Here are the specs, where to go?
 

We live in Los Angeles and want to spend 8-10 days at the end of March visiting one area with 2 locales (hopefully near each other). We'd like to spend 2-3 days in a town or city with a sense of history, cultural activities, great public architecture ( Havana, Santo Domingo or somewhere in Mexico, Costa Rica, Nicaragua or Hunduras comes to mind), wonderful dining options and choice of boutique hotels in tranquil settings.
Then no more than a 2 hour drive or flight for 4-5 days to a beach place with white, sandy beach, clear water, good swimming and snorkeling, intimate (small, personal) hotels (please recommend) with great service, spa/gym, and plenty of dining options in the area. Want to avoid large and mass tourist hotels with noise, kids.
We're in our mid 60's and enjoy relaxing, adventure travel, photography, quiet beaches and wonderful food. Since we're west coast don't want to spend two whole days getting to and from destination if that's possible.
We've been to Puerto Rico & Bahamas (years ago), US VI (loved St. John), Jamaica (beautiful,didn't like vibes from locals) Belize (wonderful resort of 10 luxury beach huts whose name I can't recall and fun town a boat ride away, Cancun (hated the big resorts and lack of real town), Puerta Vallarta (was best 20 & 30 years ago), Zihuatinejo (La Casa Que Canta was superb).
Where am I describing for our spring get away??

You say you've already been to Puerto Rico. Does that mean you've already stayed in Old San Juan? Because it would be perfect for your architectural/cultural/historical/boutique/restaurant needs. And since San Juan is a hub for American and American Eagle, which fly almost everywhere in the Caribbean, you could have your choice of the remaining islands for your relaxing beach time.

Not sure about the logistics of traveling to Havana. I'll leave that to you and other posters.

ejcrowe, you took the thoughts right out of my head! I was about to suggest San Juan -- a beautiful, cosmopolitan, and historic city -- followed by several days elsewhere, like Grenada or even one of the "Spanish Virgins" (Vieques or Culebra).

But, how about thinking a little out of the box ... why not spend a few days in Miami, the gateway to the Caribbean and Latin America? Get yourself acclimated, sequester yourself in a deliciously private and luxurious hotel like one of the Ritz Carltons or the Mandarin Oriental, and then fly out to one of the Out Islands of the Bahamas.

You may have been to the Bahamas (which many people think are limited to Nassau and Freeport), but have you visited an Out Island? I suspect Harbor Island, off the north tip of Eleuthera, would suit very nicely -- with its small hotels, beautiful pinkish beaches, and very intimate feel. Also, Andros has some very high-end resorts which also have the benefit of being very green -- consider Kamalame Cay or Tiamo. The Out Islands, while only minutes away from Miami by plane, feel like they're a world away.

The only real catch with the Out Islands is that dining tends to be somewhat limited. Resorts on Andros are pretty much limited to on-site dining, as there is not much outside the gates. Some of the other islands might have more choices, but it tends to be less-than-haute cuisine (but if you like conch and fish, as I do, you'll be perfectly content).

I say Puerto Vallarta or Costa Rica. The only large cities in all the Caribbean (outside Central America or Mexico) are Havana, Kingston, San Juan, or Santo Domingo. I guess the DR would be a possibility since you can easily get to La Romana in a little over 2 hours from there. But here are many choices in Mexico. You might also consider Guatemala, where you could spend some time in Antigua and then at the beach, though the most fabulous archaelogical sight is not particularly close to either Antigua or the beach.

I will take a closer look at San Juan and the idea of flying from there to any other destination. I did do some research on Cuba and I decided that its just more hassle than I want to deal with.
The Frommer's guide on DR gave me the impression that most beach resorts were either AIs, huge (300+ rooms) or very budget places unless you go all the way to La Romana and Casa de Campo. Can anyone enlighten me on this impression or misimpression??

I think most tourist hotels/resorts in the DR are that large. It has more hotel rooms that any other island in the Caribbean and is well known for large AI places where you never leave the resort.

On the north coast, the Cabarete area still has some smaller guesthouses with a funky surfing vibe, according to my friend who used to live there. I've never been there myself, so it's all second hand, but he is definitely NOT a resort kinda guy.

Definitely take a look at Old San Juan, which is full of 17th century buildings, many of which have been beautifully restored. If you have the money to do so, stay at El Convento, a converted Carmelite convent in the heart of the old city, not far from the old wall or the two magnificent forts. There are quite a few museums in the area, and lots of high end dining as well as funky hole in the wall dining. Touristy as well as authentic, chock-a-block next to each other. Kind of like the French Quarter in New Orleans, with beautiful antique stores on Royale juxtaposed with tacky t-shirt shops. Hidden courtyards also abound in Old San Juan.

Old San Juan does look interesting. And I'm reading much praise for Anguilla as a beach destination with day trip to St. Barths (probably too pricy to stay there).
What are the logistics to fly from LA to San Juan and from San Juan to other islands?
Thanks
I'm also looking in to Central America to see if it meets to spec and is any less transit time.

There are lots of nonstop flights from major cities in the US to San Juan. If there's not one from LAX, you'd probably have to connect in Dallas/Ft. Worth. We have a friend in Pasadena who travels to the Caribbean every other year or so, and I think he flies on American to San Juan with a connection in DFW.

From San Juan it's an easy hop over to Anguilla on American Eagle. I agree it would be a good beach h destination for you.

How about Grand Cayman (for the beach part), then a few days (flying from Cayman) in Havana ?

Would also chime in for PR/San Juan for a cpla days -- then either Horned Dorset Primaverra in Rincon/Agadilla on West coast (fly or drive) for luxe or
Viques off other coast for more beachcomber/sleepy Mexico style, tho the island's fast becoming known.

I believe American has one daily nonstop to PR from LA, but it's expensive. If you are going to San Juan, then the obvious islands from there are those that are nearby. Vieques and Culebra are natural choices, both off the eastern tip of Puerto Rico. St. Thomas or St. Croix are also close by on a short small-plane flight. Since PR is a hub for American Airlines in the Caribbean, there are many, many flights to other islands, but you'll find that the prices can be surprisingly expensive.

I think you can also fly nonstop from LA to Montego Bay in Jamaica on Air Jamaica.

You'll find that Mexico is infinitely easier to reach. I'm not sure about Costa Rica.