Luxury travel experiences, tailored to you

Olegana Travel Boutique creates bespoke European 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

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 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 me plan your dream vacation where you can escape the mundane and experience an epic, one-of-a-kind adventure.

Why choose Olegana Travel Boutique?

Tailored Experiences

Every itinerary is a work of art, meticulously crafted to match your unique preferences and interests.
Exclusive Access

With insider knowledge and connections, I can provide access to hidden gems and exclusive experiences that are off-limits to most travelers.
Unmatched Expertise

Benefit from my extensive network and expertise in European travel to ensure a seamless, stress-free journey from start to finish.
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 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.

Book A Custom Travel Consultation

Join a Group Trip for Women

Founded by Anna Fishman, a visionary travel curator and passionate connector of women, Olegana Travel Boutique began by crafting custom itineraries for families and couples seeking authentic, elevated travel. Over time, Anna recognized something powerful: many women wanted to travel — not just to see beautiful places — but to reconnect with themselves, form meaningful friendships, and feel taken care of along the way.

This is how our signature women-only journeys were born.

Today, Olegana Travel Boutique offers both private custom travel planning and immersive group experiences to destinations like Italy, Spain, Scotland, and the Caribbean. Each itinerary is designed with intention: local flavor, refined comfort, cultural depth, and unforgettable moments. Our group journeys bring together like-minded women who value joy, connection, and saying “yes” to themselves.

Buy the dress. Eat the cake. Take the trip. ✨