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Hawaii golf vacations made easy: Tips for planning a stress-free Hawaiian golf trip

By Chris Baldwin, Contributor

Maui, the Big Island, Kauai, Lanai, Molokai or Oahu? - all the choices can make planning a golf trip to Hawaii maddening. But golf courses such as Jack Nicklaus' Experience at Koele and Greg Norman's The Challenge at Manele Bay, both on Lanai, make booking a Hawaii golf vacation worth the trouble.

Puakea Golf Course
Puakea, a golf course on Kauai, highlights Hawaii's lush natural scenery.
Puakea Golf CourseHawaii BeachesMaui Plantation

Planning that first trip to Hawaii can make successful grown ups feel like they're unsure teenagers again cramming for the SAT.

There's an initial rush, that "Oh yeah" moment when you decide you're going to freaking Hawaii - the land of a million vacation fantasies. Then, there's that pregnant pause when you realize you don't really know anything about Hawaii except for those beach and volcano fantasies and maybe a postcard image your Aunt Hilda sent you when you were a kid.

It's not long before you grasp that taking a trip to Hawaii requires more planning than a golf vacation to Myrtle Beach or Phoenix-Scottsdale. Picture the difference between watching a football game and coaching a football game, and you're starting to get the idea.

Just choosing which island to go to can make you feel like you're on a game show with Howie Mandel screaming in your ear. There seem to be so many choices and you're not even sure you can pronounce some of them correctly - Kauai, Lanai, Molokai, Oahu. Even if you decide to make one of the easy choices, Maui, there's the decision on which area of that island to use as your golf base: Kapalua, Kannapali, Wailea.

Spend a night online - or in a Barnes & Noble - researching this, and you might break down and just consider throwing a dart at a map.

"My husband and I got into so many stupid fights planning our first trip to Hawaii a few years ago," New Yorker Evelyn Olvara explained, laughing. "I think because it's Hawaii you want to make sure it's perfect and it can get crazy. It really created a problem.

"I'm not saying it threatened our marriage, but there were some cold nights, let me tell you."

Never fear, there's no need to kick your partner out of bed because he's waffling between a condo on the Big Island, a rustic "hunting" lodge at Lanai and a 5-star beach resort on Kauai.

People who've been to Hawaii multiple times will tell you it needn't be that complicated or stressful. Tim Hurja, a PGA Professional who operates Hawaii Golf Central - a golf and hotel trip packaging service - has found that for first-time Hawaii visitors it usually comes down to two choices after all the clutter has been removed through questions.

They're either going to go with the Big Island, its sheer volume of possibilities (it's more than twice the size of all the other Hawaii islands put together), its big city tall buildings and its lava golf. Or they'll seize on Maui, which offers tons of high-end golf courses and resorts with a more natural lush look.

These days, Hurja often sees the pick become pretty clear-cut once he's explained the various pluses and minuses of each island.

"People typically choose Maui now," Hurja said. "Especially if this is their first trip to Hawaii. A lot of the vacationers I've dealt with want more of a nature feel while still having plenty to do. That's Maui. It's definitely in right now."

With Maui giving visitors the natural vegetation you can find on the smaller islands, along with luxury shopping that could give Beverly Hills a run for its platinum cards, it's easy to see why it's more popular than Jon Stewart in a room full of democrats.

Still, Hurja sometimes find himself arguing for the now overlooked benefits of the Big Island, the place everyone wanted to go when he first started coming to Hawaii.

"People go to Maui because they want to see things they haven't seen before with scenery," Hurja said. "But if you play some of the lava courses on the Big Island, that's something most people will never have seen before either.

"And it can blow your mind just as much as all the green on Maui."

Hurja laughed. "Most people still choose Maui though."

Maui's side trip golf magic

One of the benefits of going with Maui is that it gives you the option of taking a unique, golf-centered day trip. A ferry brings passengers from Maui to the small island of Lanai, a more secluded land with two Four Seasons Resorts, one other hotel and two golf courses dedicated duffers don't want to miss.

Hawaii vacation veterans swear by these two very different courses - Jack Nicklaus' Experience at Koele and Greg Norman's The Challenge at Manele Bay. The fact they're the only two courses on the whole island of Lanai only adds to the aura.

Island hopping between any of Hawaii's locales is relatively easy by plane. Still, there is something about getting on a boat in the morning at first light with your golf clubs that imbues extra romance into the Maui to Lanai jaunt.

"It's fun to travel on the ferry," Olvara said. "My husband loved not having to get on another plane too. He was nervous enough about the long flight just getting to Maui, and he doesn't like what he calls Puddle Jumpers. It made him happy to be able to see another island without flying."

Before you automatically assume Maui is the runaway winner choice, you want to look into Kauai's golf. Dubbed the Garden Isle, Kauai is rapidly becoming a trendy pick, with Golf Digest ranking three of its golf resorts among the Top 75 in all of North America.

This on an island that's still remote-looking enough to have been the setting for Steven Spielberg's Jurassic Park.

"I wouldn't just count out Kauai," Hurja said. "It's popular with honeymooners and people who look at the golf as almost an afterthought - just something else to do. It's a beautiful spot. You can have a great trip there too."

Hey, no one can make the choice super easy for you. It need not be a stress test though. Just remember, this is vacation and you're only a Hawaii virgin once.

"It gets a lot easier after you've already been to Hawaii," Olvara said. "It's not so intimidating anymore."

Yes, you can stop sweating.

Chris BaldwinChris Baldwin, Contributor

Chris Baldwin keeps one eye on the PGA Tour and another watching golf vacation hotspots and letting travelers in on the best place to vacation.

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Dates: November 10, 2017 - December 31, 2018
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Price range: $469