Whether by choice or chance, at some point most sailors will find themselves sailing shorthanded. Your first experience might be a trip to the fuel dock with your own boat, an end of the season delivery with a loyal friend or sailing with a group of four or five friends before realizing only a couple of them are sailors. The sooner you learn shorthanded seamanship, the sooner offshore waters become a comfortable backyard in which to play.

Docking is usually the first obstacle to shorthanded sailing. Docking a boat alone starts by being comfortable docking a boat with a full crew aboard. After that, work on docking without a reliance on lines. Think of it as parking a car without using the brakes. There is one dock line that can be your most valuable tool: a breast line. This dock line is set amidships within easy reach of the helm. Bring the boat gently to the dock and secure this line. Holding the boat in place with the breast line allows you to move around the boat to tie the most important corners first. When the boat is secure, undo the breast line. When it comes time to leave the dock, reset the breast line and untie the others leaving the breast line as the last line to go. It’s not much different than docking with a full crew, it’s just that the breast line probably comes in the form of a crewmember holding a piling or stabilizing the boat while others tie the bow, stern and spring lines. 

Docking and harbor maneuvers don’t have to happen quickly. Relax; enjoy the fun of letting them watch you do it shorthanded. 

Cate Brown photo

Once you’re away from the hard stuff and clear of the harbor, sailing gets a lot easier. The quiet wisdom all shorthanded sailors know is that timing is everything. You want to do it right, but you don’t have to do anything quickly. Slow down your expectations, take a deep breath and enjoy the feeling as the harbor slips away and you gain open space and room to set your sails. 

Take time to set up your sails, halyards, sheets and all the necessary gear before rushing to hoist your sails. Be sure the lines are untangled and ready to go. When you’ve checked everything over, methodically set the sails. The sails will flog and the noise will make you anxious but take your time and set your sails correctly. Despite the old wives’ tale that sails last forever, they don’t. Flogging wears on sails but that’s OK; sails are meant to be used and used up. Concentrate on getting them up properly and without undo delay and then get them trimmed.

With the sails set and the autopilot driving, take time to relax and enjoy the sail. Pick a fictitious destination beyond the horizon and let your imagination run. You’re in command, sailing shorthanded. By the way, did you check the weather before you left?

Weather causes anxiety in all sailors—young, old, novice or Volvo ocean racer. Knowing the weather before you leave lets you plan your future. Knowing the future makes sailing enjoyable. Without a full crew and the weather coming, we know we have to start working early. 

There’s wisdom in the old saying, “If you think about reefing, reef.”  Don’t apply the five-minute rule when reefing. It never works and always results in problems, anxiety and more work. Practice reefing on a quiet day, in 10 knots of wind. Reef and unreef, back and forth. Do it again and again and then one more time for good measure. Making mistakes in 10 knots is the best way to learn. Don’t wait until you’ve ignored two five-minute rules and the wind has built to 25 knots to learn to reef. There’s nothing in the sailor’s code of conduct that says you have to sail with the largest sails all the time. I’m often seen sailing with just a working jib. 

Practicing in 10 knots of wind will show you what’s going to break or go wrong. Maintenance is the first step to problem avoidance and problem avoidance is the precursor to problem solving. Knowing your boat, maintaining the systems and lubricating the moving parts are the best preventers onboard. It’s easier to fix something while tied to the dock than five miles offshore—with or without weather approaching. 

So, how do you know what to maintain and what to look for? Start by washing your boat regularly, twice a month, from bow to stern. You’ll get two things from this. The first is obvious: a clean boat. The second is that you’ll see every inch of your boat, and learn the pace of wear and tear. You’ll know how something is wearing and when it needs attention. This is where maintenance begins—not when something breaks unexpectedly. 

Shorthanded sailing is going to happen and it should happen. Why sit at the dock pining for a sail because you have no crew when you could be out on the water? Get ahead of the game and grab some experience. Offer to help other shorthanded sailors with their next sail or delivery, ask questions and ask for advice. They’ll help you, invite you and encourage you. Shorthanded sailors are the best codependent enablers you’ll ever find. Shorthanded sailing is easier than you think, it really is. 

Safety tips for shorthanded sailing

1. File a float plan. Let friends or the local Coast Guard know where and when you are sailing shorthanded.
2. Always have a working VHF radio. VHF communication is for everyone. You probably won’t need help, but someone else may need your help. Have your VHF installation checked by a trained professional. The difference between a good-enough connection and a proper connection can be 10 miles of range.
3. Have a current weather report specific to the waters you are sailing on. Don’t expect the morning television news show to give you the specifics you need. Get a real forecast.
4. Keep flashlights handy. Whether sailing at night or not, good, reliable flashlights and back-up batteries are worth their weight in gold when fixing the engine or finding the reflection on a navigation mark or floating life jacket.
5. Have a good knife and tools mounted in the cockpit. When the emergency strikes, knowing there’s a tool or knife in a sheath in the cockpit and on the foredeck is priceless. If you only have two people on deck, you don’t want to leave a person alone on the bow while you search for a tool below.
6. Collect sail ties in mass quantities. You can never have enough sail ties. One in the pocket, a few on the lifelines and a few dozen on the handrails below within reach of the companionway.
7. Install and use jacklines. Tubular nylon or Dynema lines running from bow to stern, along each side deck allow you to traverse the length of the boat without unclipping your tether. An even better option is a jackline running down the center of the boat, keeping you safely within the lifelines if you fall. 
8. Have the necessary items to keep you comfortable. Comfortable sailors are good, critical thinking sailors. Quick-dry clothing, warm-ups, foul weather gear, drinking water, easy-to-grab food, sunscreen and extra hats should be handy.  You may end up in a situation for an extended period of time. Being comfortable will allow you to concentrate on managing it.
9. Use PFDs and tethers. When alone on deck, always clip on. It’s not fun for anyone to wake up and find your sailing mate gone.
10. EPIRBs and PLBs are your quickest way to call for help. Carry one and make sure the registration and contact information is current.

Dave Rearick is a lifelong sailor who has sailed crewed and solo races on the Great Lakes for 45 years. He campaigned Bodacious Dream, a Kiwi FC Class 40, shorthanded in international events before sailing her solo around the world. An ambassador for 11th Hour Racing, Dave spends much of his time educating kids about the environment and the oceans.