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Aloha! October is Hawaii month at The Points Guy, so check back regularly for flight and hotel reviews, features and deals from Maui, Oahu, Kauai and the Big Island of Hawaii.

So you want to visit Hawaii. Understandable — it’s a great place. But unless you’re booking a spontaneous flight deal (and there certainly are plenty of those) you’ll want to plan ahead to ensure you’re traveling at the best time for your dream Hawaiian vacation.

Whether you’re looking for dry, idyllic weather or the cheapest time to book a Hawaiian hotel room, consider this your definitive guide to planning a perfect trip to Hawaii.

Photo by Melanie Lieberman / The Points Guy.

The Best Weather in Hawaii

Generally, the best weather in Hawaii can be experienced in June, July and September. This is when travelers can expect the least amount of rainfall along with warm water temperatures. However, Hawaii has pretty great weather year-round (after all, the Aloha State experiences only two seasons). So if traveling during June, July or September isn’t in the cards, you’re not out of luck.

The Best Time to Surf in Hawaii

Only four of the islands in the Hawaiian archipelago are suitable for surfing year-round: Oahu, Maui, Kauai and the Big Island. As for when and where you’d like to surf, well, that depends entirely on your skill level.

The waves follow a somewhat consistent schedule. In the winter, for example, surfers can find serious swells off an island’s north coast, while the south coast experiences calmer seas. During the summer, the opposite is true.

So, for advanced surfers, winter season, or ho’oilo, which runs  from mid-November to early February, is when you should look out for big wave surfing competitions on the North Shore of Oahu, also know as the “Seven Mile Miracle.”

On the Big Island, surf enthusiasts should check out La’aloa Bay and Honoli’i Beach Park.

For novice surfers, you’re going to want to spend more time on the islands’ southern coasts in the winter. In Maui, beaches in Kaanapali, Lahaina and Kihei deliver just-right waves for beginners to get their feet wet.

When to Visit Hawaii for Events

Summer Events

In the summer, visitors can attend the Prince Lot Hula Festival, Hawaii’s largest non-competitive hula event.

Fall Events

The Hawaii Food & Wine Festival is a major draw for foodies, featuring an extensive line-up of dinners, parties, cooking classes and more. In September, travelers can attend the Aloha Festivals.

Winter Events

This is prime season for surfing competitions, including the Vans Triple Crown on Oahu.

Spring Events

Heading to Hawaii in the springtime? Consider the Honolulu Festival in March or the Lantern Floating Festival, held on Memorial Day.

Photo by Tor Johnson / Getty Images.
Photo by Tor Johnson / Getty Images.

The Best Times to See Wildlife in Hawaii 

The Best Time to Go Whale Watching

Whales migrate to Hawaii in pods of roughly 1,000 between late December and early April, making Maui and the Kohala Coast of the Big Island two of the best places on Earth to spot the giants.

The Best Time to See Turtles

If you’re interested in spotting Hawaiian green sea turtles, they’re quite numerous on the Ho’okipa Beach in Maui — just don’t get too close. Visit in the summer, during nesting season, to increase your odds.

When to Visit Hawaii to Avoid Crowds

The peak tourism season in Hawaii typically starts in the middle of December and continues until the end of March or mid-April.

The off-season stretches from the middle of April and continues until mid-June, and resumes again from September until crowds tick up before the holidays.

July and August, while not considered Hawaii’s busy season, still tend to draw decent crowds — and are especially popular with vacationing families.

The Cheapest Times to Visit Hawaii

Traveling to Hawaii is usually priciest during peak season, so if you’re looking to save, wait until the off-peak or shoulder seasons.

The shoulder seasons in Hawaii run from March through the beginning of May, and from September until Thanksgiving. However, spring break and the beginning of September can yield high traffic and higher prices, too, so look carefully before booking.

Affordable Airfare

By examining two years of historical data from the travel booking site Skyscanner, airfare is at its most expensive during the winter: specifically, January. At this time of year, long-haul flight prices can exceed $1,400.

But during the shoulder seasons, or times that cushion peak periods such as late November and early March, prices can plummet.

Affordable Hotels

We looked at 2017 data from the travel search engine Booking.com to determine the most affordable time to book a hotel room in Hawaii.

Numbers from the two most visited cities in Hawaii (Honolulu and Lahaina) suggest the most expensive month for a room in Honolulu is January, by a 22% margin over the least expensive month, April.

In Lahaina, prices are 29% more expensive in February than in September, when prices bottom out for the year.

Of course, you may have more flexibility when you cash in your points and miles — though hotel award rates tend to shift with peak and off-peak seasons, too, and award flight availability is often directly tied to demand. 

Featured image by Getty Images.

The Platinum Card® from American Express

The American Express Platinum card has some of the best perks out there: cardholders enjoy the best domestic lounge access (Delta SkyClubs, Centurion Lounges, and Priority Pass), a $200 annual airline fee credit as well as up to $200 in Uber credits, and mid-tier elite status at SPG, Marriott, and Hilton. Combined with the 60,000 point welcome offer -- worth $1,140 based on TPG's valuations -- this card is a no-brainer for frequent travelers. Here are 5 reasons you should consider this card, as well as how you can figure out if the $550 annual fee makes sense for you.

Apply Now
More Things to Know
  • Earn 60,000 Membership Rewards® points after you use your new Card to make $5,000 in purchases in your first 3 months.
  • Enjoy Uber VIP status and free rides in the U.S. up to $15 each month, plus a bonus $20 in December. That can be up to $200 in annual Uber savings.
  • 5X Membership Rewards® points on flights booked directly with airlines or with American Express Travel.
  • 5X Membership Rewards points on prepaid hotels booked on amextravel.com.
  • Enjoy access to the Global Lounge Collection, the only credit card airport lounge access program that includes proprietary lounge locations around the world.
  • Receive complimentary benefits with an average total value of $550 with Fine Hotels & Resorts. Learn More.
  • $200 Airline Fee Credit, up to $200 per calendar year in baggage fees and more at one qualifying airline.
  • Get up to $100 in statement credits annually for purchases at Saks Fifth Avenue on your Platinum Card®. Enrollment required.
  • $550 annual fee.
  • Terms Apply.
  • See Rates & Fees
Intro APR on Purchases
N/A
Regular APR
N/A
Annual Fee
$550
Balance Transfer Fee
See Terms
Recommended Credit
Excellent/Good
Terms and restrictions apply. See rates & fees.

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