- When the Islands Have the Smallest Crowds
September - Maui and the Big Island
November - Lanai
February - Oahu and Kauai
April - Molokai
May - The Big Island
- More Aloha for Off-Peak Travelers
Although Hawaii's blissful weather lasts year round, the islands cradle the calmest waters and fewest guests in September. As the back-to-school breezes carry families of flip-floppers back home, the incoming tradewinds of U.S. mainland and Canadian tourists suddenly sputter, resulting in roughly 150,000 fewer visitors in September than in August (more than a 20% drop).
So with the quieter beaches, softer waves, and the decibel savings of 300,000 fewer flip-flops, you'd think they'd jack up the rates for the extra zenful paradise. But thankfully not. After Labor Day weekend, you can usually expect reductions of at least 10% for mid-week airfare and up to 55% for some hotels, with especially attractive savings for Maui and Big Island, which enjoy their least traveled and arguably most pleasant month of the year.
Savings continue through October, which is the peak month for weddings and honeymoons on the islands (so the most popular wedding spots on Maui might be exceptions). And the autumn dip lasts through most of November -- until fares and rates quickly snap back up around Thanksgiving and through December's holiday influx.
As the winter waves churn up, so do more off-peak savings opportunities. From the second half of January through the end of February, when Oahu and Kauai have the fewest visitors, you can generally save a bundle on airfare and hotel packages -- upwards of 30% or more as compared to making the same trip in summer. Packages like "stay three nights, get the fourth night free" are often common. February in Hawaii also sees the fewest number of visitors staying in timeshares, which drives down hotel rates and car rental rates even more.
The next quietest and most affordable time is April, after the spring-break rush and before families return on their mega summer vacations. The Big Island also experiences a second reprieve from tourists in May, similar to its September lull.
- Never Experienced Aloha? Tips for First-Timers
Don't ignore your vacation bookends. Focus on turning travel days into unravel days. Know in advance that you will want to savor every second of aloha... because you won't want to leave. Own it. Plan for it. So ...
Given that you're flying at least five to ten hours to get to the islands from the U.S. mainland, don't neglect a single moment of hula-happiness when you finally get there. Try to time your arrival as early in the day as you can, ideally before noon: Of course, this is much easier for west coasters, and it happens to be my personal favorite TOHA (time of Hawaii arrival). That way you'll feel like you've enjoyed your entire first day of sunshined bliss and Pacific breezes. If you arrive after dark, you won't be able to see all the beaming dreamscape and you'll feel like you've wasted a chunk of your budget solely on your first night's hotel tab. No mahalo.
On the flipside ... To avoid any sudden snaps back into reality, plan your flight home for the late afternoon, if possible, so you don't rush and ruin your island glow. Then you'll actually feel like you've spent an extra day on the islands without paying for it -- in effect saving money on one night's hotel.
One more thing. Don't overpack. You can buy beachwear, towels, and sunblock while you're there at one of the countless ABC Stores. There are more than 30 in the Waikiki area alone. You'll find beach towels to be cheaper than a gallon of milk.
- Average Temps (ºF), Always Beautiful
- January - High 81, Low 63
April - High 84, Low 64
July - High 88, Low 69
October - High 87, Low 68
When to Escape to Paradise: Cheapest Weeks for Hawaiian Trips
Once you've been to Hawaii, you'll always want to go back. Anyone can find a personal happy place there, or two, or three, or a gazillion for that matter. One of mine's pictured below, on the Pihea Trail overlooking the Kalalau Valley on the northern coast of Kauai -- ah, a land that naturally looks Photoshopped to perfection. If the islands are on your dream vacation list, learn the cheapest time-windows to help you make your Hawaiian escape a dream no longer.