Anyone else prefer paddling into a headwind as opposed to a tailwind? Coming from a road cycling background it seems counter-intuitive, as a tailwind is always much more enjoyable on a bike. In my kayak a tailwind is hotter, no cooling breeze. The waves are passing you by making it hard to feel that sense of motion, like you’re spinning your wheels so to speak. Going into the wind you seem to be knifing thru the oncoming waves and traveling much faster. I just love getting a good steady rhythm going and eat up the miles.
Same as you say when in a sailboat. Of course your not work that much harder when going to weather in a sailboat.
Depends …if the following seas and wind allows surfing it can be fun.
If the head wind and waves are together plowing through them is easier than making corrective strokes or edging to correct for beam or quartering winds.
I often point higher into the wind to gain weather elevation then fall off like the sail boater I was to play with the waves.
If wind is one way and waves are another and/or waves are “washing machine” all bets are off.
On a little river…just paddle. River will change direction.
PS…the boat makes a difference. Some are affected by wind more, some less.
If my goal is to eat up the miles, I definitely prefer a tailwind.
It is true that directional stability is easier into the wind, and the direction of the waves does provide a satisfying illusion that I’m moving faster. And I definitely feel warmer going downwind.
But the push of the wind and waves always have revealed that I move faster with a tailwind. And the game of catching free rides is a joyful one.
Tail wind? Every time I get in a kayak the wind is in my face.
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The wind in your face is from paddling so fast!
A head wind is cooler than a tail wind. Which is very important down south in the hot months.
SR, that’s funny! There was a time maybe but I’d like to meet the monster who could do that in a Tarpon.
I’m a canoe person and I enjoy a good headwind too. I do a lot of round trip paddles on rivers and also enjoy paddling against the current. I’ve been blown to a stop by wind and stopped by strong current and it’s fun to poke around (or wait for gusts to die down) and figure out a way to keep going.
We were on a club paddle at Matanzas inlet. Thunderstorms forecasted later in afternoon. Storms came early. Gusts were around 35-40mph. Coming through the bridge near the take out a gust stopped me and pushed me backwards. I could only hold position during the gusts. It was fun.
Tailwind. Or more specifically, Downwind.
Surfing for miles downwind with a 20kt+ breeze at your back is the single funnest paddling there is (generally on a OC or Surfski).
The only reason to paddle into the wind is so I can go downwind a few minutes later 
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The river that’s closest to where I live, and is therefor where I paddle most, runs a little to the south of due west. I paddle into the prevailing westerlies almost every time. Some days it’s a pain, but most days it is fine. If I have a tailwind on that river, I use extra long stakes when I camp, because a tailwind means bad weather is probably on the way.
On a lake it’s fun to ride waves with a tailwind and it’s also possible to make really good time, but on a lake with a big fetch, especially a shallow one, often the further downwind you go, the bigger the waves get. I haven’t been swamped (open canoe, mind you) by big waves often, but when I have its usually been a wave from behind me that got me. (And always when I was carrying a big load.) A person can be surprised by their size, their angle, even by their timing if you can’t see them coming. That doesn’t happen with a headwind.
Most of the time the hardest wind to deal with is a quartering wind. That is where you can get swamped.
On boats, I had an early Elaho and a Cobra Eliminator. Neither of those would got to windward, only downwind. You didn’t have a choice.
If paddling a surfski or SUP, downwind races are a blast.
If you are on a river there is no such thing as headwind or tailwind because the wind swirls around and every few feet it comes from a different direction. Upwind is always more challenging
I’ll share an interesting anecdote. It’s not really about what you enjoy more, but about the potential effects of wind on travel.
We had an experienced group of strong paddlers travelling northeast up the coast on the ocean from Ocracoke Inlet along Ocracoke Island. The wind was from the east northeast, somewhat onshore and quartering, but mostly coming straight at us. We had 15 knot winds, and around 3’ short period seas, in the form of waves in the wind that’s creating them. We wanted to make it all the way into Hatteras Inlet. We paddled a distance from shore in an attempt to minimize longshore current effects. We didn’t have anyone needing to brace about, and I figure we were paddling a strong 4 knot pace given flatwater.
I remember landing after around 5 hours, and calculating sub-2 knot progress. Given our plans, we threw in the towel. After some lunch, we started back towards Ocracoke Inlet with a bit more relaxed pace. It went fast, and I remember someone reporting a GPS showing a 6+ knot pace.
Of course, a big caveat in this is always whether a paddler can remain fully engaged in their strong forward stroke. Folks are much more likely to stiffen up, do more bracing, and fall off their forward stroke effort in following seas. As a result, it wouldn’t be uncommon to experience situations where the differences in pace are minimalized.
My preference is to paddle into the wind going out so I can get a ride back.
My worst wind experience of all time was this fall, paddling at an inland lake event into 12-15 knot headwinds with frequent gusts of 22 knots. Winds became so strong the anchors on safety boats wouldn’t hold. When I checked the Windy app and saw the gusts would increase to 28 knots, I bailed at eight miles. No fun, plus my left triceps brachii was sore from tightly holding my paddle so it wouldn’t be blown away. Later read comments by other paddlers stating the winds were so strong it took them an hour to travel a mile.
Would have been a blast had it been a downwind run. I probably would have set a personal best speed record. 
On Jocassee, we often paddle into the wind in both directions.
The perfect day of kayaking, in MY opinion, is fighting the headwind to the decided destination, then just ‘riding’ back with minimal effort. I can’t tell you how many time that hasn’t worked out . . . Just sayin’.
A slight headwind is fun to paddle into because there is the illusion of going faster, and straight tracking is pretty much on autopilot.
A strong headwind is a beotch but there can be (can be) the reward of turning around and actually going faster.
Winds in between those directions, or wind opposing current, tend to be a PITA.
I’m looking forward to getting my surf ski, so that paddling upwind will be less of a grunt and chasing the wind waves will be a blast!
My GPS often indicates an elevation change.
So up hill, up wind, barefoot, both ways against the tide? 