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I'm with Ray on raising the mast alone (but a little behind him on age). If there is a member close by who can help you the first time it will cut down your learning curve but unless my "helper" has done the job on my boat several times I don't find it to be any faster.

I'm often asked at the dock how long it takes to raise the mast and get everything ready. My usual (slightly tongue-in-cheek) answer is, "45 minutes to an hour by myself; about an hour and a quarter if I have help."

If I have two helpers, it takes even longer than that (I have to explain to each what they have to do, double-check, help the helpers, and that takes extra time). I am planning on adjusting the raising pole according to the newer design (the one with a crank on top of it) and, hopefully, that will enable me to shave some minutes by doing it alone. Such as things stand, one person is cranking the winch on the side and I am pushing the mast up from the cockpit. When the mast is almost vertical and does not require hard cranking anymore, I can scuttle to the prow and attach the forestay. Then attach the boom. Once they are in place, I have the feeling that we are almost done and crack open a beer (or enjoy a cigarette break, when I was younger) and make sure everything is on board. Then launch.
I don't like to putter around on the ramp more than I have to. Or even by the dock. Just eager to get the heck out on the water asap.

Became a pro on this past 4 day weekend out on a close to me lake and new to me 26X. We stayed at a Marina that unfortunately required going under literally an 8' bridge that not only required on each day of sailing to lower and raise the mast but also had to unbolt it from its hinge point and raise to a perfectly level stance as we went under the bridge, clearing by 10"! (We even had to duck our heads when standing in the cockpit to clear). Here are my steps:
1- At home in the driveway i levelled the boat and trailer perfectly then lifted mast and once i got it perfect I marked all pin holes with nail polish so Id know exactly which hole lines up with which hole for the pin in the standing rigging.
2- Once at the lake but still on the trailer I attached all rigging cables (Except the Fore stay of course) lining up all the nail polish marks (color coding with different colr nailpolish for each stay could be beneficial).
3- Once out on the water just had to raise the mast with mast raising winch and only had to attach the front Stay, was quick and easy!

I am not familiar with intricacies of the For clarity, do you have the boom still attached to the mast while the mast is lowered?

NiceAft wrote: ↑Fri Apr 04, 2025 8:00 am I am not familiar with intricacies of the For clarity, do you have the boom still attached to the mast while the mast is lowered?

Nope. It gets detached before dropping the mast - that's what the factory manual recommends.

I always detach mine, because I'm always doing it for storage at the end of the season. That being said, I can see how one might possibly be able to lower the mast to a certain point without doing so - for going under bridges and other stuff.

I left the boom attached once when I needed to "dip" the mast to retrieve a halyard that I'd let get away from me when rigging.

As I recall there was not enough clearance between the boom and the cabin top to lower the mast into the support. Since I was rigging at the dock I was able to lower the mast as far as it would go and then spin the boat around so that the mast was over the dock allowing me to retrieve the halyard with a boat hook. This was before I'd attached the main. If the main had been in the way it would have only made things worse.

NiceAft wrote: ↑Fri Apr 04, 2025 8:00 am I am not familiar with intricacies of the For clarity, do you have the boom still attached to the mast while the mast is lowered?

No, the boom with the main sail attached is sitting to the side while raising the mast. Then after mast raised the boom is an easy attachment with the topping lift sheet attached at the rear end of boom and the pin inserted to attach boom to mast and your done. Just need to attach sail in the mast track after.

FWIW, I do. I leave it attached, then used bungee cords to secure it to the mast for storage. KISS - Keep It Simple - Simon.

NiceAft wrote: ↑Fri Apr 04, 2025 8:00 am I am not familiar with intricacies of the For clarity, do you have the boom still attached to the mast while the mast is lowered?

March wrote: ↑Mon Mar 31, 2025 5:22 pm If I have two helpers, it takes even longer than that (I have to explain to each what they have to do, double-check, help the helpers, and that takes extra time).

Came here to say ... this hit home, so hard, I doubled over in laughter and solidarity. "But you need help, I come help you"