From orgy propositions to projectile vomit: an exposé on private wine tastings, and why I’ll never stop hosting them

I scrambled - very hungover and very late - knowing I was cutting it close for a wine tasting I’d booked for later that day. The instructions explicitly stated, “ensure you eat before arrival”. I had allotted exactly zero time to get there promptly, so food would have to wait. I banked on being a seasoned drinker, assuring myself that a few pours of wine wouldn’t do much damage. I threw on my previous night’s clothes and hopped in an Uber.

It was 2017, and I was on a solo trip in Portland, Oregon - a city I’d always been curious about and finally found the time to visit. When booking my Air BnB, an experience page popped up, showcasing various unconventional activities to try while visiting the city. Since I was travelling alone, this new feature of Air BnB sparked my curiosity.

Upon arriving at the venue - a dark, cramped, basement dwelling wine bar - I was a little unsure as to what to expect. The place was completely empty, accessed via a narrow alley and rundown stairwell. I was the sole attendee. The price was steep - $100 USD to taste a flight of wines - but I remained hopeful that I’d walk away having learned, or at least tasted, something new.

The interaction with the host, Jeff, was awkward at first. It turned out he owned the wine bar, and was also the winemaker of the bottles being featured. Since we were so close to the Willamette Valley, I assumed I’d be tasting a bunch of Pinot Noir and Pinot Gris. Jeff poured me none. Instead, he introduced me to obscure varieties like Savagnin Rose, which set the tone for the course of the tasting.

Once Jeff determined I wasn’t a total idiot - he opened up, and the conversation began to flow a little more freely. He graciously offered me top ups of any of the wines that had piqued my curiosity, was patient with his time and knowledge, and answered all my pressing questions with ease.

I left with several bottles I was elated to smuggle home and share with my wine friends - the Savagnin Rose would be the wine of the night at a dinner party hosted upon my return to Canada among a group of winemakers and sommeliers.

I’d always hosted wine tastings to some degree, being a part of the wine industry for the bulk of my adult life, yet I’d never encountered the style of tasting Jeff had hosted, nor had I ever seen anything of its kind advertised the way it was on Air BnB. It seemed to be about so much more than just the wine, and was nothing like any other wine events I’d attended - nothing like the scripted, choreographed tastings at wineries I’d become accustomed to. I didn’t realize it at the time, but I had tapped into an emerging trend about to redefine the travel industry.

Home stays and experiences have long been a part of the travel industry, appealing to the unconventional, those after something outside of the norm. Couch Surfer, Meetup, Craig’s List and even classifieds have provided a respite for mavericks and renegades after authentic interactions that offer a behind the scenes foray into how locals live, outside of the flurry of main attractions.

The late Jim Haynes - an ex pat who resided in Paris since the 60s - was renowned for hosting weekly supper clubs in his home every Sunday. It didn’t matter your background or social status - if you were keen to meet and connect with others, you were welcome. His goal was “to introduce the world to each other.” He hosted hundreds of thousands of visitors over the lifetime of his experience.

My own personal experience hosting tastings had consisted of a Kijiji ad targeting stagettes while I lived in Calgary. Most of the groups didn’t care to learn about wine, allowing me to pour relatively inexpensive bottles and make serious margins. I upped the ante when I partnered with a pole dancing instructor - I got the ladies lubricated, just in time for the pole dancing portion of the evening to commence.

Eventually, I tired of hosting bachelorette parties, akin to the exhaustion you feel after going on too many Tinder dates. I didn’t realize it at the time, but they depleted my resources instead of energizing them, because I was going about it all wrong - I wasn’t making the effort to connect with people on any real level.

My travels eventually took me all over the world - staying with families in Udaipur, a small lakeside town in northern India in the province of Rajasthan, visiting wineries in northern Slovenia, where I communed with friends and winemakers until the wee hours, passing around bottles we’d smuggled in our suitcases and smoking the local organic weed, and a homestay where I learned how to husk and roast my own Robusta coffee beans, the host, John and his family, happy to have us on their farm in remote Indonesia on the island of Sulawesi, in a small town called Rantepao.

These experiences began to accumulate and it suddenly dawned on me that my most cherished memories all had one thing in common - they had been hosted in someone’s home. I had been permitted a peek behind the veil, beyond the masquerade of the tourist trade. It provided an intimacy no 5 star hotel could rival, and before long, was what I began to seek in my future travels.

When I moved to Toronto in 2019, the thought had never occurred to me to host wine tastings in my home. I figured I’d find a job at some hot downtown wine bar, and sort out what I’d be doing with the rest of my life at some later date.

Upon meeting wine professionals throughout the city, it became apparent how poor the knowledge of BC wine was, and what an edge my experience and relationships with BC winemakers equipped me with. It was on a whim one random Tuesday, where I decided to enroll on the Air BnB experience host app, and listed a “Canadian wine tasting”.

Before long, I was slammed with bookings - hosting back to back tastings, sometimes upwards of 30 people per day. Yet, in spite of the success I was experiencing, I couldn’t narrow down a location - I tried various venues from a condo party room to a co-working space - knowing I hadn’t truly nailed that seductive energy travelers were after. The missing link had been hosting it in my home.

In my own space, I had full control of the music, lighting and decor. Ultimately though, it gave me the freedom to mix groups: putting strangers together at an intimate table, where they’d be forced to open up and share their stories. This is when the magic really started to happen.

A recent CNN Traveler article affirmed the allure of these encounters, via a Sicilian boat tour booked through Air Bnb experiences, where they observed how happy travelers are to share space with others: “when you're spending a week with the same people, especially family, it can be nice to mingle with others for a bit. Our fellow passengers, all from various parts of Europe, were such great company; we were laughing at jokes they'd made through the rest of the trip.”

I met people from all over the world: race car sports commentators from Germany, academics from Colombia, winemakers from Hungary, retirees from Kansas City. People wanted my information to stay in touch; in turn, they too wanted to host me in their homes just like I had done for them. At times, the conversations flowed so freely I’d lose track of time and realize certain guests had been at my table for 4 hours.

Though an overwhelming majority of the experiences were positive (allowing me to accumulate over 100 5 star reviews), the weird, and downright bad guests eventually came a-knocking, too.

The bad encounters weren’t only just uncomfortable, they were unsettling and downright gross. Hosting tastings in your home exposes you in a vulnerable way, relinquishing any sense of boundaries, so you’re really putting your trust in others that they’ll respect this fact.

One couple hired me to do a private tasting for them on a Saturday afternoon. When you host tastings in such an intimate capacity, you learn to read people really well, and it was evident we weren’t a fit. The conversation was taxing, and it didn’t appear they were all that interested in hearing about wine to any great extent.

About halfway through the tasting (I was counting down the minutes until we were done), the male half of the couple interrupted me, and inquired as to why I had so much nudity on my walls, followed up with, “now that you’ve given us your sales pitch, let me give you mine. It seems as though you’re pretty open considering all the nude art you have on your walls, so I’d like to pitch you our sex club.” The remaining hour was spent discussing the “lifestyle” (a moniker for swinging).

The worst experience I’ve ever hosted was with two young women visiting Toronto from New Jersey. The first indication that something was awry: they arrived 40 minutes late.

Something appeared very off, but I couldn’t quite pinpoint what until they sat down at the table, and one of the woman inquired as to whether the liquid in the water glass in front of her, was in fact, water. She took one sip, looked to her left, lifted her hand to her mouth, and proceeded to projectile vomit all over my walls, books, plants, couch and Persian carpets. To say the experience was traumatizing would be an understatement.

It would be unrealistic to expect that all the tastings I host are transcendent - I know that the bulk of them will be good, but not great. Some of my guests have now become dear friends, and I’ve received no shortage of job offers and opportunities.

The beauty of hosting such an unconventional experience is honing my skill of hospitality, learning how to talk to others, and connect.

So many of my guests arrive itching to discuss Covid and the political climate - this type of conversation gets boring quickly.

After a few glasses of wine, it’s pretty easy to get people talking about their families, favourite books, movies, or memorable trips they recently took. Before long, they sheepishly realize they’ve been regaling their life story to me. When this happens, I know I’ve done my job.

My initial purpose in hosting experiences was to expose as many people as I could to the bounty of Canadian wine being produced - and while that still remains a prime goal - an unexpected byproduct has been the fascinating education in human psychology.

If you’d like experience a tasting with me (I offer both in person and virtual tastings) you can book here.