Estero to Miami to Key west in January 2020
 

Hi, Will be doing first trip to Estero area in Jan. '20 for 3 weeks. 2-- 60 somethings. Would like to know some key things to hit while there. First week in Estero area visiting friends who moved there but is new. Then 2 weeks when we can play elsewhere around South Florida.... 1 of us has been to Miami before (30 years ago) so interested in that for food, culture, sights..love Cuban food, South American, seafood.. Also interested in Everglades and Key West, both of which are new places never visited.. Will be driving. Looking for points of interest, suggested routes. Not into amusement parks, maybe beaches (if different offerings from HI), love to see some "Old Florida" if still exists, light hiking is ok. Suggested restaurants, tours, non-chain hotels or B &Bs all welcome.
If there are recomended sites online to research or threads on here a link is great. Appreciate it all. Mahalo and aloha.

Estero is within a 30 minute drive to Ft Myers, Bonita springs, and Naples, each in different directions... a taste of old florida remains in the Edison/Ford winter homes to the north, and Naples to the south.
Day trip to Sanibel and Captiva for beach experience, some fun dining, and shell hunting...
My choice for Miami is the Deco district on South Beach... it puts you in a walkable area for drinks, dining, shopping, and wandering along the beach with access to multiple events and experiences...

Key West gives you the best taste of Old Florida... make sure you stay in "Old Town" , near Duval Street... wandering around gives you a glimpse of Key West architecture, even though the magic is mostly commercial.
Have fun!