An upcoming anniversary (not major milestone but we would like to get away for a long 3-day weekend) and I cannot decide...

NYC - we have both been but not together and since we did not see everything (how could one??? - in any of the cities I have headlined for that matter), we would have no problem enjoying its additional pleasures.

OR: Boston, Chicago, Washington...
Neither of us has been. And these are on the "list" of what we would love to experience...

Here is what we love:
Walking, stopping for morning coffee, lunch, dinner (or any time in between)...

Art Galleries, museums, architecture...

Decent, very convenient accomodations at great prices. I may sound cheap but I will pay more for dinner than I am willing to pay for sleep! (Let's use US$200 as a benchmark - am willing to pay but would perfer not to...)

Shopping - current fashion (as opposed to some discount malls - which in my experience is often not as current as we prefer), affordable art and bric-a-brac...

Not a massive amount of tourists - we love to just follow the locals to the best places in town (you know the places we NEVER want to see a bus load of tourists to know about). Am willing to trade for this info (anyone coming to Toronto)??

Let me know your thoughts...

Typhoon

Late October starts to get chilly in NYC, Boston, and Chicago -- it can even snow any of those places for Hallowe'en.

But a pretty good time to go to DC -- very much between tourist seasons but still decent weather. I'd strongly recommend that choice -- free museums, great restaurants, good art and music (check Kennedy Center), only problematic part is the shopping, because you really have to go out to the suburbs to get the upscale shopping. Not much downtown.

I think NYC is too big for a 3 day weekend, unless you don't do very much touristy stuff - which is sounds like you might be looking for this time. Same goes for Washington DC. I think Boston is about the right size for that amount of time (though I haven't been to Chicago).

However do not cross the others off the list - Washington DC is wonderful and has so much to see and October is a great time - the tourists are gone and it isn't hot.

Good luck decision making!

Nothing to keep the shopping in check like NO SHOPPING!!...
I like the fre museums part - I wish we had that in Toronto.

Not to worry about the weather...I am a Toronto Canadian (our weather is almost exactly what you would get in each of these cities and (yes I am an anomoly) any weather above 80 is almost too much for me!

Washington is a though - Do I land in Dulles?

Thanks

I've been to all the cities you've mentioned numerous times. If you've both been to NYC I suspect you would be able to focus on things you haven't seen, since you've each been there seperately. I suspect there will be a significant memorial of some sort [even if temporary] for Sept. 11 anniv. That may be a reason to go or stay away, depending on how you feel. Boston is perfect and meets everything I believe you're looking for, and is more condensed. Washington may have the best rates for a weekend visit and has wonderful museums, architecture, restaurants and very good metro system. Chicago is a great city, but of all of them, I feel this one is more difficult to get around in for a short visit. I have been there four times, and have yet to put a dent in what the city has to offer. I'd say that ultimately, you wouldn't be sorry with any of the cities mentioned. [and by the way, I love Toronto!]

Thanks!

Moved here to Chicago 2 years ago from NY. Miss NY but Chicago is great!Fantastic shopping on Michigan Ave (Miracle Mile), Top notch restaurants (Charlie Trtters, Spiaggia, Ambria, Gibsons Steakhouse), jazz clubs, comedy clubs, great hotels and many w/indoor pools unlike NYC hotels, plus a great walking city. Chicago is smaller than NYC and easy to see in a 3 day weekend. Most of the museums are concentrated in one area and are also great. Check out quickbook.com for great hotel rates. Walk out on Navy Pier that goes 1/2 mile out onto Lake Michigan (which has water more the color of the Caribbean than the Jersey Shore). End of October has been warm here the last 3 years--no jackets until the sun goes down. Any questions please feel free to e-mail me.

Go to Boston and stay at one of the 2 hotels at Copley Place (an upscale indoor mall). If weather is cruddy, you could stay inside and go someplace for a meal or coffee. It is walking distance to most of the places in Boston you would want to see - Newbury St. boutiques, theatre district, Chinatown (not much in Boston but some interesting small restaurants); easily on MBTA transportation to other places in city - museums, etc.; a longer walk to North End for dinner, but nice if weather is good; walk to Public Garden or Boston Common.

PS We loved Toronto

Though I love Chicago, I'm going to suggest DC -- great museums, good food -- shopping so-so. Depending on your interests I'd suggest staying in an inn or boutique hotel rather than a big chain. Be sure you are near a metro stop as that system works pretty well for the tourist sites.

The northern cities are all defoliated by late October and can be pretty dreary -- so I'll vote for Washington. Certainly would satisfy anyone's needs for art galleries, museums, architecture. You might like the George hotel.

I love all the cities you mention and it would be a hard decision, so KM's suggestion to make weather the determining thing seems a decent way to decide. Moreover, there's something sort of defining about DC -- the sense of history surrounding you in such an immediate, newsmaking way is interesting and gives you an insight into things American that's different from NYC and in some ways as important. Meanwhile there's a lot of touristy things to do -- the art in the National Gallery rivals anything in the other cities and the East Wing's architecture is wonderful. Rehopping -- the museum shops offer some interesting stuff and Georgetown has a lot of more usual shopping (and many many restaurants), including the quite-decent Georgetown Park indoor mall. So I don't think it's fair to say there's no shopping.

You can fly into either airport -- differences: IAD(Dulles) is rather far out from the city so you have to deal with transport in and out, almost an hour depending on where you go. But it's not nearly as congested as WAS (National), and bigger planes can use it. WAS is extremely convenient-- there's even a Metro stop right there -- but it's congested and subject to post-9/11 restrictions, including the need to stay buckled in one's seat for the last 30-40 min. of your flight.

Although I grew up in NYC and later moved to Boston, have visited DC countless times and love Chicago - I am going to push for Boston. Honestly, you have a tough choice to make!!

Boston will be slightly past peak foliage in late October, so the numerous tour groups will have moved on. Also, late October is Halloween season and there is no place better for Halloween than New England. The weather can be cool and is typically dry, but is rarely cold. (Coming from Toronto, i won't lecture you about the weather!) A light sweater or jacket during the day would suffice.

There is so much to do in Boston and you will be able to get everywhere on the "T," our subway system and my walking. Everything you will want to see is within walking distance.

Boston has the best of American history on display. Unlike other places where its history is behind a glass partition, our historical sites are right in the middle of the city. There are great restaurants and you will probably still be able to eat lunch at an outdoor cafe.

Boston is also a great neighborhood city. Within an hour you can walk rom the Italian North End to Brahmin-filled Beacon Hill, to Chinatown, to South End (a large gay community), to yuppie-filled Back Bay. Each is distinct, but all lend well to the social fabric of the cenrtal part of the city. Plus, across the river is Cambridge which ranges from Jamaican and Brazilian immigrants to aging hippies to college students, you name it. Very diverse.

Chicago and New York have more architecture to speak of, but Boston has a particular style that the others do not - low rise development, red brick sidewalks, bay windowed townhouses, white church steeples, old narrow streets. It's a city on a human scale. Other than Quebec City, I think Boston is the most European feeling city in North America. For museums, the Museum of Fine Arts has the 2nd largest collection in the western hemisphere, plus there's the Gardener, the ICA, the deCordova, the Fogg, the Sackler, ...

Shopping? Yeah, plenty of options. Not quite in the same league as NYC, but maybe a half heartbeat behind. Boston's shopping scene ranges from Chanel to second hand CD's - if it's sold anywhere, you can find it here.

You will enjoy any of your choices, so I wish you luck in choosing.

Let us know what you decide on.

Decisions decisions!

One thing I appreciate so afer is that each person who has kindly taken the time to reply has not pooh-poohed any of my selections- infact eact city seems equally beloved...

The Boston as close to European city is a tug (am a European in my soul), while the idea of the National Gallery in Washington and the wonderful monuments et al that are conjured up in the minds' eye certainly tempt. My concern about Washington (and perhaps each of the cities)...is it closed down to the extent that much of the past access is no longer possible? Thus is the Capitol, etc removed from the visitor??

I can understand if that is the case - and for the record - fear is not a factor, nor is weather.

Any other input is appreciated and when the decision is made I will (with your collective permission) start soliciting input for places-only-the-locals-know-about...

Boy, what a tough choice! The upside, of course...is that you can't go wrong. I agree with the poster who remarked on NYC being 'too much' for a three day w/e - there's sooooo much to see/do, would be tough to narrow down and, if it were me, I'd end up feeling bad about everything I couldn't get to. I think I'm in the DC-vote camp - so very much to see there, and the good w/e hotel rates mean you might get more value for your lodging dollar. I read just recently (Frommer's Budget Travel mag, I think) - a recommendation to consider flying into Baltimore because airfares are much more favorable. Just a thought....Do let us know what you decide...