Earning Your Dreams

By Tom Neale, 8/19/2010


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Too many people go to sea these days with half baked dreams in half baked boats, fortified with half baked skills. Sometimes the boat and much of the gear is given to them. The media loves it, even some in the boating media who should know better. It’s easy. You just get a boat and take off, knowing that people will come to rescue you, risking their lives and spending enormous amounts of money doing so, if you get into trouble. But there are also voyagers who do it the right way. Such were the four college friends who started talking about cruising across oceans several years ago. They graduated from Washington and Lee University in Virginia in 2003 and in 2004. After college they went different ways, working in various jobs. But they kept in touch and the dream was born: to restore an old boat, make it ocean tough and go cruising.

The Dream

Obelisk on a test sail in the Chesapeake

Jesse Smith, 28 as I write this in 2010, started sailing while young, with his family on a 1982 Skye 51' named Obelisk. He acquired it from his father as the plan began to form. He and the three other guys, Rob Burnside, Willie Thompson and Jesse’s cousin, Matthew Smith, began a thorough and rigorous job of restoring her.

They moved to Gloucester, Virginia, where the boat was located, and began sharing a very small cottage near the boat, “about as big as the boat itself.” This was important to get themselves accustomed to living together in tight quarters on a boat. They began working feverishly on the huge project of rebuilding the boat to get it ready. Even though they were putting in long backbreaking hours on the boat, they were also working on “gainful employment” jobs to support themselves and their adventure. Jobs included working as a cook, bar tending, waiting tables and anything else that came along. For example, they collected scrap metal by helping a neighbor clean out his garage and rummaging around marina junk trash bins and sold it for $1,000.

The Projects

Following are but a few of the restoration projects. They found a used generator in Annapolis and muscled the 400 pound unit into a home beside the main engine. They rebuilt the 11 Barient winches. They loaded on an all-chain rode and replaced their ancient windlass with a new Lofrans. This job included rebuilding the deck underneath it. They had the 44,000 pound boat hauled and began working on the bottom. The first day of scraping netted 35 pounds of old paint left over from all the years, and this was from only 5% of the hull. They estimate that there were around 700 pounds of old paint removed in all. This revealed around 300 small blisters, each of which they repaired. They also replaced the electronics which included making new mounts, running new wire and getting it all to work.

The Skye’s fiberglass deck was overlayed with teak, fastened with around 4,500 screws. These, with time, can cause leaks into the deck laminate. They stripped the old teak off, removing the screws. They began the 3 month job of rebuilding each screw hole, filling the surrounding core with epoxy. This project left 3/8 inch voids between the fiberglass deck and toe rails and hatches and other structures. They cleaned these with a Dremel tool, and filled them with thickened West Epoxy. They then sanded for days.

They also removed every fitting that had been bolted through the deck, routing out each bolt hole checking for water damage in the coring and sealing and refilling the holes and surrounding areas of coring with West System epoxy and 404 filler. With the old holes filled with epoxy and no longer cored, they drilled new holes through the now solid mounting areas.

Obelisk rounds Cape Horn east to west under spinnaker

After making other repairs, they sanded the deck and applied two coats of primer and two top coats of Awlgrip. They epoxied on non skid Treadmaster after making templates of roofing tar paper to determine exact sizing for the sheets.

With dampened (but undaunted) enthusiasm they completely rebuilt each head, and then repainted the head compartments. And for 1½ hellacious weeks they replaced all the hoses aboard.

Installation of an auto pilot included connecting the driving motor to the steering mechanism within parameters that wouldn’t allow wandering or allow a disconnect, such as a chain jumping off sprockets. In this instance there was already in existence the mini-quadrant for the old chain-driven unit, so they used this for the new unit and had a bracket made to mount the drive.

Other jobs included rebuilding all the boat’s hatches, installing new salon portlights, rebuilding the companionway hatch, new lifelines, restitching sails, adding a new stuffing box for the prop shaft, having the Martec folding prop rebuilt, adding a new Force 10 European Compact two burner stove with oven and broiler, replacing the bilge pumps and adding new Rolls batteries giving a combined total of over 400 amp hours. A 75 amp alternator and a Newmar battery charger (for use with the generator or shore power) were added. Thankfully the original Perkins diesel had already been replaced and the newer one was working well.

They acquired a sat phone for emergency calls and limited emailing and an ACR 406 EPIRB (with GPS). They got weather download and GRIB weather maps using the services offered by Ocens on the sat phone. They purchased Mscan Meteo (mscan.com) software with which one can download weather information in the form of faxes, NAVTEX, RTTY and GRIB files to a computer, via the SSB. They also got a 6 person life raft.

They took a few short cruises to begin to get the feel of the boat and of themselves as crew. Before they left, they took a trip around the Delmarva Peninsula in January of 2009.

The Cruise

Finally came departure. The Obelisk draws 7.5 feet with a mast of 70 feet so it couldn’t head down the east coast in the ICW. They closely watched the weather and, on March 18 2009, left Mobjack Bay in the Chesapeake and sailed out into the Atlantic between Cape Charles and Cape Henry. They headed south around Cape Hatteras, continuing on to clear Cape Fear. This area is known, for good reason, as “the graveyard of the Atlantic.” Eventually they reached the Caribbean. After enjoying this area, they departed Grenada in early June of 2009. They were bound, not south down the eastern South American coast as had been planned, but easterly across the Atlantic. Jesse explains that political unrest, wind directions, and a desire to see Gibraltar and that part of the world contributed to the decision.

Eighteen days later they made landfall at Horta on the island of Faial, Azores. They’d had 6 days of calm, a series of storms, and, overall, a fun trip. From there they sailed to Gibraltar, in search of a repair for a damaged shroud and a better tender. Then they headed south to the Cape Verde Islands, with other stops along the way. From there they departed for Brazil, back across the Atlantic.

Obelisk anchored in a caleta in Chile
Sailors on this trip fear the doldrums, long periods of windless days and nights and stifling heat. But nature helped in the form of a tropical depression, later to become Hurricane Fred. The storm began to close in as they lay at anchor in Brava, where it would have been dangerous to remain. They had to leave, and soon were at sea in 45 knot winds. But the outlying winds from this storm saw them across the equator in cool weather and good winds. However, only a couple of hours out of Brava the planetary gear of the auto pilot failed. It wasn’t repairable at sea, and they felt certain that it couldn’t be repaired back in the Cape Verde Islands.

By this time, only Jessie and his cousin, Matthew Smith, were aboard, the other two having had to return to the states. They had to manually steer the 2,500 mile passage back across the Atlantic to Salvador, Brazil. They did it and were on the other side in 15 days. It was a fast trip as sailing goes, but a grueling one because of the failed auto pilot. They then visited various ports, including, Arquipelago dos Abrolhos , Rio de Janeiro, and, the “cruising capital of Brazil,” Bahia Ilha Grande. In Buenos Aries, Argentina they replaced more gear and, although the auto pilot was to be repaired under warranty, added a wind vane—something they’d wanted from the beginning but hadn’t been able to afford. Here Matthew had to return to the States, as he’d planned, to pursue a Master’s Degree.

New crew soon arrived; Jesse’s father and godfather, both eager to join the adventure. The Obelisk headed south, toward the bottom of the Continent. As soon as they turned the corner of the tip of Terra del Fuego they got hit in the face by 50 knots of wind. The next leg took them into the Beagle Channel where they found williwaws blowing off the mountains at 35 to 50 knots. They were afraid to work their way into any of the small caletas (coves, often fiord like) where they could have anchored and rested, so they kept on under power. Soon they were in the spectacular unspoiled cruising grounds of southern Patagonia, at the bottom of South America, where they explored for around 6 weeks.

They cleared into Chile at Puerto Williams, and used the “Micalvi Yacht Club” as a staging base for what Jesse describes as a “side trip” around the Horn. Called the “southernmost yacht club,” this is an old ship, now resting on the bottom. Boats tie alongside, rafting out.

It was blowing 15 knots when the Obelisk went around the horn from west to east on February 17, 2010. The day was so nice they were able to go ashore. They didn’t want to anchor off the Horn, for obvious reasons, so friends on another boat sailing with them sent crew over to tend the Obelisk while they went ashore in the dinghy, and they did the same for that boat. Then they went back east to west, the “wrong way” around the horn, flying the spinnaker. Finally they continued up the western coast, using the Beagle Channel.

Tom’s Tips About Dream Boats

1. Many people who buy an old boat planning to “fixer ‘er up” and go cruising end up broke, broken hearted and with an unrealized dream.
2. Even if you are able to do most of the work yourself (and few of us are) it’s going to be very expensive to do it right. Cutting corners and going to sea don’t mix.

Click Here for More Tips

The night before they were to enter the Straights of Magellan to continue the long northerly trip, they anchored in a caleta. Here their transmission failed. This left them with the option of sailing back down the Beagle for several days in tricky channels or sailing the 4 miles out to the Pacific and sailing up the coast on the outside. The inside trip would have included running at night. It would be difficult enough to sail in the Beagle, but dangerous to sail into and out of the caletas for overnight anchorages. They chose the open Pacific. Under sail they exited the extremely narrow caleta where they had anchored, tacked to the Pacific, and began the 1400 mile sail up to Puerto Montt.

Because of the notorious lee shore they first put 200 miles of sea room between the boat and the coast. They knew they’d made a very wise decision when a huge low with hurricane force winds enveloped the Obelisk. They survived under storm sail and triple reefed main with waves breaking over the boat. The dodger was ripped completely off, tearing the frame mounting bolts right out of the boat. A wave breaking over the transom broke the welds on the very rugged mount for the Aries Wind Vane. The mainsail shredded near the end of storm, so they lay apole and repaired what they could. Finally the wind moderated and shifted southwest, giving them a beautiful five-day jenny run, averaging 8 knots for 800 nautical miles. Eventually they reached Puerto Montt, Chile, where they left the boat in a marina, prepped for winter and under watch by cruising friends. Jesse returned to the States to get a job to make more money so that he can return and continue.


This story has been told to me, mostly by Jesse, through words and pictures. But there is a story within this story. These people did what they dreamed, by research, education, careful planning, common sense, extremely hard work, good seamanship, and learning how to take care of things themselves. The sea requires that of our dreaming.

There were many more adventures and details than I’ve had space to share here.

See www.tomneale.com

Copyright 2004-2010 Tom Neale

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