After 20+ years of travel for sports that are almost 100% environmentally dependent on the outcome, the past 10 or so years I've adopted a new approach to taking these trips.
I decide "go/no go" at the last minute.
Really, I do. Sure it (can) cost more, but the reward is worth the added expense. Here's the rationale and how it works.
First, fix on a destination. Preferably multiple destinations. In this case, we'll go with Maui. Then, pick a "window" for travel. Typically this will be 2-3 weeks. Now, I'm not going for the entire time, but its a window of travel that I keep open and available. If you have accumulated any frequent flier miles, but are short on needed miles to get a full fare, check for "cash+miles" promotions - you'll be amazed at what you find. You can also set alerts for fare reductions on most travel websites - very handy.
Then start working ticket prices to find the "sweet spots" in the travel times. On the airline websites, select the "flexible date" options - typically +/- 3 days around a departure/arrival date. Map out the 2-3 week window and get a feel for when flights are cheap(est), from there, its all about watching the weather to catch epic conditions.
A few things you need to be flexible on. 1) crappy flight times. Cheap flights have bad departure/arrival times, sometime long layovers and weird routing. 2) sketchy lodging. 3) limited gear rental/availability depending on season and 4) crap airline seats next to an overweight, annoying tourist. Sure I usually get upgrades, but I've spent a ton of time on flights is crappy seats - who cares! I'm just happy to be there headed towards funville. ;-)
Oh, but the reward! Winter trips with days of powder, sailing trips with killer swell and more wind than you need. Sweet opportunities to get somewhere off the beaten path with a crew that makes the whole journey worthwhile.
The last time you were on a trip and got skunked - what if I said you could score epic conditions for an additional $200 for the entire trip?
Cheaper than a lift ticket and oh, so much better.
Go ahead, roll the dice and take your chances next time you schedule your trip months in advance. You might score, you might not. Use my method and score every time. ;-)
Here's the forecast for my trip tomorrow. It works for me!
...SMALL CRAFT ADVISORY NOW IN EFFECT UNTIL 6 PM HST SUNDAY...
HIGH PRESSURE WILL STRENGTHEN AS IT MOVES NORTHEAST OF THE MAIN HAWAIIAN ISLANDS. THIS WILL CAUSE TRADE WINDS TO INCREASE ABOVE ADVISORY THRESHOLD.
A SMALL CRAFT ADVISORY MEANS THAT WIND SPEEDS OF 25 TO 33 KNOTS AND/OR SEAS 10 FEET OR GREATER ARE EXPECTED TO PRODUCE CONDITIONS HAZARDOUS TO SMALL CRAFT. INEXPERIENCED MARINERS...ESPECIALLY THOSE OPERATING SMALLER VESSELS...SHOULD AVOID NAVIGATING IN THESE CONDITIONS.
FRIDAY East winds to 25 kt. Wind waves 14 ft. Northwest swell 4 ft. Scattered showers.
SATURDAY East winds to 25 kt. Wind waves 15 ft. Northwest swell 3 ft. Isolated showers.
SUNDAY East winds to 25 kt. Wind waves 13 to 14 ft. Northwest swell 4 to 5 ft. Isolated showers.
MONDAY East winds to 25 kt. Wind waves 12 to 13 ft. Northwest swell 4 to 5 ft. Scattered showers.