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  • Ken C

When in Maui...

Since my first visit nearly three decades ago, I felt more at home on the islands than any other place in the world. My first trip was to Oahu, but over the years, I revisited many more times and stayed on the majority of the other islands. Each of them offers a different character, beauty, and geographic panorama that makes them incomparable in many ways. For me, Maui offers the most welcoming atmosphere that I crave for when I am away for too long. The beauty is unmatched with just the right combination of both a tranquil and urban lifestyle.

When I visit Maui, I always stay in the Western part of the island, which is sometimes called the Kaanapali side. This section of Maui includes the incredibly charming town of Lahaina, lively resort area known as Kaanapali and the affluent community of Kapalua. Other smaller neighborhoods such as Honokowai, Kahana, and Napili weave themselves in between the larger, more well-established areas. When staying on this part of the island, you will notice the lush green mountains that complement the piercing blue water.

Each visit, I tend to alternate between Kaanapali and Kapalua based on the number of travel reward points I possess at that given time. Several years ago, I purchased a Marriott timeshare in Orlando, Florida. Although many people frown upon timeshares, the investment was excellent for me because it offered tremendous flexibility in utilization. Every other year, I trade the week for 90k Marriott Reward (Bonvoy now) points that I can use at ANY Marriott hotel property around the world. When I travel on business or for vacation, I always try to stay at Marriott hotels to further accumulate reward points. When I get enough in the bank, I will book a stay at the Ritz Carlton Kapalua, which I consider one of the most beautiful resorts in the world. The accommodations, view, and service are superb. The property sits near the water and nestles itself into the Kapalua community and Bay golf course while resting at the foothills of the legendary Plantation golf course.

In years that I do not have enough Marriott points to cover my stay at Kapalua, I trade my timeshare in Orlando for the Marriott Maui Ocean Club timeshare located in Kaanapali. Although not as luxurious as the Ritz Carlton, the rooms at the Marriott are lovely and spacious. The Maui Ocean Club sits right on Kaanapali beach, which provides direct access to incredible shopping, dining, and world-class golf courses.

When dining on this side of the island, you have so many incredible choices. If you have not visited Hawaii, be prepared for a bit of sticker shock with prices. Everything is expensive, and dining out is certainly not an exception. There are certainly lower priced options than what I will present, but if you want to experience finer dining on your vacation, the following are just a few of the favorites that we try to visit during each stay on Maui.

Lahaina Grill

Unquestionably my favorite restaurant on the island (for that matter, perhaps anywhere). Lahaina Grill is found at 127 Lahainaluna Road Lahaina, Maui, Hawaii 9676. The restaurant provides a contemporary environment and menu packed with fresh local fish, produce, and meat selections. The Lahaina Grill consistently wins awards as the best restaurant on the island for its outstanding quality and service.

We enjoy getting to the restaurant about an hour early and hanging out at the bar for a cocktail before our meal. The bartenders are so much fun, and you can watch some of the fantastic salads get produced by chefs working near the bar space. This establishment receives a large number of locals as regulars who are welcoming and open to conversation about the reality of living on the island.

As with any dining on the island, book EARLY or you may have a hard time getting a table. We try to go online at least three months before our trip to book all of our dining reservations. If you do not use Open Table, I encourage you to do so. Perhaps I will write a blog post in the future about how to take advantage of the benefits of this app, but until then know that you can accumulate "points" just for booking reservations at most restaurants through their system. Not ALL restaurants participate, but many do, and after you accumulate enough points, you receive free dining choices!

Photos courtesy of

Merrimans Restaurant:

With establishments on Oahu, The Big Island, Kaui, and Maui, Merriman's restaurants are known for producing high-quality dining using the freshest local resources available. In partnership with other leading regional chefs, Peter Merriman urged farmers to raise local products as part of a broader aspiration to create a healthier, more sustainable Hawaii. Through his efforts, Merriman has established a genuine farm to table production and in his Maui location touts that a minimum of 90 percent of the products are locally grown or caught practicing only sustainable methods.

The Maui Merriman's restaurant can be found in the Kapalua district on a fantastic beach with views of the sunset, which only experience can describe adequately. The location offers indoor and outdoor dining and bar choices. I strongly advocate for a nice glass of wine or cocktail outdoors on the lanai at sunset before enjoying your incredible dinner.

Note: If you stay in Kapalua at one of the residential areas or Ritz Carlton, you can use the free shuttle to travel around the community, and it regularly stops at the Merrimans property.

Merrimans at Sunset
Photo Courtesy of

Mamas Fish House:

Kahului Airport (OGG) serves as the primary airport on the island of Maui. From the west side of the island, it takes approximately one hour to reach OGG. Most of the flights back to the mainland leave later in the evening, so one tradition we now have is to eat dinner at the world renown Mamas Fish House on our final evening on the island. From the restaurant to the airport is only about a 15-minute drive.

The Christenson family owns Mama's, and their life story is just incredible. You can read more about that here -

The restaurant sits snuggled in a cove that looks precisely what you might imagine Hawaii to look like if you had only heard or read about it but never actually visited. The views, sounds and breezes from the ocean relax you in a way that is just magical. Although a little cloudy on my last visit, I took this video, which will hopefully give you a feel for the cove at Mamas.

Once you get into the actual restaurant, you realize the magnitude of the property itself. It is enormous! 2 bars and several dining rooms make up the legendary fish house. The menu changes daily and will provide you not only with the type of fish but also the name of the fishing boat and location/depth where the fisherman made the catch. Beyond the freshness, the quality and preparation of the selections offered by this restaurant are lovely.

Mama's Fish House Menu Photo


The Plantation Course hosts the first significant PGA tournament in January of each year. Currently, Sentry Insurance sponsors the competition, which only extends invitations to individuals who won on the PGA tour during the previous year. Consequently, the event is known as the Tournament of Champions. In 2019, the course closed for several months and went through a substantial overhaul.

There are numerous other courses across Maui which some online research will shed light on opportunities to play. If you have some extra time and money, I strongly encourage you to take the public ferry over to Lanai and play the Challenge at Manele course. The ferry costs approximately $30 each way. One word of caution: The seas are generally calm in the mornings but can be quite rough in the afternoons. The ride takes about 40 minutes each way. The Challenge at Manele course is located on the bay and is part of the Four Seasons Resort. The views are incredible with numerous shoreline holes that make you feel good despite the quality of your play. Here is a photo of one of my favorite tee shots on the course...

I'm certain I hit the green (maybe not on the first attempt)!

Whale Watching:

The North Pacific Humpback whales take up residence in Hawaii from December through April. During their time in the islands, the whales mate and give birth before heading back to Alaska to feed during the remainder of the year. I recommend the tours offered by Ultimate Whale Watch & Snorkel - The boats are smaller and faster than many of the others, and we find the service to be excellent. This video provides a brief sample of some whales we spotted on my last visit.

The Road to Hana:

I will not bore you with all the details, as there as so many things that you can see along the way. Let's just say that the trip takes a full day to do correctly, and you see amazing sights at every turn. The road can be very narrow, windy, and threatening so you must not get too caught up in the natural beauty if you're driving and if you suffer from car sickness, try to be prepared. There are numerous pitstops en route where you can encounter everything from waterfalls to pineapple drinks to parrots who want to play!

I am happy to answer any questions you might have about Maui or the other Hawaiian Islands. Just send me a note and Aloha!

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