If you wanna check out Cuba, i think Cancun is the best place for that.
If you wanna do sailboat thing, drive to Panama from Costa Rica and do the San Blas Islands sailboat tour, lots of great options for really awesome tours, i hear... But they are like 4 day tours and Panama is pretty big.
But the Panama highway doesnt really have many towns, almost no highways intersect it and zero stop lights or signs, plus no traffic police or highway patrol, so you can drive like the bus drivers at 90 MPH and make good time.
South of a few places in Mexico, sailboats have very few places to stop on the Pacific and certain portion of the year sailboats are a no go.
Stay at that place i told ya about a few nights for unforgettably awesome vacation that you be dreaming about for many years to come.
Ive travelled all the US, alot of Mexico, all C.A and I've never seen a place so colorful, peaceful and magical as those mountains.
Lots of wild blueberries and blackberries growing everywhere too, tasty snacks if you do some cool hikes.
It's not far from San Jose and the drive there is very Bonito, rural CR looks like Ireland.
Also, San Isidro is very near. Nice little city, lots of cool offerings and a bunch of excellent Pacific Beaches very nearby.
Southern CR is way better than the North, i thought the people in the North were unfriendly and pretentious.
