I’m not going to give you a list of 50 restaurants. 😂 These are a handful of places I’d actually mention to a friend — a mix of little local spots, good cocktails, coffee and fresh fish. I rechecked current reviews before keeping them on this list.
Wailuku
Esters Fair Prospect
2050 Main St #1B, Wailuku, HI 96793
Phone: 808-868-0056
Website: https://www.estersmaui.com/
From Wailuku: a few minutes
From Grand Champions / Wailea: about 35–45 min
This would be my first pick if you asked me for a cool little Wailuku bar. Really good craft cocktails, tropical feel, local neighborhood vibe and not at all resort-y.
Good to know: Hours can change, so check the day you’re going.
Tiffany’s Restaurant & Bar
1424 Lower Main St, Wailuku, HI 96793
Phone: 808-249-0052
Website: https://tiffanysmaui.com/
From Wailuku: about 5–10 min
From Grand Champions / Wailea: about 35–45 min
A good local-style food and bar option. Chef Sheldon Simeon’s menu leans into the mix of flavors people actually grow up eating in Hawaiʻi, so this is a fun place to order a few things and share.
Maui Coffee Attic
59 Kanoa St, Wailuku, HI 96793
Phone: 808-250-9555
Website: https://www.mauicoffeeattic.com/
From Wailuku: about 5 min
From Grand Champions / Wailea: about 35–45 min
Coffee, breakfast/lunch and a very local little music/community feel. It’s one of those places that feels like people actually live here — because they do. 😊
Wailea & Kīhei
Tikehau Lounge
116 Wailea Ike Dr, Suite 2104, Wailea, HI 96753
Phone: 808-214-6500
Website: https://tikehaulounge.com/
From Wailuku: about 35–45 min
From Grand Champions / Wailea: about 1–2 min
If you want a really good cocktail without the big-resort-bar feel, I like this little spot at Wailea Village. It’s small, pretty and gets excellent reviews.
South Maui Fish Company
1794 S Kihei Rd, Kihei, HI 96753
Phone: 808-419-8980
Website: https://southmauifishco.com/
From Wailuku: about 30–35 min
From Grand Champions / Wailea: about 15–20 min
Fresh local fish, poke, tacos and fish plates in a casual little food-truck setup. This is exactly the kind of simple Maui meal I like recommending.
Good to know: They work with the fresh catch and can sell out, so don’t wait until the very end of service.
Monkeypod Kitchen – Wailea
10 Wailea Gateway Pl B-201, Kihei, HI 96753
Phone: 808-891-2322
Website: https://www.monkeypodkitchen.com/
From Wailuku: about 35–45 min
From Grand Champions / Wailea: about 2–3 min
Yes, it’s popular and more touristy than the little local spots above, but it’s popular for a reason. Good cocktails, live music, a fun atmosphere and an easy option very close to Grand Champions.
Good to know: Reservations are a good idea for dinner, especially on busy nights.
On your Hāna day
I keep Aunty Sandy’s Banana Bread and Huli Huli Chicken in the Road to Hāna guide instead of repeating all the directions here. Both are currently well-reviewed and they fit much better as part of that day than as a separate restaurant trip.
Photo credits: Food cover — Life Glamorized; Wailuku — Forbes (Esters Fair Prospect); Hāna day — Flashpacking America.
