VANCOUVER ISLAND WINDTALK

This is a little of the wall but you could consider Corpus Christi.

http://www.corpuschristiwindsurfing.com/weather.html

"From April through June, Corpus Christi offers some of the best all-round sailing conditions as the winds become S, SE, ESE, and strong (20-40+ mph), 2-3 days a week or more. This wind pattern allows for great bump-and-jump conditions in the bay, high wind flat water sailing at Bird Island and in the Laguna Madre, and onshore wave sailing in the Gulf of Mexico."

You can get flights from C$499 Return to DFW and it's a great place for learners. There are cheap hotels and SW Tex-Mex for feed.

...and I hear a certain local sailor has a place for everyone to stay down there...

I'll second that Corpus Christi and South Padre Island are fantastic places for both advanced and new sailors. The Laguna Madre is waist deep for as far as you can see in many places and is perfect for getting waterstarts and jibes wired. Corpus is a super friendly city from what I remember.

Wind is guaranteed for Maui in May. In fact, you'll usually be begging for a non windy day to heal your muscles and hand blisters.

I usually go in April because there are usually still some North Pacific waves coming in for Wave Sailing. The waves taper of at the end of April. April is also the start of the Summer Trade winds, by May the wind is consistent.
For surfing there are some nice south swell starting in May. Good for SUP or Longboard

As per cost I stay for a month and usually spend about $2000 (travel,acomo,car,food), not including cost for buying new windsurfing toys that I need (want). I usually share my accommodation with 2 or 3 other people over that period. I have windsurf gear stored on Maui.
If your not windsurfing then you can easily go SUP or surfing or hiking or biking. Lots of things close to everything. Even if you stay in Kihei your only about 20 to 30 minutes from Kanaha. If the trades shift a little bit north then you can sail right at Kihei. I usually stay in Haiku which is 5 minutes from Hookipa and 10 minutes from Sprecks and 15 minutes from Kanaha.

I just checked WestJet. Take the Ferry to Vancouver. In May the cheapest way is to fly to Honolulu ($438 two ticket May 2/16) then take the SuperFerry ($50 each way) daily at 6:30 am.
Lots of car rentals in Honolulu. ~$20-$40/day.
A direct flight to from Maui from Vancouver will be about $723.

You can stay at the Hostel in Wailuku (see my previous links) with a private room for $60/night for two people or a condo in Kihei for about $80/night (Kihei Bay Surf it is close to the windsurfing beach in Kihei)
or in Haiku at Pu'u Koa Vacation rentals where I stay ($80 -$90/per night).

For windsurfing instruction you'll be hard pressed to find a better place with good quality instructors. It is where I learned how to windsurf.

Also, warm ocean water (no wetsuit needed), Palm trees, sandy beaches, awesome snorkeling and diving. You'll feel like your really on vacation.

Again,
Wind is guaranteed for May for Maui.

Maui is soooo tempting. I will have to toss this one around with the SO tonight.

Ok you win, I booked two flights to honululu for $169 each, each way. That ferry looks fun.

I mean for that price... it hardly makes going down to Oregon worth it when it is still cold in May.

Only downside is that Air Canada was way cheaper than West Jet, and so sadly I signed a deal with the Devil.

Nanmoo, let me know when you booked for....I'm looking for cheap flights there also. When did you book for..??

That sounds pretty great RK. WOW!

May 17 FO from Vancouver arrive 8 or so that night.

May 27 FO from Honululu Red eye style arrive Vancouver Early May 28.

100 more each way min. to fly direct to maui I found, yet 50 each way on the ferry, so save 100 each min. I found the cheapest ever with Air Canada was 169, still a few left, whereas Westjet cheapest was 181, most were 219, and they had less availability. After all taxes, stupid fees etc, for two of us return it was a hair over $800.. Thats pretty darn good I think. Not far off a drive to Edmonton and Back in an SUV!!! And in may, that ain't paradise!

Probably going to stay at the place suggested, but its cheaper if we find more people!!!

Oh and Pu Koa has plenty of availability at that time. We are still going to investigate stuff right on the beach to see if we can get anything nice at the same price, but I doubt we will.

I'd act fast for those flights, WestJets availability changed between when I booked my flights at work today and when I checked later tonight, I am sure its the same for Air Canada. When I picked my seats the chart showed maybe 50 or so left, but I am not sure how accurate that is.

I have been going to Maui for 23 years now and one of the best places to get a car rental rate is www.carrentalinhawaii.com. You have to send in a rate request but you will find them hard to beat on price.

used travelocity.ca and flexible date calendar, saw vancouver to maui in april/may for $421 Cdn return, tax included, via NW Airlines connecting in Seattle then maui.

I got two return to Honululu for $800 all in, after deciding the Ferry would be more interesting than paying a bit more to go straight to Maui but having to do stopovers and/or plane changes.

A friend at work is flying either United or NW, and she mentioned that they don't include bags in their prices, and was expecting to pay $50-$75 each way for just normal baggage, so I assume that would add to the price you stated.

Either way... cheeep cheeep cheeep