
Global Hitchhiking to Aruba
A 2000-Mile Crewing Passage
In 2016, I decided to take my sailing life to a new level. After working as a computer consultant for 20+ years in California, the stresses of my job and lifestyle were starting to take their toll. I was introduced to sailing in Belize in 2011, where I boarded a sailboat and didn’t get off again — except to go snorkeling or scuba diving — for a week. That experience sparked something in me and changed my perspective for the rest of my life.
Over the next 4 years, I took sailing lessons, joined a yacht club, and went sailing almost every weekend. But I wanted to take it to a different level. I was in between contracts and felt it was time to take a break.
In June 2016, I flew to Barcelona and took a 3-month course that culminated with receiving an RYA YachtMaster Offshore Certificate. Technically, this qualified me to skipper a vessel offshore, commercially. We put in 2000 nautical miles of sailing, during the course, by making passages to Portugal, Spain, France, Morocco, and Tangier. We sailed actively in the waters where orcas are causing problems today.
It was one of the best times of my life. I made lifelong friendships and memories. It was a great way to learn — living on boats and working together on the same goals — with my class/shipmates. I loved it. Not since my trip to Belize in 2011 had I felt so immersed and at one with the sailing lifestyle.

Global HitchHiking
After returning from YachtMaster school, despite having a professional certificate, I decided to get more experience on sailboats by crewing. Think of the certificate as a driver’s license. You have to get one to drive, but it takes experience in all kinds of conditions to drive well. Crewing on other people’s sailboats is a way to get that experience.
Crewing is essentially offering your experience and services to the owner of a boat in exchange for passage on that boat. Sometimes this means a berth, sometimes it means a couch or a hammock. Also, while crewing, depending on the arrangement you make, you might be responsible for your share of the consumables. Different skippers have different requirements and benefits. I preferred paying for my share of the food. I felt like it gave me more say in what we ate. It also felt like I was a contributor rather than just someone exchanging food for my services.
I call crewing, Global Hitchhiking because you can literally crew around the world. I have written articles about the topic in my publication, Global Hitchhiking, that help you get started and discuss safety and practical concerns.
Before going to Spain, I lined up a tentative Global Hitchhiking opportunity with a boat in Norfolk, Virginia, called Caribbean Reiki. When I completed my YachtMaster course, I flew home to California (September 2016). After putting my things in storage and tying up some loose ends, I flew to Norfolk on November, 4th 2016.
Caribbean Reiki
After arriving, I met the members of the crew for this 60-foot boat, preparing to sail to Aruba. The boat had been sitting in the water at a marina for 10 years, unused, and required a lot of work to get it going again. The owners — a nice French couple — were onboard, as well as a young couple from Texas, who also wanted to get some experience sailing on a sailboat by crewing. There were also two cats onboard — honorary crew members for the trip.




We knew before arriving that the boat did not have an autopilot, which is why Paul, the owner, had invited all of us to crew. Hand steering for 2000 miles can take a lot out of you, which can be made easier with others, taking shifts.
When we checked in, Paul had a small army of people there, working on refitting the boat. Because it had been sitting in the water, unused, for a long time, there were lots of issues. Electrical was one of the biggest issues— that and the motor. Electrical wiring doesn’t last long on a boat, especially a saltwater boat. The wire and connectors get rusty and brittle and eventually fail to carry a current properly. Somewhere between the power box and the top of the mast, there was a short in the wiring. So new wiring had to be run to the top of the mast. And throughout the boat.
The first day I arrived parts of the motor were strewn across the floor of the pilot house and the motor was splayed open like a corpse in an autopsy. Not being a mechanic, and seeing the motor in such disarray, it seemed impossible to me that that motor was ever going to run, let alone run in a week, which was when Paul told us things would be ready.
There was also a list of things Paul asked us to work on. Things like securing a chest with tools on the deck, going to the hardware store to buy parts and supplies, and replacing the navigation lights at the front of the boat. We stayed busy the whole week. We were all excited about this adventure and wanted to get going, so we helped as much as we could. We probably should have come a week later, because they were so behind on the renovations.
Paul had a single purpose for this boat — get it to Aruba and park it in the marina. He was going to turn it into an exotic Airbnb and provide Reiki services to guests. He didn’t want to, nor did he have the budget to spend lots of money to get the boat in tip-top shape. He did the bare minimum to get the boat functional and seaworthy for a single trip to Aruba. He had no plans to sail it after that.
Caribbean Reiki was a Douglas custom, ketch-rigged, 60-foot sailboat with two masts and three sails— the foresail, the mainsail, and the mizzen. It had two helms — one up on deck and the other in the pilot house, where one could escape the weather and steer the boat.
The Journey Begins
About a week after we arrived — by some miracle— everything was ready and we started on passage. Norfolk, Virginia is where the Intra-Coastal Waterway (ICW) begins — Mile 0 was a marker we sailed past as we began. From Norfolk, we took the ICW all the way down to Miami, Florida. From there we would cross to the Bahamas, go on to Southern Haiti, and then cross over the Caribbean Sea to Aruba, a journey of around 2000 miles. The image below shows our planned route.

Intra-Coastal Waterway
The ICW is one of the coolest and safest places to travel down the East Coast. It is essentially, an inland channel, although you could often see the Atlantic from the boat. Every 25–50 miles the scenery changes, giving you a diverse snapshot of the Eastern Seaboard, from Norfolk to Miami. There were many opportunities for photography along the way.









There are two issues on the ICW for a large sailboat — heights, and depths. We would be traveling through a lot of bridges. Some bridges raised, some swung, and others were just high enough for us to go under. The tallest point on our mast was 63 feet from the waterline. And the shortest immovable bridge we had to cross under, was 65 feet from the waterline. We often held our breath when sailing under these bridges.
The other issue is depth. Our boat had a 7.5 foot draft, meaning the keel extended 7.5 feet below the waterline. The ICW was originally designed and dredged by the Army Corp of Engineers. In the past, they guaranteed a depth of 9 feet at its shallowest for the entire ICW. But, in recent years there have been budget cuts and there was no longer a guaranteed depth of 9 feet.
Because of this, we ran aground several times, trying to guess where the deeper channels were. In most cases, we were able to free ourselves by waiting on the tide to raise us. But on 2 occasions, we ran aground hard and had to call a towing company to pull us out. Thankfully, the owner had towing insurance — normally a $1000 process — to help out.
Aside from the groundings, we also started noticing other issues with the boat, even though it was just recently refitted. It was partly because of these issues, as well as the delays we experienced, that the young couple on board started thinking about jumping ship.
Southport, NC
The day we arrived in Southport, North Carolina, the alternator quit working. That was the straw that broke the camel’s back for them. They no longer believed the boat was safe for ocean passage. Looking back, they were probably right. It really wasn’t safe for an ocean passage. They left the next day — Thanksgiving Day — and headed back to Texas. They went on to buy their own boat and started sailing full-time. I was disappointed when they left. I liked them and enjoyed having them on board. I am still friends with them to this day. I was also concerned about the lack of hands to steer the boat on passage.
Looking back, they were probably right. It really wasn’t safe for an ocean passage.
Paul, his wife, and I spent the rest of the day looking for supplies, including calling shops to find a replacement alternator. Because it was the holiday weekend, we didn’t have any luck. We decided to wait until the weekend was over and try to find an alternator further down the ICW.
We made good use of our time in Southport, met new friends, and enjoyed the fantastic sunsets on the ICW. I found some warmer gear for my feet and face as the weather was getting cold this late in November. I was expecting to be in warmer climates by this time and didn’t prepare for the frigid wind that blew across my bare feet and face while steering up on deck.



The Great Loop
The ICW is part of a much larger route, called the Great Loop. To participate, you start anywhere on the route below, follow it in either direction — although most cruisers do it counter-clockwise, to take advantage of the south-bound river currents — and when you get back to where you started, it’s called, “crossing your wake,” and you are done.
One of these days I’d like to join the hundreds of cruisers who take this journey every year. They usually do the northern sections in the summertime, to avoid the ice and cold. There is no set time or limit — it’s not a race. It can be done in as little as two months, but most people take about a year. It has been done in boats as small as a kayak or as big as a 70-foot yacht. For more information google America’s Great Loop Cruisers’ Association or AGLCA.

Back to the Journey
After arranging to meet an electrician in Jacksonville and ordering the alternator to be delivered there, we sailed down to that gorgeous harbor where we tied up to another dock for a couple of days to get the alternator installed.
The ICW has many towns that allow you to tie your boats up to their public docks for free. We stayed for free in several towns along the way including Southport and Jacksonville. We also anchored several places along the channel, just on the side of the “ditch,” as the ICW is affectionately called.
I remember many relaxing nights as we anchored near some reeds, or at a river intersection, and swayed in the water flowing by. It seems to me that the moon and stars are always brighter and more fascinating to watch when you’re on the water. The weather had started to warm, as well, the further south we got, which made it nice for sleeping out on the deck.
The closer we got to Miami, the busier and more challenging it became to stay on the ICW. There were more boats, the bridges were closer together, and it became troublesome to safely continue. We finally decided, several hours North of Fort Lauderdale, to sail outside the ICW, along the coast. It was while doing this we attempted to put up the mainsail for the first time.
The sail hadn’t been raised in a decade. Combine this factor with our unfamiliarity with hoisting this massive sail. It sheered in half as we attempted to raise it — in part because it was so old and it was also still reefed. This was a disappointment for all of us, as we sadly put it away again.
That night we arrived in Fort Lauderdale and anchored in the harbor there, surrounded by the warm and picturesque lights of the buildings around us.



No-Name Harbor
The next day we sailed to the Miami area and anchored in a little bay called No-Name Harbor on Key Biscayne. The harbor is part of the Bill Baggs Cape Florida State Park. We were there, mostly, to prep and provision the boat for crossing the Gulf Stream, and over to the Bahamas. We wanted to ensure we had sufficient supplies and work on any last-minute issues with the boat.
A week or so later, we attempted our first crossing of the Gulf Stream. While doing so, a bolt — connecting the shroud to the chain plate — broke. Shrouds are the rigging or cables that hold the mast upright, especially when the sails are up and there is pressure and force against them from the wind. I found a shackle below the decks and was able to replace the bolt with it, connecting the shroud back to the chainplate, although not snugly. It wasn’t the best solution, but there was less chance of the mast teetering with it there. This allowed us to return to the anchorage in No-Name Harbor without losing our mast.
That was when Paul’s wife decided she didn’t want to carry on with us. Losing the shroud bolt put her in a panic, and she made plans to leave after Christmas. This left Paul and I to sail the rest of the way to Aruba by ourselves. I say “sail” but if you haven’t been able to gather by now, we weren’t doing a lot of sailing — mostly motor sailing.
In hindsight, we should have attempted to find more crew members. I’m not sure why we didn’t. But, I was committed to going all the way to Aruba with Paul, despite the safety concerns. I don’t know if it was stubbornness on my part or just the sheer excitement of being on my first sailing adventure.
Honestly, I was having the time of my life even with all the issues. I was learning from all of these experiences on someone else’s boat and expense account. Every challenge taught me why safety standards are in place and what can go wrong when they aren’t followed. And my sense of adventure was stronger than my fear of what could go wrong.




More Repairs in Miami
Upon further inspection of the shroud bolts, all of them were rusted — a lot! So we replaced all four with stainless steel bolts that are resistant to rusting. After we made those repairs, we made plans for another attempt to cross to the Bahamas a few days later. On the next passage, we got about an hour into it, when we felt the seas were much rougher than predicted. We decided to return once more to No-Name Harbor — feeling uneasy about things — and wait for the next weather window. Upon returning, just as we set the anchor, we lost our steering.
Yes, our steering went out completely! We learned that the steering hydraulic system had been slowly leaking, and at the exact moment when we set the anchor, it dropped low enough to cause the steering to stop functioning. We were lucky. We could have lost the steering in the middle of the Gulf Stream, and who knows where we would have ended up. Alas, one more thing to fix on the boat.
Repairs were made on the hydraulic system during the refit in Norfolk. However, they were a mix-match of imperial and metric pipes and fittings. It should have all been replaced completely, but with Paul’s budget, it hadn’t been done. We made many trips back and forth to the different Miami hardware stores, trying to find parts that would work.
Also, the auto-pilot — the one that didn’t work — was tied into this system, and it had leaked as well. We patched both systems as much as we could and bought a 5-gallon bucket of hydraulic oil, to top off the system when it got low. We didn’t fix all the leaks, but we felt like we slowed them down enough to proceed.
Something else I discovered was the boat’s emergency steering system — every boat should have an emergency steering system in case the normal steering fails — was in pieces below the aft bed. For it to work properly, a hole would need to be drilled in the deck and tested. Did we do that? No, we didn’t. I did pick up some empty buckets at Home Depot because I read they could be used to steer the boat in an emergency, by dragging them on one side of the boat or the other.
I can hear all of the captains and responsible boat owners reading this and criticizing me for staying on this boat and ignoring the many safety concerns. But I remind you, that I was not the skipper or owner of this boat. I was simply acting as crew. Many, if not all of these safety issues should have been resolved by the owner.
In hindsight, I should have demanded they be repaired the right way before sailing on. That’s why they call hindsight 20/20. I can see it all now, but at the time, I was just enjoying my first time crewing on a boat to the Caribbean.
Bahamas
We finally got the boat functional enough to make the crossing to the Bahamas. We decided to do it at night since that was the best weather window for us at the time. The passage itself went off without a hitch. It was my first time sailing at night and I had to figure out whether we were going to cross paths with a much faster boat or not.
We didn’t have AIS on board or a plotter system that would calculate this for us. We were just eyeballing it. There were a few cruise ships we had to change course for to avoid a collision. But as the sun was rising, we saw land on the horizon. We had arrived at the island, Bimini, and got checked-in to the Bahamas.
The first thing I noticed was how clear the water was there. I may have just been excited about being there, but everything had this clear and beautiful aspect to it. This was one of the first photos I took, while tied up to check-in.

We spent the next 22 days meandering through the Bahamas. Paul wanted us to go faster than that, but we ended up getting locked in by a storm, moored at Farmer’s Cay. The wind blew 35–50 knots for seven days straight. Here’s some video from that storm, with a couple of shots of Farmer’s Cay below.




























