Dole Whip from Lappert's Ice Cream
Lappert's is famous for extra-indulgent ice cream in Hawaiian-inspired flavors like Guava Cheesecake, Kona Coffee, and Caramel Coconut Macadamia Nut, all of which have between 16 to 18 percent butterfat. They also sell pineapple flavored Dole Whip, a frozen dessert that's a bit like a cross between sorbet and soft serve. It's great by itself or as a float (with pineapple juice), but I like adding a "shot" of it ($1.80) on top of a scoop of a complementary ice cream, like coconut.
Creamy Chocolate Coated Paletas from Neveria Tocumbo
This Mexican ice cream shop stocks some legitimately unique ice cream flavors (mamey, corn, and strawberry with cheese, to name a few), but I like the paletas best. They've got a ton of fruit flavors, several creamy flavors, and a few creamy bars wrapped in chocolate and rolled in nuts or coconut. I made friends with this strawberry-chocolate-coconut paleta last fall and have never looked back.
4686 Market Street, San Diego CA 92102 (map); 619-264-0391
Hawaiian Shave Ice from Ice Blast
There are 26 different flavors to choose from at this Hawaiian shave ice shop, so it's great that you can get up to three different options in one cup. The "tiny" size ($2.75) is plenty for one person, and comes with free condensed milk, sour spray, ling hing mui (salty dried plum) powder, or Hawaiian salt. My favorite combination so far is lychee and guava syrups with condensed milk and mango jelly.
4206 Convoy Street, San Diego CA 92111 (map); 858-430-6104
Milkshakes from Hodad's
One of my favorite things about going to Hodad's is watching people's reactions to how gigantic some of the food is. Jaws tend to drop when people see their double bacon cheeseburger for the first time, and the same thing happens when milkshakes ($5.25) appear. There's so much superfluous ice cream and chocolate syrup on top that it's practically like getting a milkshake and a sundae in one. All of the flavors (chocolate, vanilla, and strawberry) are great, but my personal favorite is the (off menu) Neapolitan.
Ice Milk Drinks from Infinitea
If you like boba, but not tea, these ice milk drinks ($3.85) are the way to go. Under a cap of frosty, frozen milk, you can slurp up chewy additions like coffee or grass jelly, plain or caramel pudding and red bean. I like the first option on the menu—ice milk with plain pudding and honey boba, made with half of the usual sugar. There's got to be at least a quarter cup of chewy boba, and a generous portion of silky pudding. If you want to introduce some bitterness and even more texture, the coffee jelly and starchy red beans are a great combo. Just be sure to stir it up before you start sipping so the sugar can get right to the bottom.
4690 Convoy St #111, San Diego CA 92111 (map); 858-268-8836
Stirred Ice Milk Drinks
Brownie Ice Cream Sandwich from The Baked Bear
I think we all know that absolutely nothing can go wrong when you make an ice cream sandwich out of two fudgy Ghirardelli brownies and mint chocolate chip ice cream. Best part: at The Baked Bear, this will only cost you $3.95