The Traveling Steve's

Exploring The Wailea, Kaanapali, and Kapalua areas of Maui

This post is a continuation of our pre-Christmas 2021 Maui visit. While we stayed in the Wailea area, we made a few day trips around the island during our visit. This post visits (and compares) the Wailea, Kaanapali, and Kapalua areas; all of which are upscale tourists areas with deluxe hotels, on or near the ocean and/or golf courses. As there are so many nice resorts and condos for rent on Maui, it’s nice to look at the different areas to get a feel if there is a good fit for you, your family and/or significant other, and especially to see what else is available for a future visit.

In the last post I showed the condo we stayed at in the Wailea area, as well as the nearby mall and Waldorf Maui resort where we ate dinner one night. I’m expanding this post to include a few more photos in of the Waldorf in daylight , and other adjacent resorts adjacent to it in the Wailea area.

Starting with the Waldorf Astoria, there is a direct and flower-lined foot path to the resort (though not well marked) from the outdoor Wailea Mall.

The Waldorf is a huge and ultra-deluxe complex of rooms and buildings with meticulously maintained grounds (as are all of the resort hotels), overlooking the ocean and beautiful Maui sky and mountain backdrop. The open air lobby has beautiful fountains, sculptures, paintings, artwork throughout the resort and grounds.

Here are some daytime photos of the Waldorf, including a couple pics taken from inside their very own wedding chapel.

All of the hotels offer cabanas either oceanfront and/or poolside, and Waldorf appeared to have the most cabanas and pools due to its sheer size and luxurious grounds.

There are also umbrella and beach chair rentals on the public beach, or you could bring your own fold- up chairs, umbrellas, and beach towels as well.

The public oceanfront walkway connects several of the upscale resorts and condos, and is a great place to take a walk, even if you don’t like to walk or lie on the beautiful beaches. Like Kaanapali, the beach in Wailea is narrower and wider in places, and there are patches of rocky coast as well scattered among the resorts, which adds to the beauty of the Maui landscape in Wailea.

The Four Seasons Resort is next to the Waldorf, connected via the public walkway, although it’s distant enough to make both resorts feel private and self-contained from each other.

Like the Waldorf, the Four Seasons is an ultra-deluxe Resort with beautiful grounds, fountains, shops, restaurants and artwork galore. Compared to the Waldorf it is smaller and more intimate in size, and appeared to host mostly well-heeled adults who want quiet and relaxation by the pools and cabanas, without the need for lots of organized activities. Here are some photos of the gorgeous pool area and fountains.

While we didn’t eat at the Four Seasons Resort this trip, we previously had wonderful breakfasts there and an evening dinner one night at Ferraro’s, their outdoor and romantic Italian restaurant. Hint: they offer 1/2 price bottles of wine after 8pm at Ferraro’s Italian Restaurant only. Not to be confused with Spago, their ultra high end and chic restaurant.

We did browse thru the gift shops, and we each got a Four Seasons logo hat. And believe me, DOS made sure we each got a separate fancy shopping bag for each cap! LOL!

Down from the Four Seasons and past the Waldorf again, there are low-rise condo resorts and a huge Marriott Resort, and an Andaz Resort (by Hyatt). The beach pathway also connects these resorts, and the walk itself offers picture-postcard views along the way, alternating between sandy beaches and a lava-rocky coast.

The Marriott Maui, (Wailea Beach Resort) is a huge and deluxe resort as well, and like the other Wailea oceanfront resorts, has a private feel to it due to generous spacing and landscaping between the resorts.

By the time we toured the Marriott resort we were getting a bit hot, hungry and a bit tired out, so we took a break on a couple of the rockers on the super long entrance porch, overlooking an Aloha sign.

The Marriott Hotel’s front porch area is also a great place for people watching, coming and leaving the hotel for activities, check-in, lunch etc.

The hotel is also walking distance (via the front driveway) to the Wailea Mall, where we went once again for lunch at the Waikiki Brewing Company.

For comparison to the Wailea area, we drove one day to the Kaanapali resort area, scouting possible future Maui visits. Like Wailea, Kaanapali also has both Hyatt and Marriott Resorts, and as we have top status at both hotel chains, it’s always nice to see what our options are for using points or upgrades. Kaanapali has a similar oceanfront layout to Wailea, with a large outdoor shopping mall serving as a spoke for the oceanfront hotels adjacent to it.

Kaanapali is beautiful with several large oceanfront resorts, golf courses, restaurants, shops and water sports galore, and it has a busier, i.e. more lively vibe to it than slower-paced and more exclusive Wailea. Kaanapali (pronounced Ka-Ah’-napoli, that is both of the A’s are pronounced separately and distinctly), is about a half hour drive from the Wailea area, or about 45 minutes from the Maui airport. Like Wailea there is a large outdoor mall area; this one called Whaler’s Village, which has lots of shops, tour and excursion desks, kids playground climbing tower, and several family-friendly restaurants, all with bars and many offering a nice view.

Both Wailea and Kaanapali have a beachfront walkway that connects the various resorts. There are also luau facilities along the beach walkway in both areas, as well as scenic golf courses.

After browsing around the Whaler’s Village Mall for a bit, we walked along the ocean pathway, which leads to the oceanfront resorts there. We walked for quite a distance, passing several large resort hotels, including the Westin, Marriott, and Hyatt Regency, the latter two which also have Vacation Clubs.

The beaches at Kaanapali were beautiful and in some places much wider in parts than Wailea, (although the beach width varied among the resorts), with plenty of beach activities, such as surfboards, snorkeling and other equipment etc for rent.

We even saw a beached ship along the Maui beachfront!

Towards the end of the oceanfront walkway, we saw the Hyatt Regency (and Club Vilas), and walked thru the hotel and grounds for a while. The open atrium style of the resort reminded me a bit of the Hyatt Regency in Orlando, and even had there own parrot mascot like Orlando’s does!

The Hyatt Regency also had a beautiful swan garden with a both black and white swans, playfully having fun in the waterfall stream.

We had an oceanfront lunch at Libby’s Restaurant, which was good for a burger and soda for us, with others enjoying a brewski or fancy Hawaiian cocktails.

We passed by several other spots along the beach which were offering a refreshing beverage or meal including Longhi’s:

and even a swim up pool bar cave for guests at the Hyatt Regency. We weren’t staying there so we didn’t go in the pool bar area, but it looked similar to the cave pool area at the Orlando Cypress Creek Hyatt Regency. The cave pool area is really ‘cool’, literally as the cave shields you from the hot sun for a refreshing swim and drink.

In our opinion, the Kaanapali area seems more suited for families, beach lovers, honeymooners, sports enthusiasts, and active adults young and old, although we saw people of all age groups enjoying the sand and sun. Kaanapali was definitely a busier area than Wailea, and the beach walkway was quite active in places especially near Whaler’s Village, although was less busy the further down the path you walked.

The resorts felt a bit more clustered together than at Wailea, and while they were all nice, the grounds at some resorts were smaller in size and seemed more crowded with people laying out on the wide open lawns soaking up the sun. There were cabanas and some umbrellas, but at some resorts many people young and old were laying out on the lawns uncovered directly in the sun. Ouch – those days are over for us!

There were also a couple booths along the walkways where people were pitching their time shares for Marriott Vacation Club and separately for Hyatt’s Club, and a jewelry stand here and there which you didn’t see in Wailea.

Not that one area is better or worse, but we preferred the much quieter and more upscale and “exclusive feel” of the Wailea area over Kaanapali, but then again we don’t have kids, lay around in the sun, or do any of the surfing or other water sports activities either (although Wailea does have water sports available too). Kaanapali seemed to appeal to active people and families ‘on the go’ and a bit more of a party crowd, while Wailea was a slower pace in more residential surroundings.

Finally, we drove out to Kapalua later in the day. While we didn’t go there on this visit, there is a gorgeous Ritz Carlton Resort in Kapalua. We toured the Ritz on our last visit to Maui, and my sister and her family stayed there a few years back and loved it. The Kapalua area is a bit out of the way compared to both Wailea and Kaanapali, but is a golfer’s paradise, mixed in with the ocean.

Kapalua has a quiet and exclusive feel to it and does seem much more geared to golfing, and it doesn’t have the close walking proximity to restaurants, shops, and the large outdoor mall areas like Wailea and Kaanapali. Kapalua is on the far north side of the island so it is a bit away from the other areas, which is great for adults who enjoy the quieter side of Maui and golfing; probably not so much for families with kids. There is a small village area in Kapalua on the golf course that has a couple shops and a restaurant overlooking the golf course.

We went by the Kapalua Golf pro area we visited last time, and once again bought a cap and Kapalua polo shirt. We love the Kapalua logo, which resembles a butterfly!

Maui is a gorgeous island and there is so much to see, but these are three of the well known and popular tourist areas, each with their own vibe and personality. You really do need a car in Maui to see the island, unless you’re planning on staying at your beach resort the whole stay. Like The Big Island, venturing out to see the lava fields, a volcano (Mt Haleakala, and even a winery as you will see in the next post) are fun places to visit when you need a beach break. Until next post, Aloha!

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