Which hotels are cool for a nice little girl in the city by herself for the first time? I prefer modern boutique hotels or old world sophistication.  

Better yet, where do I eat yummy San Diego exclusive foodie bucket list delicacies besides Extraordinary Desserts

In downtown SD (i.e Gas Lamp District), I've eaten a few times at Gaslamp Strip Club - A Steak Place (https://www.cohnrestaurants.com/gaslampstripclub).  It's an unusual restaurant where you grill your own steak/seafood on a hibachi grill or the restaurant staff will cook it for you.  There's also Ballast Point brewery near the airport. but it fills-up quickly (standing room only) after work lets out.  La Jolla is another good spot for restaurants.  Karl Strauss has a brew pub with full menu in La Jolla as well as the Sorrento Valley area in north county.