During the summer of 2008, Jay came with me to the house my friends and I rented in the Hamptons. We rented a car and drove the two hours to get there, but since the Hamptons is basically a relocation of all of our friends from New York, I do not count that as an official "first trip."
My first trip with Jay was to the Hunter Valley in New South Wales, a three-hour drive outside of Sydney. Hunter Valley is wine country, and a lovely place for a weekend getaway. And anyone who really knows me knows that I just love a good road trip. Love it!!
This was a fairly easy trip in theory, but we had not taken into consideration was that it would be my first time driving on the “wrong” (ok fine, the left) side of the road. Whenever Jay and I travel anywhere, I am automatically the driver; no discussion. Maybe it is because he cannot keep focus enough to drive, maybe it is because he does not have a license, or maybe it is because I am the safer driver. We do not have to speculate, just know that Jay does not drive.
So we rent our car at the King’s Cross Budget Rental Car Company and hop right in. Except I hop in on the wrong side. Red flag #1. After we switch places and are in the correct seats, I turn on the car and attempt to turn onto the road, and turn on my windshield wipers instead of my turn signal (as they are in opposite spots in cars down under). Red flat #2. When I finally feel comfortable getting onto the highway after driving around the block a few times, I merge into the highway and start drifting left…into the wall in the tunnel underneath Sydney CBD. It was a close call, but Jay gently screamed “Wall!” and I moved back to the right side of the lane. Red flag #3. But Jay was a good sport and thanks to his lack of focus, he didn’t seem to really notice how dangerous this excursion was going to be and was just happy for a little break from work.
We spent two days and one night in Hunter Valley. I had stumbled across an adorable B&B online and booked one of their 8 rooms. What a treat this was! Their “rooms” were actually massive suites with king-beds, luxurious robes and slippers, overflowing amounts of L’Occitane amenities, and a fully-stocked all-inclusive mini-bar (with lots of local wine and champagne from the vineyards of course!). We were in heaven! We had a quick snack after we arrived, and headed off to put a dent in the list of vineyards that we wanted to visit on this trip.
Learning about wine was new for the both of us. We both knew what good wines tasted like and knew what we liked in regards to our favorite grapes, but we had not learned about the process that goes into making it and the proper tasting techniques. Soon enough we were drinking and spitting (or in Jay’s case, just drinking). We picked up a case of wine along the way, and even stopped at a cheese shop to taste-test the marinated fetas and triple-cream brie. After that stop, we left with a feast of dairy in the backseat.

(Bimbadgen Estate, where we ended up picking up a few bottles for the road.)
Our dinner that night was at the Restaurant Botanica on the hotel premises. Another lucky turn of events was that one of the best restaurants in Pokolbin was at our B&B and dinner with a paired wine flight was included in our stay. I had one of the better filet mignons I had ever had, and Jay enjoyed have a special wine pairing for the first time. The next morning we did not want to leave!

(The vineyards of Pokolbin in the Hunter Valley.)
Before departing Hunter Valley, we stopped at a few more vineyards and picked up a few special bottles of wine which are keepsakes for 20+ years (and that we still have today). We then popped back onto the highway and headed back to Sydney. It was a good first international trip together, and one that I will always have fond memories of.
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