I of course could not go to South Africa without spending some time in wine country. I had heard great things about the Stellenbosch valley, which along with Paarl and Franschooek, forms the Cape Winelands, the largest wine region in South Africa. According to friends that had been there, it is stunningly beautiful, affordable and accessible from Cape Town. After spending two nights in the area, I’m happy to report that I agree with all three points.

I took an Uber from the POD Hotel in Camps Bay to my Stellenbosch hotel, Clouds Estate. The drive took just under an hour and cost about $45. Accessible, check. Pulling up to Clouds Estate, I was immediately impressed with the dramatic setting. The boutique hotel and villas were set on a landscape of hilly vineyards overlooking a couple of craggy mountains. In addition to a tasting room, dining area and indoor living area, the hotel also featured a large outdoor space with a beautiful pool and plenty of cozy seating options.

Outdoor scene at Clouds Estate – not bad, right?

Oh, and the price? My room set me back a mere $160/night, which included breakfast, a complete tasting of the Clouds Estate wines and a bottle of rosé. I had booked the only “standard” room in the hotel, but it was far from standard; modern and spacious, the room contained a king-size bed, a seating area and an outdoor terrace larger than the living room of my NYC apartment. I instantly fell in love with the place.

$160 got me this private seating area and outdoor terrace

My plan for the afternoon was to hit up a couple tasting rooms, and then head into the town of Stellenbosch (~15 minute Uber ride) for dinner. I had booked an Airbnb Experience that was described as a winemaker dinner; the winemaker James had worked in Sonoma, New Zealand and Chile before moving to Stellenbosch, so I was curious to chat with him. 

Since my stay at Clouds Estate included a tasting of their wines, I decided it made sense to start onsite. Why leave the property if I didn’t need to? The tasting room didn’t seem to be a big destination for people that weren’t staying at the hotel; in fact, I didn’t see anyone else tasting there during my entire stay. The wine was fine, but nothing that I liked enough to take home with me.

The Clouds Estate repertoire
The tasting room bar at Clouds Estate

Next up was Molenvliet, a wine farm down the road that is also a hotel and a popular wedding venue. My friend Johnny had recommended the place (potentially a venue for his wedding to my good friend Erica in the future?), so I wanted to check it out.

Remember how I said that wine tasting in Stellenbosch was accessible and affordable? There are many reasons why this is the case, but two to be noted: 1) You don’t need to make appointments for tastings at most places, and 2) Uber is affordable and readily available, so it’s easy to get from place to place without needing to hire a driver or rent a car.

Back to the present moment. Unfortunately, Molenvliet was not open to the public for tastings. What? Apparently, Johnny had steered me wrong. I had mentioned to the manager at Clouds Estate that I was going to taste at Molenvliet and he didn’t seem to think it would be a problem either. However, they wouldn’t even let my car through the gate, insisting that they only offered tastings for hotel guests. Okayyyy. I was still in my Uber, so I just asked my driver to turn around and take me to Tokara instead (another Johnny recommendation). Tokara was within walking distance from Clouds Estate, so I could just walk back to the hotel and get ready for dinner after the tasting.

Tokara was of course beautiful, and popping with couples and small groups enjoying the sunny afternoon. I grabbed a table and ordered a flight, taking in the surrounding ambiance. It was my first time wine tasting solo, and I’ll admit that I felt a little awkward watching the people around me chatting and laughing with each other. However, I pushed the self-conscious feelings aside and focused on appreciating the view and the wine. I was in South Africa wine country and I was going to make the most of it.

Even from my vantage point indoors, the views at Tokara were unbelievably beautiful

After finishing my flight, I ventured back to Clouds Estate. While it was technically walkable (about ten minutes door-to-door), I would not recommend going on foot. I had to cross a highway and then walk on the side of the road (no sidewalk) as cars whizzed by. I scurried along and prayed that the people operating the cars hadn’t been drinking. Fortunately, I arrived back at Clouds Estate unscathed.

The late afternoon view back at Clouds Estate

Winemaker Dinner

The “winemaker dinner” Airbnb Experience was held at a restaurant called Spek et Bone. I was the only person who had signed up for the experience, so it was just me and James. He sounded cool from the description of the experience, and I was hopeful that it wouldn’t be weird to have a one-on-one dinner with a stranger that wasn’t a date.

Fortunately, James ate and drank with me, so he wasn’t just watching me indulge. He was younger than I expected, probably in his late twenties, and also from the States (Fresno). After spending some time traveling after college, he met a South African girl and had recently moved to Stellenbosch to be with her. We started talking about wine, but gradually moved on to talking about our lives, and how James had gotten started doing Airbnb Experiences. He had only hosted a handful of groups (I was the first solo traveler he had hosted) and was eager to discuss ideas on how he could improve the experience.

We also talked a lot about travel, and I brought up the topic of wealth inequality since it was something that was top of mind throughout my travels, particularly in Africa. After a couple dishes and carafes of wine at Spek et Bone, we decided to move to the bar next door for a whiskey nightcap, where the conversation spiraled into a full-on political rant (we were contributing equally). After one whiskey, I decided it was time to call it a night and got an Uber back to my hotel. While it was not the evening I was expecting, and we certainly didn’t come up with any solutions to the world’s problems, it was nice to have a deeper conversation with someone. 

The next morning James sent me a very sweet thank you message, saying that he had learned more with me than he had with any of the other groups. I took that compliment with some humility since I’m sure the dynamic was different hosting just one person than with a group, but it was kind of him to say, and I’m glad that I was able to help him.

Day Two: Delaire Graff

I lucked out on my only full day in Stellenbosch: it was one of those perfect, warm, sunny days that make you happy to be alive. I spent the late morning lounging by the lovely Clouds Estate pool, and then got ready for my one big excursion of the day.

It was hard to tear myself away from this magical scene

The plan was to go next door to Delaire Graff, which is the fanciest, most spectacular wine farm in the area. I had made a reservation for lunch at Indochine, one of the two restaurants on the property. The other restaurant (simply, Delaire Graff), was supposedly the nicer of the two, but I couldn’t make a reservation for just one person. I debated booking for two, showing up solo and apologizing when my faux date had to cancel at the last minute, but Indochine also looked quite nice. I figured it would do.

Another perk of staying at Clouds Estate: they had a partnership with Delaire Graff and could drive guests on a golf cart through a wooden gate between the two properties. I felt like a VIP as the Clouds manager escorted me into reception at Delaire Graff and delivered me to the manager onsite. Delaire Graff is also a hotel, but the rooms will set you back about $1,000/night (at least on the dates when I was in town). I felt like I was getting quite the steal next door at Clouds Estate.

The expansive dining room at Indochine was beautiful, but completely empty. I was literally the only guest when I arrived at 1pm, and I remained the only person dining throughout my entire meal. But the food was excellent, and I was able to enjoy a lovely table outside in peace.

Prawn curry paired with DG chardonnay at Indochine

After lunch, I told the manager at reception that I wanted to do a tasting, but didn’t know where the tasting room was. It was downhill from the main entrance to the hotel and Indochine, so he would arrange for another private golf cart to take me there. Sweet!

Arriving at the building that housed the tasting room and the Delaire Graff restaurant, I was in awe. The tasting room featured a large patio framed by leafy green trees, and overlooked the same dramatic mountains facing Clouds Estate. Unlike Indochine, the tasting room was packed, but they managed to find a table outside for me. My server was a sweet guy named Simba. When he introduced himself I had a naïve moment struggling to keep my composure. I didn’t realize that Simba was a traditional Swahili name used for humans, not just a Disney character.

I had no other plans for the afternoon, and after laying eyes on Delaire Graff, I had no intention of leaving anytime soon, so I decided to order the biggest flight of five wines, opting to taste a rosé, two whites and two reds. It turned out that the Cabernet I selected was only included with the Reserve tasting (not the regular tasting that I had chosen), but Simba let it slide. Each time he came to my table, we chatted a bit more; I told him stories about my travels and we talked about different wine regions around the world. 

The view from Delaire Graff

At some point I decided to ship some wine home, and even after I had finished my five pours, Simba kept bringing over additional glasses for me to try. I ended up tasting nine different wines (I think)! He also stopped giving me any descriptions of the wines, and instead asked me about the notes of the wines I was tasting, as well as the pairings that I thought would be best with each bottle. By then I was enjoying a nice buzz, so I just went along with it and had fun. 

Me, my wine, and I

I told Simba that even though it was my last night in South Africa, I was considering coming back next year, and I hoped to be able to bring friends to Delaire Graff with me next time. As I paid for my tastings, Simba suggested that we keep in touch and asked for my contact information. Sure, why not? I thought, although I figured I probably wouldn’t ever talk to him again.

Hold that thought… after a final golf cart ride back to Clouds, I felt my phone vibrate and saw a WhatsApp message from a South African number I didn’t recognize. “Hey, it’s Simba,” it started. “I really enjoyed meeting you and I learned so much talking to you.” He asked about my plans for the evening and suggested getting a glass of wine in town, offering to pick me up when he was done with work in about thirty minutes. Wait, Simba was asking me out? I was not expecting that.

My mind raced as I thought about what to do. On one hand, when would I ever have a chance to go out with a guy named Simba?! It would at least make a good story. And he did seem very nice. It couldn’t hurt to have a glass of wine and some conversation. On the other hand, I had been drinking for about four hours already and had a long, long, long trip home the following day (one “long” for each flight). I was looking forward to a quiet night and a good night’s sleep. I had also told the Clouds hotel staff that I would have dinner at their restaurant on my last evening, and I suspected they were keeping the kitchen open just for me. Finally, I knew nothing about Simba, besides the fact that he had a name from the Lion King and he worked at a fantastic wine farm. He had been asking me all the questions earlier.

Ultimately, I made the adult decision and told Simba that it had been really nice to meet him. A glass of wine sounded nice, but I had a long day of travel ahead of me and needed to stay in. But I’d keep in touch and let him know when I came back to town (white lie). He was very understanding about it and even checked in a few times over the next week to see how I was doing. Oh Simba.

Last sunrise in South Africa… for now

Just like that, my first trip to Africa was over. Going into the trip, I had been anxious about traveling to so many new, exotic places solo. Fortunately, I made it everywhere without any major hiccups, and I was proud of myself for seeing all the distant sights on my own. I felt invigorated and excited to continue on my travels, and to see what else the world had in store for me…