I'd like to get away for a couple of weeks sometime in October. I picture sleeping in late in a relatively nice luxe hotel, breakfast room service, easy mornings with a jog or a snooze, then off to a local attraction whether it's a church or a landmark, museum, store, park, garden, theatre, basically anywhere beautiful with no set agenda. Rest up, drink up, then back out for a nice dinner. A walkable city with cabs or Uber so I don't have to bother with a car. Thank you.

Two come to mind . .

- Charleston ( less decadent than New Orleans )

- New Orleans

Charleston
Savannah

New York
San Francisco

Lee Ann

San Francisco

San Francisco

Sorry I should've specified SF, NYC as no-go zones as I'm there frequently enough. Charleston or Savannah will be new. Kinda wanna try something new. Loved New Orleans but will skip that too. Los Angeles? Chicago? DC?

Philadelphia.

Minneapolis and Saint Paul, spend a week in each.

DC would be nice in October.

Santa Monica has everything you mentioned.

without a doubt: Vancouver BC Canada - my favorite city in North America by far ... and early Oct is a great time weather-wise. Lots of great hotels, very much a new and exciting and clean city with something for everyone ... it has one of the best jogging routes anywhere -the Seaside Greenway (also formerly called the Seawall), a 30 km separated jogging / strolling / biking trail that follows the entire waterfront with its many beaches. I could easily spend a dreamy week or more there.

The other week you may want to consider:
* Victoria, a 2 hour ferry ride away.
* Whistler ... a totally walkable mountain resort north of Vancouver, or Banff National Park.
* Seattle, just south of there.

I can't resist including some links about Vancouver (and no, I'm not related to Vancouver):
http://www.hellobc.com/vancouver.aspx
and
http://www.tripadvisor.com/Tourism-g...Vacations.html
and
http://vancouver.ca/parks-recreation...e/seawall.aspx

<Sorry I should've specified SF, NYC as no-go zones>
Ya think? Might have mentioned you've been to New Orleans, too.

<Los Angeles? Chicago? DC?>
Sure. Yes to all of those.

Luxury hotel on a beach in Puerto Rico, close to Old San Juan.

You'll need a car for LA

These are great ideas. I think it might have to be LA or Vancouver unless someone can come up with a better idea. I've always wanted to go to Vancouver but I kind of miss LA. You think I can get away with Uber in LA?

I'd pick Victoria BC over Vancouver. It's like a little bit of England in North America.

Yes, if you stay in Santa Monica or Westwood you can easily get around with Uber in LA. Depends on what you want to see and do, lots of visits to downtown/ball games/concerts etc would be a traffic headache, but sounds like you mostly want to relax/walk/enjoy.
Sheraton Delfina is @ 275 and Le Merigot is @ $300.

In Vancouver, the Metropolitan is a steal @ $159 for a luxury king with wifi & complimentary morning car service around town.

I'm sure you can use Uber to get around LA but you'll be sitting in a car for a lot of the time if you want to venture farther than just one area.

Vancouver can be lovely in October, or it can be wet. Same for Seattle.

But for "a couple of weeks" you might run out of things to do in Vancouver; maybe you could combine Seattle with Vancouver, or Philly with DC, or LA with San Diego or Santa Barbara.

I was also going to suggest Montreal, maybe combined with a couple of days in Quebec City. Quebec is gorgeous in the fall.

where are you traveling from?