Maui is 'no ka oi' - the best of the islands. Riders flocked to Maui for its warm waters and super consistent conditions in the early days of the sport to be surrounded by the most progressive talent than anywhere on the planet. Plus, of course, there's Hawaii-size surf, but actually, Maui offers lots of riding opportunities for kiters, beginners through advanced.
Kitebeach Maui is ground zero for kitesurfing. Year-long trade winds blow from the northeast, providing side to side-onshore conditions. Upwind, west of the lifeguard station, is Ka'a Point, a small inlet offering a protected area called the 'Swimming Pool' or 'Pro Pool' for flat-water tricks. Further offshore from September through May, large north and west swells pound the reef, from Pier One to the west, the 'Boneyard' in the middle and 'Lowers' to the east. Sizeable left and right handers can be found, often reaching 25 foot in size. Closer to shore these waves re-form and set up a fun zone for intermediate kiters also wanting to ride waves or pop off the ramps. Apart from the occasional extreme low tide Kitebeach is not tide-reliant. 30 minutes from Kitebeach are the world famous spots of Ho-okipa and Lanes, offering advanced wave riding for the vastly experienced. Kitesurfers are not generally allowed to ride at Ho'okipa.
Elsewhere the west and northwest coasts have several spots that are kiteable in northerly trades, the premier being at Embassy Resort in North Kaanapali. Kite right out front of the hotel and next door at Kaanapali Shores and Maui Kai. Head north to Pelican Point AKA: #216 / Kahana Villas also works great with the northerly trades and 'Windmills' or 'Punaluu' is a very good wind and wave spot with the same exposure as 'Lanes'. Head south to Lahaina which gets kiteable in 'Kona South' winds or a strong northerly. Kehei is further south and gets waves in Kona conditions. The swell exposure is limited but can be fun at times.
The weather is comfortable year-round on Maui. Summer-time sees brisk winds with small to no surf (June - August). Winter can be wetter and maybe 12°C / 10°F cooler with the temperatures seldom dropping below 21°C / 70°F. Northeast trade winds blow year-round. The occasional west wind and Kona wind (south/south east) blow from November - April and usually last for short periods with the passing of a storm. The strongest winds blow in the summer months, sometimes exceeding 30mph. Kitebeach has its best waves in the winter months, November - February. A 9m is probably the most popular kite at Kitebeach, but bring your seven to 12 metres. You don't need to worry about getting cold at night, unless you are staying at higher elevations, otherwise a long sleeve shirt will be enough. Summer is definitely boardshort weather on the water, you may need a thin neoprene top in the winter.
Everything is between 30 and 40 minutes from everything else and taxis are expensive and unreliable, so hire a car. This is America, so everything is well connected.
Expect a good range of accommodations, but Hawaii isn't cheap. Stay in luxury world-class resorts in Wailea through to budget vacation rentals and back-packer hostels; all are within 30 minutes drive from most places. Paia near Ho'okipa is popular with kiters due to the range of low-cost accommodation and proximity to Kitebeach. There are camp-sites, shared accommodations and a couple of hotels and vacation rentals which offer a less expensive option.
FOOD AND DRINK
There are supermarkets and health food shops, delis and big box stores all over the island. The nightlife usually shuts down between 10pm and midnight though. Watersports is a serious business here and pervades everything, from bars to restaurants. Those iconic watermen need their sleep too, you know!
You're spoilt for choice! Go stand-up paddling, surfing, snorkelling, horse riding, parasailing, kayaking, take a spectacular hike, watch whales, play golf on some of the most beautiful courses in the world, dive under waterfalls, bathe on stunning beaches, take a ferry to Lanaii or Molokai, drive to Hana, visit the Haleakela Crater...
Kahului (OGG) is 5 five minutes from Kitebeach. In fact, you'll see the planes coming in while you're kiting!