I pulled a Sawbill permit for May 21 with the plan to head up tp Wine and camp there for a couple days. I’ll be going with my son (an experienced tripper) and two of his friends (complete newbies). I realize the Lujenida portage is good at thinning out crowds, but I’m concerned about the relatively smaller number of campsites on Wine - if they’re all occupied getting a campsite on another lake wouldn’t be an easy task. So, I’ve been thinking about heading to Cherokee instead, where there are many more campsites. My question is this - should I worry about the Wine sites all being occupied, or is that so unlikely that it shouldn’t be a consideration?

I arrived on Wine July 3rd last summer and left on July 5th. I saw no else the entire time. I stayed on the island site, but paddled around on the 4th to check out the other sites. The one in the southern most arm looks like it is hardly ever used. The other 2 get regular usage but definitely more like weekly usage not daily usage.

We stayed on Wine for a night during the first week of August two years ago. We didn’t see another soul on, or close to, Wine.

When you pick up your permit at Sawbill Outfitters, ask them how many people are headed to Wine Lake.

Just FYI, there is a 200 yard section in the middle of Lujenida to Zenith that you will likely have to wade. It may be as much as knee deep. That early in the season "cold" will probably not even begin to describe the water temp.

On the other hand, one of the nicest stringers of lake trout I have ever seen came out of Wine Lake.

May 14 is fishing opener, and both are LT lakes. Sawbill permits are gone (11/day) on May 18, 19 and 20. I'd have a back-up plan regardless of what the outfitter (who may be a really nice college student who arrived on May 20) tells you. If you find Wine full (as I did in May, 2020 when the BWCAW re-opened from the COVID closure), try the single site on Frederick. It's known as a "1-star" site, but any port in a storm after Lujenida. Wake up on Sunday and either check sites again on Wine for folks departing, or head to Mesaba.
Or scrap that plan and go to Cherokee. With five times as many sites, you'll find something there. But it's also an LT lake, and the fishers will be fishing!
Either way, heed the wisdom of Michwall2 - the water is liquid ice that time of year. Wet-footing will be the reality even if it's not the plan, regardless of which route you choose, including Ada Creek.