We took my mother last year, who has Type II diabetes, and she had a blast! We noted her diabetes on every ADR and then I mentioned it to the waitress/waiter at the beginning of each meal. The chef personally came out each time (except for Chef Mickey's) to ask more specific information about the kind of limitations she had and then advised her about what to avoid. My mom eats no refined sugar and very few carbs (only whole grains). Anyway, she was served amazing desserts at each meal....with very few repeats.
The best experience was at BOMA. The Chef gave her a personal tour and when she asked about a coconut seafood soup, he offered to make her a new batch with Splenda because it had sugar in it. She said "Oh , don't worry about it". He insisted and about 10 minutes later a huge bowl heaping with seafood and broth was brought to the table. She loves seafood and was in her glory. He also offered to prepare steak for her with a different rub since the one of the menu had brown sugar in it. She didn't have room......with all of the seafood. At the end of the meal, out came an absolutely beautiful piece of SF cheesecake drizzled with a SF pineapple sauce and garnished withe pineapple slices. It really was beautiful.....
At every restaurant, the desserts were fabulous...and she really enjoyed it because usually she just watches everyone else eat dessert or settles for the inevitable bowl of sugar free jello or vanilla ice cream. Here are some of the things she was served:
Askerhaus- chocolate mousse
Boma- cheesecake with pineapple
Cape May Cafe- more cheesecake
Chef Mickeys- sf brownies (not very exciting)
Mama Melrose- lemon creme
Biergarten- carrot cake (I think...)
Also, there was a SF brownie in many bakeries that my mom just loved. I went back to buy her extras with our snack credits at the end. It was just nice that for once, her diabetes meant special attention, not a hindrance.