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What’s more appealing: DC, Boston, NY, Chicago, SF, Denver, Seattle
Posted on 7/22/26 at 6:07 pm
Posted on 7/22/26 at 6:07 pm
Have a work / family vacation with conferences coming up in September.
Given the work conferences, we’ll be confined one the aforementioned cities. I’ll probably be solo for 2, 3 nights with work and then the family will come up.
Which sound best for 2 nights solo and 4,5 additional family days in terms of sights, attractions, food and drink etc.
Kids 11, 13 and 17.
Given the work conferences, we’ll be confined one the aforementioned cities. I’ll probably be solo for 2, 3 nights with work and then the family will come up.
Which sound best for 2 nights solo and 4,5 additional family days in terms of sights, attractions, food and drink etc.
Kids 11, 13 and 17.
This post was edited on 7/22/26 at 6:08 pm
11
Posted on 7/22/26 at 6:10 pm to GentleJackJones
Boston has Fenway Park and the Freedom Trail.
Posted on 7/22/26 at 6:26 pm to GentleJackJones
When in September? What do you like to do on your own?
Could go see the aspens outside of Denver and spend some time in the mountains, Seattle should be nice still before the rainy season (could go hiking, whale watching, explore downtown), Boston fall weather as well with freedom trail, NYC should be good before it gets cold, SF explore the city then head to Muir Woods and go hiking, DC all the national monuments.
Honestly all good choices for September
Could go see the aspens outside of Denver and spend some time in the mountains, Seattle should be nice still before the rainy season (could go hiking, whale watching, explore downtown), Boston fall weather as well with freedom trail, NYC should be good before it gets cold, SF explore the city then head to Muir Woods and go hiking, DC all the national monuments.
Honestly all good choices for September
Posted on 7/22/26 at 6:56 pm to GentleJackJones
Assuming all things equal, I’d go Boston, Chicago, DC, then NY. But that depends on what you want to do. San Fran used to be near the top of that list but that was 10+ years ago. Not a ton of experience with Denver or Seattle.
Posted on 7/22/26 at 7:40 pm to GentleJackJones
Chicago IMO... Stay on the magnificent mile. Quarter mile south and you;re at the Bean and all the musuems and stuff to do there. Quarter mile east and your at Navy Pier. Tons of food throughout that part of town. Jump on the L and head up to Wrigleyville to catch a cubs game.
Boston and DC would be fun, but I love Chicago through and through.
frick NYC, Seattle, and Denver.
Boston and DC would be fun, but I love Chicago through and through.
frick NYC, Seattle, and Denver.
Posted on 7/22/26 at 7:50 pm to GentleJackJones
Denver, Chicago and Seattle are at the bottom of the list.
Boston or DC will be more relaxed (I can't believe I said that about DC), NYC is good but feels like it will generate more anxiety than Boston or DC. I don't think you can go wrong with those three.
Boston or DC will be more relaxed (I can't believe I said that about DC), NYC is good but feels like it will generate more anxiety than Boston or DC. I don't think you can go wrong with those three.
Posted on 7/22/26 at 9:07 pm to GentleJackJones
I've been to all of those locations and feel Boston is the best
Posted on 7/22/26 at 9:26 pm to GentleJackJones
For many years, New York was my favorite American city to vacation in because the restaurants are fantastic and there is so much to do.
Same with San Francisco which I always considered the most beautiful city in the country.
Things are changing in both.
DC is great and I like Boston.
Denver is nice if you can drive to the surrounding areas.
Same with San Francisco which I always considered the most beautiful city in the country.
Things are changing in both.
DC is great and I like Boston.
Denver is nice if you can drive to the surrounding areas.
Posted on 7/23/26 at 7:24 am to GentleJackJones
Everyone should go to DC and see the memorials and smithsonians IMHO. The Metro is clean and reliable.
You should be able to find something the kids are interested in between the space smithsonian, spy museum, ect.
You should be able to find something the kids are interested in between the space smithsonian, spy museum, ect.
Posted on 7/23/26 at 8:08 am to GentleJackJones
If I had the choice, it would be NYC. Weather will be great, and if you really want to you can get to Boston or Philly in a short time.
Chicago would also be a good option and like NYC, lots for you to do solo until the family shows up.
Seattle would be higher but unpredictable weather can make planning activities for the kids a little difficult. But you wouldn't regret the trip out there in the long run.
Chicago would also be a good option and like NYC, lots for you to do solo until the family shows up.
Seattle would be higher but unpredictable weather can make planning activities for the kids a little difficult. But you wouldn't regret the trip out there in the long run.
Posted on 7/23/26 at 8:54 am to geauxpurple
quote:
Denver is nice if you can drive to the surrounding areas.
Lots to do right outside of Denver, but the city itself is meh....
Posted on 7/23/26 at 9:16 am to GentleJackJones
With kids, I'd probably do DC, Boston or Chicago. Weather will be extremely pleasant in September, as well. New York has very obvious advantages in September, as well, but wasn't sure if you'd prefer something at a 'smaller scale.'
This post was edited on 7/23/26 at 10:31 am
Posted on 7/23/26 at 11:35 am to GentleJackJones
I've been to every one of those places and live in Seattle. I think it is highly dependent on what you and your family enjoy doing. Are you more into checking out the city (art, museums, tourist attractions) or more broadly considering checking out the area/getting out of the city/enjoying nature?
If you're in the former camp I'd rank them Boston > Chicago > New York > San Francisco > DC > Seattle > Denver
I think Boston and Chicago are pretty neck and neck, followed by New York (amazing city, but ambitious with 3 kids).
If you're more into enjoying nature, I think you my ranking would look something like this:
Seattle > Denver > San Francisco > the rest
Consider SEA/DEN/SFO if you want to maybe spend a couple days in the city interspersed with some traveling outside of the area to get into nature.
Seattle you could ferry to the peninsula, go to Olympic or Rainier National Parks .. among so much more. The city itself would definitely be fun for a couple days too.
Denver you could head west into the mountains - Silverthorne/Breckenridge area is pretty family friendly and lots of nature to enjoy. Denver itself is probably the least interesting city on your list but there is still a lot to enjoy.
San Francisco you could get out to Muir Woods and go check out redwoods .. pretty awe inspiring. The city gets shite on a lot, but I've been several times (including when I was around your kids age) and always had a blast.
Very cool you get an opportunity to treat the family to any of these places. They're all great cities in their own right.
If you're in the former camp I'd rank them Boston > Chicago > New York > San Francisco > DC > Seattle > Denver
I think Boston and Chicago are pretty neck and neck, followed by New York (amazing city, but ambitious with 3 kids).
If you're more into enjoying nature, I think you my ranking would look something like this:
Seattle > Denver > San Francisco > the rest
Consider SEA/DEN/SFO if you want to maybe spend a couple days in the city interspersed with some traveling outside of the area to get into nature.
Seattle you could ferry to the peninsula, go to Olympic or Rainier National Parks .. among so much more. The city itself would definitely be fun for a couple days too.
Denver you could head west into the mountains - Silverthorne/Breckenridge area is pretty family friendly and lots of nature to enjoy. Denver itself is probably the least interesting city on your list but there is still a lot to enjoy.
San Francisco you could get out to Muir Woods and go check out redwoods .. pretty awe inspiring. The city gets shite on a lot, but I've been several times (including when I was around your kids age) and always had a blast.
Very cool you get an opportunity to treat the family to any of these places. They're all great cities in their own right.
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