Lessons are probably the quickest way to progress, and Maui has the conditions to learn pretty much anything. Compared to European centres it’s not cheap, at around $100 per 60 to 90 minute private lesson.
Al West has full on windsurfing vans with racks, $299/wk for the mid age ones, $199/wk for older ones, plus insurance. Not the cheapest option but they are big vans and the racks are great if you have lots of gear.
Kimo’s Rent a Car has mini vans which are fine for 1-2 people plus gear at $140/wk or $500/month including liability insurance.
Others
If you’re staying longer than 6-8 weeks I’d consider renting for a week or so and trying to find a van to buy. It’s a bit of a hassle but can be much cheaper. Craigslist and the noticeboard at Kanaha are good places to look.
Wind
For current conditions iWindsurf has a sensor near Kanaha which gives a pretty good indications of the conditions there. They also have sensors at Kihei and Hookipa. If you’re not a member iWindsurf have a 10 day trial which gives access to all sensors.
The iWindsurf Kanaha forecast is also good for predicting the wind pattern though it seems to underestimate the local effects that accelerate the wind. Also worth a look is the NOAA forecast for Maui, though the forecasts are only given to the nearest 5 knots so for windsurfing it’s only useful for a general idea of if it’s going to be windy or not, i.e. a forecast of 10 knots probably isn’t worth it, 15 knots and up probably is. If you’re looking for slightly lighter conditions for intermediates then getting on the water at 11am can work as the wind may still be building, or getting on later in the day after 4pm may also be worth a try which also keeps you out of the sun.
It’s definitely worth adding some local windsurfing insight into the mix by following Jeff Bennett’s Twitter Feed and his blog. The Marine Winds section of Glenn’s Daily Weather Narrative can give you a good overview of what’s happening.
Waves
The NOAA surf forecast gives you an idea of what size waves to expect. Remember that local conditions will affect this to, for example Lowers will probably be breaking smaller than Uppers and Hookipa.
Whether you’re checking out the conditions or just wishing you were there, check out the Kanaha web cam. A great way to get in the mood for your windsurfing holidays!
Remember that most sites here probably have more kit available than they list, or their online list might not be up to date. So asking around when you arrive is the way to go, but from these listings you can still get an idea of the range and price of the available gear.
Craigslist - lots of great deals on here.
Neil Pryde Maui - used and ex-rental Neil Pryde boards and sails
Hot Sails Maui Shop - used, prototype and closeout Hot Sails gear
Naish Maui Specials - ex rental and closeout deals.
Second Wind board & 2 sails - 7 days $290, 14 days $522, 28 days $783
Maui Windsurf Company board & 2 sails - 7 days $319, 14 days $561, 28 days $890
Kanaha Kai - board & rig - 7 days $290, 14 days $529, 28 days $820
Naish Maui - boards & 2 sails - 7 days $290, 14 days $495, 1 month $795
Hawaiian Watersports - Board & rig - 7 days $279
Obviously this is a pretty competitive market, so the prices don’t differ that much between places. So it’s the details that make the difference, it’s worth checking