Meet Anna Fishman

We’re excited to introduce you to the always interesting and insightful Anna Fishman. We hope you’ll enjoy our conversation with Anna below.

Anna, so good to have you with us today. We’ve always been impressed with folks who have a very clear sense of purpose and so maybe we can jump right in and talk about how you found your purpose?

Early on in my life, I knew that travel was my passion and that seeing the world was such an important part of my personal and professional lives. After spending many years in the “corporate world,” 9 years ago I had the courage to start my own travel business and share my joy of travel with others. It wasn’t until after the COVID pandemic that I finally found my purpose – bringing together a small group of women who share their love for European travel. Since then, I’ve built a community of like-minded women (we’re over 200K+ strong on Facebook!) who share my passion for uncovering new off-the-beaten-path experiences in Italy, Spain, Scotland and more. Seeing their smiling faces during our small group trips and hearing from women about how transformational the experience has been for them makes it all worth it for me.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

I’m the proud mastermind behind Olegana Travel Boutique, a boutique travel company offering custom-curated trips for families and couples to Europe and authentic, luxury small group tours for women.

I live for family adventures with my travel-loving husband and our two little jet setters in training. With 31 countries under my belt, I’ve combined my personal globetrotting escapades with the expertise of local destination gurus. My secret sauce: being born and raised in Europe adds that extra sprinkle of charm to every adventure.

My team and I offer white-glove travel planning services, where every detail is handled with precision and care – all you have to do is look forward to waking up in Europe filled with anticipation and excitement.

I am very excited about our newest small group trip for women that has JUST launched – “Wine, chocolate, and you – in Sicily!” which will take place on October 5 – 13, 2025.

Because of overwhelmingly positive client feedback and how popular these women-only trips are, we’re also repeating our trips to Puglia, Italy in 2025 and 2026. I invite you to join us for an unforgettable adventure in Italy!

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

I think the most important qualities and areas of strength for me have been my grit and determination, and an unrelenting pursuit of delivering the most epic, one-of-a-kind adventures for my clients. I take the time to really listen and read between the lines to understand what it is that’s going to have the “Wow!” impact. I always try to under-promise and overdeliver because I know just how much it means to my clients to have that amazing trip of a lifetime with their loved ones. I’m always working on building new connections with our travel partners in destination, and I travel a lot to visit hotels and resorts firsthand.

My advice is to never stop learning and growing your business – put your fears of failure aside and try something new even if it’s scary and you’re not sure if your idea will succeed. Sometimes the best ideas seem wild and crazy at first, but in retrospect they are the universe’s way of telling you to lean in and embrace the next stage of your journey. Don’t focus on what others in your industry are doing, even if they seem to be more successful than you – keep your blinders on and be unapologetically you.

All the wisdom you’ve shared today is sincerely appreciated. Before we go, can you tell us about the main challenge you are currently facing?

Sometimes we are our own worst obstacles (and critics!) in business and in life. My focus recently has been on giving myself permission to dream big and then being intentional about putting in the hard work to make my dreams happen. Not having a Plan B for your next wild idea can be liberating. I knew I wanted to take a group trip to Venice in December because it has always been my dream to come back to Venice and see the city decorated for the holidays. It took over a year but I finally made it happen – I am so excited to take a small group of women this December to experience the beauty of Venice and the magic of the Venetian Carnival.

As women, we have to overcome the challenge of self-limiting ourselves and give ourselves permission to do all the amazing things that bring us joy and fill our cup. Buy that dress, eat that cake, take that trip – and leave the guilt behind.

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