$1k A Day Part 3: Bullets in the Headboard
by sorrydog on Nov.29, 2008, under How to see the Caribbean on $1000 a Day
Now, you must be wondering about our boats, the Hiatus and the Lehac, still anchored out in a bend in the harbor. We left the local party at about 9 or 10. We didn’t want to overstay our welcome.
Unbelievably, we threaded our way back via the dinghy, without a local guide. Dumb luck? Most certainly. Especially in light of the local pirates. Knowing the danger, we discussed our defense plans on our journey back.
Both Shelton and Island Eddie knew that area of the Caribbean. They believed that it was unlikely that any regional pirates would strike until the wee hours of the morning, when most sane people would be asleep. Surprise was their most potent weapon.
Our boats were anchored, side by side. We figured that it shouldn’t be very difficult to secure a perimeter so that only one guard would be needed. Fortunately, we had a plethora of alarm materials readily available. Not being ones to waste time, we set to work immediately.
We stretched a line of high-test fishing wire around both boats. Then we attached clusters of empty beer cans across any potential point of invasion as well as a string of cans in any place that we thought they might try to gain access to the lower cabins. If one line were broken, it would set off a chain reaction that would readily alert us to intruders aboard. Overall, we were nervous about being in pirate waters but ultimately grateful for Shelton’s armament.
I took the first watch, amply equipped with an awesome Magnum. Four hours passed with no significant signs of intrusion. Right on schedule, Joe Bob, Shelton’s 17 year-old son came up for his shift. I laid the Magnum on the dash and told him it was loaded… then I asked if he knew how to use it.
He bowed up in typical teenage fashion and pronounced, “I’m from Texas. My Dad has an arsenal hidden in the hold. What do you think?”
Not being one to argue, I headed for my berth on Island Eddie’s boat. Dodging our traps, I finally made it next door to Eddie’s boat. The first thing he asked was, “Who’s on guard?”
I assured him that Shelton’s son, Joe Bob, was on guard and that he seemed to be very capable in the gun department. My eyes and my body were screaming sleep. The only thing I wanted was to be horizontal. Trust me, it didn’t take long. I stripped and was out like a light in record time.
Less than 3 hours later, I was rudely jolted awake. I didn’t know what triggered my internal alarm, but I wasn’t taking any chances. I called out to Joe Bob but got no answer. Fearing the worst, I grabbed the pistol I had hidden in my cabin and headed for the bridge.
Most Island Wanderers tend to sleep nude and I am no exception. Getting dressed was not an issue. I crept out of my cabin, clad only, in a 357 magnum.
In the salon, I met up with Eddie. He too was resplendent with nothing but a fully automatic machine gun and the belts that went with it. Bleary eyed, but tense, we quietly agreed not to shoot each other and went in search of the real culprits.
We were both crouched low, awkwardly duck-walking toward the hatch, every nerve poised on a pin at the slightest sound. Oblivious to the potential danger, I took the lead. I probably could say that it was sheer bravery and manly bravado that made me take the point, but it wasn’t. Considering our current mode of attire, I simply had no wish to inspect Island Eddie’s dangling jewels up close and personal.
I crawled up the stairs, conscious of every swell of the ocean and the odd creaks that every boat makes when it’s at anchor. Cautiously, I tried to peer through the inky blackness of night, but saw nothing.
“Joe Bob,” I hissed. There was no answer and my hackles cranked up another notch. “Joe Bob?” a tad louder this time. Again, nothing.
I snaked out onto the deck and low crawled down the port side of the boat. Still not seeing anything that would merit alarm, I motioned for Island Eddie to cover me. I slipped over the rails onto Shelton’s boat and finally spotted Joe Bob in the pilot house across the cabin.
He looked dazed and confused, staring down at his hands as if they’d suddenly become alien appendages. He too was clad only in a gun belt with his pistol clasped loosely in his hand.
“Joe Bob” I softly urged, “who fired that shot?” He didn’t answer; only shrugging his shoulders as he blindly stared back. “Were we boarded?” I asked, my voice more urgent this time.
Still no answer but he finally looked at me and not through me. My nerves were still coiled like a spring. “Dammit Joe Bob, what happened?”
He gave me that guilty shrug that is characteristic to almost all teenagers. “I dunno,” he mumbled. “It just went off!”
Finally, he confessed. He’d started getting sleepy. To keep himself awake, he started playing with the gun and boom….it went off. Now we had to figure where the bullet went and where his girlfriend and dad were.
We traced the trajectory through the dash and finally found that the bullet had lodged in the headboard over his girlfriend’s head.
It’s a good thing that they serve great rum in the islands. With the gunshot, Joe Bob’s girlfriend screaming and the imaginary pirates, Shelton never heard a thing. He slept through it all. It would seem that the good Lord does look after drunks and sailors.
The next morning we got the single side band radio working but my 7 day vacation had now stretched into 30 days. We had not been around an actual telephone for weeks but I knew that there were two calls that I had to make.
First, I called my boss. Determined to get the jump on him, I started speaking as soon as he answered. “Now, before you say anything, I just wanted to let you know that I quit.” That was the end of that story. Come to think of it, I never did get that final paycheck.
Next, I called my girlfriend. The iciness of her tone came through loud and clear over the staticy connection. Then, she said something about a new boyfriend. End of story number two.
Oh well! I leaned into the wind, staring out at the broad expanse of endless blue ocean and my siren muse take flight in my mind. “So what if you don’t have a girlfriend?” she cajoled dreamily, “look at what you do have.”
Ahhhh, my siren muse is always right. I have the singing surf, sugar sands, gentle breezes, and lots of islands left to explore. So enough with the reminiscing. Let’s hop on over to St. Croix.
Tune in next Month for Chapter 4: “St. Croix or bust (and why do I have to make a choice?)”
$1k A Day Part 2: “Oh the funnel we’ll have…”
by sorrydog on Nov.24, 2008, under How to see the Caribbean on $1000 a Day

As all good sailors do, we had to go into Georgetown to kiss all the girls goodbye the night before we left for St. Croix. Now it doesn’t take much to entertain an Island Wanderer so we took our funnel to town in hopes of finding new members for the FUNNEL ISLAND CLUB.
Yellow Bird, a local islander, placed the funnel neck in the front of his pants just as we showed him. He then laid a quarter on his forehead to drop it in the funnel-best out of 5 tries wins-right?
When he closed his eyes and leaned his head back to aim and let the quarter fall into the funnel, all tried and true members of the funnel club, poured their drinks into the funnel. Yellow bird immediately raced out of the Two Turtle Inn and disappeared down the street. This was somewhat strange, but we continued trying to find new members of the Funnel Club. After a short time, we saw Yellow Bird shyly peeking around the door. I motioned him in, he said he was to embarrassed. I asked him why-he said that when his quarter landed in the funnel, he was so excited he ‘wet his pants’. He wanted to try again so, being the nice guys that we were, we let him.
We had a millionaire from Texas join the club that night. Shelton joined on his 42’ trawler “NoLease” along with his 27 guns and a 22’center console that he towed from Texas. Shelton told his divorce attorney he would see him in 6 months to see how much money he had left. Butlike any true Texan, he was making sure she wasn’t getting his gun collection, his boat or his wine collection.

We had anchored next to Shelton in the Bay along with about 25 other boats. We we all got back aboard his boat around 2:30 am, we had to see his gun collection. We also decided to test fire all of his 27 guns at bear cans floating in the water. (I liked the WWII Thompson submachine gun the best but the automatic shotgun was a blast). The next morning at daybreak, we were surprised to to find that we were the only boats left in the anchorage (go figure).
3 days later, south of Long Island, we dropped anchor in a harbor along with Shelton. It didn’t take but a few minutes and we heard on the radio “there goes the neighborhood”. We weren’t sure if they were talking about us until they said something about the ‘Apple Dumpling Gang” and a midnight shootout at Red Hook Bay. Yes, things do get a little crazy in the Islands, but one thing you will never see is a MENTAL HEALTH CLINIC.
Next stop Mayaguana Island and wouldn’t you know it, we have a full freezer and we hook a 60lb wahoo. The cruising guide tells you two things about this island:
- Pirates still work the area so stand guard on board at night.
- A native named Reggie is the unofficial mayor of this abandoned WWII fuel dump (pop 75).
Now who would you rather give your fish to? We got Reggie on the VHF and he sent out 2 guides to help us get through the sand bars and to get the fish. Reggie had decided to cook us all diner along with the rest of the village locals. He said a guide would come out to our boats around 5:00 that evening.
The guide led us in Shelton’s 22’ center console dinghy. Reggie and all the other Pirates wanted the Dinghy and the radio. We ignored them and stayed for the fresh fish, rice and peas for diner. Local bongo drums, Island surf, wine and beer and stars that go on forever-just another shitty day in paradise.
About the pirates and our two boats, still anchored out around the bend in the harbor. Reggie said he would put in a good word with the local ‘bad guys’. He said they listened to him sometimes. We posted a guard and were very glad that Shelton brought his gun collection.
How to see the Caribbean on $1000 a Day
by sorrydog on Nov.24, 2008, under How to see the Caribbean on $1000 a Day
Little did I know that cold, drizzly day in early January of 1985, in Jacksonville, Florida, that when I answered my office phone, I had just quit my J.O.B.
The voice on the phone tugged at my heartstrings. It was my old friend, Island Eddie. “Go to the airport,” he said, “get on a plane, and fly to Georgetown in the Exuma’s. I’ll meet you on the dingy dock at the Peace and Plenty Hotel at happy hour.”
Naturally, I was never one to argue so I left the office, mumbling something about an errand. First stop was my newly purchased, as yet unnamed, 50-foot boat. (Later to be known as ‘Sorry Dog’…hmmm, I wonder why?) After all, I did have to pack something. However, Island Eddie’s girlfriend, Joanie, a longtime traveler of the islands had taught me well.
- Rule 1: When traveling through the islands wear just enough jewelry that if you get over there and get broke you can sell it and buy a ticket home.
- Rule 2: Travel light. You can always swap a beer for what you need.
- Rule 3: Always take enough beer to get back home.
Moreover, I’d only be gone seven days.
I threw seven t-shirts and seven swim shorts in a tote bag and slipped on my faithful flip-flops. I looked around, my mind reeling with the decisions of what to take and what to leave behind. Then I thought, heck, I don’t need anything else. I’ll be back in a week.
Time was of the essence. Unaccountably, I felt this inner siren rising, urging me on, her whispered voice, breathless with heated anticipation, blinding me to the past… and to the consequences. I turned off the lights of my now defunct Christmas tree and left.
The siren continued to serenade me with wild, yet barely glimpsed visions all the way to the airport. Once I had my ticket to Georgetown firmly in hand, it was time to face that one last chore. Both my boss and my girlfriend were less than thrilled when I called them from the airport saying, “I’ll be back in a week!”
My first clue that I had quit my J.O.B. (I still can’t say the word.) came during happy hour at the Peace and Plenty Hotel. By that time, Island Eddie and I were both well oiled. “I’ll make you a deal. If you get on the boat and go with us,” wheedled Island Eddie, “we’ll go all the way to St. Croix in the Virgin Islands.”
I had no real knowledge of St. Croix but the siren was once again calling. “How far is that?” I asked.
“About 2000 miles from Jacksonville,” Eddie replied casually. “It should only take two to three weeks.”
Now any responsible person would have jumped ship immediately to save their J.O.B. and girlfriend. I agreed to go. After all, that siren’s call is irresistible.
( He told me later that once I got aboard his 38 foot trawler, aptly named the ‘Hiatus’, that had I not agreed, I would have been kidnapped and taken along anyway.)
Since I was never one to waste an opportunity, I traded the remainder of my round-trip airline ticket to the bartender for a round of drinks. It was only proper to make a toast to our newest adventure.
My boss and girlfriend sure are gonna be happy. Seven days-yeah right.
To Be Continued…
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