Two of us have run a 38-foot cruiser up and down the French coast for four seasons now, and the boat came to us set up for a racing crew of six. The first year was a fight. Every manoeuvre needed three hands, the headsail was a brute to tack, and reefing in a rising Biscay swell meant one of us on the foredeck while the other wrestled the helm. So we changed things, one item at a time, and I can tell you exactly which bits of deck gear turned a two-handed slog into a two-handed cruise.
This is not a list of everything you could buy. It is the order I would buy it in, with the cheap wins first.
The autopilot is the third crew member
If you fit one thing for short-handed work, fit a proper autopilot, and fit it before anything fancier. On a two-person boat the pilot does the steering while you both deal with sails, anchor, fenders or lunch. Ours holds a course in anything up to a real blow, and on a long leg it steers far better than a tired human at 3am.
The modern systems are not cheap but they are not silly either. A Raymarine wireless remote and starter kit was set to land around 549 US dollars in 2026, and that remote is the upgrade I would buy next if I had a basic pilot already, because it lets you adjust course from the mast or the foredeck without going back to the helm. For a fuller autopilot the cost runs into four figures once you add the drive unit, but spread over the hours it works, it is the best value gear on the boat.
A pilot that can tack on command is worth seeking out. Some Raymarine units turn the boat through the wind on a button press, which on a self-tacking rig means one person can tack the whole boat solo. That single feature reshaped how we sail tidal gates like the Chenal du Four, where timing matters more than crew muscle. The biscay passage planning notes go into why steering relief on a multi-day leg is a safety item, not a luxury.
Reefing you can do from the cockpit
The foredeck is the dangerous place on a short-handed boat, especially in the steep tidal seas off Brittany. The aim is to never go there under way. That means all reefing led aft.
Slab reefing run back to the cockpit is the workhorse. Single-line reefing looks tidy because one line does luff and leech together, but it drags a lot of friction through multiple blocks, so on anything but a small main it is a sweaty job. A two-line system, one for the luff cringle and one for the leech, asks far less of the winch and drops a neat reef in seconds. We went two-line and never looked back.
In-mast or in-boom furling removes the reef-versus-no-reef decision entirely, letting you set exactly the sail area you want from the cockpit. It costs more and adds failure modes, but for an older couple or a genuinely short crew it can be the thing that keeps you sailing rather than motoring. Whatever you choose, pair it with a wet weather gear brittany channel setup, because the cockpit is where you now live in a blow.
Winches that do the grunting
A self-tailing winch is the baseline for short-handed sailing, full stop. It holds the tail while your second hand does something useful, which when you are the only one on deck is every hand you have.
The next step up is electric. An electric self-tailing winch takes the load off your arms entirely, which matters most for the genoa sheet and the main halyard on a heavier boat. Prices start around 2,800 pounds for a mid-size electric self-tailer, so this is a serious spend, but if a wrist or a shoulder is the limiting factor on your crew it can extend your cruising life by years. We fitted one to the primary winch only and left the rest manual, which is a sensible compromise on a budget.
A cheaper halfway house is an electric winch handle, a powered drill-style unit that drops into any standard self-tailing winch. It costs a fraction of a fixed electric winch and you move it from winch to winch as needed. For most two-handed cruisers that is plenty.
The small stuff that punches above its price
A self-tacking jib or a small staysail on a track is the cheapest way to make upwind work painless. Tack the boat and the sail looks after itself, no sheet to grind across, which for tidal-gate sailing in Brittany is transformative. Even a modest furling staysail set inside a big genoa gives you an easy sail for windward bashing.
Decent jammers and clutches at the cockpit, properly sized to the lines, stop the slip-and-regrip dance that wastes time and skin. Lazy jacks and a stack pack mean the main flakes itself when you drop it, so neither of you has to leave the cockpit to tame a flogging sail.
Good non-slip and solid jacklines from cockpit to bow are not glamorous, but on a short-handed boat the person who goes forward is alone, and the lifejackets meeting french rules requirements around harness clip-on points are worth meeting properly rather than minimally.
A remote anchor windlass control, ideally wireless, lets the helm drop and recover the hook while one person conns the boat in a crowded Riviera anchorage. Anchoring two-handed in a packed bay is one of the real stress points, and taking the foredeck dash out of it calms the whole operation. The best anchor french holding ground piece covers the ground tackle that goes with it.
Cockpit organisation is the unglamorous multiplier. Label the clutches, colour-code the line tails, and keep a spike, a knife and a winch handle in a fixed pocket within reach of the helm. When you are the only one awake at night and a sheet jams, the seconds you lose hunting for a tool are the seconds the boat rounds up. We spent an afternoon sorting the cockpit so every line and tool has one home, and it did more for our short-handed sailing than half the gear on this list.
Ground tackle you can handle alone
Anchoring is where short crews come unstuck, because the loads are real and the foredeck is far from the helm. A windlass sized properly for the boat, with a chain counter at the helm, lets one person drop and recover while the other steers, and the chain counter means you know how much you have out without a crew member shouting metres back from the bow.
We rig a snubber permanently to hand so we can take the load off the windlass the moment the anchor sets, which protects the gypsy and quietens the boat at night. A trip line on the anchor saves a fouled hook in the rocky Brittany anchorages, where a single fouled anchor with two tired people aboard can ruin an evening. None of this is glamorous, but a calm, repeatable anchoring drill is what lets two people use the wild anchorages rather than always paying for a marina berth.
The same logic runs through every short-handed upgrade: take the panic out of the loaded moments, and the boat shrinks to a size two people can manage.
Where I would start
If I were kitting out a short-handed boat for France from scratch, the order would be autopilot, all-lines-led-aft reefing, self-tailing winches, then a self-tacking headsail, then electric assistance only where a body actually needs it. Do it that way and each upgrade pays back before the next one.
The boat we sail now is the same hull we started with, but two people run it without raising our voices, and the foredeck stays empty under way. That is the whole point of short-handed deck gear: not to sail harder, but to keep both of you safe and rested for the bits of France worth being awake for.
