suze

I say back to the drawing board... Puerto Rico or Martinique. I also am a pool preferring swimmer. I love being near the beach/ocean but not so much actually *in* it!

sassy_cat

Patrick,
I think you'll be happy with several of these options but St. Martin with a day trip to Anguilla sounds lovely.
The beaches even if you're only there for the view and not to swim are stunning on Anguilla plus the food options will tempt you to return.. if your a pastry fan (Yes I know you're trying to eat healthy when it comes to deli meat but this is vacation...!) go to Gerauds!
St. Martin I think, is more relaxed and laid back than Puerto Rico. Excellent food options too..

If you choose Puerto Rico then I'd stay in or close to San Juan for at least part of your stay. You won't be beach front at El Convento but you'll be able to walk to all the sights. Condado might be better if you want beachfront but you might find yourself at a bigger hotel than you'd like.
Hire a car for a couple of days and get out to the rainforest.
If you go for a week include an overnight in Vieques for the Biobay (or take the evening trip by catamaran).

NeoPatrick

Thanks, sassy_cat.
Part of the issue is neither of us are really very good at relaxing. While it sounds good, we need lots to do. We go to my place in Naples a few times a year, but an hour at the beach is about all we can stand until we have to get going again.

Meanwhile, I just started a new thread about a condo in PR. Check it out if you will and see if you have any comments. I was intriqued by it's closeness to San Juan and the idea of being so close with even a bus to go back and forth for dinner or daytime sightseeing. It would be nice to just stay in one place for the full week and not more around, but we aren't opposed to breaking the week into two if that really makes more sense. We are also more into renting a car and doing our own thing than we are into signing on to a tour for the day.