I know summer only ended yesterday, but today hasn't even broken 60 degrees yet and I'm already thinking of winter vacation planning.
Looking for a spot that is bike friendly (decent road bike rentals, good roads), guaranteed warm (80's or above), and has stuff for kids (tweens) to do. Oh, did I mention not too far away and not too expensive?
Is this the impossible dream or does anyone have a recommendation?
Hawaii - anywhere in Hawaii. Shop for good airfare and it is no more expensive than anywhere in the US. You can rent a bike from a good Tri store out there. Lots of tri clubs and running clubs to hook up with and the weather is always perfect.
Off the top of my head, I think San Diego/Palm Springs, Tuscon or Austin would meet your criteria - if you can swing Hawaii, of course, that would be ideal. I've heard crazy things about Florida drivers and bikes, so I wouldn't chance it down there.
A small group of people are heading to Puerto Rico in January to do La Vuelto Puerto Rico. Flights are very reasonable and it looks like a great weekend. I'm jealous that I can't go this year.
If you wind up in Hawaii, specifically, Oahu, the Waikiki Swim Club has several ocean swims each week and welcomes visitors. Great chance to get in some beautiful open water swimming.