Maui vacation advisors We've been asked this question for many years and it will continue to be a good one, especially given the amount of "false info" out on the internet these days, with all sorts of "reviews" being written and taken as "truth". Both of these sides of Maui have been developed for "tourism" by virtue of their geographical location, though the westside was developed first, mostly in the 70's and 80's because of the prior existence of Lahaina town, with the southshore being a little later to develop in the 80's and 90's.
Wailea Beach Villas

Here's our opinion, along with some facts, about the southshore of Maui vs. the westside, based again on 15+ years of not only living here but guest feedback during all that time:

1) The southshore typically has warmer and drier weather thru the critical "winter/spring" months of December thru April. While both are "leeward" shores, the westside gets about the same rainfall and wind conditions as the northshore. The southshore tends to be much less rainy and even less windy the further south you go.
2) The beaches, all of which are open to the public, including the ones in Wailea where the hotels are located, are superior not only in number but they could be called more "user-friendly" in that they are less prone to get surf most of the year and provide better swimming, walking, and snorkeling given their geographical location on the island.
3) It's more centrally located so that you can use it as a good "home base" from which to enjoy the whole island, which is really what a vacation on Maui is all about, without being somewhat "isolated" as you would be staying on the westside. It's just a 15- 30 minute drive to the northshore and 30 - 45 minutes to the westside, depending on where you're staying on the southshore.
4) There's less "density" of development on the southshore in terms of condos, hotels, and commercialized areas. Of course, no one is attracted to the "suburban sprawl" of the southshore, that's not what you come to Maui for, but it is nice to have modern conveniences of shops and restaurants close by without having to "look" at them or be surrounded by them during your stay, which is why we only recommend properties in the northern end or southern ends of the southshore, not in mid-town Kihei, so that the busiest parts are "out of sight/out of mind".
5) The sunsets are better. (OK, that's not true, sunsets here are wonderful just about everywhere.)

Makena Surf Rumor vs. Reality

For those who’ve made the northshore their “home base” for past vacations, the experience of being in an uncrowded lush tropical environment far outweighs any negative issues that they have presupposed. For those who haven’t stayed on the northshore, some misconceptions can preclude them from even thinking of staying here, and thereby perhaps have them miss an opportunity to have a unique vacation. These negative “rumors” and the “reality” include the following:

Rumor: the northshore is too windy.
Reality: it’s no more windy and often less windy than other popular tourist locations on the island, with the exception of Wailea and Makena on the southshore. Both Kihei and Ka'anapali routinely get higher wind speeds on most “tradewind” days. But this is good news since the trades cool off the hot island air to make it very pleasant during all times of year.

Rumor: the northshore is too wavy.
Reality: it’s flat like a lake at the beaches most of the year, with the exception of the “winter” months of December - March. Waves usually break on an offshore reef located 100 - 300 yards offshore anyway though there can be some shore break at popular beaches like Baldwin on the northshore, but even there it’s usually fun for boogie-boarding. During the “summer” months, however, shore break is common at southshore beaches. At all beaches on Maui, it’s usually not dangerous at any time, though there are days of rare exception so caution should always be exercised.
Baldwin Beach

Rumor: the northshore is too rainy.
Reality: it does rain more on the northshore than the south or west sides, hence the more “lush/tropical” northshore appearance, but rain is usually in the form of “passing showers” that come in on the tradewinds and usually effect areas to the east like Haiku much more. Infrequent storms do effect all the islands and there’s just as much likelihood of them effecting all shores equally. Statistically, though every year is different and weather is unpredictable, the northshore still only has about a 10 - 25% chance of rain in the areas close to the beaches, near Paia town, which still means a 75% chance of sun during the “winter” months, more like a 90% chance of sun during the other months.

Rumor: staying on the northshore would take you "out of the loop" of "where the action is" on Maui.
Reality: if you're looking to be close to some great outdoor activities like windsurfing, hiking, and biking, the opposite would be true. But if you still want to have the flexibility to enjoy the other shores, the really nice feature about Maui, as opposed to the other Hawaiian Islands, is that it's very easy and convenient to get from one side of the island to the other. It's just a 30-minute drive from Paia town to the best beaches on the southshore and just a 45-minute drive to Lahaina town on the westside. There's certainly more nightlife available on the southshore and westside but even that's in short supply here on Maui.

Rumor: there's too much jet noise from the airport on the northshore.
Reality: jet noise is NOT an issue at most of the properties we offer on the northshore (the exception being those with direct windsurfing access). There are several good oceanfront properties that offer beach access with no jet noise whatsoever.
In other words, none of these issues is worth considering when making a decision whether to stay on the northshore. What should be considered is what type of vacation experience you want to have and in what type of accommodation you wish to stay, cottage vs. condo, rural/residential vs. resort, and what do you want to spend, since northshore accommodations are approximately half the cost of what you can get comparably in other locations on Maui, making it the most affordable location on the island.

Paia town is at the center of the northshore, about 10 minutes from the airport in Kahului. It's an old sugar cane plantation town that has since turned into a "funky meets trendy" little gathering place, real little, as in one stoplight. But the tiny-town atmosphere of Paia boasts many boutiques, quaint coffee shops, and various restaurants of all kinds in all price ranges, including some of the best on the island nearby. Just up the road from Paia, world-famous Ho'okipa Beach attracts surfers and windsurfers alike from around the world. Makawao, a few miles up the mountain from Paia, is another small town that time forgot which contains many boutiques and restaurants.

There are several uncrowded sandy beaches on the northshore, with mile-long Baldwin Beach near Paia being the main one, a perfect place for strolling, sunning, swimming, or boogie-boarding. The northshore is ideal as a base for jumping off to explore more remote parts of the island like the tropical rain forest past Haiku which extends to Hana, the upcountry area of Kula and Haleakala Crater, and the West Maui Mountains. Kahului is conveniently close by as well with supermarkets, restaurants, and the island's largest mall, which includes a multiplex movie theater. The northshore has developed slowly over the years but still offers the best of both worlds: a laid-back casual culturally-diverse atmosphere with modern amenities and conveniences.