by Victoria Shepherd

Originally from England, Victoria has always been an avid traveler. In 1992, she moved to New York City and currently resides and works in San Francisco. She has traveled to numerous places around the globe, including India, Africa, and Brazil.

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Accompanied by the new Harry Potter, I departed out of San Francisco Airport in June. Armed with boarding pass and picture ID, I headed to the end of a very long security line, and realized that perhaps the one hour I’d allowed wasn’t quite enough time to get to the airplane. But the queue began to disintegrate immediately, and within minutes security guards herded the passengers through the metal detectors, like sheep about to be thrown into a trench, dipped, and sheared—all within record time.

The flight was uneventful, except that I was moved twice, with someone asking if I would kindly switch places in order for them to sit next to her Aunt Flo or five-year-old Timmy (whose lower lip practically touched his knees because the airline, to his horror, was not going to give him his very own TV screen). Being single, I was more than happy to move anywhere. And for my charitable actions, a flight attendant rewarded me and moved me up to Premium Economy section near the front of the plane, as opposed to Toilet Class in the rear. There was the slight problem of the seat not reclining an inch—which eventually led to lower back pain, tingling in my legs, and lots of fidgeting proved problematic—but hey, I was going to be one of the first off in the rush when we reached our destination, and that’s what mattered. (Unless of course, the numbness in my legs was the sign of one of those fatal blood clots I’d heard about…)

My home for the week would be a brand new resort in Poipu, which is located in the south of Kaua’i, approximately thirty minutes drive from Lihue Airport.

The accommodation was surprisingly large. I had two bedrooms, two bathrooms, living room, a dining area for eight people, full kitchen, plus washer and dryer, all to myself. And three television sets. It was amazing. I would need to make friends fast. I stripped my clothes off at a rate any man would be impressed by and quickly changed into one of the alluring bikinis I’d purchased for the trip. And with factor 15 suntan lotion, sunglasses, beach towel, and a bottle of water, not forgetting The Order of the Phoenix, I headed for poolside and the bar. I situated myself on the only available sun lounger, breathed a sigh of relief, and laid back to strategize and plan my itinerary.

One negative of going away on vacation alone is that no matter how hard you try to push your arm down your back covered in lotion using the other arm, you’re never able to ensure satisfactory coverage and protection from the rays of the sun. I therefore arrived back at my villa accompanied by a very red and painful (not to mention embarrassing) warning stripe stretching across my back that would hopefully be enough to remind people to STAY BACK FIFTY FEET.

I spent Sunday evening at a delightful ocean-front restaurant located in Poipu. My date was Harry Potter. We situated ourselves at the bar, where an amazing view of the sunset ensued. Two hours later when I departed the restaurant, having eaten the most amazing raw fish ever to pass my lips, Harry and I took the long way back to the parking lot and walked along the torch-lit beach front. The comfortable, relaxed silence between us was beautiful.

Ride ’em Cowboy

On Monday I awoke before five a.m. The drive to Kapaa would apparently take approximately one hour, and I had to leave enough time to account for the rush-hour traffic. On an island with only one main road? Turns out that Lihue, on the east of the island, comes to a stand still most mornings between the hours of seven and eight a.m. I did as I was told and arrived at the riding academy right on the dot of eight thirty a.m.

Mandy would be our guide and companion for the next four hours in the saddle. There would be a total of five of us on the outing: four women, including Mandy and myself, and one southern gentleman. We demonstrated we knew how to mount and dismount a barrel with a saddle attached to it, and start and stop using reins attached to a branch, and then we met the real thing. Prince was a frisky paint horse that thankfully had a mind of his own and was not totally predictable.

In addition to Mandy being full of general knowledge about the local flora and fauna, she also had a sense of humor, which can be helpful when it comes to taking your mind off the ache that eventually starts in your buttocks.

All of us spent the next few hours bonding while walking, trotting and loping, learning many interesting things about The Garden Island. For instance, the great Captain Cooke was chased from the shores of Kaua’i by the natives who believed he and his crew had very kindly bestowed upon them some rather uncomfortable STDs. Although he did survive this humiliation, later when he upset locals on the Big Island, and his ship was anchored eight feet out from the shores, to save himself from being impaled by spears he was going to have to sink or swim. And, as he couldn’t actually swim a stroke, he did the latter and never resurfaced.

In addition to being able to taste fruits such as guava, which grow prolifically on the trails, and smell the lavender flower (or natural orchid), you can hear the legend behind the “Sleeping Giant” Mountain, or have your photograph taken with the breath-taking views as your backdrop. One thing you won’t get to see during your stay on Kauai is a snake. These scaly reptiles have been totally eradicated from the island and not even a grass snake will be seen slithering across the path in front of you.

For dinner that evening, Harry and I visited the bar at a four star resort located five minutes drive where I was staying. Although, if you happen to be directionally challenged like myself, feel free to take the rather circuitous route whereby you arrive at your destination approximately one hour later than planned. Having already been advised this was one of the more elegant places to dine, I opted for a pretty flowing floral sundress and high heels. And nothing else. The dress was fabulous to look at but was very sheer. Consequently, I had to lose the underwear. Not surprising therefore that by the time I left the bar, I had a dinner date lined up for the following evening. I stand firm on my belief though that the two things have absolutely no correlation whatsoever.

Sea Legs

Rising early on Tuesday, I headed for the north of the island, to Anini Beach, approximately 70 minutes’ drive away. Yet another activity I had on my list of “things to do during my life,” I was to go windsurfing. A local company offered “easy, fun and safe” lessons at Kaua’i’s safest beach. In just two lessons, or six hours of tuition, I would be able to use this flotation device as a form of transportation.

By the end of my first lesson, I was able to stand up on the board, pull up the sail and travel out to sea, even turn—albeit in a wobbly sort of fashion – and come back to the place on the shore that I had set out from. According to Brad, my long blonde-haired and bronzed instructor, I was “a natural.” I was also very tired and hungry so as soon as I’d rinsed the salt water from my hair, I waved goodbye and headed in the direction of Princeville, the town where the elite of the world vacation, live and play, where one of the more enticing past-times is a round of golf at “Hawaii’s Number One golf course.”

Hanging with the Locals

While desperately searching for a lid to match my medium-sized cup full of diet cola at a local over-priced supermarket, I met Fred, a funny and flirtatious 50-something. If it hadn’t been for the fact that low blood sugar was sending me into a shaking, giddy state of lucidness, I would probably have remained chatting away quite happily with this friendly local for hours. Instead, we exchanged numbers and I headed for the deli counter, before continuing along Highway 560, just north of the Napali Coastline. This is the most amazing, most beautiful untouched and unspoiled area of land that I have ever seen. The landscape is lush, green and faaaabulous! This is where movies such as Six Day, Seven Nights, King Kong, and Jurassic Park were filmed. If, by the way, you’re that way inclined and like to spend a vacation stuck on a bus with other individuals, you will be pleased to know that there are companies based on Kauai that will be more than happy to take your money and show you all of the places where movies have been shot. This is not my cup of tea, but the bottom line is, whatever rocks your boat, someone out there will be able to take care of you.

Baby Face

Later that evening, after I’d showered and changed, I headed over to the hotel to pick up my young date for the evening. For the first time since we’d been together, I left Harry behind.

A very cute and weathered twenty-six-year-old named Richard (whom I was thankful considered me eight years his senior), my date for the evening, was visiting the island with his parents. In fact, sharing a room with his parents…I found this rather puzzling but was certainly not going to complain.

For dinner we visited a local restaurant. Although frighteningly busy, the food was excellent and they mixed a very mean margarita. So mean in fact that by the time our food arrived, I’d turned into a giggling, very cheap date and I’m sure mentioned more than once that it was strange how Richard didn’t have his own room. Perhaps though, this was the first family outing they had ever been able to afford and in fact, in addition to his parents, Richard’s grandparents, aunts, uncles and cousins were squished into the room like sardines. Guilt suddenly swept over me and I immediately felt sorry for this child and wanted to take him under my wing and protect him. He was in desperate need of comfort and I would be more than happy to oblige.

Needless to say, after spending a wild (but “safe”) evening with this little engine running on “bunny” batteries, I will think twice before speaking negatively about Demi Moore again.

Row, Row, Row Your Boat

The next afternoon I headed to Lihue to go kayaking. I was greeted by a very cute blond named Summer Dawn. Working at the store during her school break, Summer very kindly turned my kayak around to face the beach, and then left me to it, having relieved me of my two cameras and cell phone. Hopefully, I would make it back…

I tried to push the kayak out into the water through the waves, without it turning sideways, bashing me in the legs and flipping over, forcing me to run around grabbing the oars and life jacket, all before they were swept out to sea never to be seen again. This was definitely the most difficult point of my vacation. Apparently, there is a certain knack to ensuring a graceful departure from the sandy shores and getting into your vessel. But because of how things go in life, no one had told me “the rules” and everyone around me giggled at the sad “single” who laughed away to herself while getting soaked to the bone. I tried to push the small boat out to sea again and then ease my weight into it, while at the same time trying not to fall out over the other side. Five miles and a couple of hours later I returned, worn out and wet. Having only had myself to talk to for the duration of my boating expedition, I headed straight for the nearest bar seeking civilization. Even though I was covered in saltwater and sand, wearing no shoes and a pained expression, I was able to relax and feel welcomed. I spent the next couple of hours chatting to anyone at the bar who’d listen, including the adorable fifty-something Fred, who stopped by to buy me dinner.

It’s a Wrap

It was my last day to play in Paradise and once again I was up at the crack of dawn. By lunchtime I was “certified,” having gained the art of windsurfing and its terminology, including tacking, jibing and down-wind.

After all the excitement of my all-to-brief stay on this magnificent island, I headed to a day spa in Lihue to experience a much-anticipated Hawaiin massage, or Lomilomi. Nate was going to be my masseuse, and Heaven would hopefully be my destination. I left Nate’s very capable hands one hour later feeling relaxed, rejuvenated and refreshed, with just about enough energy to pack my suitcase and get a good night’s sleep before returning to reality.

The Upshot

The brilliant thing about being thirty-something and single is that it’s actually possible to date someone who’s nearly young enough to be your son or old enough to be your father. We’re at that ripe age when pretty much anything goes and anything is possible. So ladies, grab your ambition, throw it over your shoulder and run with it. Run as far and as fast as you can and one day, you’ll be very close to realizing your goals. Ralph Waldo Emerson once said that “nothing great was ever achieved without enthusiasm.” Having enthusiasm and a passion for life is key to being a successful, independent single woman. At some point in my future, when I’m busy enjoying being me, I have a feeling that the “actual” Mr. Right, and not all the Mr. Maybes who have gone before him, will appear on my doorstep and I’ll trip right over him in my rush for happiness—and he’ll be the one chasing me this time around.

Feel free to contact Victoria at

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