BEST CHAT WITH A BARTENDER
Dina's SandWitch @ 145 N Kihei Rd., Kihei
Rating: 🍹🍍 😀 💵
Dina's is technically a sandwich spot, but their bar serves up a long list of tropical drinks (the kind that come in pastel colors, served with an umbrella) that somehow avoid feeling cheesy. It could be the layers of character that the place in steeped in, the friendly, chatty bartender, or that the cold, sweet drinks are exactly what you want after a day of baking on the beach. Relax and let the evening slide by.
MOST LIKELY TO MAKE QUESTIONABLE DECISIONS
Kihei Town Center @ 1913 S Kihei Rd., KiheiRating: 🍻 🎉 🎶 💋
If anyone's really trying to tie one on and see what kind of trouble they can get into, chances are they'll end up in Kihei Town Center, where a cluster of five or six bars serve according to various themes (beachy, cocktail, tiki, Irish, fratty, local) and you can easily check a different scene if your first or second try doesn't scratch your itch. To be honest, I've never seen it get all that rowdy, but there does seem to be quite a bit of thirst for one little area. My preference is for the most prominent bar, Life's a Beach, which looks out at Kalama Beach Park, serves up big ass steins of beer, and has a house band that kills it on reggae and dub jams. A close second is Ambrosia, just around the corner, which predictably attracts a sunburnt cocktail crowd and plays your Top 40 Hits. It's also been claimed by the LGBT set, so check it out if you're looking for a local gay scene. The drinks are pricey but OK.
HANG WITH ROCK ROYALTY
Charley's Restaurant & Saloon @ 142 Hana Hwy., Paia
Rating: 🍺 🎸 🎤 📀
Although Charley's food and booze are decent, what really sets it apart is its contributions to the local music scene. It regularly hosts touring bands (Questlove DJ'd a set one night while I was on island) and Willie Nelson's platinum records glisten on the wall. Nelson has a place in Paia and is known to play there from time to time, which my mom has talked her way into before (go Mom!). It's not a bad place to catch some shade and have a beer in the afternoon, but it can get turnt up at night so check their calendar to see if someone interesting is rolling through while you're there.
BEST PLACE TO HEAR A STORY/WORST PLACE TO TAKE YOUR PICTURE
Steel Horse Saloon @ 1234 Lower Main St., Wailuku
Rating: 😎 🍻 🚲 👊
Steel Horse is basically a biker bar with an aloha bend, and it's a pretty great combo. It's no-frills, great for people watching, and they had a couple bands coming through later in the evening when we were there. If you would never go into a dive bar in any other part of the country, this isn't your spot, but if you like a place with some character, go check out Steel Horse in Wailuku and don't exit through the gift shop...