San Diego or Key West for relaxing vacation?
 

We're wanting to take a 7-10 day vacation to San Diego or Key West in the beginning of May. We are looking for a relaxing beach, shopping, good eating, and nightlife. Any suggestions on which one, or is there a more perfect spot?
Thanks

Can't comment on Key West, but here in San Diego we have "May Gray & June Gloom." That time of year it's usually overcast until early afternoon, albeit with comfortable temperatures (highs around 70 on the coast). I suspect you'd get more sun in Key West, if that's important to you. Other than that, there are many places in San Diego County that would meet your requirements: Coronado, Del Mar, La Jolla, and Carlsbad all come to mind.

Key West is not much for shopping unless you like that Jimmy Buffet look all year round. The beach is not much either as there's not a lot of it, mostly rocks and mangroves. But there's plenty of good eating and nightlife.

I'd suggest a few days in South Beach followed by a trip to Key West. May is a wonderful time of year in Florida.

The Florida Keys = RELAXING! There is nothing else like them.

Interesting dilemma. Your first two requirements would seem to rule out Key West-- but for relaxation, good grub and fun nightlife, it's great.

However, you can find all four qualities in the San Diego area. I'm a huge fan of La Jolla (great beach, charming little shops, fantastic restaurants), although its nightlife is somewhat reserved. But it's only 15 minutes out of downtown San Diego, and the Gaslamp District has plenty of good nightlife. Good eateries there as well. Del Mar and Carlsbad are comparable to La Jolla in their relaxation level and are truly lovely.

The drawback is that SD is an actual big city-- you will have to combine relaxation with occasional highway driving and big city crowds (mostly if you venture into SD proper-- La Jolla is quite laid back).

Key West is definitely 100% set up for relaxation, so if you factor shopping (and beaches) out of the equation, it's perfect. Also definitely NOT a big city. It all depends on what you really want....

The two are completely different. I enjoy San Diego and Key West for totally different experiences. Key West is unique. If you go, stay in a guesthouse or inn in Old Town. You walk to everything (though get off the beaten track for shopping), theater, museums, etc.

Thanks everyone! Shopping is not nearly as much of a requirement as relaxing. If we go to Key West, I'm thinking about flying into Miami and spending a day or two at the beginning or end of the trip in that area. Will it be warm enough in either local for water sports in early May? Thanks again

Two totally different places. I have been to Key West and San Diego.
I have a few thoughts for you.
The weather is more predicable that time of year in Key West, although if you are going for a week, you will definitely get some sun. If you go to either place you can drive around a bit.
Clearly there would be more to see, and more to do in San Diego. I think that I would plan a little drive up the coast or into the Palm Springs area. There really are some great resorts and hotels in and around San Diego.
There are some nice beaches in the area, LoJolla is great. The night life in San Diego is fantastic, not quite like Key West, But still great restraunts and "hang outs" We did not go to Coronado, but you should consider it.
If you want hotel recs, email me I will be happy to tell you about our recent trip.

How is the weather usually in November? Thanks,

Oops, I should have said, how is the weather in SAN DIEGO usually in November. Thanks,

arguably, november is one of the best months in terms of weather. personally, as a native i like november because the weather has mellowed. lots of clear days, almost never any rain. slightly cooler in the eve (low 60's/high 50's?), perfectly mild during the day.

November is also my favorite weather month in San Diego. Lots of sun but comfortably cool, and most of the tourist crowds are gone (no offense!).

Didn't you want to go in May? The water will be fine. By May, the winter storms have stopped -- they always manage to churn up some cold weather. And the winter storms dump cold water which makes the water cold in the Gulf. The Gulf stream keeps temperatures wonderful in Miami. What kind of water sports? Marco Polo (haha)?