Why Dinking Alone Can Be Your Wine Connection Transformation With Tsvety Roo

Feeling intimidated by the idea of solo travel or dining out alone? Episode 37 of the Everyday Sommelier podcast is your go-to guide for transforming solo wine tasting into a gateway for genuine connection and cultural immersion. Host Kristi Mayfield welcomes seasoned solo traveler Tsvety Roo, who shares her real-world experiences leveraging wine tasting as an effortless “ice breaker” on journeys across Spain, Portugal, South Africa, and beyond.

Learn how to break through the awkwardness of dining solo, shift from loneliness to empowered solitude, and use the communal spirit of wine to meet locals and fellow travelers—no matter where your journey takes you. Get practical, confidence-boosting strategies to help you put down your phone, strike up meaningful conversations, and make every glass of wine a celebration of both self-discovery and connection.

If you’ve ever worried about being “that person” alone at the bar or felt anxious booking a wine tour solo, this episode will give you the actionable wine travel tips and mindset shifts you need to create memories (and friendships) that last a lifetime.

BY THE TIME YOU FINISH LISTENING, YOU’LL DISCOVER:

• How solo wine tastings can transform loneliness into meaningful connections and community—anywhere in the world
• Practical strategies to overcome common fears of eating or drinking alone, including actionable conversation starters
• Why putting down your devices is key to creating both self-connection and real-life interactions over wine
• Proven tips for booking wine tours or tastings solo—and how to make the most of every experience, even as the “odd one out”

TIMESTAMPS:

00:08:14 – Overcoming Fear: How to Stop Feeling Judged When Dining Solo
Discover the mindset and simple steps to escape the fear of being alone—and turn solo dining into a confidence-building experience.

00:11:28 – From Loneliness to Empowered Solitude with Wine
Learn the powerful distinction between loneliness and solitude, and how solo wine tasting can be a path to inner peace and connection.

00:14:09 – Real-Life Connections: Using Wine to Meet Locals & Travelers
Unlock practical ways to start conversations and make lasting friendships—plus how a single glass can lead to a day of adventure with new friends.

00:20:28 – Top Solo Traveler Wine Tasting Tips You Can Use Anywhere
Hear Speti’s proven tips to build connections in any tasting room, wine bar, or international setting by putting away distractions and being open.

00:23:06 – Book That Tour: Why Solo Wine Experiences Are Easier Than You Think
What to expect, how to make the most of group wine tours as a solo guest, and why you may not be the only solo adventurer in the room.

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Transcript

Kristi Mayfield (00:00)
Solo travel sounds glamorous. Just you, your suitcase, and a world of possibilities. I know what you're thinking. Maybe for someone else. But for me, seriously, I would feel intimidated, lonely, awkward. People would stare at me if I was sitting at a bar or restaurant having a glass of wine alone, wouldn't they? Walking into a restaurant alone while everyone else seems to be paired up.

not for me. Wanting to meet locals or connect with other travelers but not really knowing how to break the ice? Well the good news is wine can be your common denominator, an invitation to connect, a universal language that transcends borders and opens doors. And my guest today is going to share tips you can take on every adventure with you so you never have to worry about dining alone

or traveling solo, but you can leverage the communal elements of wine to transform your next journey.

Kristi Mayfield (01:28)
Throughout my 20 plus year corporate career, I spent more time on the road traveling internationally than I did at home a lot of times. Well, at least it felt that way. Most of the time though, I would find myself flying solo when it came to dinner plans or weekends. And I'd simply pack my iPad or a magazine, head out to a local spot and spend my time catching up on a movie or a great article. What I didn't do was leverage the time and experience to meet new people.

over a glass of wine. Had I met today's guests during that time, I would have totally taken a different approach to solo traveling and solo dining. And you should too.

Kristi Mayfield (02:09)
My guest today has explored the world from South Africa to Portugal, from Spain to France, and all over the US as a solo traveler. And regardless of her location the culture she's exploring, Tsvety Roo has learned wine can be the common denominator, the universal language, and the start of lifelong friendships. So Tsvety welcome to Everyday Somalia. I am thrilled to have you.

on the show today. And I would love for you to just give a little bit of background on how solo travel not only transformed your world, but also how that transformed into a wine journey as well.

Tsvety Roo (02:54)
Thank you. of all, Kristi thank you so much for having me on. Whenever there's an opportunity to talk about wine, I am there. This is incredible. And so, yes, I've been a solo traveler for two and a half years now, I was doing very much the traditional lifestyle back in the States. My last permanent home was in San Diego. California has amazing wines as well, you know, both of us know.

And so I started ⁓ to travel and the idea of a solo traveler when I gave up my apartment and I just put everything in storage and I set on this journey. And the first year for sure, I made it a point to whatever city that I was going to. And sometimes there were specific cities that are very wine focused, like Bordeaux, France, to go to wine tastings.

Because as a solo traveler, that's one of my my tips to people is to say if you are missing that connection with people and Sort of find yourself a little bit lonely on your travels ⁓ Definitely sign up for wine tasting in that new country and you are gonna find You're gonna meet so many different people there. It's it's gonna open up the conversations about where they've traveled from how you got

to that specific country and you're sipping on some wine, maybe your cheeks are getting a little red and all of the sudden you become best friends, which is exactly what happened. So my first destination as a solo traveler and I've never had never been there before to that specific city, it was Malaga, Spain. And I spent a month there as by myself, didn't know a soul.

I just, that was so scary for me to do, but I knew that I didn't have anything to go back to, because that's how I structured it. Like I said, I needed this huge change and it was to start traveling because I finally dug deep inside myself to figure out that it was a dream that I was stifling. And so when I finally...

Kristi Mayfield (05:12)
how.

Tsvety Roo (05:15)
you know, ask myself the question, what have I been putting off to do? What has been just ⁓ on the back burner? I was too afraid. was so afraid to touch that part. And then finally, when I tried to basically address it in so many different ways, nothing else was working. And so I had to face myself and I had to ask some important questions. And when I did that, I realized I really wanted to see the world.

And I said, okay, then you know, everyone else is busy. Everyone else has got their own thing going. I'm just going to do it by myself and see how it goes. And I thought it would be only three months. It's two and a half years now. So it evolved quite a bit. And so that from that first point, Malaga, Spain, I went to a wine tasting. By the way, Alberino wine is my absolute favorite. It's not from that region of Spain though. It's from Galicia.

From the northern west part of Spain is alberino. I hope that's correct. I'm not a sommelier ⁓ but Yeah, and I met a wonderful person she has transformed my life ⁓ as one of my closest friends and ⁓ She just we met on the very last day in Malaga with this wine tasting. We spent ten hours together and ⁓ Like after the wine tasting we went

We got some whiskey and she's Australian Completely kind of different world. She looks very different than I do It's like much shorter and like blonde and yeah, I was just like how how We would have never met Had it not been this wine tasting and had she not sat down on the bus next to me like for his gum Jenny when they were meeting in the movie and and then

Kristi Mayfield (07:07)
Hehehehe

Tsvety Roo (07:13)
She was so pivotal in just helping me. had a situation in Lisbon and I just called her up and I said, can I come back to Malaga and stay with you? And that was like a year into our friendship. it just such deep bonds that can happen from just sharing wine and loving it.

Kristi Mayfield (07:32)
That's such an interesting perspective, not only ⁓ the life decision to become a solo traveler, but also to take wine as that pivot point, because many people do feel awkward or very self-conscious about, well, dining, of course, but also going to a wine tasting, whether that's at a winery or at a city wine shop. What are some of the common feelings that, well, or

really common fears that you hear from solo travelers or maybe you've experienced yourself when it comes to that dining or especially that wine setting.

Tsvety Roo (08:14)
Yeah, that's such a good question because a lot of people fear that they're going to get pointed at if they go to a restaurant by themselves or if they go to a bar. And I've heard that from others. I've given some talks and I've done some podcasts now that we've talked about why there's not as many people that just kind of go out to dinner by themselves.

And a lot of them say, you know, I'm afraid to be judged. I just don't want to be judged. I don't want people to pity me like, oh, this person is here by themselves. couldn't find anyone to go with. And from that perspective, I that this is one of the steps that I would say, if you want to do a little bit of solo travel, perhaps start small.

start going to a restaurant or a bar in your city or go do a day trip somewhere and that can give you the confidence that No one's really gonna point at you. I promise

All I've experienced is I've made friends with servers and waiters and...

and I got to hear their stories that, you know, I make it a point to put the phone down when I am dining or sipping wine alone because I want to savor the experience. I want to be present when I'm there. And if I'm in Porto, in Portugal, I want to basically absorb the surroundings.

Kristi Mayfield (09:52)
Soak it all in.

Tsvety Roo (09:53)
Soak it all in, including the wine.

Kristi Mayfield (09:56)
I traveled for years as ⁓ a business person and most of the time I was traveling solo. I was the person sitting at the bar with my iPad or a wine magazine, a glass of wine and dinner. ⁓

not soaking it. And so what are some other mistakes that people do make if they are going out to dinner, traveling solo, and instead should be focused, like you said, more on that soaking it up or maybe making some connectivity over that glass of wine? What are some of the common mistakes?

Tsvety Roo (10:27)
in the press.

Exactly.

The phone is the biggest deterrent. there's so many people just, sit down or they just look at their phones and they kind of eat really fast and they just kind of want to get out of there. That's not the point of this. And that's also a good segue into kind of taking that time to be with yourself. And so when you put the phone down,

you're gonna you're taking in, you you're being with your thoughts. And this is exactly the transformation that I know we started to talk about a little bit, but ⁓ going from me being a very, very lonely state ⁓ before I started solo traveling to now solo traveling, helping me transform and understand solitude and the difference between loneliness and solitude, which I feel a lot of people.

don't know, I didn't, that they're completely coming from a different place and loneliness is emptiness and it's sort of disconnection from the world and disconnection from yourself and feeling unfulfilled and you're not feeling at peace at all. And solitude is sort of coming into yourself. It's embracing that time alone and embracing ⁓ so many aspects that you were probably afraid to touch before.

And so when we eliminate some of those distractions, like putting our phones away, or maybe closing the laptop for let's say just an hour, you're going to eat. know you're on there for a business trip, but just an hour while you're eating, closing all of those devices, looking up and having a sort of the other aspect of it. So first devices put away. And then second is having this body language.

of being receptive.

And then obviously the third one, is hard for people is kind of leaning over the next person next to you or the table and kind of saying, what wine are you drinking? You know, is it, is it, is that one a good wine? And then I'm thinking about what to order. Would you recommend it? And so when you do those three things, you know, you're putting the phone away or your laptop or whatever. You're having a sort of like the attitude, the body language of I'm open.

Kristi Mayfield (12:28)
Yeah.

Yes!

Tsvety Roo (12:57)
for new connections and that mindset. And then you actually begin a conversation, which I know is very hard. And a lot of people tell me, they're just like, that's too hard for me. But even if you do the first two, you'd be surprised that other people might approach you. So between those three things, I think you're gonna have a recipe to start sharing some wine with someone.

Kristi Mayfield (13:14)
Right.

So we talk frequently in the wine world about, know, wine is such a people connector, unlike any other beverage. You put a bottle of wine at the table and it brings just a different dynamic because that's a commonality, but yet it's an individual experience, right? We're all drinking the same bottle, but we're having a different experience with it, whether it's based upon what we're eating or our own palates. So I love what you just said that wine can...

Tsvety Roo (13:30)
Mm-hmm.

Kristi Mayfield (13:48)
really act like an instant, we'll call it an icebreaker or that bridge when you're in a new place or a new culture. So can you share a couple of examples of when you've been at a restaurant or at a wine tasting? mean, what are some things that you've done? What are some success stories you've had in engaging people around that wine experience?

Tsvety Roo (14:09)
Yes, ⁓ Porto in Portugal, I'm mentioning again, that was very wine focused trip for me. And I do like port wine, but I still like Albarino better. And when I went to lunch by myself and I knew that I was going to be exploring the city that day. And so I started at this one place lunch and I kind of overheard there were three girls that were just having a good time. And for some reason,

the server and I were chit chatting and I was like, you know what, well, I just asked the server, what's an interesting line that you have. And he brought out this humongous bottle of port. This bottle was half the size of me. I mean, it was so ridiculous. It was so big. I'm sure you know the exact ⁓ quality.

Kristi Mayfield (15:02)
Yeah, the nebuchadnezzars,

the magnums, all the in-between, right? ⁓

Tsvety Roo (15:05)
Yeah,

it was so huge and I was kind of like, I was like, could you mind taking a photo of me? I was pretending to be drinking this ginormous bottle and I saw that the ladies next to me really kind of looked over and were very receptive and then I was like, oh my God, isn't this the huge bottle ever? And they started to laugh and then all of a sudden we find ourselves six hours later, we explored the city together. Two of them were from the UK.

One of them was local from Portugal and it happened, just, because of this big, funny situation and me kind of creating this funny photo and they were receptive to that. And so it made such a moment. And when you have, created that moment. And then that sort of said, listen, like you guys seem very accepting to conversation. And so we started and spent the rest of the day.

I said, touring the city and had to learn a little bit about them. And they learned that I was a solo traveler and it was, it was very, very cool. And so that, that's one of my favorite stories. And that, that wasn't even in a specific wine environment. It just naturally was a fun, brought to you by wine.

Kristi Mayfield (16:03)
touring together.

Yeah.

So you mentioned that in in that group alone, you had local from from Portugal, you had a couple from gals from the UK, your best friend is Australian. So what are some other ways that exploring, you know, different cultures through wine, so let's say local wine in Portugal can help either a solo traveler or somebody who's, you know, traveling even in a small group.

Tsvety Roo (16:36)
Australian.

Kristi Mayfield (16:53)
learn about that culture and take that as a cue to kind of feel more included, less like a traveler or a visitor, but more like somebody soaking up that cultural local experience. How does wine do that?

Tsvety Roo (17:08)
I think it just, not only brings people from different parts of the world, ⁓ it educates you also for the culture of that region. And so I think that's important because then when you go wine tasting, you let's ⁓ the Malaga one specifically, I found it on Facebook and I just put in the search on Facebook, the wine tastings in Malaga. And it popped up that it was

someone who had just started a business of doing wine tastings. She was from the UK. She was still learning Spanish. So she was technically like not even a local yet, which made it even more interesting. Cause you know, she's building the relationships then. ⁓ when I joined that, it was in English, thankfully. And most wine tastings are in English. feel like that's, we're lucky in that way. ⁓

Kristi Mayfield (17:58)
You

Tsvety Roo (18:05)
And when we went, was so amazing to have the wine owner, the proprietor of the wineries that we went to, to share about their history as a winery in Spain. And then just kind of tell us like, you know, this grape is 250 years old and like all of the stuff that you're just, you're soaking it in and at the same time, really enjoying it. And it's hitting all the senses. So you're learning.

You're outside, you're breathing some fresh air, you have the taste buds that are being met with amazing taste. It's so fulfilling in that, in your making conversation and making friends. It just hits so many different points of creating a great atmosphere for you, inner for yourself inside and outside.

Kristi Mayfield (19:03)
That's such a great segue because I studied art history. I never really enjoyed history itself, the written history, but you put it into a painting or a sculpture, a piece of art, and that's when it connected with me. And so I have traveled a lot and learned a lot about culture through museums, through art. I also now, because of my passion for wine, do the same thing, just like you said.

leveraging that wine culture because of the stories and the history, the way it pairs with the local foods. It's a completely different, it's part of a lifestyle in so many places. It's not just a liquid beverage. It's truly a story and part of culture and part of history unfolding right in the glass.

Tsvety Roo (19:53)
I feel so much more at ease and it's so peaceful at wineries There it's beautiful it's gorgeous and I don't know I'm just like maybe I was born to be on one on wineries all the time

Kristi Mayfield (20:08)
It's

like time stands still sometimes.

Tsvety, for our listener, what are some practical tips that you would give to one of our listeners who wants to use wine as a way to build those connections when traveling or just going out alone for an adventure?

Tsvety Roo (20:27)
again, think it's very, it's pivotal that they understand the distractions in the phones, they're just blocking you from making connections with other people and yourself. And once you start with that and then you're at a restaurant and you start this conversation, ⁓ like, ⁓ why aren't you drinking? And I think,

90 % of the time, if you are afraid, and a lot of people are just like, ⁓ but what if that person just doesn't want to chat? Like, I don't want to be that annoying, ⁓ creepy person to approach them. And it's like, 90 % of the time, they want to chat back. And that's what I found. And they would love to share wine stories. And if you are vulnerable about what you like about this wine, a little bit about yourself.

And I found people are gonna be vulnerable back. So that's kind of the biggest tip is, start by expressing what you like, a little bit about yourself. being inquisitive, know, kind of.

ask a few questions about this and I find that people just open up and then you end up sharing perhaps the rest of the day together.

Kristi Mayfield (21:46)
Sounds like it's been working great for you and all of your solo travels for the past couple of years, Tsvety That's really amazing. in wrapping up, could you give our listeners, say, your top three tips for leveraging wine, whether they are out traveling solo like you are, or they're just maybe on a group trip and break away for a few hours by themselves, they're on vacation, or even that business trip.

Tsvety Roo (21:55)
Thank ⁓

Thank

Kristi Mayfield (22:11)
where they are traveling solo. What are your top three tips that you would share?

Tsvety Roo (22:16)
So one of them is definitely don't be afraid to have a lovely lunch by yourself and, starting that conversation. starting conversation over wine. And then the, I think a lot of the times when I was booking wine tours or wine tastings, there's some that say eight or nine or 10 hours and

Don't feel intimidated because it's gonna go by in a heartbeat. think that's, that seems like, like for us Americans, it seems like such a commitment to, yeah, like, my gosh, that's way too long for wine tasting. What are we gonna do with strangers all day? I think like you're afraid you're gonna be bored, but then all of a sudden you look down and it's 6 p.m. and this wine tasting started at noon and you're just like, where did the?

Kristi Mayfield (22:46)
So true.

Tsvety Roo (23:05)
Where does time go? Because you had, say you were on the little minibus on the way there and then you stopped at this, like all these three different wineries and all three of them are different and all of the, like one is like, let's say a Pinot Grigio and another one is like from more of the Reds and like Sauvignon. ⁓ I'm sorry. Cabernet and Torreo. I was forgetting that first part of.

Kristi Mayfield (23:28)
Cabernet Sauvignon We'll just go that.

Tsvety Roo (23:32)
And so like each of the wineries have their own thing and they're telling you about the story and all of sudden eight hours are gone. And so please don't feel that like that's too much of a time because what you're doing is you're giving the space to really like understand the culture of those wineries, the taste and making those connections. So ⁓ that's my second tip. Definitely still book it. And then ⁓

For my third tip is ⁓ don't feel like you're going to be the only person there that's solo. ⁓ I think a lot of people are just like, only couples go to wine tastings or, ⁓ you know, I'm going to be such an outsider. I'm going to be the fifth wheel or the seventh wheel or whatever.

Kristi Mayfield (24:11)
Hmm.

Tsvety Roo (24:25)
I'd have to say like there's usually there's two or three of us that are solo travelers on these wine tastings. It's predominantly couples. This is true. There's a lot of couples. cause that's sort of, it's a romantic thing to do, but I feel like I still enjoy it quite a bit. And there are other solo travelers with me that go to these wine tastings. So don't feel like you're going to be the only one.

you're gonna enjoy it. Just book it.

Kristi Mayfield (24:56)
Those are such great tips and I definitely feel that they're all super usable. Again, whether you're just out for a little bit of a break from the group or solo. So I think this has been just so enlightening on how Wine can create connections, even if it's not just at the table with people that you already know. You're using it as a connecting device or a connector.

globally in all of your travels. you know, from our listeners perspective, if you take nothing else away from this episode, remember that you're never really alone when you have a glass of wine in your hand or a bottle of wine to share. And wine can be more than just a beverage or a drink. It can be a bridge to new cultures, to new conversations, to belonging, and as Tsvety said, to new friendships.

And being curious and open really is that fast way. Put your phone down, close your device, in my case, put that magazine away and allow yourself to be engaged and to be receptive to that connectivity wherever you are. So next time you are traveling solo, whether for work, play, otherwise, don't be afraid to pull out that stool, pull up a stool at the bar, order a glass of wine, see where the conversation may take you.

with other people who are in a similar situation or really just want to connect over a glass of wine, just like you. So Tsvety, any final comments or thoughts that you would share with our listeners?

Tsvety Roo (26:32)
Please don't be afraid to take that first step. I think that's the hardest part. It took me nine months of overthinking before I finally booked my one-way ticket to Malaga, Spain. And so I would just, I'd love to tell the listeners, if you need a little bit more support with that, please come find me on Instagram and also on my website and I can help you take that first step to doing a bit of solo traveling and also...

recommend some good wines.

Kristi Mayfield (27:03)
I will absolutely

have your Instagram and your your website in the show notes and this has been just such a true pleasure to have you on the show today, Tsvety I've learned so much and I'm inspired to really leverage wine in a whole new way on my next journeys as well.

Tsvety Roo (27:22)
Wonderful. Thank you so much for having me.

Kristi Mayfield (27:25)
Cheers.

Kristi Mayfield (27:25)
Are you as inspired by Tsvety's journey as I am? Are you willing to take the next step and dine out solo or grab a glass of wine at the bar by yourself the next time you're either on the road or breaking away from a group during your travels?

it may not be for you. I guarantee you have a friend or family member who is just as adventurous as Tsvety is. So please share this episode with them today because they can gain so much advice from what Tsvety has learned and how she's leveraging wine to make her travels less solo.

And don't forget to follow us on Instagram at Kristi Kri Sti Everyday Sommelier where we're going to continue to transform your wine journey. we are going to continue next week's food and wine pairings and explore some of the other taste elements that can truly dramatically change the way food tastes or wine tastes when you get it right. So cheers.

And here's to Learning Line your way.