One afternoon, bellied up to the bar at Angel’s Rest, I fretted aloud about a package that had just arrived for me at Connections in Cruz Bay – St. John’s biggest town, all the way across the island. I was concerned that, without prompt pickup, it would be returned to the sender.

Tough wind conditions + sea state + general laziness (it would take the entire day to sail there and back) made taking the big boat an unsavory scenario for all five of us. Land travel was my only option.

Trouble is, the island bus system (a bargain at $1 per ride) does not venture out to our current anchorage in remote Hansen Bay. As I mulled the logistical and financial challenges of getting a taxi to come pick me up, Peter chimed in.

“Taxi? That’s nonsense. Hitchhike, like everyone else!”

I shuddered at the thought. As a total chicken/rule follower, the idea awakened a very specific, imaginary scenario of being kidnapped, held in a secret room behind a basement wall, tortured, and eventually murdered.

But desperate times got the best of me, and unbelievably, there I was, the following morning, standing by the road, waiting for a car to drive by so I could stick out my thumb at it – just like in the movies.

I waited. And waited. Annnnnnd waited. No cars.

Walking until someone came along seemed like the most sensible option. But, there is no such thing as a casual walk on St. John. The entire island is made up of a bunch of steep mountains, all clumped together. By the time a car finally approached me, I was 45 minutes into a strenuous hike (in flip flops) and sweating from head to toe . I stuck out my thumb. By some miracle, they stopped.

PS – The act of someone get into the tiny back seat of a 2-door Jeep in a sundress on a road so steep that the heavy car door won’t stay open is a pretty comical thing to witness.

My first benefactors were a vacationing couple from Kingston, NY. Brian and I have family there, and it turns out there was lots of common ground. Originally from Long Island (just like Brian), they too enjoy sailing and used to charter Island Packets in the Virgin Islands. Their son, who is our age, used to live aboard his sailboat in the marina across from ours and commute to his professional job in NYC, so nothing about my lifestyle seemed at all strange to them.

They dropped me at the junction where the bus picks up near Coral Bay. Heartened that I hadn’t been kidnapped, held in a secret room behind a basement wall, tortured, and eventually murdered, I relaxed and waited for the bus.

And waited. And waited Annnnnnnd waited.

As I continued to wait, I was joined by a local engineer, who’d relocated to St. John from Virginia, after falling in love with a woman he met here on vacation. They did the long distance thing for a while, until he finally moved here, and they have been happily married for 11 years.

After chatting a while, he told me that he was concerned that the bus was not showing up. He speculated that it had gone to lunch. Yup, that’s a thing that happens here – the bus drivers up and decide to stop for an hour and eat.

Just then, two ladies he knew pulled up in an SUV to say hi. They were en route to the chiropractor in Cruz Bay, and offered us a lift. I sat back in my seat, downplayed my carsickness, and listened as they compared the virtues of various island chiropractors and acupuncturists, discussed the menacing wild island donkeys (one lady was attacked while out walking with her dog), and swapped assorted island gossip, as we bounced along corkscrew turns all the way to Cruz Bay.

I made quick work of my errands in town, and caught the next bus back. I got to talking with a young musician and composer who had moved here from Boston one year ago without a plan and had fallen into his dream job at the St. John School for the Arts.

45 minutes later, the bus deposited me back in Coral Bay. I stuck out my thumb one more time, emboldened by my day of positive experiences. A man in a truck scooped me up on his way to the dump.

I was promptly kidnapped, and am being held in a secret room behind a basement wall. Please send help. I think he’s going to kill me.

Just kidding.

He was totally sweet. He and his wife came to the island 9 years ago and made a life here, sustained by an internet connection with his company in the mainland US + income from a vacation rental property.

Back on the boat, I recounted the events of the day, and how, the more local people I meet here, the more I become more enchanted with St. John. I probably won’t be hitchhiking again anytime soon (certainly not in mainland USA or on most of the other islands we’ve visited, for that matter), but I’m proud that I faced my fears and was rewarded by a deeper appreciation for this island that I love.