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My wife and I will be heading down for the first time early next year.  We're starting with San Jose.  While there we may touch nearby central valley locations but really want to focus on one city at a time.  With hope we'll be able to meet people locally and see what they recommend. 

Retirement is a ways off for us yet, but we have many of the same desires as retirees: access to health care, lower cost of living, good transit, lots of things to do nearby, and access to at least a small airport.  (I plan to have my pilot's license next year.)

Good luck to you - I'll be curious to watch this thread and see what suggestions come through.

My husband and I (both in our Mid-50's) and Canadian, went with a friend to Costa Rica in November-December of 2010 for 3 weeks with the intent of finding a place where we would like to retire.  We had contemplated Mexico and Belize and had already ruled both out.  Our requirements were:  moderate temperature 24-30, quiet lifestyle but still accessible to amenities such as groceries, restaurants, hospitals, clinics, etc.  We started out in San Jose driving 2700 km. in a period of 3 weeks going past La Fortuna, several other towns and ending up in Lake Arenal.  From there, we went back down through Sarchi, Grecia, Santa Ana and down the Osa Peninsula through Santiago de Puriscal, Puntarenas, Dominical, Parita, Colon, Palmar Sur and several other places.  We made the mutual decision that our place of choice was a community close to Santiago de Puriscal.  We are at the age where the extreme heat and humidity were not something we wanted and being on the ocean was not a priority for us either. If you'd like more info., please feel free to message.

Fortuna - Arenal -Monteverde and then perhaps Peninsula Nicoya - Manuel Antonio

Depends alot if you speak Spanish or intend to learn it well.With Spanish your optiond are without limits, little/no Spanish and you have to stay in tourist areas,Jaco, Heredia has a large English population, Cartago and the Caribean coast. Second is the climate you want to live in. It changes with the altitude you are at. 1/2 hour driving can change 10 derees, higher is cooler, sea level is HOT.
Cities cost alot more for land and housing than rural towns, also security is less than in a small place. I recommend a small village to small town, within 1/2 hour of a clinic and gracery store, bank, hardware store ect..

My hubby and I did the same thing starting in Dec of 2008.  We got REALLY lucky and found some beautiful cabins to stay in outside of San Ramon.  From there we drove to Jaco (beach), to Monteverde (cloud forest), to La Paz Waterfall Gardens (touristy but worth the trip and it's beautiful scenery the entire way), to Poas (volcano and national park), Sarchi (shopping), Grecia (not so impressed as we thought we'd be) and way up to Berlin where we visited a couple I'd found online.  Our second trip, in 2010, we stayed in a cabin in San Isidro de General and drove to San Vito (way south), Domincal, Cartego, and then up the west coast to visit our friends in San Ramon.  We made a day trip to Zarcero.  We do not speak more than a few words of Spanish and never had a problem.  Our favorite places for sight seeing were Monteverde, La Paz, Sarchi for sure! and Zarcero.  We are leaning towards San Isidro as our retirement destination but that's a purely personal decision.

If you'd like to know about the places we stayed (both of which we can highly recommend) and/or have some names for introductions, let me know by return post.  Sometimes I think I have more friends in CR than I do here at "home."

I am a single american considering moving to costa rica.  i am in need of a web site or contacts who can give me info on cost of living, (in dollars please), and overall lifestyles and what my reasonable expectations should be.  small things count..price of gas, homes, health care quality, jobs for an americans, biggest differences in laws from usa to costa rica. and how do u learn of the local laws so one stays out of trouble while learning? so many questions i need answered before i invest in a trip there.  thanks for any and all help you can provide.

all the best

For living I recommend San Ramon but it's not a touristy area.
However you can pass through San Ramon on your way to Arenal which is a touristy area and in my opinion is a "must see" in Costa Rica.

My wife and I love to stay at Los Lagos resort in La Fortuna where you get amazing views of the volcano, can swim in the volcanically heated pools, the grounds are beautiful, sometimes there are monkeys on the edge of the grounds (ask the desk or groundskeepers), there's a swim up bar, and a great buffet breakfast included. hotelloslagos.com

San Ramon is a nice smaller city to live near and you can buy property there among the lowest prices in the Central Valley and you can "dial in" your altitude in the surrounding hills and mountains to be as cool or cold as you like (we prefer 2800 feet - warm days and cool nights! ;-D ).

From Arenal you can go back down the hill and - if money is not too much of an issue - you can stay at Villa Blanca in a private cloud forest! villablanca-costarica.com

I wouldn't plan to spend much time in San Jose', it's okay for a night or two but it's a bit dicey at night and dirty/smoggy in the day. I do enjoy it but only in very small doses.