We've never dined in Wailea or Kihei as we're more Kaanapali/Lahaina people, although we do play golf sometimes at Wailea. I would like to stay in one of the nice hotels in Wailea sometime for a day or two to get a better feel for the Wailea resort. We've never liked the feel of Kihei, however.
We've been to Merriman's on the Big Island and loved it. Where is the Merriman's on Maui? I can't seem to place it. Will need to add that to our rotation on our next visit (hopefully, 2019)
Wailea is more like Ka'anapali. It is beautiful and perfectly landscaped and master planned so not really Hawaiian countryside dotted with funky cities that were allowed years ago but it is getting better in newer neighborhoods because of better city planning. We like Kihei because our first
timeshare we bought is there but we also get a better idea how local people live and work in Hawaii and they enjoy the sunsets and come to the beach to watch and play. They really enjoy
their dogs and I love watching them right in front of our resort in the park on the beach. It is amazing how well all these dogs behave together but they come every day. If it is windy, we see them flying kites, wind surfing or even sailing but Ka'anapali beach is also fun for people watching.
In Wailea you'll have to stay in a hotel or private condo. They do not allow timeshare resorts unless it will change in the future but I doubt it. They do not want and have the room for heavy traffic.
There are nice restaurants too that Luanne has mentioned already. This was our first time to have lunch at the Hali'imaile General Store in Makawao at her recommendation. It was further out than we like to go plus it was raining but it was a really good lunch so we are glad that we finally made it.
Try the Tai Mai, a Mai Tai recipe by Wendy (bar tender) and she made it herself that day and brought it over to our table. The friendly service made it special too but I am always afraid to recommend restaurants because next time may be different. You can read about the history on their
website plus see the menu and pictures. Make sure that they are open because they cater privately too and the same for Gannon's by the same Chef. That restaurant has a beautiful view besides good food and service.
We'll have to try Merriman's in Kapalua next time. The one on the Big Island is a must do for us every trip. If we add Merriman's to the rotation, I think we're covered for all seven nights the next time we go - Kimo's , Longhi's, Duke's, Hula Grill, Lelani's, Merriman's, and Cheeseburger in Paradise. May have to leave one out or stay longer to sample new places!
That is a beautiful spot too but we only had a casual dinner and cocktails there on the terrace and not in the restaurant inside. Try to be there for sunset. You need reservations for the restaurant.
We went this Jan/Feb, a few adds/points:
Trilogy books pretty quick during peak weeks
We did Capt Steve's zodiac tour: more of an adventure ride than cruise, but fabulous! Not for the 'motion sick' crowd during swells.
We had a bad experience at Longhi's. Kimo's would be 10x times better in my HO. I won't go back to Longhi's. Nuf said.
Maui brewery has happy hour, good bear, decent food and 'logo wear Wednesdays' I figure in just 5 years, my Maui Crazy Shirt will be free if I drink enough beer on Wed's!!
I would really plug a visit to Merriman's for a happy hour cocktail, music and fantastic ocean view. Some frites make it perfect. Best when the whales are performing.
Agreed with most that watershed wrote but we haven't been to the Maui brewery yet so need to try that too. Someone mentioned Monkeypod and there is going to be one at the Whaler Village soon. It should be open this summer. Mama's Fish House is also very far away from Ka'anapali (MOC) but we still liked it very much in March but you need reservations in advance and a good hour to get there because the traffic is really bad.
They still seem to get good reviews in both locations. Maybe we just had an off night. But, I'm not willing to try it again. So many other restaurants that are so much better, with better atmosphere.