Lahaina Day Drinking – Island Style Bar Crawl

On day five of our Maui journey, and Peggy’s last day, we decided that we needed to spend the afternoon in downtown Lahaina. 

We naturally dedicated one day in Lahaina to just drinking adventures. 

It is our self-assigned duty to help you out with what to drink, where to drink, and what to not miss while drinking.

Plus, on this trip, we had some extra family members in tow:  Patti’s husband, Pat, plus Peggy’s daughter, son-in-law, and new grandbaby:  Syd, Austin, and Baby Beckham.

Sister Side Note (ssn) – we kept it pretty PG this time but still managed to have a fantastic time with tropical drinks and tasty food!

Brunch before leaving Kaanapali

It’s always best to face day drinking with a solid meal in your stomach. 

As it was Sunday, we booked reservations at Duke’s Maui.

Duke’s on Sunday?  Cue Jimmy Buffett (although his song is about the Waikiki Duke’s, you can still make this work).

ssn – I wish we had theme music playing while you read this blog…who remembers MySpace?

Probably the best server we had on our vacation.  She talked tattoos and food recommendations with us and was funny and attentive. 

Duke’s is found in Kaanapali, within the Honua Kai Resort, on the backside facing the ocean and pool area.  Of course, we get mimosas and Bloody Marys to start.

Loco Moco with fried rice, Banana Mac Pancakes, and a burrito to fill us up. 

Loco Moco is a local Hawaiian breakfast favorite with meat (usually Spam, brisket in this case) and eggs served over rice topped with a brown onion gravy. Get it with the fried Rice, is so good!

And while I’m not usually a sweet for breakfast person, don’t pass up banana macadamia nut pancakes when you are in the islands.

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Lahaina

About 80% of all Maui tourism takes place in Lahaina, which is usually reason enough for me to avoid it. 

However, Lahaina is also a cute little historic town on the water that has great bars and restaurants, art galleries, and Banyan trees.  It was the former capital of the Kingdom of Hawaii, and the largest Census Designated Place on the island of Maui.

In fact, Front Street has been ranked in the “Top Ten Greatest Streets” by the American Planning Association.

So, yes, you should probably go spend an afternoon there.

Time to get to drinking

There is a parking lot on the far end of town (south east), public parking for free, so get your designated driver to park there. Then just start walking.  By starting on this end, you get to walk by the Lahaina Banyan Court.  It’s this beautiful old Banyan tree on Front Street, marked as the oldest Banyan tree in Maui, I’m assuming they know better than me so I’m sure it is. 

Just a Little Push and You’ll be Smiling

We tagged our first stop at Captain Jack’s Island Grill. 

Obviously, any place with Captain in the title is a place we should be drinking at.  And, hey, a toast to Billy Joel’s Captain Jack doesn’t hurt. 

It is an upstairs grill, with an old timey pirate theme. All wood and tropical décor, big open windows overlooking front street.  They have a bar area, but they also have family seating and room for groups.

The service was great, we loved the staff, and you can now find a #sisbehaving sticker planted firmly on the cooler behind the bar!  Tropical drinks for all! 

My first drink to kick off our tropical adventure:  Tropical Pirate, made with the local Hawaiian Kula  Toasted Coconut Rum (we toured the distillery and I regret not having some shipped home), and of course POG (Pineapple, Orange, Guava, a Hawaiian staple).  This drink definitely screamed “I’M ON VACATION”! 

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Choosing stops based on their name

We definitely had the Dirty Monkey on our list.  Because, hey, a place called Dirty Monkey has to make amazing cocktails, right?  Yes, the answer is yes!

We loved having a table overlooking front street (yes, another upstairs bar!).  It really looked like they would have a great night life, just giving off a “come see us for Karaoke and dancing vibe”.  Big signs encouraging fun, debauchery and drinking.  Cherry Blossom cocktail is definitely my wheel house, they had some great different concoctions that still fit within the Hawaiian dive bar vibe of the Dirty Monkey.

ssn – I had a REAL Mai Tai – not one of those resorty, poolside bar or luau ones. It was a night & day difference and it was delightful!

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Make a reservation when in Maui

There’s your tip.  There are a lot of places that are constantly full, so reservations are a great idea when you are planning your trip.

This happened to us at Cheeseburger in Paradise.  They were full, it was 20 minutes to get a table. But I mention this not only as a cautionary tale, but also because the service staff was so nice.  Funny and friendly, and we would have gone back 20 minutes later for some seats overlooking the water if we hadn’t been knee deep in cocktails by the time they texted.

ssn – we had eaten lunch here the day before and it was fantastic. I was skeptical the first time I went there because I did not go all the way to Hawaii to eat a burger. Turns out that there is never a bad time for a burger and especially ones this good. Great place!

Also, side bar, we really wanted to hit Fleetwood’s on Front, it checks the box on everyone’s lists of places to go.  But they didn’t open early enough for us to fit them in on this trip.  But see the SSN from Peggy’s last trip.

ssn – Fleetwood’s is owned by rock legend Mick Fleetwood. It’s a little upscale, a little bit beachy speakeasy, a little dark wood Polynesian vibe. Iconic (like the owner) and a must-visit place in the evening to watch the sunset.

Our Best Cocktail

We wandered Front Street, we shopped a bit, we bought cheap, tacky Hawaiian shirts, and we made our way down to Tommy Bahama’s Marlin Bar & Store. 

This is where I found my heaven:  The Pineapple Paradisio, Pineapple, banana, rum, YES PLEASE, oh and garnish it with a pretty flower too! 

We found this beautiful bar to be charming, light, airy, just so pretty.  Big open windows let you watch the world go by, and the white interior and flowery décor just instantly brings a relaxed happiness.

ssn – We also decided we better grab some snacks. We had ahi tacos and Hurricane Tots (tots with furikake, sriracha and soy glaze!!!) – they were so amazing that we went back for seconds! We didn’t get pics but found the one below by the gracious Elaine (Elaineeatsjax on FB and IG)

Time for a beer

Almost to the end of the touristy section of Front Street you will find the Waikiki Brewing Company

I am always a fan of trying local breweries, especially ones we can’t get at home. 

Another open air restaurant, we opted for a patio seat.  Waikiki Brewing offers not just beers but beer cocktails, and a variety of their own created craft cocktails.

It is the perfect place for casual, relaxed fun.

Time for Food

We had waited all day to finish off at Down the Hatch. 

A Diners, Drive-ins, and Dives spot on Front St that boasts a Lobster and Crab stuffed grilled cheese. 

We weren’t really sure what to expect but had to have that sandwich.  Off of Front Street you take the stairs down to a big courtyard.  Down the Hatch shares their space with several other restaurants.  You order at the counter and find yourself a picnic table.

They have a separate bar for you to order cocktails, there’s a Hawaiian Shave Ice bar, and Taco spot, so a little something for everyone.

We call this a score because there was a live band, outdoor patio bands are the best! 

And while the sandwich was ok, the Mermaid Fries stole the show for us!

ssn – the Mermaid Fries (fries with bacon, ranch, lava lava sauce and homemade cheese sauce) are in the running for best fries ever. We also had Kahlua pork quesadilla and calamari – both delicious. Sadly, the lobster grilled cheese was a huge disappointment (and it still hurts me to write that)

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Finish off our tour of Front Street in Lahaina

Back to the parking lot.

And a little bit further.

Just a few blocks down

Spanky’s Riptide is the bar to hit at the end of it all. 

Nothing fancy, just a good name, solid drinks, and great people.

Close it down, and don’t miss the sunset over the water.

Check out our other Hawaiian adventures:

• Maui Doors-Off Helicopter Tour

Other Day Drinking adventures

• Boise
• Seattle
• Seattle – part 2
• Savannah
• Dallas