Creating Unique Wine Experiences Through Travel With Gail Sherman of Wine Lovers Travel

by Drew Hendricks
Last updated Oct 26, 2023

Legends Behind the Craft Podcast

Creating Unique Wine Experiences Through Travel With Gail Sherman of Wine Lovers Travel

Last Updated on October 26, 2023 by nicole

Creating Unique Wine Experiences Through Travel With Gail Sherman of Wine Lovers Travel 11

Meet Gail Sherman, the passionate Founder and CEO of Wine Lovers Travel. With a deep love for wine and travel, Gail has built a reputation for curating distinctive global excursions. Based in California’s wine heartland, she nurtures personal ties with winemakers, offering unparalleled access to the industry. As a Wine Specialist recognized by WSET, Gail designs immersive land trips, ensuring clients experience the world’s finest wineries and cultures. Her dedication guarantees travelers unforgettable, exclusive adventures, making Wine Lovers Travel a cherished choice for wine enthusiasts seeking unique journeys.

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Here’s a glimpse of what you’ll learn: 

  • Gail introduces Wine Lovers Travel and its mission to create unforgettable wine-centric land trips
  • Learn about partnerships, itinerary planning, and the balance between structured activities and free time
  • Gail shares insights on the ideal group size and examples of their wine travel adventures
  • Explore upcoming road trips and special events
  • Gail reflects on the challenges of starting a travel company just before the pandemic
  • Learn about airfare inclusions and options for Wine Lovers Travel trips
  • Gail highlights what distinguishes Wine Lovers Travel from other travel companies, particularly their land-based approach
  • Explore the benefits of wineries partnering with Wine Lovers Travel to connect with their clientele
  • A discussion on wineries’ participation and their role during trips
  • Gail offers advice for wineries considering booking travel experiences for their club members

In this episode with Gail Sherman

Explore the fascinating world of wine-centered travel experiences. Gail Sherman provides insights into the heart and soul of Wine Lovers Travel, covering topics such as meticulously planned land trips, group sizes, and even an upcoming road trip with special surprises. 

In today’s episode of the Legends Behind the Craft podcast, Drew Thomas Hendricks and Bianca Harmon are joined by Gail Sherman, Founder and CEO at Wine Lovers Travel. Discover their wine tasting experiences and itineraries and gain valuable advice on how wineries can leverage these trips for their clients. In addition, learn about Wine Lovers Travel’s innovative approach to virtual wine tastings during the COVID-19 pandemic and what it’s like traveling in 2023. Whether you’re a wine enthusiast or a travel aficionado, this episode promises to quench your thirst for unique travel experiences centered around the love of wine.

Resources Mentioned in this episode

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[00:00:00] Drew Thomas Hendricks: Drew Thomas Hendricks here, I’m the host of the Legends Behind the Craft podcast. Today we’ve got a really special guest. Bianca and I were talking with Gail Sherman. Gail Sherman is the CEO of Wine Lovers Travel. Welcome to the show, Gail. Welcome to the show, Bianca.

[00:00:15] Gail Sherman: Hi, Drew and Bianca.

[00:00:18] Drew Thomas Hendricks: Gosh, thank you so much for joining us.

So, Gail, I hear you just got back from a fantastic trip. Before we learn more about you, I want to hear more about this trip to Portugal.

[00:00:26] Gail Sherman: Okay, cool. Yes, I just came back a week ago. For about two weeks there, it was truly my… First real-time, other than a half a day I spent in Lisbon when I started a cruise 10 years ago, and for this trip, it really focused on wine.

So I was in Porto and then I was in the Douro Valley and it was, it was very interesting because when people think of Portugal, they think of Port wine, and obviously they should because Port is is where, where it is. But they also produce a lot of fine wines that people don’t think about in Portugal.

And so that was really interesting. Yeah. So the only downside of my trip is that like the rest of California, it rained every single day I was there.

[00:01:15] Drew Thomas Hendricks: Oh, did it? So step back. So you, you also went to the Azores as well, didn’t you?

[00:01:22] Gail Sherman: I did. And, and that was very interesting. You know, I didn’t know too much about the Azores, but now I do.

First of all, it’s part of Portugal, it’s overseen by the Portuguese government, although I was told they have their own president, but at the end of the day, the president of Portugal will oversee or overrule what goes on in the Azores. But it’s, it’s an archipelago of volcanic archipelago.

It’s about a thousand miles off the coast of Portugal, sort of right in the middle of the Atlantic.

[00:01:55] Drew Thomas Hendricks: Yeah. Were you on Pico Island? I know there’s a lot of wine growing there.

[00:01:59] Gail Sherman: I was not. And I had wine from Pico. We were only on the main island which is San Miguel, and I was only there for about three days, but I am mostly when I was there, the indigenous, I don’t even know if they’re indigenous, but the crops that they grow there now are tea and baby pineapples. And it’s interesting.

[00:02:25] Drew Thomas Hendricks: I don’t think I’ve seen a baby pineapple. Pardon? I don’t think I’ve seen a baby pineapple.

[00:02:30] Gail Sherman: It’s about so big. I mean, it’s very cute. And they’re very sweet. We got to taste them. I don’t know that this is the exact time of year, so I believe during the summer time they’re, they’re really sweet and they farm them in greenhouses because the climate is not really suited for pineapple production.

So it’s very interesting, but they’re, and then they grow a lot of tea there, which I didn’t know either.

[00:02:57] Drew Thomas Hendricks: So now stepping back for our listeners, you’re, you’re in charge of Wine Lovers Travel. Tell us a little bit about that.

[00:03:04] Gail Sherman: So Wine Lovers Travel is my passion project. I have always loved travel ever since I was a kid and I’ve gotten into wine for most of my adulthood.

And after spending a number of years working in technology and outsourcing solutions. I finally decided that life was short and I needed to focus on what was important to me. So I got some experience in travel starting in 2017 working for another company that sold cruises, but that were hosted by wineries.

[00:03:39] Drew Thomas Hendricks: Oh all the winery winery tours that we see go up and down the Rhine and the road.

[00:03:44] Gail Sherman: Yes, so I sold those to a lot of wineries and then I decided that I wanted to break out on my own in 2019 not the most auspicious time because I was shortly cut off at the knees by Covid, but, you know, I’m here. I survived.

I can. But, so what I do is I decided early on that a lot of people don’t like cruises. And that was a real impediment. And so I decided that while I will sell a cruise to be hosted by a winery, I’m focusing more on land trips. Because they’re more immersive and they’re more, you really can get into the culture and you can really spend time versus, you know, being on a cruise and having three hours to go visit a winery.

[00:04:33] Drew Thomas Hendricks: Yeah, for sure. So going through, so these land trips that you set up, are they with wineries or do you, like do you have a local partner with a local winery and go with the guests like these river cruises or tell, tell us how they, how they’re set up.

[00:04:47] Gail Sherman: Pretty, they’re set up pretty much like that, where I will, and I partner with primarily boutique, artisanal kinds of wineries, not so much the big guys that you can find in, you know, Costco and your local supermarkets. So I deal with the smaller production wineries that sell primarily direct to consumers. So they are, it really behooves them to grow that business as much as possible. And one of the ways they do that, of course, is with their wine clubs.

They’re always trying to grow their wine club, mostly always trying to grow their wine club. There are a few that are at capacity. But,

[00:05:25] Drew Thomas Hendricks: They’re trying to grow their waitlist so they can brag about how long their waitlist is.

[00:05:30] Gail Sherman: Like our friends at Saxum on the wait list for years already, and I’m not sure if I ever get to the front of the line that I’m going to want to spend that kind of money, but that’s another conversation. But in any case, so I partnered with these wineries and explain to them that this is another marketing event for them.

And I take care of everything from the, you know, all the operations, the booking, the payments, everything. Their responsibility is to promote these trips to their customers. In their tasting room, at their events, and digitally. And I even provide all the materials for them. I produce, you know, all the collateral and give them a page on my website.

I give them everything they need. And they just need to get out the word and then we do these trips. And I’m starting my 2023 trips in May, actually. First one is to the road.

[00:06:28] Bianca Harmon: When you’re doing this, are you coming up with the whole plan of where all they’re going to be going? Where they’re going to be staying?

Or do the wineries come to you with suggestions of where they’d like to go? What they’d like to do?

[00:06:41] Gail Sherman: Well, it’s a good question. And what I do is I start off by having a conversation with them to find out what’s important to them. And yes, where they would like to go. And sometimes it’s based upon the type of wine that they produce.

And for example, I do a lot with wineries in Paso Robles. Which produce a lot of Rhone varietals and so it seems obvious that they would want to go to the Rhone but not always and of course, they produce a lot of Cab and maybe they want to go to Bordeaux. Or maybe they want to go to Australia for that matter.

You know, it’s so first I need to have this deep dive with the winery owner or winemaker, sometimes the same person, sometimes two separate people. And from there, I designed the trip. And what I, in order to do this, I have partners in the various countries where I do these trips. And I develop these personal relationships with people in places like France and Spain and Italy and Croatian, Slovenia, which is an up-and-coming market for me.

And so I put together the program. If they have, if the winery has some special requests or they have personal relationships with anywhere where we’re going, then I would certainly include those, but that’s not their responsibility. I put together the trip and I present the itinerary to them. And we talk about what it would cost and all of that.

And then once we’re in agreement, then we start promoting. And the winery, you know, it varies a couple of things. One is that I want to keep the group size small because I want to keep them intimate and I want to keep them authentic. And I don’t want to, you know, come to the various places we’re visiting with enormous tour buses. And so, we keep the groups small.

[00:08:34] Drew Thomas Hendricks: What’s the ideal group size that you’ve found?

[00:08:36] Bianca Harmon: What’s the average?

[00:08:38] Gail Sherman: I’ve been saying between 10 and 20, I’m thinking between 10 and 16 is probably really the sweet spot because, and I can go, and in fact, my group to the Rhône will be 20. It was sold out. That was my max and we sold out.

And I’m thrilled about that. But you want, you don’t want people to feel like they’re in a crowd and we never go to places that are the commercial places that, you know, you do see all the tour buses lined up. These are all based upon personal relationships and getting people behind the doors to places they wouldn’t be able to find.

[00:09:15] Drew Thomas Hendricks: Yeah. Give us an example. Like talk to us about maybe this road trip coming up, some of the special prizes or special like events that the consumers can see.

[00:09:25] Gail Sherman: Sure. So, on the wine side, for example, one of the famous wineries there is Regale, and yes, you can find Regale a lot of places in the United States. But my person, my, I have a – who is actually an expat American who lives in France, and I’ve been working extensively with him, and he has personal relationships with the people over there. So we’re getting a special tasting that is not available to the general public, and they’re even.

If we’re lucky, and I think we will be, get it, get to taste their LaLa, which is their ultimate premier wine. So, so that’s an example. Another example is, and this is not a wine thing, but this is, you know it’s, we do, we specialize in a lot of wineries and but we also have to do some culture and things like that.

Yeah, you know, you can only drink so much wine too. First, the first trip I did, I’ll have to say it was last year and we were in Croatia and we were going to four or five wineries a day. And people were saying, enough, I can’t drink anymore. So, I mean, you know, you learn and, and so we, we max out at three wineries a day, but anyhow, so we do other things.

And one of the really cool places in the South of France is called the Pont du Gard. Are you familiar with that at all?

[00:10:50] Drew Thomas Hendricks: I’ve not been there. No.

[00:10:51] Bianca Harmon: I haven’t been there, but I’ve heard of it.

[00:10:54] Gail Sherman: So the Pont du Gard is a Roman aqueduct, not too far from Nîmes in, in Provence. And it was built 2, 000 years ago for the purpose of bringing water to Nîmes.

And it’s when you go there, and I was there for the first time last summer and I’ve been to the south of France many, many times and it’s sort of like going to Paris and never seeing the Mona Lisa. I, I’ve been to the south of France many times and it took to last year till I saw it. And it’s pretty magnificent.

It’s a three-level aqueduct that goes up, I don’t know how many hundreds of feet. And if you make special arrangements, you could go onto the very top level, which I did not get to do last year. And you can see how the water actually flowed, flowed through the aqueduct and down into Neem. And I believe we’re going to do a wine tasting or have a little snack, not really a meal, but you know some food line up there also.

[00:11:50] Drew Thomas Hendricks: That’s incredible.

[00:11:52] Gail Sherman: Yeah.

[00:11:52] Drew Thomas Hendricks: That’s incredible. Now on your, on this upcoming road trip, are you partnering with a winery?

[00:11:58] Gail Sherman: I am. One of my favorites, I don’t want to, but they are a favorite. I’ve had a long-time relationship with them. It’s called Caliza. And they are at Paso Robles, the winemakers, Carl Bowker, who I’ve gotten to know very well over the last several years.

And I really think Carl’s a genius when it comes to winemaking. And he has never done a trip like this before. I’ve been talking about this with him for years. And we were talking about a river cruise and all this, and then there’s COVID and blah, blah. And so finally he said, “Yeah, let’s do it.” And so, and we sold out because he’s got, he’s not a huge winemaker.

He’s under 5, 000 cases a year, but what he produces is really, to my mind, it’s magic.

[00:12:43] Drew Thomas Hendricks: Is he a Rhone-inspired producer? Like, does he?

[00:12:46] Gail Sherman: He is. He is. He does a lot of Rhone. Yeah, you know, I’m thinking he doesn’t, he does Zinfandel, which is not Rhone.

But, and he does, he doesn’t do care. Yeah. So I guess he is pretty much Rhone. He also, I believe he does a Tempranillo also, which is Rioja, but, no, no Bordeaux, Bordeaux particularly.

[00:13:09] Bianca Harmon: On your trip where like it’s, there’s no wine tasting involved. It’s maybe a free-for-all all for guests to do whatever they would like because they’re going to these areas or a beach day or, you know, anything, or is it wine tasting every single day?

[00:13:25] Gail Sherman: No, there’s actually, one day in particular where there’s no wine tasting because it’s a Sunday and Sundays, it’s, I mean, once in a great while, if you pull a lot of strings, you get a wine winery to open for you, but generally not. So we are going to, again, this trip is actually started in Leon, which is a couple hours south of Paris, and then we’re going to go south to Avignon.

Which is an hour or so out of Marseille, which is on the coast. And on Sunday, we’re going to go to a place called L’Isle-sur-la-Sorgue, which is an adorable town where they are known for their antique art. And it’s a big deal, and we’re going to, we’re going to go there and spend part of the day there.

And then we’re, there’s some other towns nearby that are very charming. One is called Roussillon. And it has to do, the word red or rouge comes from there. It has to do with the red cliffs that are surrounding the area. So that day, not that people won’t be able to find a glass of wine, but it is not a winery day.

[00:14:38] Bianca Harmon: That’s fascinating. So the winery is out there, not open on Sundays.

[00:14:42] Gail Sherman: They’re not and often not on Saturdays either, but I have,

[00:14:46] Bianca Harmon: That’s amazing.

[00:14:48] Gail Sherman: Yeah, I know. And I suppose some of the more commercial wineries are open. On the weekends, but those I had a lot of revisit.

[00:15:03] Drew Thomas Hendricks: Yeah. As you’re laying out your itinerary, how important is it for like downtime for your people and how do you balance that kind of free time with group time and organized itinerary?

[00:15:13] Gail Sherman: That is always a challenge, you know, because there is so much to see and do and drink that, you know, I could fill them up, you know, all their waking hours, but people do want the free time. And so normally what we do is we have, we, we don’t start at the crack of dawn and also who wants to drink wine at the crack of dawn, so, you know, they, they have their breakfast in the hotel.

We’ll start somewhere between 9 and 10 o’clock and we’ll start and we’ll use the usual plan as you do a winery in the morning, and then you do lunch in a, in a really nice restaurant, a paired lunch, and then maybe you do something else, or you go to another winery, and then you return to town at the end of the day, and then you’re on your own. And we, we, I’m trying to think, I’m hardly ever, maybe never do two planned meals a day, because it’s just, first of all, it’s too much food.

If you’re having this, this multi course lunch with wine pairings, you may not even want to eat dinner. You might just want a little try. And so we do give people time and the other thing too because one of people’s favorite activities wherever they go and I’ll include myself in this is shopping. And stores in Europe are usually open at least till seven o’clock and sometimes later.

So if we get them back by, you know, five they have some free time and then they go to dinner on their own. We certainly can recommend places, but free time is really important. And when, again, this first trip I did last year to Croatia, I didn’t give the people enough free time and they wanted it.

And so there were a couple of times where some of the people just bent off and they said, “You know, this hotel is wonderful. A couple of them have spas. We just want to do the spa, sp we’re gonna do our own thing.”

[00:17:06] Drew Thomas Hendricks: That’s good. So I want to talk for a second about, you started your company right before the pandemic, a travel company. And then there was the pandemic and the whole world was shut down. And now we’ve come out of it. Talk to me about what it’s like traveling now in 2023, now that the world’s open back up.

What is the same? That’s different? How do people navigate?

[00:17:29] Gail Sherman: You know, it’s evolving. And since I would say the world started opening in the early part of 2022, and, and that was a time where there were still a lot of requirements for vaccines and COVID testing and until sometime middle of late 2022, you had to get a covid test before you could reenter the United States. And that was always very scary because even if you were sure you didn’t have COVID until you got that negative test result, you weren’t sure if you were going to come home or not.

So that was, that was a challenge.

[00:18:10] Drew Thomas Hendricks: Yeah. I have friends trapped in, trapped in Europe last year in the summer of 2022, just a few months ago. And coming in now we’re in April of 2023. What’s it like traveling to Europe now from the U. S.

[00:18:24] Gail Sherman: It’s it’s pretty much back to normal. It’s there’s a lot of people traveling. There’s no, there’s almost I’m thinking because just being in Portugal, I don’t think there were any mask requirements.

Now I did choose to wear a mask on the, on the flights because I just thought that was a smart thing to do, but I was in the minority for sure. But it’s pretty much back to normal. And I’m finding too that within Europe in the hospitality field, people are so happy to have tourists back. They just, they just are.

And so they’re very gracious and hospitable and that’s really nice.

[00:19:06] Drew Thomas Hendricks: And then the exchange rate’s really good right now too.

[00:19:10] Gail Sherman: It is, although it’s going up a little bit. A few months ago, the dollar and the euro were almost at par. Yeah. In fact, there were a few days where the dollar was actually stronger than a euro. It’s now I didn’t, I haven’t looked the last couple of weeks, but it’s about a dollar 10 to the euro. So it’s still pretty equivalent. And if certain countries like Portugal, as an example, is very inexpensive. So even though the euro has gained, it’s still very inexpensive there.

And the cost of wine is so inexpensive. Same in Spain, same in the Balkans, and

[00:19:49] Drew Thomas Hendricks: Yeah, you’ve got a cider trip coming up in Spain. Talk to me about that.

[00:19:53] Gail Sherman: I do. That one is being sponsored by a cider company in Santa Barbara and, and so I’m trying to branch out a little bit on

[00:20:03] Drew Thomas Hendricks: Which cider company?

[00:20:05] Gail Sherman: It’s called Santa Barbara Cider Company.

[00:20:07] Drew Thomas Hendricks: Santa Barbara Cider Company. Okay, I’m a big cider fan. I’ve not had theirs yet.

[00:20:12] Gail Sherman: And you know, the good thing about cider is that it is, it’s more appealing I think to a younger demographic than wine. You know, there are younger people who I would say the cutoff is sort of age 50, and people under 50 are not as big into wine as they are into cocktails and and ciders and the alcoholic seltzers and that kind of thing.

And so cider is there and Spain is known for its cider, so we’re going to be doing a trip from sort of the, I’m looking at the, I’m thinking about the map of Spain, sort of north-central Spain, all the way into San Sebastian and the Basque country. And we’re even going to slip over into France, into the Basque side of France to go to some cider producers.

So that would be really exciting and different.

[00:21:07] Bianca Harmon: Is airfare included in your, or are the rest?

[00:21:14] Gail Sherman: No, it is. Well, the international airfare is not included. If there are flights involved within the trip, which domestic, then yes, they’re included. For example, I have a trip coming up right after the round with a winery called Harmony Cellars, and they’re going to Spain.

And then there is an extension to an optional extension to Portugal. So the flight between Malaga, Spain, and Porto is included in the price of the trip.

[00:21:46] Drew Thomas Hendricks: I think that makes sense. Cause a lot of people, if they’re making the trip all the way to Europe, they might want to bracket a few days before, a few days after your, your portion.

So they just have to get to a point A in whatever country you’re starting at by a certain date.

[00:22:00] Gail Sherman: Yeah. And they usually do. And, and if somebody needs me to help them with air, I have, I have an air partner that I work with who does all the air booking so I can provide full service. And if they want extra time in the in the hotels, I can help with that. I have one client who is going on another trip to Bosnia and Croatia with Alma Rosa Winery, which is out of there in Solvang, and,

[00:22:29] Drew Thomas Hendricks: Oh, I know them well. My aunt was a tasting manager, Arlene – for many years. She’s passed now, but we Alma Rosa and Sanford before that were very close to us.

[00:22:42] Gail Sherman: Yes. And Richard Sanford still owns the land that it’s produced on. So you know the whole story about Sanford and how he sold everything including his name. So he couldn’t even use his name.

[00:22:55] Drew Thomas Hendricks: Oh yeah, he got a raw deal.

[00:22:57] Gail Sherman: Apparently so. I’ve met him. He’s a very nice man and he lives, he lives on the property and we did an event a few months ago and he was there.

But I have a couple that’s going on that trip. And at the conclusion of that trip, they want to do self-drive up to Italy and I think they’re meeting some friends at Italy. And so I was able to help them to map out the whole program and book their hotels and everything. And that’s through the relationship I have with my partner in Croatia.

[00:23:26] Drew Thomas Hendricks: Oh, that’s fantastic. So the Alma Rosa trip’s going to Croatia?

[00:23:30] Gail Sherman: Yeah.

[00:23:30] Drew Thomas Hendricks: Oh, that’s gonna be great.

[00:23:32] Gail Sherman: Yeah, that’s, and Croatia, have you been there, either of you? I have not. Croatia is just beautiful. And what people don’t know about Croatia is it’s actually the birthplace of Zinfandel. And when you were asking earlier about Caliza and their Rhone varietals, and I said they produce Zinfandel, which they do, but it’s, people don’t know that, but Zinfandel got its start there, and it wasn’t even discovered, I think, until the 1980s, when there was a professor up at UC Davis.

Who realized that the grapes that are what we call Zinfandel are the same grapes that they make in Croatia that have been going back for thousands of years. And, and the trajectory was that the wine was, went from Croatia to Italy, where it became known as Primitivo and then came to the U. S. And we, you’ll notice sometimes American wine, we still call it Primitivo, but it’s all the same wine.

[00:24:25] Bianca Harmon: Yeah, I actually worked with a girl that was from Croatia. And she spoke a lot about Zin because Zin had always been one of my favorite varietals. And then she shared the whole story about it with, you know, with Croatia and how it got started and pretty fascinating, but I think I’d have a hard time going to Croatia.

Cause if I’m pretty certain there’s a lot of islands and beachy places in Croatia, and I’d want to be there.

[00:24:58] Gail Sherman: Well, I have a plan for you because one of my upcoming trips, that’s not even on the website yet because it’s still finalizing development, but we’re going to be doing a yacht trip to Croatia in September.

Go into all the islands. It’s not necessarily going to be a wine trip. In fact, I will probably be the one hosting it versus the winery, but it’s, it should be pretty awesome. So watch my website.

[00:25:27] Drew Thomas Hendricks: Oh, that’s fantastic. So let’s, I want to step back to kind of the business of Wine Lovers Travel and what, what separates you from some of these other travel companies, other than that you’re on land and they’re on a river?

[00:25:39] Gail Sherman: Well, I think what separates me is I have a very strong business background because I didn’t start out in travel. So I look at this as a business venture with my clients. They’re my, the wineries are my business partners. I’m trying to help them to expand their DTC business and through travel because travel bonds people.

And you watch Shark Tank like I do. They about the, the customer acquisition costs, which is very high. So if you’re constantly having to acquire clients, it could be very expensive, but if you’re able to retain them by giving them this kind of travel activity, it can really help to grow your business and you’re building a reputation as not just a winery, but sort of an experience and people want experiences.

[00:26:35] Drew Thomas Hendricks: Yeah. So instead of like the travel company saying, “Hey, help me sell this river cruise.” Because it’s the benefits for you come in more of a strategic partner with the wineries and help them devise a way to really add value to their club and add value to their members.

[00:26:50] Gail Sherman: That’s very true. And I think that does set me apart.

And then the other thing too is the type of trip that I do. I have to say, if I wanted to do river cruises, my life would be so much easier because I don’t have to do anything. I, you have no control over the itinerary of the river cruises. I have great relationships with, with several of them, and the best I can do is I could add perhaps a shore excursion or a pre-trip or a post-trip, but basically I’m selling a commodity just like anybody else.

But with my trips, they are totally unique. And the other value proposition I provide is that no two trips are the same. So I have, and I will be doing other trips to the Rhone, for example, it will never be identical to what we’re doing with Caliza. They might be similar. It’s hard not to be similar, but for wineries, I mean, they will be different.

[00:27:44] Drew Thomas Hendricks: They fit the clientele of the winery and they match the winery’s goals. Now talk to the benefits, but how, how, your advice to wineries to kind of utilizing these trips for their clients?

[00:27:57] Gail Sherman: In terms of, it’s building the relationships, it’s making, it’s making the customers feel more aligned with the winery, that they don’t just see that as a wine, but it’s a whole relationship that they’re having with the winery, the people that work there.

And I think that really goes a long way. And it’s small, obviously. If I’m doing groups of 10 to 20 people, I’m not bringing thousands of new members to the wine club, although most of them wouldn’t have the capacity for that anyhow. But what I’m doing is I’m helping them to build a whole new way to work attract and retain club members and

[00:28:40] Drew Thomas Hendricks: Mature and retain is two of the biggest components of running a wine club. You get them in, but if they leave in 3 months, it doesn’t really do any good. It’s keeping them as raving fans who then spread the word. So talk to me, so does it, do all the wineries attend? Or is there a member of the winery on the trip too?

[00:28:59] Gail Sherman: Oh, yes, absolutely. That’s critical because they are. They are the host. I may or may not. S score. I use the word S score because in addition to, in addition to the winery representative, I always have what’s called a tour manager on these trips. And the tour manager is… a person, local person who will be with the group throughout.

They are not the guide. I mean, they might have some guiding and they certainly know their country, but we would have guides or Psalms or restaurant owners or whoever, wherever we’re visiting, those would be the guys. But the tour manager is the legit person to make sure everything runs smoothly. They will get checked into their hotels.

You know, the transportation comes on time, that kind of thing.

[00:29:42] Drew Thomas Hendricks: So Gail on the, as you’re going, as someone attends this event, do the winery, and especially for the wineries, I can see some of them might be intimidated to be spending seven days with a select group of their clients. How involved are the wineries with like, conducting the dinners or doing special tastings?

[00:30:01] Gail Sherman: They are, generally they’re almost like one of the guests. They are, they are not responsible. What they are responsible for is attending everything that’s on the itinerary. So…

[00:30:15] Drew Thomas Hendricks: They can’t have a spa day.

[00:30:17] Gail Sherman: Yeah, pardon? Yeah.

[00:30:18] Drew Thomas Hendricks: They can’t have a spa day.

[00:30:20] Gail Sherman: No, no, they cannot have a spa day. But that said, when they’re off the clock, so to speak, you know, at breakfast, at the end of the day when they’re when we have free time, they’re free to do whatever they want.

You know, there is a challenge that some people will try to sort of take over and try to just, you know, sidle up with the winery owner and, and try to be with them all the time. And so I tell them, the winery owners that, you know, it’s your vacation too, and while you want to be kind and gentle with the people that, you know, helped you to get to where you are, this is your vacation too.

So don’t feel like you’re obligated to spend time with them when you need your own free time.

[00:31:05] Drew Thomas Hendricks: Sure. Sure. So as we’re, as we’re kind of wrapping down on this show, is there anything we haven’t talked about that you want to, we can discuss?

[00:31:15] Gail Sherman: Well, one thing we went really briefly over what happened during COVID.

And I just want to say, because I think this is a differentiator for me, is that I didn’t just sit and wait for travel to come back. What I did was pivot, as many people did. And I decided that I would organize virtual wine tastings for wineries that I could keep in front of them so that they knew I was there, I wasn’t going away, and until they could host trips again, I would help them with virtual… virtual tastings.

And the way I did it was different because a lot of people were doing virtual tastings. And the first ones were the wineries would get on Zoom and they would hold up some bottles of their wine. And they would say, you know I’m drinking this wine and it’s got floral notes with a little bit of vanilla and tobacco or what have you and it was really boring to watch to taste the wine.

And so what I did was I worked with a number of wineries, including the ones that I’m traveling with now, and arranged for them to re-bottle their wine into tasting flights, either two or four ounce tasting flights, very similar experience to what you would have in the tasting room. It was really labor intensive for them because you can’t the little bottles are bottled very differently from corking the wine and, you know, making sure the -.

And so we have a whole logistics with shipping and, and to make sure the wine was shipped out and arrived promptly. And then the other change was that I brought them the people. I was able to network with all kinds of organizations, reaching from groups of people who like wine. Lawyers, accountants, financial planners, real estate people.

I had a lot of people I did, I did all told about 40 different tastings. I had hundreds of people with tastings and I also got some corporate clients. I had Amazon did a tasting with me, T Mobile, Morgan Stanley. So, and some nonprofits like my, my alma mater UCLA. So, so that’s how

[00:33:26] Drew Thomas Hendricks: They’re playing today in the college game and they’re playing my alma mater, Gonzaga. Today is March Madness.

[00:33:32] Gail Sherman: Okay. Okay. Well, yeah, UCLA had generally has been pretty been dubbed basketball powerhouse.

[00:33:39] Drew Thomas Hendricks: Yeah. They’re in the sweet 16 playing later today. Hopefully, Gonzaga will win, but for your sake. I’m rooting for UCLA, too.

[00:33:47] Gail Sherman: Isn’t Arizona State still in there?

[00:33:50] Drew Thomas Hendricks: I’m not sure. I’m not sure.

[00:33:55] Gail Sherman: My son went there, so that would be my second choice. Arizona.

[00:34:00] Drew Thomas Hendricks: Very good. So these virtual tastings, are you still doing them now? Because I see the value with corporate bringing disparate corporate teams together.

[00:34:09] Gail Sherman: They are, but I am not. Quite honestly, it was more of a PR effort than anything else. I mean, I didn’t make any money on these, and neither did the wineries. It was very labor-intensive and sort of a logistical challenge. So we made it happen. And the whole idea was that not only did I keep up the relationships with the wineries, but every time they did a tasting, I gave them all the contact information.

So they acquired new people for their mailing list. I acquired new people for my mailing list. It was, it was a win-win, but it, you know, I have to have a whole staff person to do that. It’s like, I’m glad that’s over. But it was really a good way to build your network during that time, starting off.

[00:34:56] Drew Thomas Hendricks: And I mean, I do see the people that came out of the pandemic that kind of just plowed right through it and didn’t give up or didn’t hide in a hole for two years. It came out even stronger. And it sounds like that was the case with you.

[00:35:08] Gail Sherman: I certainly hope so. I think so. There were a lot of travel companies that went under.

They just, because they, they didn’t, they just didn’t have the creativity or the confidence or whatever, but gee, I had just started this business and it was as I said, it was my passion project. I was not going to let it fail. And I just plowed right through. Yeah. And I’m, I’m real proud of myself.

And then the other thing too, I’ll say, and I don’t know that this is as meaningful for your, your people, but it was important to me when I first started in travel, one of the ways to do this is to work under the umbrella of a, an existing travel agency and be independent contractor, but hosted by another agency under their licensing and all of that.

And that was fine. And that helped me to build a lot of relationships with my travel vendors. However, I realized that that wasn’t a long-term solution. So as of February, I am 100 percent independent. So I actually fully own Wine Lovers Travel. I do not have a host anymore.

[00:36:13] Drew Thomas Hendricks: Oh, that’s great.

[00:36:14] Gail Sherman: And, and I’m very proud of that.

[00:36:17] Drew Thomas Hendricks: That’s great.

[00:36:17] Bianca Harmon: Congratulations.

[00:36:19] Drew Thomas Hendricks: Thank you. One, one question. So what advice do you have for wineries who are considering, booking one of these travel experiences for their club members?

[00:36:29] Gail Sherman: I would say do it. If you have the opportunity, give it a chance. There’s really no downside to it. And the upside is that you, well, first of all, you’re going to get to travel. And number two, you’re going to have this amazing experience to offer your club members and other people who visit your winery.

It’s going to help set you apart from other wineries. And I used the word earlier and I’ll use it again, it’s an experience. And people really are looking for experiences. They don’t just want to go taste wine or they want something that’s more holistic. And they also want hidden gems. They want to feel like they’re getting, gaining access to something that they couldn’t do otherwise.

And this is what I provide the winery and this is what they can offer their customers. And it’s just really special. And one of the trips I’m doing this year, the trip to Spain with Harmony Cellars, they are a repeat. They did my trip to Croatia last year, so they were so pleased that they came back for a second trip.

And I’m hoping to be able to build that way too. And then also, I do want to expand the people who host my trips. So I’m starting, well, like for the cider trip, for example, I have another trip that’s coming up. It’s, matter of fact, it’s on my website. It’s to Burgundy and champagne, and it’s being hosted by a Wine Educator.

I, we’ll have trips that are being hosted by chefs or sommeliers. So people who are prominent in the food and wine industry who have a following, who want to help grow their business, I can help them with travel.

[00:38:17] Drew Thomas Hendricks: Oh, very good. Well, Gail, where can people find out more about you and Wine Lovers Travel?

[00:38:23] Gail Sherman: Well, they can start at my website, which is They can also go to my Facebook page, Wine Lovers Travel. I do have a private group, which I’m happy to let anybody join, and it’s called Wine Lovers Who Love to Travel, it’s a Facebook group. And you can always email me at Gail, G A I L dot, I’m sorry, G A I L

[00:38:55] Drew Thomas Hendricks: Fantastic. Well, Gail, thank you so much for joining us today.

[00:38:59] Gail Sherman: Well, thank you. I’m very excited about this opportunity. And Bianca, I thank you for all the pre-work that you did and getting acquainted with both of you and hopefully we’ll get to meet in person at some point and consider coming on one of my trips.

[00:39:16] Drew Thomas Hendricks: Absolutely.

[00:39:20] Gail Sherman: I’m always looking for hosts or people who can introduce me to hosts. So, so seriously, if that’s something that is of interest to you, we should have an offline conversation. Okay.

[00:39:32] Drew Thomas Hendricks: Absolutely. Well, thank you so much.