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4 seasons papagayo Costa Rica, hands down. Incredible service.
Costa Rica. Stay at Westin Guanacaste. It is all inclusive.
Ditto this. Stayed here and loved it
Costa Rica might be a bit far for a 4 day trip but much nicer than PR in my opinion. Why are you only considering these 2 locations?
Pro
Yea Costa Rica definitely a longer travel time
Pro
They're quite different. Since money isn't an issue we'll leave that out. Costa Rica is like paradise on earth - the most lush and gorgeous place. Agree with others that PR is more of a 4 day destination and for CR you'd want some more time. Both are nice but Costa Rica is inherently nicer. Rainforest, beach, volcanoes and a pura vida lifestyle. Puerto Rico also has a small rainforest and an old colonial style town but CR is more lush and tropical.
Pro
PR is great
If it’s only 4 nights, go to PR. I’ve stayed at Condado Vanderbilt. Close to everything and Ubers to old San Jan were very cheap.
If you have more time, definitely suggest CR
Rising Star
St. Regis or Ritz in PR are awesome! Prob go for a week if CR
Costa Rica...
If you want a bit of adventure, the Canopy villa at the Pacuare Lodge.
CR if she likes ecotourism
No visas or passport required for PR.
No visa for CR either for US citizens. Stamp on arrival.
Rising Star
What does she like to do? Are you seeking posh resorts, or would you prefer going hiking in the jungle?
I love both places, lots of different options in both.
Chief
Of course money isn’t an issue when you’re an MD
CR is better but with 4 days, do PR. The food in PR is AMAZING. Verde Mesa is one of the best meals I’ve ever had (and I LOVE good restaurants and food). Buy her a blue coral necklace when you’re there. Super special.
Lol just use points
Costa Rica is by far nicer than PR. But I don’t know if it’s just a 4 day trip. I did it in 10 days and still feel like there was more to do and see.
It's all about what you want to do in country. Costa Rica is amazingly beautiful, but Puerto Rico has amazing food & culture (and is lovely also). If you're purely looking to find an amazing resort and relax the time away Mexico would likely be your best bet. Costa Rica has some amazing zip lining, hiking & caving. Mexico has beautiful cenotes & caves as well.
Consider Bermuda if you are from the NE and have flex on budget - it’s an easy and quick flight