I am planning to take my son on a trip in early/mid September 2025. I have extensive experience in backcountry but have never done boundary waters and have no idea where to start with deciding where to go.

-We would like a trip that is 4 days/3 nights, but are open to 5 days/4 nights.
-We want solitude.
-We would love to have good fishing.
-We are great with a challenge.

I would love any specific recommendations.
I would also value any direction on where to start in looking (western side vs Eastern side).

A few general comments. There are a lot of options and variables involved. Your backcountry experience will serve you well, but does that include paddling and portaging experience?

You can't really go far in 4-5 days. Of course it depends on how fast you travel and how long, and there could be weather delays. How much you want to travel vs. fish. There are lots of good options out of Ely, the Sawbill Trail out of Tofte, and the Gunflint Trail out of Grand Marais. Some examples: Mudro EP, Moose River N EP, Moose Lake, Lake One, Sawbill Lake, Baker Lake, Missing Link Lake, to name a few at random. No matter where you go, you'll need a permit and permits are limited.

There's lots of general and specific information here under the tabs at the top and in the various forums. Information about permits, the rules, about outfitters, etc. There are guidebooks for sale in the books section. Most outfitter websites will list some specific route options for the area they serve.

You'll get many helpful responses. Feel free to email me also if I can provide any helpful information/suggestions.

How old is your son? That will probably be the biggest driver.
Most of our trips are late fall so there is almost always solitude, and the fishing is hit or miss.

Some routes out of ely that I've done that fall into a long weekend with my son when he was mid teens and above.
In at Mudro, then to jackfish bay (camp), basswood river (camp at lower falls), day trip to the pictoglyphs, and fish the area, when ready to leave canoe out through the horse river back to mudro. 4 day trip

Leave a car at fall lake, put in at wood lake (used outfitter for shuttle). Work your way up to the portage between back and pipestone bay and then down to fall. that was about 4 days. check out the steam engine (donkey not train) and the trestle piers Fishing was good in back bay. Indiana is said to have some good fishing but we didn't loop that way.

Moose lake, up along the boarder to knife and then back via ensign. 3 day, this is also a route where you could get a tow up to the birch or ensign portages

Snowbank lake loop 3 day up snowbank to gibson and back down through disappointment.

One thing that you'll be a bit surprised by is that the portages between lakes are short in comparison to hiking in backcountry. The longest portage I've ever taken was a one way 45 minute walk. To the average BWCA goer that is a massive distance but after spending a week backpacking in the Winds in WY last year, BWCA was a cakewalk. So don't be too scared to toss in that extra weight in your pack, it's not going to ruin your time. The vast majority of it will be spent on the water in a canoe. Make your time at camp enjoyable.

For a 3 nighter - maybe start at Missing Link > Tuscarora > Gillis > Bat? Out thru Brant lake back to Tuscarora Outfitters.

Or if you are down for 4 nights, several times we've paid Rockwood lodge to drop us off at the Cross Bay EP, parked at their joint, then canoed right down to their landing over the course of 4 days. Some real good fishing in there along the way and it's not often that people do a thru paddle like that so you won't see quite so many on those lakes in between. But regardless, even in the busiest times of summer, maybe most I've seen is 5 groups in a day. It's never super busy out there.

There is no wrong answer, I think we would all attest to that. But one more point for folks with inexperienced paddlers. You might want to watch the maps for routes that give you skinny lakes that go straight east to west. Be mindful how much you plan to try and go west on a long skinny lake, as prevailing breezes usually give you a headwind and a wind tunnel. Yeah. it might be fine, but you may find yourself laid up for a day.

Landon: "I am planning to take my son on a trip in early/mid September 2025. I have extensive experience in backcountry but have never done boundary waters and have no idea where to start with deciding where to go.

-We would like a trip that is 4 days/3 nights, but are open to 5 days/4 nights.
-We want solitude.
-We would love to have good fishing.
-We are great with a challenge.

I would love any specific recommendations.
I would also value any direction on where to start in looking (western side vs Eastern side)."

Landon...prepare to be pleasantly overwhelmed with suggestions. Gauging from solitude being high on your list, I would suggest a tow to get deep on day 1 so you can maximize time fishing. You can organize your day trips to be challenging.

For best fishing hit the Bald Eagle/Gabbro lakes but, for solitude plan on camping on one of the chain of the lakes north off of Bald Eagle. Ironing out the wrinkles in my soul