Custom-planned European, Asian, African & Caribbean travel
I'm a luxury travel planner at Olegana Travel Boutique, specializing in one-of-a-kind custom Europe travel itineraries as well as Asia, Africa, and the Caribbean, tailored to your unique preferences. Whether you're dreaming of a bespoke European honeymoon, a private guided tour of Italy, or a luxury family vacation abroad, I'll handle every detail with care to ensure a seamless, unforgettable experience.
As your dedicated boutique travel agent, I'm here to turn your "maybe-one-day dreams" into an "it's-all-booked" reality.
Get ready for a journey that’s tailor-made for you!
Tell me your idea of the perfect getaway and let’s turn that vision into an unforgettable reality. Each detail of your adventure is meticulously crafted, from luxurious accommodations to pre-arranged transportation and private adventures to off-the-beaten path gems.
What our clients say
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![Couple honeymoons in Europe withe the help of Olegana travel]()
"I found Anna & Olegana Travel Boutique by chance and I'm so eternally grateful we found her!"
Stefanie Spector
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![Retired couple travels to Italy with the help of Olegana Travel Boutique.]()
"Anna and her team did a fabulous job of planning a trip to Italy in short time. The itinerary was great."
David Guida
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![Family participates in cooking class in Italy, arranged by Olegana Travel Boutique.]()
"I contacted Anna and she did an amazing job coordinating and scheduling both the cooking class and our day trip through Tuscany wine tours."
Linda Pollock
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![Photo looking out of kitchen into Italian landscape.]()
"Anna planned a beautiful trip to Italy for my family of 12! The experiences she arranged for us would have been very difficult to do on our own. "
Nicole Watson
Sample Itineraries
Click to get inspired:
Discover the Olegana Difference
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First-hand experience
I personally visit the places I recommend. I explore the world, get to know the destinations, accommodations, and service providers. I invest my time, money, and energy into traveling for research.
I go so you’re “in-the-know.”
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White glove service
One of my core values is to always “wow my clients” – under-promise and over-deliver. Every time.
From hand-curated hotels, private local guides, off-menu restaurant access, to the perfect honeymoon or an unforgettable family getaway.
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It’s all about who you know
Over the years, I’ve built strong relationships with local travel companies around the world. This means I have “boots on the ground” to create unique, off-the-beaten-path itineraries and provide immediate support if things don’t go as planned.
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I work for you
As an independent company, I’m not tied to any hotels or tour operators. I don’t have quotas to meet or rooms to fill – I choose the best hotels and tours based entirely on what’s right for you.
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No cookie-cutter itineraries
Every trip is custom-made for you, tailored to your needs, wants, and dreams. From custom trips to Italy, Portugal, Spain, and Africa to Japan, your perfect journey starts here.
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Authentic and off-the-beaten-path
With me, you’ll avoid the crowds and tourist traps. I design authentic itineraries that engage everyone in your family, from ages 5 to 85, with culturally immersive experiences and hands-on workshops
Meet Anna Fishman
––your trusted travel planner
Have you ever searched for “the best travel agent” only to be disappointed by the results? At Olegana Travel Boutique, I know you’re searching for a travel agent to take the stress away – not add more! That’s why booking with Olegana Travel is a no-brainer.
I’ll work with you to find the perfect vacation destination that checks off every box on your vacation list. I’ll design a custom itinerary tailored to everyone’s preferences, ensuring every detail is just right.
I’ll handle booking and logistics, so you never have to stress about the details—everything is organized and accessible in a simple app. Plus, I’ll be available to you throughout your travels so you can travel confidently knowing your trusted travel advisor is by your side.
Mention ‘Olegana’ for $100 off your trip!
Meet Jennifer Day
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.
Start planning your next trip
Let me craft your next adventure, tailored to your dreams and desires.
Grab a spot on my calendar, and let’s get started!