Hubby loves the cigar shop.
We both love Two Brothers restaurant for breakfast.
Bo's fish market for fresh fish sandwiches and conch fritters for lunch.
Kino Sandals...hand made leather sandals for men, women and kids..like $8 per pair. They are great.
We always must stop at Boarshead (is that right, or am I thinking of the lunchmeat..lol) for a beer and t shirts, margaritaville for any souveniers, the Fresh Produce store for key west t's, Sloppy Joes for sounveniers and a sloppy joe.
Sotiel's studio for artwork..love it love it.
I avoid the made for you tshirt shops..better/cheaper t's in grand cayman or cozumel.
The big souvenier shop where the conch tour train lets you out is great for trinkets, postcards and mailing the postcards.