smart travelers work with a luxury travel advisor. And if you already know, I’d love to hear where you want to go.
That’s Olegana.
Anna Fishman, the visionary and soulful force behind Olegana Travel Boutique, orchestrates transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Let’s plan something worth going on
Whether you’re dreaming about a trip for two, a family journey or a week with a small group of women, it starts the same way: a conversation about what you want the trip to feel like.
Custom trips for couples and families. Small group trips for women. Whatever you’re dreaming about, let’s talk.
Email: anna@oleganatravelboutique.com or call: (917) 345-5792. For the women’s trips, book a call with me.
About Olegana Travel Boutique: frequently asked questions
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Olegana Travel Boutique is a luxury travel company founded by Anna Fishman and based in Ridgewood, New Jersey. It designs custom trips for couples and families, mainly to Europe and the Caribbean, and hosts small group trips for women of sixteen at most.
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I’m the founder and lead travel advisor at Olegana. I came to the United States from Ukraine as a child, built a career in tech advertising and compliance, and started Olegana in 2015. I specialize in Europe and the Caribbean.
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It combines two names: Oleg, my husband, and Anna. He believed in the business before it existed, and the name came from him.
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I plan Europe and the Caribbean myself. Jennifer Day plans Asia and Africa, and Tracy Schatz plans river and ocean cruises. Our women’s group trips go to Europe, and from 2028 to the Caribbean and Japan as well.
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Yes. We’re based in Ridgewood, New Jersey, and plan trips for clients across the United States and beyond.
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It starts with a call. Tell me where you’re thinking of going and how you like to travel, and I’ll tell you honestly how I’d approach it. For the women’s trips, there’s a short application and then a one-on-one video call with me.