Despite our reluctance to eat in a clothing shop chain, we always have a great time at Tommy Bahama’s, and it’s one of our favorite Happy Hour places in South Maui. Tommy’s menu is filled with hyperbole (every item reads like the most extravagant, to-die-for dish you could ever hope to eat) and Wailea’s characteristically high dollar signs. But the food that’s presented is consistently fresh, well-prepared, and delicious. The staff is uniformly gracious from the hostess to the busboy.
We love the appetizers, especially their ahi poke, a simple, fresh, delicious representation of the Hawaiian-style sashimi. The ahi tuna is uniformly chopped small, mixed with creamy mayonnaise and plenty of spices, then layered with guacamole to smooth out the flavors. Served over crispy flatbread and tortilla chips, it is one of our favorite ways to celebrate.
The scallop sliders are a lighter takes on the beef slider — replace the red meat with the tender seared scallop and you get a fresh burst of sweet fish that perfectly sets off the spicy slaw on top. The simple, macadamia-nutencrusted goat cheese served with mango salsa is also a favorite. Texture and flavor are well-balanced in all of their appetizers. We also like the buttery crab bisque, the crab cakes, and the coconut shrimp, which are usually well prepared and not overcooked.
The cheeseburger has a good sear and sweet and melty honey roasted onions. The pork sandwich with the blackberry brandy sauce continues to be one of our favorite items; savory and sweet and generously sized. The chopped salad with chicken is chunked up with apples, nuts, bacon, and corn, and completely satisfying as a light main entrée. Ribs fall off the bone (and we always take some home).
The steaks are good cuts and prepared well. They often have good specials, and sometimes excellent deals on three course fixed price menus (the portions are often smaller, but we still leave plenty full).
Desserts are excellent at Tommy’s, and we often come here late just for a little something sweet. We were skeptical when a reader (who is now a friend) told us that the butterscotch pudding was “the best dessert on Maui,” but we were converted upon the first taste. Made from scratch and spiked with plenty of whiskey, the creamy, beautifully browned pudding comes in a giant (giant) goblet coated on the inside with a chocolate ganache and topped with homemade whipped cream. While we like the brownie and the key lime pie, this pudding is what we talk about later. (And you will, too.) Ask for the smaller size unless you are splitting it with your companion.
There’s live music at night, and the open-air restaurant features wide, comfortable booths and large tables. It’s even prettier with its recent renovation, which left the central bar intact: big, square, and comfortable for hanging out at Happy Hour or any other time.
Address: 3750 Wailea Alanui Dr., Wailea, South Maui
Location: at the Shops at Wailea
Meals: Lunch, Dinner
Hours: Daily 11am-10pm