Most people who visit Maui spend their evenings in the same rotation… resort bars, oceanfront restaurants, maybe a luau. Which is great! 

But if you love a really well-made cocktail and you want to feel like you’ve actually found something special on this trip, you need to know about Esters Fair Prospect in Wailuku.

Esters is a craft cocktail bar in downtown Wailuku with major tiki vibes. The interiors are genuinely cool… rattan furniture, anglerfish wallpaper, the kind of design where you just KNOW it was put together by people who care a lot. It has a local bar energy and it’s a million miles from the upscale resort bar experience even though it’s only about 30 minutes from Wailea.

Who This Is Perfect For…

If you love tiki bars this is an absolute must. Full stop. But even if tiki bars aren’t usually your thing, Esters is worth the drive because the drinks here go well beyond the typical sugary tropical concoctions… we’re talking cocktails like the Mercury in Retrograde with mezcal, Aperol, a pineapple-coconut shrub, lime, and absinthe. 

These are serious, creative, beautifully balanced drinks made by people who actually know what they’re doing. The bartenders are the types who will ask what you like and make you the perfect thing. 

Happy hour runs from 3 to 6pm with discounted daiquiris, seasonal beer, and glasses of wine, which makes it a great early evening stop before dinner. 

Speaking of dinner… Wailuku is genuinely worth exploring while you’re out this way. It’s a real local town with cute shops and restaurants that hasn’t been totally transformed for tourism the way Paia has. For dinner, Tiffany’s is a great option nearby, or call ahead and reserve bentos at Shimeda Bento Patisserie to pick up before you hit happy hour.

This is a great spot for anyone who wants to get out of the resort bubble for an evening, anyone who appreciates craft cocktails over frozen drinks, and anyone who likes feeling like they’ve found the place the locals actually go rather than the place the hotel concierge sends everyone.

Extra Details

Cocktails are creative and inventive with a focus on craft spirits, rum, amaro, mezcal, and tequila. The daiquiris are a standout and the small bites menu, while short, is well worth ordering from… the burrata and the ceviche both get raved about consistently. Happy hour daiquiris run around $7 to $8, which is an exceptional deal for the quality. Outside of happy hour expect to spend around $15 to $18 per cocktail, which is completely reasonable for drinks this good.

There’s a free parking lot adjacent to the building. 

I’ve made it my job for the last 10 years to explore Maui.

And after hundreds of beach days, rainforest hikes, snorkeling trips, and reconnaissance missions to find the best hotels… and mai tais… I put everything I know into one place.

This is my Maui Digital Map — hundreds of my favorite spots. Beaches, snorkeling spots, hikes, farm tours, scenic drives, places to eat.

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Get access to my Maui digital map and itineraries here.