My Boat-Owning Background
I’ve been sailing for 50 years. I’ve owned and sailed four cruising boats and made dozens of offshore deliveries between Maine and the Caribbean. Each boat, each voyage has taught me something. Most of those lessons came from getting my hands dirty and venturing outside my comfort zone.
My first boat was Quinta, a 1947 34-foot Alden wooden sloop. I bought it in 1969 in Shelburne, Vermont, on Lake Champlain for $6,000. I fixed it up, and we motored down the lake, through the Champlain Canal, down the Hudson River, around Manhattan, out to Long Island Sound and Cape Cod, Massachusetts, then up to Maine. For the next 10 years, Quinta and I sailed up and down the New England coast with a compass, a radio direction finder and a sounder. I learned to anchor, managed to keep the Gray Marine gas engine running, and navigated by running aground, frequently.
In 1979, friends joined Kate and me on a two-week bareboat charter in the US and British Virgin Islands. The boat, a Morgan Out Island, was a floating Winnebago, but it introduced us to a world I thought existed only in literature: the tropics.
I was hooked. The islands of the Caribbean were everything I’d been dreaming about since I could read. There was warm, crystal-clear water. Colorful fish. Coral reefs. Islands, each one different, with strange languages, dancing music and spicy food. The sun shone all day. The trade winds blew steadily from the same direction. At night, a warm breeze wrapped around my sunburned hide like a down comforter.
I had to get back—on my own boat.
Fair-Thee-Well was another wooden sloop built in Maine in 1947. It was 42 feet and cost me $42,000. I was moving up.
That boat and I sailed to the Caribbean in 1980, and back to Maine in ’81. Then back down the Intracoastal Waterway in 1984 to hop over to the Bahamas, and then back in ’85.
By then, I’d had it with leaky wooden boats. That fall, I bought Afaran, a Lord Nelson 41 cutter. She was brand-new and cost me $125,000. With another $20,000, we outfitted her in Fort Lauderdale, Florida, and sailed to the Virgin Islands.
I owned that boat for 10 years, sailing back and forth from Maine to the islands for the first five years. In 1987, Afaran and I rode out Hurricane Emily in Bermuda; then, in 1989, Hurricane Hugo in St. John, USVI. In 1995, we rode out Hurricane Luis in St. John, but a few weeks later, Afaran was lost in Hurricane Marilyn. I was not aboard to move the boat out of the way.
Yes, I still miss that boat. It showed me what it needed, taught me how to care, and gave me back twice as much. You might say that we had a relationship.
I’ve heard that you are supposed to own a boat whose length on deck is equal in feet to your age. In my case, that held true. After losing Afaran in 1995, I bought Searcher the following year. It was a 57-foot Bowman ketch built in 1976. It cost me less than $200,000, and with another $20,000, I outfitted it, and we sailed to the islands.
We made three round-trip voyages to the islands in the 14 years that I owned it—and I realized that I would not have been prepared to own and sail such a large, complex boat if I had not owned my three previous boats.
Boats are built of systems that need to be learned, maintained and occasionally replaced. Certainly, modern systems make the offshore voyage less stressful, but there’s still the weather, seas, currents and other ships to contend with, and the knowledge that you are out there, 300 miles from the nearest technical help.
You are on your own, as you have perhaps never been. The only people farther away from help are the astronauts in space.
Shopping Advice
The first piece of advice that I give people who are shopping for a boat is not to buy a boat.
Let me repeat that: Do not buy a boat. At least not yet.
Sail on other people’s boats—as many different kinds as you can. Walk the docks and ask if anyone needs crew (assuming that you can properly cleat a line, tie a bowline, and pump the head). Pay for a bareboat-charter class or a DIY class.
Before you even think about going offshore on your own boat, go with someone who has many voyages under their belt. This might cost you $4,000 to $6,000, but it’s a bargain as valuable research. For starters, it will teach you whether offshore sailing is your thing, and what to look for in a boat that fits you.
When you get to the actual buying, start small. I suggest a boat smaller than 30 feet. Within a year, you’ll learn a lot—and spend even more. There’s the cost of the boat, insurance, a mooring or slip to rent, the cost to haul and store your boat for the winter—it gets expensive. While doing all of that, you’ll also see if you actually use the boat enough to receive an adequate return on your investment. If not, charter a bareboat until your lifestyle justifies ownership.
If your ultimate dream is to sail amid the islands of the Eastern Caribbean, or even around the world, then your preparations take on an even greater significance. The boat needs to be designed and built for long-distance offshore voyages. You’ll be spending weeks at sea, separated from any assistance, so you must be able to fix stuff that breaks, change fuel filters and bleed the injectors, rig an emergency rudder, patch a sail, and keep going. You will have acquired these skills working your way up while owning smaller boats.
Today’s offshore sailboats are technological marvels. If you are a gear person who loves fiddling with stuff, then these boats might not pose a problem. I’m still of the old school, and when navigating between Maine and the Caribbean, and through the islands, I use just Navionics on my smartphone.
Top Considerations
I was walking the docks at the Newport International Boat Show this past year, looking for an offshore cruising boat. I found few. Only 20 percent of the boats at that show had masts. All the rest were power yachts. I did find two offshore sailboats that I liked.
Exodus, a Hylas 57, was impressive, but at $2 million, it’s a boat that only an experienced and wealthy owner could manage. A full-time captain might be required.
The Island Packet 349 was a bit short at less than 40 feet, but Larry and Lin Pardey completed two circumnavigations aboard engineless boats under 30 feet. And the Packet has a full keel with an attached rudder to track well on long passages, along with smart bluewater features such as handrails along the entire coachroof.
When I’m evaluating boats like these, I look for a number of key things.
First is hull design: Sloop, cutter, ketch, yawl or schooner? They all qualify. A full or partial keel makes for better tracking over long distances. Narrow fin keels create less drag, meaning a faster hull and quicker turns around the buoys, but they require constant helm work to keep on course. Long keels and rudder skegs protect the prop and rudder.
Waterline length: Longer is faster, but it’s also more costly to buy, operate and maintain. Many boats these days range from 38 to 48 feet, but more and more 50-plus-foot yachts are on the water. The difference in speed between a 45-footer at 6 knots and a 50-footer at 7 knots is 24 more miles in a day. On the 640-mile voyage from Newport to Bermuda, that 1-knot advantage gets you there half a day earlier. At 8 knots, Bermuda is whole day closer.
Catamarans: They have less wetted surface, are faster, have more living space, and have less heel, but my son, a yacht designer, tells me that once a pontoon leaves the water, stability begins to deteriorate drastically. “A cat is the most stable upside down,” he says.
Tankage: If you’re going offshore to anywhere, you’ll need at least 100 gallons of fuel, enough to motor for 100 hours, four days, with another 30 gallons in jerry cans lashed to the deck as a backup. A few boats run out of fuel each year from inadequate tankage. Know your engine’s burn rate at different rpm.
Water: Two tanks are better than one because one could become foul. A watermaker? Sure, but that’s just another piece of expensive gear to buy and maintain. At a gallon per day of drinking water per person, a crew of four will need at least 60 gallons for a two-week delivery. Carry enough drinking water in extra jugs for emergencies.
Rig: A cutter rig is preferable to a sloop for going offshore. It’s easier to reduce sail and hove-to. A cutter or ketch affords more options in sail management. An inner forestay can carry a staysail or a smaller storm jib, but you’ll need running backs to support the mast. All headsails should be on furlers so that there is no need to go forward of the mast once at sea. Should you need to go forward, jacklines rigged from the cockpit exit point to the mast are better than those along the deck. Jacklines along the deck are fine for dragging you along in the water should you fall overboard, but jacklines rigged to the mast keep you from falling overboard in the first place. Look for handholds along the cabin top all the way and 30-inch-high lifelines—or, better yet, stainless-steel rails. Those 24-inch stanchions can catch you at the back of the knees and flip you over the side.
Furling: How easy is it to reef and furl the main? Can it be done from the cockpit, or does someone need to go to the mast or climb onto the boom?
Anchoring: A windlass that’s hidden makes for a neat bow but is inconvenient. When it comes to setting and retrieving multiple anchors, the windlass needs to be on deck with a chain gypsy and a rope capstan—side by side, not stacked up—one above the other. You’ll need at least two anchor rollers on a well-built platform over the bow to accommodate a heavy working anchor on chain, as well as a second, lighter anchor on chain and rode. This lighter anchor can lower into the dinghy, run out, and set when there’s concern about dragging. A chain brake just forward of the windlass is a must, and I’d like to see a strong point on the foredeck—a Samson post—to secure snubbing lines, chain or a 1-inch mooring pendant. The deck cleats on many modern boats are barely adequate for dock lines. The windlass is not there to secure lines or chains. You’re apt to bend the shaft and render the thing useless.
Convenience versus practicality: I recently delivered two modern cruisers. Compared with my previous boats, which were like camping in a tent, these were like motor homes. But with all the convenient push-buttons came a 50-page technical manual, or the need to bring along a technician. If you are buying a boat, remember the KISS principle: Keep It Simple, Stupid. Your new boat should be within your technical ability to keep it going.
Overall, if you’re up for the challenge and want to explore the world from the water, start small and learn as much as you can. Most of all, remember to enjoy the journey.
David H. Lyman is an author and award-winning photojournalist who contributes regularly to Cruising World and other publications. Find him at dhlyman.com.
Useful Clicks for the Offshore Curious
Sailing Totem: Jamie and Behan Gifford are circumnavigators who provide practical guidance and exceptional coaching for safe, comfortable, happy cruising. sailingtotem.com
Lady K Sailing: Tim, a popular YouTuber, gives genuine unbiased advice about boats and boat ownership. ladyksailing.com
Sailing Avocet: Marissa and Chris Neely share their sailing adventures, from the technical aspects of cruising a classic sailboat to the challenges and triumphs of liveaboard life. svavocet.com
Yacht Hunters: Captain Q on YouTube provides a fresh, entertaining look at used boats. yachthunting.com
Offshore Passage Opportunities: OPO is an organized crew network that aims to create quality offshore passage opportunities for its members. sailopo.com
