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Inspiring Conversations with Michelle Yoshinaka of Many Escapes

Today we’d like to introduce you to Michelle Yoshinaka.

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
Many Escapes was born from my love of wine, travel, and the desire to live with intention. What started as sharing stories from wine regions and European cities has grown into something more: a reflection on how we experience joy, connection, and place.

As a WSET Level 3 certified wine professional, I’ve become fascinated by how wine connects people and tells stories about culture and family. I’ve also learned that you can enjoy wine fully while still prioritizing wellness—it’s about appreciation over excess, and taking the time to slow down.

Many Escapes is a space for people who share that mindset, or want to. It’s a gathering place for stories that inspire you to travel intentionally, sip mindfully, and live fully.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It’s been challenging in many ways. I started Many Escapes while juggling another career—and then I changed careers. Add family life and two kids heading to college, and finding time to post consistently has been my biggest struggle.

I’m also solo on this journey, which I love but can be isolating. Bringing creative ideas to life requires a lot of initiative and I’m not skilled at every aspect, so finding the right partners and collaborators is important and takes time and effort.

And, although my background is in marketing, marketing for clients is very different from marketing myself. It’s easy to hide behind a post and not expose your actual self. I finally started showing up in the stories and photos, and it was hard at first. It’s certainly very vulnerable. But over time it began to feel more natural now.

That said, when I’m in the process of creating a post, I find myself in a flow state. Time disappears. I’m deep in the work of bringing my experiences and perspectives to life to share with others, which I love. Those moments remind me why I’m doing this. It’s an ongoing journey, but it’s worth it.

Alright, so let’s switch gears a bit and talk business. What should we know?
Many Escapes is more than a blog. It’s become the foundation for my career and my passion. As I dove deeper into exploring Italy through wine and travel, I realized I wanted to buy a home there some day. Looking into it further, I realized the process of finding property, navigating legalities, and understanding the market was incredibly complicated. I saw an opportunity to use my interest to help others.

I decided to make a shift, got my real estate license and my CIPS (Certified International Property Specialist) designation, and then vetted and set up meetings in Italy with brokers in two regions I had never visited. I flew to meet them in person a few months later. I wanted to connect and build relationships with people on the ground who I could trust to support my clients.

I’m now a real estate agent with Compass, helping buyers and sellers in San Francisco’s East Bay, specifically Lamorinda (Lafayette, Orinda, Moraga). I’m also set up to support clients interested in finding a second home or relocating to Italy.

What sets me apart is my blend of experience, desire to learn, and a belief that there’s a way to live life that honors both enjoyment and wellness—with grace when we don’t get it perfect. I approach things in a grounded, unpretentious way that makes people feel comfortable and genuinely supported.

What has been the most important lesson you’ve learned along your journey?
I’ve been working on Many Escapes for years and I’ve learned two important lessons. First, things don’t happen overnight. We often see the end result of someone’s years of hard work, but we forget the “years of hard work” part. It takes consistency and commitment to build something meaningful.

Second, any idea is bound to shift over time. There are bends in the road that begin a new path. Approaching Many Escapes with the understanding that it’s going to evolve makes it more fun, brings more ease, and keeps me open to new opportunities—the ones that are connected, but often unexpected.

Contact Info:

Woman with long brown hair smiling outdoors, wearing a dark blazer over a white shirt, with trees in the background.

Cliffside overlooking the ocean with clear blue sky and calm water, rocky terrain with green vegetation in foreground.

Vineyard with rows of grapevines, green trees in background, clear blue sky, and open field.

Cliffside buildings with white and beige facades overlooking a small beach and the sea under a clear blue sky.

Woman sitting on a stone wall with ancient hillside buildings in the background, wearing sunglasses, a dark jacket, and white pants.

Stone archway opening to a scenic landscape with trees, a building, and distant mountains under a blue sky.

Pasta with meat, garnished with purple and yellow edible flowers, on a gray plate, with a glass of white wine in the background.

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