How to Make It All Worth It During Your Hawaiian Getaway at Hyatt’s Maui Regency

Story by Kelly Kusumoto, photos by Colleen Cahill & Kelly Kusumoto

It’s all in your head. Every image you’ve ever seen of Hawaii, every story you’ve ever heard. There’s majesty, serenity, and in February, warmth that just appeals to you in the throngs of an East Coast winter. Well, the images and the stories can’t even do Hawaii any justice. There’s nothing like being there. But as I’ve learned the last four years on the right coast, getting there is a big reason Hawaii is such a mystery to those who’d rather fly south to the Caribbean.

First off, you have to come to terms that any trip from the East Coast to Hawaii is going to be an odyssey. And for us Philadelphian’s flying out of PHL, there is a guaranteed layover or two. You have to get it into your head that the travel is less a rainbow leading to a pot of gold and more like working in a coal mine and stumbling onto diamonds. Once you come to grips with the fact that you will lose a day there and possibly more on the way back, you have already won the battle.

But just in case you need extra incentives, I suggest signing up for TSA Pre-check. It is absolutely worth it. No taking off my shoes or separating my laptop from my bag. And the lines are usually quicker and shorter.

My wife and I decided we would spend nine February days in Maui. With the travel, it was actually seven days but let me tell you, as soon as I felt that warm, 72º, moist air hit me, the full day lost in transit evaporated away. At 9 p.m. Hawaii time, Kahului International Airport was empty and so were the lines for the rental car. The drive to Ka’anapali Beach was about 40 minutes and the staff at the Hyatt Regency understood what we had just gone through and offered to upgrade our room. Nice! We had a balcony and partial ocean view. After some room service, we left the sliding door open and let the waves of the Pacific sing us to sleep.

I highly recommend staying in or very close to Ka’anapali Beach. If you want to lounge, they have cabanas if that’s your thing. If you want to be active, they have everything from snorkeling and scuba to parasailing, paddle boarding, kayaking, and of course, surfing. There are restaurants and pools up and down the shoreline and everyone is super nice and accommodating. My wife and I are Hyatt members, and the Maui Regency is one of their best Category Four hotels. But there are many places to choose from. Even condos and Airbnb‘s are a great option.

No trip to Maui is complete without a taste of the fare. A Maui staple is Aloha Mixed Plate. Anything on the menu is a sure bet, but I usually go for the Kaula Pork or Lau Lau. The view and ambiance are spectacular and the price very affordable. It’s located in Old Lahaina, about a 10 minute drive from Ka’anapali. There, you can shop around or catch a flick, or pick up a shaved ice at Ululani’s Shave Ice. There’s a slew of bars as well. Fleetwood’s, owned by Mick Fleetwood of Fleetwood Mac, has nightly live bands, and Kimo’s Maui boasts a Hula Pie that is to die for!

Now, because we were there in the middle of winter, we didn’t get to do all the things we set out to when we wanted to do them. The water was choppy at times, which made for less-than-optimal snorkel and kayak conditions. But when you are on a budget, these are the things you have to weigh and be prepared for. Whenever the weather kept us from snorkeling or paddle boarding or kayaking, I would think about life back home. All of a sudden, settling for just lying on the beach or at the pool wasn’t so disappointing. In the end, there was enough good weather for us to do all of the above, and the few times the weather was too windy or rainy, we were able to discover places we probably wouldn’t have.

Exhibit A: The Mill House. By far, this was the best meal we had in Maui. I’ve been to this island on four other occasions and I’ve never been to a better restaurant. The setting is idyllic. The service is unmatched. The food is superb. We wouldn’t have found it if it weren’t raining in Ka’anapali. *Note: another thing about Hawaii is no matter what island it can be sunny or rainy at any time, but it will almost always be between 75º and 85º no matter what time of year.

If you spend enough time in Maui you start to notice that everything is for sale. Even things that you don’t need to buy in order to enjoy. Case in point: Haleakala. Tour guides swear by the sunrise and sunset views Haleakala offers. Don’t buy it. Instead, drive up there yourself and enjoy the view at a fraction† of the cost. But dress warm. Like, back home in the snow, warm. You will be 10,000 feet up in the middle of the Pacific where land collides with ocean winds. If you dare to brave the cold, you will be rewarded with these sights.

Another experience for sale is the Road to Hana. Again, don’t buy it. You already have a rental car, so use it and save over $150 per person. Let the person in the party who likes to drive, drive. They will love it. The roads wind and rise and fall, with waterfalls, black sand beaches, cemeteries, plantations and more for passengers to observe. Stop at the Twin Falls and do a little exploring. Get some Kona coffee and local pastries at Hana Harvest. And make sure to stop at Waianapanapa and curl your toes in the black sand, see a blowhole, and a natural cave.

There’s just something about Hawaii that always has me wanting to go back. When I look at pictures or see it on TV, it’s never as good as actually being there. Feeling the warmth of the island and the people isn’t something you can read about. Swimming up to a sea turtle isn’s something you can live vicariously through your friends. You have to experience it for yourself and when you do, you don’t think about the travel or the cost. You come back home with experiences money can’t buy and you come back home wanting to go back. That’s when you know it was all worth it and that you’d do it all again in a heartbeat. There’s nothing like a Hawaiian sunset, and there’s nothing like a Hawaiian getaway. There’s a reason it’s always referred to as “Paradise.” It’s because your normal life dies when you get there and when you get back, you’re never the same.

†Haleakala sunrise tours start at around $130 per person, whereas permits and entrance fees are around $20 per vehicle (good for three days).