Surfing is one of my favorite things to do on Maui. Maui has some of the best surfing in the world. Near the Wailea condo is a world class, expert only surf spot called La Perouse Bay. It's a shallow reef bottom that breaks left on a big south swell. It's a fickle wave, doesn't break often but when it does look out. From the condo head towards Big Beach and keep going until the paved road ends. There's a parking lot on the right. Park and walk down the path until you get the bay. It's also a great snorkeling spot.
Another great surf spot is Hookipa on the north shore, just past Paia Town. Hookipa breaks 300 days out of the year, but mainly likes a north swell. In the winter it can hold a 15 foot wave before it starts closing out. This is an advanced spot not good for beginners. Go early before the wind picks up in the afternoon, unless you are wind surfer, and then you are in for a treat as this is THE best spot in the world for Windsurfing. Windsurfers can be seen nearly every afternoon jumping the waves, do flips and other amazing tricks.
Honolua Bay, on the upper west side of Maui past Napali, is one of the top ten surf breaks in the world - experts only, people die here! It's a right handed point break. When conditions are right, with a large North West swell that wraps around into the bay, 400 yard rides can be had. The spot has about 5 or 6 take off points, starting from the outside: Coconuts, The Point, Middles, Caves, Inside Caves. Taking off right at Coconuts is an easy drop, then it starts to barrel and if you are lucky you can make it all the way through going between the two rocks at the point, past caves into the bay. Then it's a 400 yard paddle back to your take off spot, but worth every stroke.
There's a good beginner spot near the Wailea condo in Kihei called Cove Park. You can rent foam boards and take surf lessons from instructors at the park. You may want to rent booties or reef socks as it's a rocky bottom. If you fall or jump off the board without protection you can cut your feet.
Here's a good resource for all the surf spots on Maui:
http://www.wannasurf.com/spot/North_America/USA/Hawaii/Maui/index.html
This the best surf report page: http://www.omaui.com

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