Raising a Glass with Lindsay

Lindsay Smith - Owner/Founder/Wine Nerd of Flight Cleveland

By: Woman Up Cleveland

Lindsay opened Flight Cleveland in December 2018 and since then has poured endless glasses of tasteful wines, hosted incredible events, and so much more.

Sharing a glass of wine between friends, acquaintances, or even strangers can be the key to forming meaningful connections from a place of deep understanding. Not only is it important to bring to the table a willingness to listen, but it can be equally important for us to feel heard by others. The idea of gathering and sharing is fundamental to our personhood, especially as women, and few understand this fact better than those in the hospitality industry.

A pillar of the community, Flight Cleveland has been lifting spirits and pouring wine for almost a decade. At its helm, Lindsay Smith has curated a space filled with intention and a comfort that welcomes all to unwind and uncork without any intimidation.

Growing up in a Chicago suburb, Lindsay’s life always contained a meaningful connection to togetherness and the importance a meal can play in creating a moment to gather. She absorbed and maintained these values all her life, proving that the root of the hospitality industry lies with a love for hosting. 

Choosing to further her studies and enter the workforce while living in Illinois, Lindsay gained lots of experience and knowledge about the industry before ever setting foot in Cleveland. She began her schooling with the goal of becoming a photographer and quickly decided, after working in restaurants, that there was a better path for her. Hosting, serving, and even working retail had Lindsay falling in love with customer service and the meaningful connections she was creating in her work.

After college, wanting to explore these feelings deeper, Lindsay enrolled in culinary school and got her degree. “I love being around food and wine. I grew up in a family that had a lot of respect and love for the art of dining. So it didn't surprise me that it became kind of an interest for me as well,” she said.

Her first few roles out of school were with various catering companies in the area. Following a mentor and a new opportunity, she finally found herself moving to Cleveland. On what she now calls a ‘whim’ Lindsay landed in a role in a new sector, contract trade service. She credits both of these steps in her journey with teaching her more about the in’s and out’s of service.

Their space is perfect for you to host your next gathering, just like our 'Cheers & Charms' event in July 2026.

Truly trying a little bit of everything, Lindsay began to flesh out her likes and dislikes, creating a clearer vision of her dreams. She shared, “All along that time I had this love affair with food. I had learned how to cook, I was spending a lot of time with chefs in my industry, and I was planning a lot of events. I started falling into a special events / catering coordinator kind of role early on and I really loved it and decided this was something I wanted to pursue a little bit more.”

Following the winding road of possibility and curiosity, Lindsay found herself gaining interest in the detailed and intentional world of wine. What started as a yearning to learn more and ultimately led to the completion of the Wine and Spirits Education Trust program, she was officially immersed. “I zipped through the first three levels of WSET in a year. I just really dove in and loved it and it was really fun. That was sort of the moment where I thought to myself ‘you're really enjoying the wine industry and learning more about it you should figure out how to get closer to it,’” she said.

Finally, wine had made its appearance in Lindsay's life and the rest was history. The dream of Flight began far before she ever realized and manifested from her combination of hard work, genuine curiosity, and willingness to learn. Lindsay spent somewhere around eight years imagining what Flight could become before ever bringing her visions to life.

Before the name, decor, and wine partnerships could come to life, Lindsay had to master the planning, saving, and learning of what it would take to make her dreams a reality. In December 2018, all of her dedication paid off when Flight opened its doors and became a staple of the neighborhood and Cleveland as a whole.

“I am very blessed and very lucky to put this thing together,”  Lindsay told us, “It started as a little whisper in my head and then all of a sudden I get to work in the wine industry in a way that feels very unique to me. I get to do it the way I want to do it and I think that's a lucky position that I find myself in. I love it. I think it's my favorite thing I've ever done.” 

Ten years after she originally moved here, Lindsay finally found herself as captain of her own ship and truly began to shine as the entrepreneur and connoisseur she had always been. As a truly knowledgeable and approachable person, she had built Flight in her own image. Every member of her team is hyper focused on creating an inviting and inclusive space for those who are both interested in wine or simply looking for a place to settle down for happy hour.

A photo of Lindsay stocking wine bottles.

Whether you’re a wine newbie or a seasoned pro, Flight offers a welcoming and serene space to enjoy some sips, snacks, and socializing. After all, it’s in the name. “I always wanted our menu to be composed of flights. The idea of our menu and the way that we do things is so specific to my hope and dream that the guests can approach us in a really easy way. I always felt a little intimidated by wine bars and wine information in general. So Flight to me from the very beginning has always been about approachability,” says Lindsay.

Knowing that wine trio tastings, named with fun puns or cutesy themes would be more approachable to most guests, Lindsay built Flights menu and offerings based on this idea of inclusivity and friendliness. Encouraging customers to try new things and get out of their comfort zone is a main focus as well. She told us, “We aim to take the pressure off the ordering process of wine which I think can be really stressful to people. We sort of opened up the idea that the adventure of wine and showing you things that you're not already familiar with is one of the most wonderful things about this industry. It's truly endless, there's so much out there to try and so many great people making great things.”

As she understands better than anyone, it is undeniable that the world of wine can be intimidating, exclusive, and even snobby, often deterring beginners from exploring their interests and expanding their experience. Lindsay aims to do away with this outdated approach to wine and she curates a space, menu, and energy that invites all to dive deeper and ask questions.

This extends to the entire Flight team as every bartender and staff member is willing and ready to help with anything a customer may need. Whether it be advice on a bottle to buy from the in house shop or a suggested pairing with your charcuterie spread, the experts at Flight are ready to help.

Even with an incredible team and the support of an inner circle, there is almost always more to be said about the importance of collaboration and partnership when building a business. Especially in such a community driven place such as Cleveland, brick and mortar businesses serve as more than just an exchange of goods and services. 

As a staple of Gordon Square, Flight has become a true gathering place for the community and Lindsay credits a lot of this to the people who saw something in her vision from the very beginning. She said, “There have truly been so many people who have touched this space in such a unique way and been part of this experience.” 

They center on education and discovery, truly hoping to take each and every guest on a beautiful wine journey the minute you enter their doors.

Lindsay describes herself as not only a prepared person but an organized one and admits the beginning of this journey had her feeling a bit out of her depth. When she started exploring spaces for rent and tackling renovations and contracting work, there was a definite learning curve that she credits a welcoming community with helping her navigate.

“I feel like there were a lot of people who saw something in this place and saw something in the idea and really believed in what I was doing. Early on when I was getting the whole thing going and we were just starting to build, I was thinking about who my team was going to be. I was introduced through mutual friends to someone who would become our general manager. His name was Matt Blink,” Lindsay told us of a special connection that impacted Flight in a way that lasted well beyond the early phases.

Eventually becoming a business partner of Flight, Matt really invested himself into the idea of the wine bar right away and hung on tight to his involvement, and subsequent friendship with Lindsay throughout the journey of building the space into what it is today. Lindsay spoke so highly of him saying, “Had some of the most amazing wine knowledge you'll ever experience. He’s just one of those people who hears it once and never forgets. Given this insane library and catalog of information in his head, he's just someone that had an amazing memory which made for an amazing way to frame his thoughts about wine and talk about wine.”

Matt became Lindsay’s other half when it came to running Flight and after his passing in 2022, she felt such a huge loss from someone who had believed in her and her vision from day one. Coming in with no connections and taking a chance on something new, Lindsay gives Matt his flowers for helping her create and maintain a thriving place for people to gather in the community.

“He really hitched his wagon to me and I feel so lucky because he very much influenced what Flight is today. His mark is still here which is one of the luckiest things I could say. He was one of the most influential people in my world when Flight opened and still to this day,” Lindsay said.

During the turmoil that accompanied grief and an ever changing business structure, Lindsay found herself in the caring hands of her sister, Charlotte, who stepped in to help in any way she could, eventually becoming Lindsay’s business partner. “Now she kind of runs our whole financial package behind the scenes. If we had titles like a company, she would be the CFO.  She's done so much work for the business to get us to this place where we're financially responsible and comfortable and doing all the right things. Her brain is amazing to me because I'm the creative and she's so good at the technical stuff,” she said.

Lindsay went on saying, “Watching her work and not just be my sister, but help me shape Flight as a business has been a really really amazing experience. I wish in all of my heart that I had her with me the whole time and she had been doing her role from the beginning. But people come in when they're supposed to. That was an interesting transition time for me and she stepped in and totally changed us which was amazing.”

With her sister Charlotte, Lindsay has seen the way that a trusted confidant can help ease the roughness of change and transition in a business. It has shaped her and Flight and has carried on the legacy that began with Matt’s initial faith in the success of this idea. The welcoming energy Matt embodied from day one can be found in so many throughout Cleveland and is such an essential part of what makes entrepreneurship in all industries so successful here. Lindsay knows well that thoughtful and creative collaboration can be transformative and for her, proved to be the key to a successful venture. 

She went on to name countless chefs in the area such as Jill Vedaa, Liu Fang, Tom McIntyre, Doug Katz, Dave Kokab, and Marie Artali, all of which have partnered with Flight throughout the years. Lindsay told us, “The list goes on and on of all these incredible people that I've had the pleasure of getting to do fun projects with. I'm just constantly amazed by the folks that come through this place and how people find ways to be creative with us here in our space. It's really lucky and I've had some amazing conversations and amazing learning moments from a lot of these folks too because everyone here in Cleveland is so willing to share and help.”

Lindsay ended up in Cleveland with the idea that she wouldn’t stick around for long and that she would see where the wind takes her. Now, nearly two decades later, she has put down lasting and impactful roots in the community and continues to praise all of the camaraderie and support that got her here. She said it best, telling us, “I am very Cleveland all the way. It's a pretty amazing place that really surprised me with how much I fell in love with it and how much I feel part of the hospitality scene here.”

This love for the community that has shown up for her has translated into the way Lindsay runs her business. Embracing the inclusivity and sense of togetherness has influenced Flight to become a place of peace and comfort. She describes her initial visions for the space as being different from the traditional dark, swanky, and moody wine bar. Instead, Lindsay’s goal has always been to make Flight feel like a home away from home.

She describes the aesthetic as cozy, bright, relaxing, and filled with authentic and warm people. Truly balancing the luxury of being taken care of and the comforts of your own home, Lindsay has curated the perfect in between and a well rounded experience.

Soft lighting, lots of foliage, and welcoming energy complete the space and transport guests to a place that feels both new and familiar. With an almost silly way of naming and branding her menu, Lindsay has captured the essence of feeling right at home among others. The patio especially is built to embrace Cleveland summers and is often packed with people enjoying their after work happy hours or spontaneous weekend plans with others.

Lindsay knows better than anyone that aesthetics can help dictate feeling, but ultimately, the interactions guests have with staff and each other is what can make or break their experience. She said, “You want to make sure that we're being really kind to people because I think we've all been to a restaurant or a bar somewhere where we don't get acknowledged when you walk in the door. You're not sure if you see yourself or if you should be waited on and you don't know what you're supposed to do when you walk into a space. We want to make sure that we're getting in front of people right away and understanding how they want to use the space in that moment and then directing them to where they need to go.”

She hopes more than anything that Flight feels bright and lively with an  overall positive energy. The bar's ability to accommodate any type of person with any motive for walking through the doors is astounding and truly reminds us that hospitality is all about the guest experience. At the end of the day, those drinking and dining at Flight feel a sense of belonging and relaxation that is a direct result of Lindsay’s keen ability to stay true to her vision and execute the perfect blend of inclusivity and curiosity.

Pulling back the curtain on the hospitality industry, Lindsay wants people to know that not only is it not a life of glitz and glamour (as most entrepreneurs can attest to) but that the everyday workings are not as straightforward as some may think. Her daily responsibilities for example often include errands and bar management. Lindsay aims each day to set her team up for success in whatever ways they need and acting as a support system providing the tools and encouragement needed to ensure a positive guest experience.

When it boils down, hospitality has a specific energy that someone can either love, or feel isn’t for them. Those who embrace this feeling, and its often accompanying chaos, really allow the job to become a part of them and value creating space for others. As with many roles in service based industries, without that deep pull to host and enhance an experience, it can feel grueling and without purpose to work in service of others.

Enjoy a beautiful Cleveland evening on their patio complimented by a sip + snack.

Lindsay embodies the spirit of what it means to serve others and create a place for people to unwind and truly embrace the experiences available to them in life. She told us, “I love the fact that I have an opportunity to be one of those people that's creating an experience for guests. It's such a privilege.”

Understanding the difficulties that can accompany this career as well has only deepened Lindsay’s love for her craft, “It can be a very challenging thing too and I think maybe I had some Rose Colored Glasses on when I was starting a business about what it was going to entail. But gosh, it's so fulfilling and rewarding and I still pinch myself even now, and feel so delighted when people come in,” she said.

Ultimately, Lindsay is so obviously the perfect candidate for this exact role and it all leads back to her unwavering sense of values. She continues to put much of what she first learned and cared about in the beginning of her journey at the forefront of her work today. Further proving that she is a natural in this industry, Lindsay continues to hold herself at an incredibly high standard, ensuring that her guests at Flight are receiving nothing but the best possible experience from the moment they enter to the minute they leave.

“I'm so enamored with the people that come here. I'm so grateful for them that they enjoy the space the way that they do. It brings me so much joy,” Lindsay said.

Finally, we asked Lindsay a fun question that we couldn’t resist, given her background: if you could share a glass of wine with any woman, who would it be and why? Her answer, as expected, was incredibly suited to all that we had discussed previously and even further proved just how meant for this life she is.

“Picking a historical figure, I would have to go with Julia Child. I'm blown away by her in so many ways and her life was just one trailblazing moment after the other. She was doing things that women were not doing at that time. She just seemed not to care what other people thought and just did the things the way she wanted to do them,” Lindsay answered.

Someone who knew the importance of food in our lives and the value cooking can bring to gathering and sharing is the perfect example of Lindsay’s understanding of hospitality and her welcoming nature. Fascination with the way Julia lived her life along with a desire to learn more about the choices she made makes her an easy choice for Lindsay’s dream wine chat. She has such an appreciation for this piece of food history and knows that the life she holds herself today is a direct result of Julia’s impact on the world.

She then went on to tell a more personal story of why she would choose her grandmother as a wine drinking partner. Having been too young to do so before her passing, Lindsay was glowing at the idea of being able to share a glass and chat with her beloved grandma about just about anything. Comparing her lovingly to Julia Child for her sense of family and value of the dining experience, Lindsay knows her grandmother would love to hear about the concept of what she has created today.

“Just so ahead of her time and so progressive and I think she would be so curious and interested in what I'm doing today. If we sat down and had a glass of wine to talk about it all I think that would be one of my favorite conversations that I would absolutely love to have,’ Lindsay said.

The whole idea of enjoying a glass of wine is the basis for not only Flight’s entire business model, but at its core, the hospitality industry as a whole. The idea of a third space, being somewhere besides home and work for people to unwind, is most clearly present in places like Flight. A true hub for the community and destination for all those in Northeast Ohio, the wine bar has perfected the art of a welcoming and approachable meeting place. 

Aiming to make wine more accessible and less intimidating has also resulted in the creation of a sanctuary for people to relax, celebrate, and feel the coziness of lounging at home mixed with the luxury of elevated dining service. Lindsay Smith has expertly built a haven for sommeliers and beginners alike. A self proclaimed ‘wine nerd’ she understands not only the unique complexities and beauty of the beverage, but also the casual and laid back nature of gathering over food. She is eloquent, knowledgeable, friendly, and creative, leading the way for an excellent team of experts to help her serve the community. It was a privilege to hear her story and that of Flight's creation and we are so thrilled to be hosting our July networking event in their lovely space!