Pearl Harbor

Visiting Hawaii: 3 Bootstrap Tips for Your Paradise Vacation

You’ve made the choice to enjoy an upcoming vacation in Hawaii. You get excited when you think about the warm weather, the sun and the beautiful beaches. But, the plane tickets aren’t cheap. So, how do you have the best possible time visiting Hawaii without taking out a second mortgage? Follow these 3 bootstrap ideas to get the most out of your Hawaiian vacation.

Value Housing

On any Hawaiian island, including Maui and Oahu, the cost of housing rises as you get closer to a beach. It makes sense, since there’s only so much beach to go around.

But, if you want to have more money to spend on your vacation, there are a few things you can do while planning that can pay big dividends.

First, consider Hawaiian vacation housing that’s not close to the beach. Even a distance of a few blocks can make a huge difference in cost, including hotel rates. And, while we’re talking about hotels, there are lots of alternatives to traditional hotel chains when coming to Hawaii for vacation.

You can use sites, including and to find people who are renting portions or all of their home or condo. And, you can pick and choose based on location, amenities and other things that are important to you. Want a place with a pool? No problem. Someplace close to lots of restaurants? Done.

But, the real benefit is looking for a place that is more than a few blocks from a beach. In Waikiki, this means looking for a place that’s closer to the canal than the beach or further up in the surrounding Honolulu hills. You can find great accommodations for less than $100 per night, often much less, depending on how many people are traveling with you.

Now, before you wonder how to leverage that distance, let’s move on to the next Hawaiian vacation bootstrap tip, transportation.

The Joy of Motion

Maybe it’s the thought of cruising around a Hawaiian island in a Jeep with the top down that drives (sorry, bad pun) the crazy amount of visitors who think renting a car is a great idea. Think again. Remember the earlier point about Hawaii only having so much beach? What do you think that does for parking opportunities and cost?

If you just couldn’t resist and booked a suite at a swanky Hawaiian resort, the daily parking rate can easily outrun the daily cost of the car rental itself. And, why do you need a car in the first place?

Hawaii is not a 3rd world country. Every possible means of transportation is available. Let’s look at a few, before you burn lots of vacation time hunting a parking spot.

The most popular Hawaiian Islands all have solid public transportation systems. If you’re headed to Oahu, there’s The Bus. On Maui, you’ll find the Maui Bus System. Even Kauai has a public bus system. And, smart tourists use the buses to move about the island for pennies.

If you want to check out the largest open-air mall in the world, Ala Moana Mall on Oahu, you can grab a bus for $2.50 per person and do a roundtrip, as long as you head back in under 4 hours. You can even take the bus from Waikiki to the world famous North Shore, although there’s probably a better way to get there.

Pro Tip- Most of the public bus systems don’t allow full size luggage on board, so the bus is not an option for getting from the airport to your vacation rental. Book a roundtrip, prepaid shuttle for that trip.

You’ll also find a plethora of transportation rentals, including bikes and scooters, that can be parked almost anywhere and pedaled or motored around town for peanuts, or less.

Uber and Lyft also have a strong presence across much of Hawaii. If you’re dressing up for a night on the town, let someone else drive while you see the sites. Even if you took a roundtrip rideshare every day of your vacation, you’d still likely pay a fraction of what a rental would cost and you’ll be a lot less stressed, although listening to your phone’s GPS try to pronounce Hawaiian street names can be pretty funny.

And, finally, let’s revisit that Waikiki to North Shore excursion again. Scattered throughout every Hawaiian city are lots of smaller car rental services. You can also find them in most hotel lobbies and they aren’t restricted to hotel guests.

Longer trips across the islands make a single day car rental an inexpensive way to go, without paying car rental fees while you lounge on the beach or losing half the day to the bus rides.

And, now that you have a place to crash and wheels, or a lack thereof, you’re only missing one thing- Hawaiian activities.

Having fun in Hawaii

It’s highly unlikely that you’ll see everything that there is to see on your first visit to Hawaii. So, you’re going to have to make some choices. Do you want to visit Pearl Harbor? Volcanos? A Luau? Pick a few things that you want to do, but remember that there are a ton of free things, including the dozens of unique beaches, that you can spend time doing.

Once you have your list, head over to an activity booking service, like and book your fun. A site like this is a huge time saver, because all of the best activities are available in one place. Plus, how many websites do you want to trust with your credit card information?

PRO TIP- avoid the “vacation clubs” that offer free activities for a “brief” presentation. You’ll probably also want to skip people handing out activity flyers. The prices might look great, but these tours are usually short or poor versions of activities. Do you want to parasail for 3 minutes and wonder about the crew or for 20 minutes and enjoy the view?

Try to avoid over-booking your vacation. It’s understandable that you want to do a lot, but vacation is also about relaxing by the pool or surf and hiding behind a great book or whatever you love to do when there’s nothing you have to do.

There you have it, 3 simple bootstrapping ideas for your visit to Hawaii. And, with the money that you’ve saved, you can buy more t-shirts and chocolate-covered macadamia nuts to take home to your poor frozen friends who couldn’t visit paradise with you.