San Diego vs. Santa Barbara?
A good place to start is staying at the Upham hotel on West Sola and dining in their LOUIE'S restaurant for California cuisine in this lovely historic old Victorian mansion B&B, right next to Magellen's travel retain store.
Then moving your way down State Street only a few blocks to West Figueroa street smaller modest restaurants and bars.(The SPORTSMAN definitely ranks as a "dive-bar" and at one time had really hot music) and then to the upper end ones clustered around the 1200 block of State Street: ARIGATO, BUCHON, EPIPHANY, OLIO ET LIMONE, DOWNEY'S
For pretty good dining: SOHO upstairs in VICTORIA COURT is great for acoustic music in its roof top setting. OPAL'S is consistently good. CAFE BUENOS AIRES is magical at night under the stars with their fountain courtyard and lampiones. CAFE BIANCO tucked inside Victoria court runs circles around the new Starbucks sitting on the corner for great European coffees, desserts and light breakfast/lunch and quiet atmosphere. The MOROCCAN restaurant also in Victoria Court has a really good feast if you want the full on belly dancing package, but in a small intimate setting for a change of pace.
And going the other direction on West Victoria is CA CARIO for intimate N. Italian
Maybe you can be the first to try the new FRESCO's at the corner of Milpas Street and Cabrillo Blvd at the beach - the ocean view is the best and Fresco's has always had a good reputation in their more modest spot in Five Points and as a caterer. Be among the first to set the record straight on their more upscale adventure.
Hole in the walls for breakfast would be ROSE'S Cafe on East Haley for Huevos Rancheros which would require a good morning walk or short drive. Or closer to Dining Ground Zero, Anderson's Bakery in the 1100 Block of State Street for Danish specialties and a full breakfast. For local funk, see the huge fig tree growing up in the middle of the IHOP on West Valerio and State just up from the Upham for their Swedish pancakes with lignonberry jam - as good as they get, and a chain to boot.
Cantwell's deli and market at West Arrellaga and State (again all in the same neighborhood) can provide good picnic items and some lovely parks are only a few blocks away at Santa Barbara and East Micheltorena Streets.
So if you want to spend more time dining than moving around finding places to dine, you couldn't go wrong with this potential combination -- plus about a dozen other suggestions still using this as your base.
Try San Francisco! And if that is really the standard for your dining interests, neighther SB or SD will match it. Yes, you can have some interesting dining experiences in a much smaller and more ambient area in Santa Barbara that meet some of your needs. Right around the 1200 block of State Street can be your dining ground zero in SB, absent the sea side view and the dirty dive bar - though those could only a short walk/drive or shuttle ride away at the harbor and lower State/Chapala Street
Santa Barbara simply does not have the range of population to support more than an artificial dining experience and it is too expensive to support the truly unique and adventurous. OldTown Ventura along Main Street near their mission may in fact be more of the sleeper range of dining experiences these days on the Central Coast.
Does Joe's Cafe on State Street count as a "dirty dive bar"? Does everything on Lower State Street on a Friday or Saturday night count as dirty dive bars when they are loaded with wealthy college students? Does Mel's count tucked into Paseo Nuevo or the Sportsman down another but more modest "dining row" on West Figueroa - and why? Stiff drinks, dark atmosphere, regulars during the day time?
For compactness of the experience with more variety in a smaller, more easily accessible space with all the features you want in walking distance probably SB wins, but it does have more ....artificiality than autenticity ...... (duck).
Tough choice. SB is smaller in scale and easier to manage. The wineries on Foxen Rd are within easy striking distance along with Los Olivos Cafe and Matteis Tavern, both excellent.
San Diego has great places to eat spread over a larger area. Temecula wine country is 60 miles to the north. Again, some very good food there to go along with very good wines (seriously)but plenty of choices in SD - refer to the board for them.
I was in SB last weekend and give it the edge. I admit it is more beautiful even than our fair city.