Luxury travel experiences, tailored to you
Olegana Travel Boutique creates bespoke European, Asian, African, and Caribbean vacations for couples and families, and intimate small-group journeys for women. We handle every detail with care, so you can stop stressing over research and simply arrive and exhale. Give yourself permission to travel boldly and beautifully.
Meet Anna Fishman
Europe & the Caribbean specialist
Hi — I’m Anna, the founder of Olegana Travel Boutique. Born and raised in Europe and now traveling the world with my husband and our two little explorers, I bring insider knowledge, trusted local partners, and a passion for meaningful experiences.
With 33 countries (and counting!) under my belt, I design trips that feel personal, seamless, and extraordinary — no crowds, no tourist traps, just beautiful moments.
Olegana Travel Boutique is a luxury travel design studio specializing in bespoke European, Asian, African, and Caribbean vacations and intimate small-group journeys for women. If you’re overwhelmed by planning and endless Google searches, you’re in the right place. We handle every detail with care, so you can simply arrive and exhale.
What We Offer
• Custom luxury itineraries
• Curated women-only small-group journeys
Buy the dress. Eat the cake. Take the trip. ✨
Let us plan your dream vacation where you can escape the mundane and experience an epic, one-of-a-kind adventure.
Meet Jennifer Day
your Asia & Africa specialist
Hi — I’m Jennifer, the owner and lead advisor at Destination Days Travel. I’ve spent my life exploring our beautiful world, and I’m passionate about designing journeys that truly change perspective.
My love for travel began with a teaching position in Japan that was meant to last a couple of years, but turned into nearly a decade of living and exploring across Asia. That experience shaped the way I see the world and ultimately led me to turn in my classroom keys and build a career in travel.
I specialize in bespoke journeys throughout Asia and Africa, crafting immersive experiences that go far beyond a typical vacation. From private safaris and conservation-focused camps in Africa to culturally rich itineraries across Japan and Southeast Asia, I design trips that are intentional, meaningful, and transformative.
As a mother of three, I believe deeply that shared experiences and time together are some of the most valuable investments we can make. Travel has the power to expand horizons, strengthen connections, and shift the way we see the world, and I love helping my clients experience that for themselves.
Whether it’s a life-changing safari, a culturally immersive journey through Asia, my goal is always the same: to create travel that inspires, connects, and stays with you long after you return home.
Mention ‘Olegana’ for $100 off your trip!
Meet Tracy Schatz:
your luxury cruise specialist
My personal journeys have taken me to more than 30 countries and I'm a passionate advocate for the power of travel as a means to strengthen our connections with one another. By stepping out of our comfort zones and exploring new places, we can break down barriers and cultivate a deeper understanding and empathy for different cultures and ways of life.
Whether it's through exchanging smiles with locals in a remote village, sharing a meal with new friends in a bustling city, or simply witnessing the stunning landscapes that our planet has to offer, I am committed to promoting travel as a powerful tool for unity and connection. Let's discover the beauty and diversity of the world together.
Mention ‘Olegana’ for $100 off your trip!
Why choose Olegana Travel Boutique?
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Tailored Experiences
Every itinerary is a work of art, meticulously crafted to match your unique preferences and interests.
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Exclusive Access
With insider knowledge and connections, I can provide access to hidden gems and exclusive experiences that are off-limits to most travelers.
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Unmatched Expertise
Benefit from our extensive network and expertise in tailor-made travel to ensure a seamless, stress-free journey from start to finish.
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Privacy is the New Luxury
You’ll enjoy private tours, seamless transportation, and a curated selection of hotels that offer stunning locations, impeccable service, and unforgettable memories.
Discover the Olegana Difference
Whether you want to sip wine in a sun-drenched Italian vineyard, explore charming coastal villages, wander historic cobblestone streets, or simply wake up each day with excitement — we’re here to make it seamless, personal, and extraordinary.
Olegana Travel Boutique is a luxury travel design studio specializing in bespoke European, Asian, African, and Caribbean vacations and intimate small-group journeys for women. If you’ve ever found yourself with 24 tabs open, overwhelmed by Google searches, or unsure where to begin planning your dream trip — you’re in the right place. Here, travel planning is a white-glove experience. Every detail is curated with care, so you can simply arrive and exhale.
Buy the dress. Eat the cake. Take the trip. ✨
Learn What it’s Like to Travel with Us
Need restaurant recommendations in Italy?
Dozens of restaurant recommendations from Venice to the Amalfi Coast, from Milan to Rome, from Cinque Terre to Florence – we’ve got you covered!