Planning ahead on how best to escape for 3 weeks next winter or early spring and looking for some ideas. I'll be working in the mornings and have the rest of the day free to explore. I'd like somewhere warm as I'm in the Midwest, but not necessarily Florida as I've been there many times. It can be in the US or not, but prefer English speaking. I'll have family members come and go but will be by myself for the most part. As I hate driving in big cities that I'm unfamiliar with, I'm looking for small- mid size city that's easy to navigate, warm, and interesting. Mid range budget.
I do like great natural scenery, the charm of walkable downtown areas and to be close to that walkable area..
Any good ideas?

Almeria or Valencia.

When I have to work on vacation, I like going west as the time change means I can be done with work earlier in the day. Hawaii is perfect because I feel like I can quit checking emails around 1 pm Hawaii time as it's 5 pm in the Mountain time zone.

Asheville NC

We stayed in Savannah for 9 days in February 2020 and really enjoyed it. Lots of walking, good food and great weather. I can't recommend the apartment we stayed in, because it was on Broughton Street and was very noisy.

We were in Florida this past winter and it was very nice. We were in Naples but there are many areas that are nice and not as pricey as Naples. (My mom has a condo there).

Our daughter moved to San Diego and I have to say the weather is unbelievably nice all year round. So if you like pleasant temps and a nice atmosphere, somewhere near there. I liked Encinitas as a town to hang out in. That would put you three hours behind, but you would get to enjoy most of the day then.
East coast, I would say SC and south would be warm but you don't get really warm until you get past Tampa in Florida in my opinion.

I did love Asheville as Starrs mentioned but doesn't it get cold there in the winter? Nice area. Lots of outdoor activities. I would love to go back. We were there as the country was shutting down in March 2020.

South Texas?

If you go to Ashville, say Hi to Willowjane

I always love our Florida vacations, Delray Beach in particular, and I'm hoping we can get there in December/January for a couple of weeks.
Otherwise, I like both Savannah and Charleston but Charleston wins out by a bit.
Also, I really like Santa Fe. We've been a couple of times and I hope to get back there one day.

With a title like " Where to go", be careful

A lot of people just might tell you where to go.

I'm done : The zebec

I second Hawaii. Or maybe somewhere in one of the California wine regions.

"I did love Asheville as Starrs mentioned but doesn't it get cold there in the winter?"

Highs are around 50F in the winter.

The temperature issue is interesting.
We usually go to south Florida because anything more northerly than that isn't warm enough for us for a winter vacation but considering global warming, that may change.

Especially the mods, who will recommend a different forum ⭐️

Does that mean you have to start checking those emails four hours early?

I like Carlsbad, Ca. Nice downtown to walk around in. If that gets boring, you have all the beach towns between Carlsbad and San Diego including La Jolla. The train runs between SD and Carlsbad so if you don't want to drive, you can take the train. The train also stops at many of the beach towns.

I usually start checking at 6 or 6:30 am because that's when I tend to wake up in Hawaii. On this last trip, I did have a Zoom conference call that I had to be on at 5 am (and it lasted for three damn hours). It's just nice that I can take care of a whole mornings worth of emails by 9 am.

"I'll be working in the mornings and have the rest of the day free to explore."
I did this a lot when pup sitting for friends in NYC. Walked the dog in the morning. Worked. Had lunch. Walked the dog and was "off" by 2 pm. Maybe a bit earlier if I was going to a Broadway matinee. Loved it!

You should go from the Lounge to the Travel Tips forum. Just kidding.

I would recommend Puerto Vallarta because it's easy and I love it there, but you said English speaking. So I'll go with the Hawaii idea. Can't go wrong with that. Oahu would be my island pick.

I would recommend Puerto Vallarta as well given your criteria. And I wouldn't worry too much about the language. Probably more English spoken in PV than in south Texas, lol. I'd say the top 3 resort areas in Mexico where English is spoken almost as much as Spanish are PV, Cancun & Cabo. At least in the tourist zones. Budget friendly too, compared to many places in the US.

goddesstogo, my sister in law lives in Delray. I agree that is a great town too. Lots of great restaurants.

Palm Springs. Nice walkable downtown, lots of cool architecture and art (including a dynamite small art museum) as well as plenty of cool places to stay in all price ranges. Great food, and in an hour you can be in Joshua Tree National Park, or you can take the aerial tram up San Jacinto Peak to the snow. Easy access to greater LA if that appeals, reliably warm weather...