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…And when he handed me the emergency life beacon and told us to put lifejackets on, I knew it was time to pray.

If you were following our latest Bahamas trip aboard the motor yacht Mermaid Tales on social media, then you might have caught on that the trip wasn’t going quite as planned. Sure, the photos we were posting on Facebook and Instagram showed smiling faces as we fed the swimming pigs of Big Majors and chowed down on conch burgers and rum punch at Chat N’ Chill beach bar on Stocking Island, but pictures can mask the real happenings.

Yes, those experiences where enjoyable as were a few others. It’s just that the boating lifestyle and mother nature had other plans when it came to our trip.

I’m a very glass-half-full type of guy and know that when you’re boating things can go wrong and weather can be a bitch. Those two antagonists just seemed relentless this trip. While being stuck in a place like the Exumas doesn’t sound too bad, expectations can be hard to adjust.

Here is a brief run-down of what the trip was suppose to be and then I’ll go into a day-to-day account of what did happen.

The Trip of a Lifetime – The Trip That Wasn’t

As you know I’ve been working with Captain Mike of Tropical Escape Yacht Charters. For almost two year we have set up Castaway Cruises aboard his 70ft. Hatteras motor yacht named Mermaid Tales. For a relatively low price people could book a charter on the vessel and experience islands and the boating lifestyle.

Captain Mike is doing Caribbean charters the end of this year and next year so he needed to move the boat south from his home port of Miami.

Myself, Castaway Crystal, and 5 other Castaways booked a two-week charter traveling one-way from Nassau to the Turks and Caicos. We would be hitting Bahamian islands that most people never get a chance to visit. Places like Cat Island, Rum Cay, Conception, Long Island, Crooked Island,  and Mayaguana were all on the itinerary.

The anticipation for this trip was unbearable. There was the excitement of not only spending two-weeks at sea and experiencing unimaginable island beauty, but I was going ask Castaway Crystal to be my wife on Cat Island at the highest point in the Bahamas. Throw a hurricane into the mix and yeah, I was a stressed out excited mess.

But things don’t always go as planned.

What Really Happened – The Trip That Was

This is the account of what really happened on our two-week trip. It’s a behind the scenes look at how the exotic boating lifestyle isn’t always very exotic.

Day 1-3: 

Plans change. You have to adapt. Mermaid Tales had been going through 3-weeks of repairs before our trip, and with Hurricane Matthew disrupting repairs, captain was no longer able to get the boat to Nassau in time to pick everyone up. Instead, everyone would now meet in Miami to board the boat. We would then leave from Florida and island hop down to the Turks and Caicos. Not a huge deal, I just had to eat my Nassau flight.

First impressions are everything. When you miss an opportunity to make a good one, it’s hard to recover. We arrived to the Miami marina along with the other Castaways and found the boat not really ready for people. Repairs were still being made and things were messy. Being that I had been on the boat before it didn’t register with me as much, but I could tell by the reactions of the others that they were less than impressed.

Once everyone arrived I thought it a good idea for everyone to go out to dinner and have a good time. I stayed behind to help captain clean and get the boat more presentable. When everyone got back it was better, but like I said, a bad first impression is hard to recover from.

The next two days consisted of some problems with the heads and the two engines not firing up. We saw three mechanics come and go and nothing seemed to work.

The understandable frustration hit a limit on the third day, and the five castaways decided to pull the plug on the trip and make the best of their time. Two headed home to Tampa, two flew to the Turks and Caicos, and one headed to Key West. Castaway Crystal and I talked it over and decided to give it another day.

On a high note, it’s funny how unique experience can bring people together. These five castaways are great people and I’m now happy to call them friends. Scott and Kathy, Nate and April, and Sherri…It was awesome meeting you guys and I look forward to a different adventure with you in the future!

Day 4-5:

The next two days where spent running errands for captain and trying to stay away from the boat so he could do what needed to be done. If the boat didn’t start by Thursday we’d go home or hit the Keys.

We distracted ourselves by exploring Hollywood Beach (love the boardwalk!) and soaking up the best the area had to offer.

Hollywood beach mermaid

Hollywood beach margaritaville

Thursday came, the engines fired up so we took on fuel and discussed our options.

Winds were blowing out of the NE at about 15mph. Not ideal for crossing the Gulfstream. Captain wanted to wait one more day to make the crossing because the winds would fall off a couple mph, but I thought we could make a go of it.

That was a bad idea.

The Gulfstream is one of the most powerful currents on the planet and it flows north between Florida and the Bahamas. If a north wind is pushing against the north-flowing current you can get some tightly packed unpredictable waves. That’s what we hellishly experienced for 7 hours trying to get to the protection of Bimini.

We battled 6-8ft seas with the occasional 9-footer. Things were falling out of the refrigerator, glasses were breaking, things flying off the top deck…it was hell. It’s a passage I don’t suggest in those conditions. Captain’s bike even flew off the top, now lost to the thousand-foot abyss of the Gulfstream. The video shows what the good conditions looked like before we got out into the middle of the stream.

Day 6:

This day was the passage between Bimini and Nassau. After the hammering we took the prior day, we were treated to the calm seas of the Great Bahama Bank.

The sun was shining and the water glowed blue with an occasional squall rolling through. We entertained ourselves by dancing on the top deck to hip hop and cold beverages.


Castaway Crystal

Bahamas squall

yachting sunset

We didn’t find an anchorage until way after dark.

Day 7:

We woke to the blue waters of our New Providence (Nassau) anchorage. Castaway Crystal whipped up her famous scrambled eggs with sausage and cheese and we raised anchor. Destination…the Exuma Islands, Norman’s Cay.

This 5-hour passage was calm and we enjoyed blue skies the entire way. We dropped anchor in Norman’s Cay in the early afternoon and quickly set out to explore this protected area via dinghy.

Norman’s Cay is home to the postcard perfect island of Castaway Cay. It’s just a small spit of an island with just a couple palm trees, little beach and small bench. Hurricane Matthew was not kind to the little island knocking down it’s one talk palm, sending it crashing on top of the bench. We did our best to fix it and I’ll detail that experience more in a future post.

Norman's Cay and Castaway Cay


RumShopRyan Caribbean blogger

This was the first real good island day. While Castaway Crystal and I really enjoyed our solo explorations of this beautiful location, we did miss our new castaway friends…wishing they were there enjoying the beauty as well.


That was the first week of our trip that wasn’t. It was filled with highs and lows, but isn’t that life? Here is Part 2!  It will give you a glimpse at more good and bad island adventures and one of the most intense moments of my life. Yes, I’m referencing the life jacket and emergency beacon moment!

We all create expectations of things in our mind, that’s especially true when it comes to vacations. We spend a lot of money to do and see things that we dream about. We want the experience to be absolutely perfect, and when life throws you a curve ball it hurts. You just have to adapt and make the best of what you have at the moment.

Part two coming soon!!!


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About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.