Sailing the GypSea

Sailing the GypSea

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Follow the crew Tracy, Kimmie, TiKi & Charlie as they sail “GypSea” along the East Coast and Caribbean

20/04/2026

I wrote this down a couple of years back but just realized that many don’t realize who Bernie, of Bernie’s trail acclaim in Kimmie’s last post, was.

Ragged Island Yacht Club is a haphazard structure of drift wood and palm thatch, assembled by cruisers and some of the mere 50 odd inhabitants of this beautiful archipelago of isolated wind swept cays. It’s complete with kitchen, lounge , volleyball court and of course a rather large salt water pool. You’ll find it adorned with whimsical offerings made by cruisers who have passed through on their way to distant destinations. Among the offerings you’ll find an understated life ring proclaiming “RIP Bernie 2022” as well as a scenic trail that traverses the island from flats side to ocean side that bears Bernie’s name.
Kim and I first met Bernie by happenstance in 2022 when we dinghied ashore in Thompson’s Bay, Long Island and randomly turned north to walked along the desolate sun-baked road. We came upon a sign declaring “cold beer” whose paint was faded by the relentless sun and salt saturated air but apparently was none the less attractive to ourselves than to a pair of weather worn sailors approaching from the opposite direction. We simultaneously reached the plywood shack and took seats at what was a liberal interpretation of a bar and whose sum total of electrical power seemed dedicated to the beer and mixer filled fridge.
We made our introductions and found that Bernie was making his way north through the Bahamas and had enlisted the help of his younger friend to complete the longest segment of the trek. From here, they planned on moving on to Georgetown in Bernie’s motor trawler where his friend would depart, leaving Bernie to solo his way the remainder of the way north. Over cold beers we learned that Bernie was German and were treated to an entertaining dissertation on German-euro politics and the obligatory, but much enjoyed, tales of his many travels.
We saw Bernie in Georgetown a handful of days later where his friend was awaiting transport back home.
A short time thereafter, we heard fellow cruisers report that they had passed Bernie closely broadside the following day and could clearly see him sitting at the helm. He was heading north and they south. They found it odd that he did not answer to hails on the VHF nor respond to their waves and smiles. The next day Bernie’s trawler was found grounded on Andros Island, its engines running and, in true seaman fashion, Bernie sitting lifeless at the helm. A devout mariner standing his watch to the end.
Bernie’s trail is adorned with numerous colorfully painted sea Beans with words of affirmation as well as various funky remnants gathered from along the island’s storm riddled beaches.

In my mind, Bernie’s trail is a metaphor for this life and it’s journey from one side to the other where the path is often steep, rock strewn with uncertain footing, and boarded by inhospitable terrain but none the less, littered along the way with breathtaking views and displays of peace, beauty and affection. Some man made and some painted and sculpted by nature’s hand. The trail begins at a modest marker on the white sand beach bordering a beautiful, protective and peaceful anchorage that feels like a mother’s embrace to those who have sailed across waters from distance shores. At trail’s end, one is rewarded with the view of a breath taking shoreline looking out over a seemingly endless ocean. It fills you with questions of what might lay hidden beyond the sea’s distant horizon. One that seems to have no regard for time.
May we all be as fortunate as Bernie to have lived such a life that at its end, like Bernie, we are granted the privilege of passing from this side to the other while doing what we love most and then be paid tribute to by the many whose wakes we had crossed in such an appropriately simple way on such a ruggedly, ragged, beautiful patch of earth.
Well done Bernie!
Eight Bells and
RIP

20/04/2026

We walked the art trail (Bernie’s Trail) last week. Cruisers are getting more and more creative with flotsam collected on the windward side.

17/04/2026

Not a bad place to wait for your laundry!

Photos from Sailing the GypSea's post 17/04/2026

Tiki had a great day swimming and making friends at . Then it was naptime.

Photos from Sailing the GypSea's post 08/04/2026

Sunday we anchored at the southern end of Ragged Island. Crew enjoyed the many hues of blue water and endless shallow water beaches. Tiki was off leash (finally after some dog unfriendly islands)

Photos from Sailing the GypSea's post 06/04/2026

Easter in the The Raggeds. The tree outside of Hog Cay Yacht Club looked Easter egg-ish.
Today we hiked over on Bernie’s Trail (RIP) to the windward side of the island and I found my first sea bean!! I have been looking for years. Then I found 20 more. It was like an Easter egg hunt but with no chocolate or peeps 😕
Would really love a Cadbury Egg about now.

01/04/2026

Sailing perfectly explained 😂

Photos from Sailing the GypSea's post 30/03/2026

Incredible display of seamanship and a step back in time!
After a 3 night passage we sailed into remote and lightless Great Inagua at 4 am. Just before dawn this sketchy, lightless boat sailed in and anchored abreast of us. Being that there were no other boats around, I was admittedly a bit concerned about safety until I spoke to local who said they were very pleasant Haitian traders who sailed here when possible with farm goods to barter for goods to return home with. Kimmie and I gathered together some old fishing gear, old reels, a rod, lures, hooks, a few lengths of large rope and some DR dollars that we hadn’t exchanged in 2 years along with a pint of Virginia Gentleman which I dinghied over. They couldn’t have been more grateful. They insisted on giving us what are the best tasting mangos we’ve ever had. While there was a language barrier, the smiles and fist bumps worked just fine.
Last evening as the anticipated winds arrived, their 2 crude anchors began to drag. As the first of the wind paused, they hoisted a sail apparently made from anything they could find to stitch together. Four of the crew hoisted the anchors and then immediately hoisted and backwinded the jib to turn the boat away from the wind but DIRECTLY at us 200’ away. The motorless beast slowly bore down on us but gained enough speed for the helmsman, grasping a tree branch of a tiller, to finally gain control to trim the jib and turn up just across our bow! I was honestly racing to drop our dinghy to act as a tug when they cleared.
They then proceeded to sail parallel to shore past the blasted manmade coral boat basin which has a 150’ wide entrance to a 7-11 parking lot sized concrete bowl. I said “No way are they going to try what I think they are going to try”. They tacked, reached down to gain speed to the basin’s mouth, turned up dead into the wind while dropping sails and coasted into the dock like a Captain Ron boss! If things went south, there would have been no way to recover! BLEW ME AWAY!
They awaited the arrival of today’s “mail” barge and loaded an entire 20’ shipping container of goods into their “freighter” (their term). It completely filled the interior and is stacked on decks beneath tarps. There’s no room below for crew so they sleep on deck.
This is as far north as they can travel because of government restrictions on their boat. Actual trees for mast and boom. No electronics at all. No lights, no navigation, no radio, no communications, no AIS, no radar, no auto pilot, no plumbing, no refrigeration and NO MOTOR. Leaks like a sieve requiring constant manual pumping. They will wait like us for reasonable conditions and sail back home to Haiti. A 75nm open sea passage to nearest point.
We made a point to go over and tell them how impressed we were. They acted like it was just another day and just wouldn’t stop thanking us. All 6 came over with huge smiles to thank us, one wearing an apparent tattered modified woman’s dress because it was all he had.
Barge day is a big day for locals as they gathered to get goods and the Haitian traders worked as dockhands loading other’s goods.
Made us reflect and be thankful for what we have.
Safe journey guys!

29/03/2026

Night three. Almost there. The moon leading the way.

26/03/2026

Unmanned autonomous winged sailing drone, sailing into the wind and seas in Mona Passage! Transmitting AIS signal as NoComms/Unmanned.
I’m made of questions🤣
Creepy.

https://youtu.be/juZdke0mzv0

26/03/2026

Gypsea is departing for our 4 day passage across the Mona Passage between Puerto Rico and Dominican Republic and onto Great Inagua.
Today’s tech is great, but it’s still a bit unnerving with so much to worry about; boat, weather, crew. You can drive yourself crazy analyzing the 8 different weather models, confirming your progress compared to computer polars and looking for a weather window that will get you there above water, in one piece and still married!
When the model lines are close together, it indicates they are in agreement. We’ll see!

Photos from Sailing the GypSea's post 23/03/2026

Morning photo and evening photo.
We had the first real rain in weeks, mixed with Puerto Rican sun. Rain means GypSea got some laundry done and decks scrubbed cleaned.
Tiki did get a beach day ashore. She chased a heron and ate some very odiferous sea debris which will surely show up later tonight at about 2am. 🤮 In our cabin.
We spent some time at the “Bananas Beach Bar” during downpours 🤪 Drinks were ok but plentiful and local entertainment was included (see below)
A stray horse meandered down the street in front of the bar. 35 minutes or so later, a cowboy on horse dramatically collected her up. He had food in a bucket. She followed.
Five bar cats were in residence. Kitties paid no mind to patrons, street noise or the awful American 80s music playing. You had to wait behind crime scene tape to get seated 🤷🏻‍♀️
Overall, a weird experience but it was actually another normal day sailing on GypSea.
GypSea is now prepared to sail off early morning to Salinas. A few more stops after that while staging the weather crossing of Mona Passage. Slowly migrating to Bahamas then home around June 1st. .

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