Looking for a five day resort trip with interesting things to do nearby

I'd third Costa Rica, but I'd go to http://www.tripadvisor.com/Hotel_Review-g309274-d673363-Reviews-Arenas_del_Mar_Beachfront_and_Rainforest_Resort_Manuel_Antonio_Costa_Rica-Manuel_Antoni.html. It is literally exactly what both of you want -- a luxurious, welcoming hotel with a stunning private beach plonked down (ever so gently) in the middle of a rainforest. As much or as little adventure (hiking, ziplining, diving, etc.) as you want is there for the taking or leaving. If you don't properly close the "monkey door" monkeys will come into your room and take your breakfast cereal. (Why yes, that did happen to us, why do you ask?) I never recommend anything on MeFi (or anywhere on the Internet) but Arenas Del Mar is the best resort I've ever been to. Feel free to MeMail me if you want more gushing details.

I'd do the http://www3.hilton.com/en/hotels/costa-rica/hilton-papagayo-costa-rica-resort-and-spa-SJOPAHH/index.html where it's luxurious and all inclusive and there are cool wildlife hikes and surfing lessons nearby.

I'm thinking Puerto Rico. Easy flight from the east coast, neat culture and history. No passport required.

We went to San Juan, Puerto Rico. Spent a few days on the beach; a few days up in the rainforest swimming under waterfalls; a little time in Old City carousing; and one great night kayaking through bioluminescence. Easy flight. No passports. Eazy peazy.

I agree with Ipsguy, although we didn't time things well enough to make the bioluminescent bay trip. But basically you can stay in San Juan at any one of the large hotels if that's your companion's thing (feels more "all inclusive") -- that's what we did -- stayed at one of the Marriots -- and then we took taxis (there are city buses too but harder to coordinate the schedule) to Old San Juan for sightseeing (El Morro, old fortress, and other interesting sightseeing), more interesting restaurants, the old cemetery,etc.. and then you can sign up at your hotel for the El Yunque rain forest trip, a bioluminescent bay trip, and other trips for more physical-type activities (a van will pick you up right at your hotel for these trips). And, yes, it was a very easy I think 4-hour direct flight (we took Jet Blue), no passport, no need to change money, but you feel as if you're in another country (because, really, you are, despite the politics). I went with my grown-ish son for 4 days and it worked out very well. Something for everyone! (Another possibility that I'm curious about (haven't been) is Cartagena, Colombia. I hav(e a feeling that Puerto Rico is an easier place in which to get that diversity in a few days, though. )

Not sure if this is helpful at all but I'm a Gold Status member with Hilton if anybody knows of any great Hilton locations.

This might not be exotic/foreign enough for you but have you considered Hawaii? Some beautiful and seriously relaxing beachy properties on almost all of the islands, and there's lots to do: hiking, exploring volcanoes/black sand beaches, snorkeling, diving, etc. I'd also second Costa Rica.

rmless, I looked at that one but it got some terrible reviews. Have you been there? I'd love to go to Hawaii but it's too long of a flight for a 5 day trip. Thanks, all!

Try the http://www.tripadvisor.com/Hotel_Review-g147323-d151671-Reviews-Hilton_Ponce_Golf_Casino_Resort-Ponce_Puerto_Rico.html, Puerto Rico. It's across the island from San Juan, about 1.5 hours. You can rent a car, and do some exploring from there.