Mundane Moments

I’d do a Californian road trip, with a few days in SF followed by a couple of nights in Yosemite, then maybe a drive through Death Valley to Vegas. I’d end with a return to the coast for a few days, somewhere like Santa Monica so you can do the Universal / Disneyland stuff, or further south towards San Diego. La Jolla is nice. We did all of that many years ago with young teenagers and everybody loved it.

Have been to SF many times for work, loved it there, great beer & food scene. But friends who live there say it's gone downhill in recent years.

I would also consider going north west, Portland & Seattle are both great cities.

I've heard similar on Sam Francisco from colleagues there.

This sounds awesome

I'm waiting to get my hair cut.

At a barbers. On a Sunday.

Game's gone.

It absolutely does but unfortunately not possible in the four or five days we had in mind.

4-5 days feels like not very long to go to the US. Not tempted by a European destination?

He is. The US.

If you're only going for 4-5 days then I'd skip the West Coast, it's an extra 4 or 5 hours in the air.

Toronto is great, but obviously I'm biased. Depending on what you like to do, the downtown tourist plaza has a ton of things to do with the kids - the CN Tower obviously, but also there's a brilliant aquarium, a big entertainment centre called the Rec Room which has restaurants and bars and a huge arcade filled with games, and when Dad needs some time alone the Steam Whistle Brewery does a really fun guided tour complete with beers along the way. It's all right on the waterfront which is super scenic and you can get a 10 minute ferry or water taxi over to the islands which are beautiful and give you a stunning view of the skyline. There's also a ton of cool neighborhoods and markets dotted around, and our transit system is pretty good.

I obviously don't know Boston or Chicago so well, I'll let our resident experts give you the skinny on those but I also love both of those cities. I don't think you'll go wrong on any of the three tbh.

I also love DC but I don't know if it's worth a family holiday, and October is just before the midterms so I would have a mild concern over protests, rallies, and an excess of jackbooted security. Probably recommend skipping that to be on the safe side.

Was perfect for New York last year (well, for us anyway). Obviously still loads to do next time, but managed to tick a bunch of things off the list in four days.

I guess if you're trying to stay East Coast, which you probably should, then Russ' suggestion of Toronto is good. We enjoyed it a few years ago. I particularly enjoyed Toronto Island and the Aquarium is top notch as Russ mentions. Plus the brewery area.

We also did a Boston - Salem - Provincetown (ferry from Boston) trip which might be fun for you?

I have been to Toronto once before but more than 30 years ago as a kid. I don't remember much apart from the SkyDome (likely not called that now), CN Tower and the underground malls.

Advantage is you can also hire a car or take a train to Niagara pretty easily from there.

Boston appeals because of the Freedom Trail stuff and chance to see Harvard. Again, have done that before but in the early 90s. Not been to Chicago, San Francisco or Chicago before.

That looks awesome. Did the trip take in Cape Cod and Martha's Vineyard?

All this holiday talk annoys me. There is so much of the world to see. I've seen quite a bit but I'm mid 40s now and there's many many places. I don't just want to visit places for a few days, I want to go live in them for a few years, and it feels pretty impossible that it's ever going to happen, especially with a kid.

My top places to relocate to would probably be in no particular order:

1) West Coast North America (though never been, so not sure what that's based on!). Portland. San Francisco. LA. Vancouver.
2) Barcelona. Been many times. Love it.
3) Somewhere a bit insane like Dallas Texas. Again, never been, but surely great.

All this talk has got me planning a trip next summer to do Vancouver + Portland + San Fran. Maybe if I love them as much as I think I'll go insane and talk to my boss about relocating.

Skydome is called the Rogers Centre these days, but everyone knows what you mean when you say Skydome.

In October you'll likely have the Leafs playing, although it's eyewateringly expensive to go to a game.

Cape Cod yes, but not Martha's. Province town had such a relaxed beach vibe compared to the city feel of Boston. Then all the witchcraft stuff in Salem was interesting to see in person.