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Pimp in Paradise: 9 Ways to Do Hawaii Without Tapping Into Your 401K

Mouthwash blue water (ok, smartass, you describe the water without using the same old clichés), long stretches of deserted white sand, endless tiki drinks by some sun-drenched poolside oasis: vacationing in Hawaii seems like a cure-all for every one of life’s heartaches.

But, what if you’re stuck in a financial cul-de-sac and can barely afford a bus ticket to Vegas, let alone a plane trip to the Aloha State?

Well, first, charge it (duh).

Then, follow these tips to have a budget Hawaiian vacation while still looking like a baller:

Show Some ID

costco wholesale logo

We know, we know: the last thing that you want to do is maneuver that convertible Mustang rental into some underground parking lot and then traipse through the aisles at a big box store to score some deals on blueberries.

Buck up, guy: you’ve got a car payment and prolly child support. (Besides, you won’t be renting, home fry: see tip #6.)

The major islands in the chain—Oahu, Maui, Kauai and the Big Island—have enormous Costco’s that are complete blights on the landscape, but total boons for your wallet.

Stock up on the essentials, whether that’s beer and Hana Bay rum or kale chips and protein bars. Grab that SPF you forgot in Tulsa and a variety pack of chocolate mac nuts, while you’re at it.

‘Cause trust us: hitting up corner markets for souvenirs, sunblock and water adds up faster than you can say wtf, when those pretty little Asian cashiers at ABC tell you your total.  Let your parents support ABC.

Go Eco With Your Lodgings

As in economical, Ben Bernanke.

True, there’s nothing quite like staying at a five-star resort frequented by the likes of Hilton’s scantily dressed daughters and featuring pools so heavenly that they make the Pacific look a wee-bit disappointing.

But, you also don’t look like the kind of guy who’s in control of his financial future, so…

Hush, hush, K-Fed: we’re not asking you to stay at a hostel, which, bee tee dub, have become so popular on the islands that private rooms are now upwards of $90 per night.

Rather, get cozy with vrbo and Airbnb on your home screen. You can find sweet deals on condos, cottages, even rooms in locals’ homes, if you’re traveling alone are really that broke, but still have something resembling good hygiene.

Bonus points: these digs come with kitchens, where you’ll be eating the lion’s share of your meals, before heading out for what’s really important: libations. Which brings us to #3.

Scour Happy Hours

Red Bar at Gannon's
Gannon’s Red Bar

Otherwise known as pau hana, happy hours are a godsend for blokes on a budget. From chicken wings to live jams, you can get your buzz on without breaking out that super-predatory credit card.

The Red Bar at Gannon’s, on Maui’s south side, lets you imbibe in style while savoring one of Wailea’s one-of-a-kind sunsets. Apps start at $6—try their kick ass Volcano Fries—and domestic brews go for $3 a pint.

On Oahu? Check out Bevy without having to dish out bevies of bucks.

This swank little spot in Honolulu serves up champagne for five bones a glass and $1.50 oysters for those looking for an aphrodisiac. Little too fancy pants for you, former football, ahem, star? Order a house beer: they’re only twelve quarters.

Oh, you really were a football star?  And now, just a fan like the rest of us?  Head to Snappers, especially on game day (and double especially if you’re a Packer’s fan).  They run all types of specials and no one will really notice you counting quarters to cover your tab.

Kicking it on Kauai? Check out Duke’s Barefoot Bar, for a taste of quintessential Hawaii—or at least mainlanders’ cookie-cutter version of what tropical oughtta look like.

Dukes Barefoot Bar in Kauai

Nawiliwili Bay sits right in front (and is crazy fun to say when you’re drunk), the peeps are sweet and all their beachy drinks come with the requisite pineapple and umbrella.

La cucarachas, take note: they also boast Taco Tuesdays (or, as they say at Duke’s, Tuesday Tacos because, you know, it’s Hawaii, not Cancun).

On the Big Island? Sorry, pal—can’t help you there; the place is dead as hell. Might as well grab that handle of Hana Bay from Costco and stare at the lava.

Sneak Into a Pool

Espy a luxe resort whose pool looks pimp AF?

Mentally prep yourself, ‘cause there’s no reason why you can’t play with those beach bunnies and ten-year-old CEOs either.

The key to a smooth entry necessitates some down low recon.

Stroll on by those gorgeous spas and slides, late at night the evening prior, when lazy, entitled douches often leave their hotel towels in puddles on the sand or tossed on lounge chairs as they schlep around waiting for others to pick up after them. Hang dry (the towels, not the douches—well, whatevz, yogi’s choice and all that, so do what you must), approach from the lobby and assume a posish on a chaise for the better part of an afternoon.

Order the cheapest drink on the menu (or go virgin and hit up the bathrooms with that water bottle filled with Costco vodka), as most libations come with a complimentary plastic cup of bar munchies—enough to keep you going until you have to sneak back to your airbnb at sunset for a bowl of Top Ramen.

Feeling extra ballsy?

Make a date with a daiquiri-dumb cougar and charge a cheeseburger to her room while she’s in the Jacuzzi. (It’s up to you to make it up to her later, but please manscape ahead of time.)

Bro tip: some posh spots require a wristband. Scope out the other swimmers and either play dumb, if you’re confronted by security or hop, skip and jump to the next pool. This is Hawaii: we’re not exactly at a loss for resorts with some theme on water.

And Crash a Luau While You’re At It

Sound sketchy? Not with these tips:

Suck it Up and Take Da Bus

Da Bus App LogoSweet cheeks, we know: you wanna cruise the island in a 1957 roadster, top down, drinking a roadie and listening to Bon Jovi. Maybe when you’re fifty, momma’s boy.  You’ve still got student loans.

And, while renting an island cruiser might sound budget-conscious, you don’t need a head gasket blowing when you’re gliding down the Pali.

Your best bet is taking public transpo, otherwise known on Oahu as Da Bus. This baby’ll take you where you need to go and, while you won’t look dashing while you do it, there’s a reason why God made hats and sunglasses.

Get the app on your phone to save yourself some trouble—and score some stories about locals to take home while you’re at it.

Score Souvenirs for a Song

Nice guy in you feeling a little guilty for your Hawaiian vacation while the rest of your fam stays back in cold-ass, why-do-you-live-there Wisconsin?

Bring a smile to their face, when you come home (sunburned, smelling like spiked Hawaiian punch and introducing that cougar you couldn’t lose the morning after) with souvenirs that’ll cost you next to nothing.

For the ladies in your life: hit up Hilo Hattie for free shell necklaces—it’s the thought that counts and all that—and get a cup of free juice while you cool off under their air-conditioner.

For the lads (bros, colleagues and dads): slip into a Salvation Army some morning and comb the racks for old surf shirts. Wash when you get home, wrap in an ABC bag (no doubt you’ll be inside one {the store, not the bag, jackass} at some point) and dub it island vintage.

Eat Local Grindz

Can’t bear the thought of calling a Costco-sized portion of Chex Mix dinner again?

Seek out local eats (or cheap dinner cruise) and save those singles for the strip club.

Plate lunches go a long way towards fueling you for a whole day of fun. You’ve got your protein in Teriyaki or Katsu Chicken, enough starch with their two-scoop rice to feel like a Sumo wrestler and what passes as a veggie in the Midwest in their Hawaiian style mac salad.

Looking for some sugar, sugar? You need not dip into your savings with good ole’ shave ice: most cones will set you back less than six bucks (even with ice cream!)

And, if you’re turning your Hawaiian vacation into some nostalgic wave at your Spring Breaking self, lace it with some love from the jug (we told you that Costco trip would come in handy).

Sit Through a Timeshare Spiel for Some Swag

Recover from a hangover with AC and free coffee at a timeshare spiel.

Word: they’re annoying as all get out—and don’t those salespeople have any integrity? But, sometimes two hours (ok, maybe more like 5 or 6) of nodding along and saying “no thank you” pays off big time.

Think: free seats at ‘Ulalena, proper luau attendance, discounted booze cruises and, if you’re lucky, a night at one of those resorts you’ve been lusting after like a motherf***.

But, stick to your guns, cheapskate and refuse to cough over the dough for what they’re peddling.

Because if you really had the moolah for ten days every three years in Hilo, you probably wouldn’t be reading this, would you?



  • Brian K

    Brian K has been a writer and publisher for 10+ years and has worked for LiveYourAloha as a freelance author and content manager for several of them. There's not much about Hawaii he can't tell you about!