Teaching Objectives

By the end of this article, you will understand how to assess whether your boat is suitable for shorthanded sailing

How to prepare both your vessel and yourself

How to build the confidence required to sail safely and effectively without a full crew.

What does it take to sail shorthanded? When people ask this question, it typically reflects two underlying concerns: is my boat suitable, and am I personally prepared to sail without a crew?

From the perspective of the boat, the answer is often reassuring—most boats are suitable. In 2017, I raced my cruising boat, a Catalina 350 MkII, in the Bermuda 1–2, a 635 nm race from Newport to Bermuda sailed solo, followed by a doublehanded race return. The boat was not purpose-built for offshore racing, but it was well constructed, and more importantly, I knew it intimately. That familiarity translated directly into confidence.

It is worth remembering that much of the sailing done worldwide is already shorthanded. Couples routinely cruise doublehanded on production boats. While such boats may not initially be equipped for ocean passages, they can often be modified relatively easily. Most shorthanded sailing and racing is coastal, and with a few thoughtful adjustments, it is entirely accessible.

In an ideal setup, a shorthanded boat allows key control lines to be managed from the cockpit. This reduces the need to move forward to the mast or bow in difficult conditions. Personally, I prefer all reefing lines to be led aft. While there may be minor advantages to going forward, they do not outweigh the risks of leaving the cockpit in heavy weather. On Fearless, I can reef in approximately 30 seconds while remaining clipped in at the cockpit—a significant safety and performance advantage. Squalls often arrive unexpectedly, frequently when a partner is off watch, and the ability to reef quickly and independently becomes essential.

There are several core elements that define a shorthanded-ready boat. The reefing system must be simple and quick to deploy. The autopilot must be reliable, with a backup steering solution available. Lines should be controllable from the cockpit without excessive movement. Organization is critical—sail storage, sleep arrangements, navigation systems, and access to food and water should all be efficient and intuitive. Systems should be thoroughly tested, and above all, the sailor must be familiar with the boat and confident in its operation.

While there are many safety considerations before heading offshore, these are largely the same as for fully crewed sailing and are not the focus here.

 In reality, the primary barrier to shorthanded sailing is rarely the boat—it is mindset. Do you feel ready? This question is best answered through experience. Start with a simple day sail doublehanded. If you are considering going solo, take someone along for reassurance, but perform all maneuvers yourself. You may be surprised at how quickly your confidence builds.

There are simple steps that you can take. Set incremental goals. Aim to say 10nm away from the harbor and return. Take notes while you sail. What have you learned? What can you improve on? Do you need to rig something differently? Don’t beat yourself up if it’s not perfect. Perfection is the enemy of execution. Celebrate the things that you can control! You did it, celebrate that success. Next time, address any concerns and try again, or even try a longer sail. Again, take notes.

For many sailors, the next hurdle is sailing overnight. The first night offshore can feel intimidating, but in practice, it is far less daunting than expected. The primary difference is simply that it is darker. In fact, sailing at night can be a remarkable experience. As visual input decreases, other senses sharpen—hearing, balance, and motion perception become more acute.

A useful strategy when building confidence is to control your exposure. For example, when sailing from Newport, Rhode Island, one can sail south overnight and then return north. By heading away from land initially, you eliminate the risk of a lee shore during the night.

Preparation is key. Study charts in advance. Identify hazards such as wind farms, islands, and shipping lanes. Determine safe heading limits and mark no-go areas. Create a written plan and annotate charts with areas of concern. This builds confidence and reduces uncertainty offshore.

I strongly advocate maintaining a written logbook alongside electronic systems. Electronics can fail. With a logbook, a headlamp, a compass, and an understanding of your recent course and speed, you can estimate your position and navigate safely.

Ultimately, what holds many sailors back is the feeling that they are not fully ready. But we are never completely ready. The key is to start and progress incrementally. Set small goals. Build experience step by step. Remain calm, breathe, and work through situations as they arise.

Sailor Takeaway

1) Shorthanded sailing is defined less by the boat and more by preparation, organization, and mindset.

2) Most boats can be adapted, and most sailors are more capable than they believe.

3) Confidence comes from experience.

4) Start small, prepare carefully, and expand your limits progressively.

5) Offshore, calm thinking and structured preparation matter more than perfection.