If Savannah, Charleston and New Orleans are the 3 southern cousins,

Albany, Syracuse, and Buffalo?

Newark, Long Island and Providence.

Boston, New York, Philadelphia

R3, the OP was looking for cities with charm.

No Chicago?

New Orleans likes to think of itself as totally unlike anywhere else. In it's universe, Charleston and savannah would be more like cleaning women than cousins, and of those two only Charleston seems like a real city. Savannah is like a pretty little girl who grew-up and got fat and a little ugly.

What r3 said. Those were the first major cities in America.

In the first American census back in 1790, the biggest three cities were New York, Philadelphia and Boston. They are shared history to the founding of America.

The Twin Cities of Minneapolis-St. Paul!

Detroit, Cleveland, Pittsburgh- the blue collar cousins....

Chicago would need to go with other midwestern cities r5.

Probably Chicago, Milwaukee and Indianoplis would be a good threesome.

They have a shared history and culture. By the time Chicago came along NY, Boston and Philly were already two centuries old.

I’d agree with Boston, New York and Philadelphia. Chicago is different.

Scranton, Pittsburgh and Allentown

Seattle, San Francisco, and Los Angeles are the 3 Western Cousins.

Cincinnati, St. Louis, and Milwaukee are the German triplets

Cooperstown, Springfield, and Canton are the Hall of Fame triplets: baseball, basketball, and football

Albany, Harrisburg, and Trenton are the political ghetto triplets.

New York City, Boston, Philly.

Duh.

Although Baltimore and Philly are similar so too.

Are they cousins who speak to each other?

Hartford, Worcester, Manchester, NH.

I disagree R13, All three of those cities are way too different. IMO I would say Seattle, Portland and Vancouver,BC are the three cousins of the North west coast, and L.A., San Diego, and San Jose are the cousins of the South West Coast. San Francisco is its own thing. Las Vegas, Phoenix and Albuquerque are the Southwest cousins, and Salt Lake City, Denver and (perhaps?) Boise would be the Rocky Mountain cousins.

R21 Denver, Salt Lake City and Calgary would more accurate. Boise is too small.

R17 NEw York has no "cousins." New York is an only child, no siblings, no aunts and uncles, no cousins. A Singular, unique entity.

Montreal, Boston and (specifically) Manhattan?

Houston, San Antonia, Dallas make up the Texas cousins.

The Great Lakes cousins: Chicago, Toronto and Detroit.

Cousin cities?

1) Providence, Boston, and Portland ME

2) Troy, Albany, and Schenectady

3) Harrisburg, Lancaster, and York

R24 Montreal is like a friendlier, french-speaking third cousin of NY and Boston. San Francisco really is its own thing ( architecture ,climate and even culture) . R23 not really, there are still too many similarities between NYC, Boston and Philadelphia ( history, culture, architecture, attitude, language, climate).

R26 Detroit is too run-down, poor, dangerous and ugly . I think Milwaukee, Chicago, Cleveland and Toronto are the great lake cousins.

R29, i thought Detroit didn't fit either but it is the third largest great lakes city.

R28, funny you say that, when I was in Quebec City, I told my uber driver we were in Montreal for a few days before QC. He said he didn't like Montreal because he felt it was dirty and run-down but he LOVED Boston and far preferred it to Montreal. Historically, many French Canadians have moved to Massachusetts/Boston, so there is a shared history there.

R31 Any city is dirty compared to Quebec City. However, Montreal is NOT dirtier than Boston, that is absolutely ridiculous. That being said, I'm not suprised the cab driver likes Boston better. Boston has prettier architecture , has more character, has a nice seashore, and has a better climate.

R32, I haven't been to Boston but I found Montreal pretty clean, especially the subway. And i only saw one crazy person on it the whole time I was there. In Chicago, I see at least two or three crazy people on the El per day. Based on pictures, I actually like Montreal's architecture more than Boston's. And I think Montreal has a ton of character.

R33 I'm familiar with both cities. Lived in Boston and have been to Montreal many times. Montreal, like pretty much any Canadian city, is much cleaner than practically any American city. The Montreal Metro is spotless and puts Boston's T to shame. Vieux (old) Montreal has lovely architecture, but it is concentrated in only one part of town, whereas Boston has nice colonial architecture throughout the metropolitan area. As far as character goes, Montreal does have character but unfortunately it still suffers a little bit from that Canadian blandness that other Canadian cities have ( Though it still has more character than any other Canadian city except Quebec City).

Miami is like the love child of Jacksonville and San Juan

Atlanta, Charlotte and Raleigh as a whole are more alike than Savannah, Charleston and New Orleans.

Savannah, Charleston and New Orleans share a long history as old southern port cities. They were the major cities of the south in the early stages of our country (or "deep south", ignoring VA/MD)

Detroit, Cleveland, Buffalo - hollowed out industrial rust belt cities

Los Angeles, Tijuana and Mexico City

Miami, San Juan and Havana.

R29 Toronto is a midwest city that desperately wishes to be an east coast city. Sad and disappointing. Reminds me of Meghan Markle, who shuns her real family ( that gave her everything) to try and fit in with a family that will never really accept her. I'm not surprised she lived in Toronto before meeting Harry.

Wow, the Meghan Markle freaks really are something else. Trying to force a conversation about cities into being about their demented obsession. Get help r41 and quit trying to derail the thread.

Fall River, Bridgeport, Camden

Bedrock, Frostbite Falls, Springfield.

This thread is so much fun to think about. Like a little geography puzzle. Especially when you throw in some differing opinions and people give reasons for choosing a different combination.

Just to broaden the scope: St. Louis, Kansas City and the twin cities. Or should it be Twin Cities, Denver and KC?

R45, How about Minneapolis, St. Paul and Winnipeg.

The Mountain-West Siblings: Denver, Salt Lake City and Calgary.

The Geriatric Mothballed Guilded Age Resorts: Lenox, Newport, Bar Harbor

Twin Cities, Madison, Milwaukee

Sheboygan, Hoboken, the Catskills

Yes, R36, because the former are upcountry Scots Presbyterians vs. cosmopolitan Episcopalians and even Catholics in the port cities. Very different outlooks and outcomes.

R41, both Toronto and Chicago suffer from a "second city complex", Toronto even more than Chicago.