Are you sure he wants this to be a family trip and not a mini getaway just for him?

Try https://www.roseriverfarm.com

It’s not too far and is beautiful.

Fly fishing - go up to Central PA. Super peaceful.
Inshore - Chesapeake bay, but I would wait for opening day of the annual striper run. Usually April or May. He will 100% bag a few big ones and they are great for eating.
Offshore - best to go south. VA beach will start hopping in a couple of months.

Ultimately, your decision comes down to the following:
1. what does he want to catch? Bigger fish = bigger boat, longer trip, more $$$. Does he want to eat what he catches or sport-fish? And how much of a fight does he want? A striper will give some fight but end up in your boat for you to eat. A marlin is “ old man and the sea” shit. Can’t eat or keep, but the hour-long fight is the fun. Yes, the fish lives.
2. When does he want to go? If you go now, you’ll have to travel further for desirable conditions. Wait until April/May and your options are wide open.
3. If it’s a family trip, I wouldn’t advise offshore. It’s a hard day. Most charters start at 6:00 am or earlier and last 12-14 hours. But if it’s a dude trip, offshore is exactly the kind of adventure that middle-aged dudes love. Hunter gatherer and all that stuff.

Also, factor in 15% tip for the first mate on top of base price.

This will give you some ideas what's out there

https://fishingbooker.com/

Travel or sport board?

I have a friend who fly fishes out near CHarlottesville...

Anonymous wrote:I’m the PP, Flyfishing is for old retired guys, he needs a trip to the canyons; if you’re in DC it’s three hours to Jersey or it’s 3 1/2 down to North Carolina.

Aw, I’m a 35 yr old female and actually really enjoy fly fishing! Guess I’m an old retired guy at heart...

I’m the PP, Flyfishing is for old retired guys, he needs a trip to the canyons; if you’re in DC it’s three hours to Jersey or it’s 3 1/2 down to North Carolina.

Get that man a tuna trip!

https://www.jennyleesportfishing.com/

We went fly fishing near Carlisle, PA for a couple of days. We hired fishing guides for the day and stayed at the Allenberry. It is definitely family friendly. It’s gorgeous and you can get a little house for everyone to stay together. We had a great time and caught a bunch of trout!

OP, I'm not an expert, but you're not getting much advice here, so I'll add my two cents. Fly fishing is usually done from the banks or while standing in the water wearing waders. I think "boat fishing" is what you want -- in this area, I think that would mostly be bass fishing? I don't have a particular recommendation, but there are lots of companies who offer fishing packages on the Chesapeake. I wanna say prices are around $500-700 for a day.

Anonymous wrote:Asheville, NC has some amazing fly fishing and a fun family friendly city

And also 7 hours away. If driving that far plenty of other options.

Asheville, NC has some amazing fly fishing and a fun family friendly city

Anonymous wrote:Fly fishing or boat fishing?

Fly would be better, but excuse my ignorance, I was assuming the only organized trip I would find would be boat-based.

Fly fishing or boat fishing?

Anyone have a recommendation for a pre-planned trip like this? Extra points for family friendly, and within 2/3 hours of DC.