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With plunging waterfalls, lush foliage, and unspoiled beaches, Hawaii is the quintessential tropical paradise. If you’re contemplating going to these magnificent islands for your next vacation, you’re likely wondering, when is the best time to cruise to Hawaii?

In Hawaii, there are certain seasons that are more appealing depending on what you’re planning on doing. Whether you’re hoping to go whale-watching, escape on a couple’s getaway, or avoid crowds, this is the best time to cruise to Hawaii.

What’s the best season to cruise to Hawaii?

Aerial view of Oahu


Shoulder season, or the period of time right before or after a destination’s high tourist season, is one of the best times to cruise to Hawaii. During summer, kids are out of school and families flock to Hawaii, which leads to higher prices and larger crowds.

Hawaii’s shoulder season, which includes the months of May and September, also boasts some of the best weather, making it a prime time to enjoy a vacation there.

When should I go to Hawaii to see whales?

best time to cruise to Hawaii for whales

Humpback whales go to Hawaii in search of warmer water to conceive and birth their calves. Planning a Hawaii cruise earlier in May will increase your chances of seeing them before they migrate to cooler waters for the summer.

If whales are on your must-see list, arrange a whale-watching shore excursion during one of your days in port.

When’s the best time for families to cruise to Hawaii?

best time to cruise to Hawaii for families

Avoid the summer crowds in Hawaii and plan your family cruise vacation in May, just before the school year ends. In May, the rainy season will be over in most regions of the Hawaiian Islands, guaranteeing sunny weather for you and your kids.

Plus, you might even get to see a few whales from the ship (as this is prime whale-watching season), which is sure to delight everyone in your group.

When’s the best time for couples to visit Hawaii?

With the kids back in school in September, this is a great month for parents to go on a couple’s cruise to Hawaii. It’s the perfect way to celebrate an anniversary or birthday, or simply spend quality time together resting and reconnecting.

Couple walking on the beach

September is decidedly more relaxed than during the high season months. While you’re there, enjoy some of the islands’ best waterfalls, swim with turtles in the turquoise ocean, or experience an authentic luau and gain a new appreciation for this natural paradise.

Cruises in September visit multiple Hawaiian destinations such as Hilo, Kailua Kona, and Lahaina.

Read: Best Way to See Hawaii

When should I go to Hawaii to avoid crowds?

Aerial view of a beach in Hawaii

Families with school-age children are likely to time their Hawaiian vacation during spring break or when school’s out for the summer, so the best time to cruise to Hawaii and share the island with minimal crowds is during the month of September.

When is the best time to see Hawaii’s flora?

Aerial view of a farm in Kailua Kona

Summer is the season with the most sunny days in Hawaii. However, during the summer it can also get quite hot and dry, and Hawaii’s typical lush vegetation may suffer from drought.

Avoid running into an arid landscape and instead cruise to Hawaii during shoulder season, when you’ll get to see plenty of sunshine with pockets of rain that won’t hinder your trip, but will keep the scenery fresh and vibrant.

Flowers blooming in Hawaii

May is the best month to witness the lush Hawaiian scenery covered in pops of vibrant colors, as it’s typically the season when the islands’ gorgeous tropical flowers are in bloom.

Be mindful that the weather can change drastically depending on which island you’re visiting and your location. The leeward sides of the islands tend to be calmer and sunnier than the windward sides, where you’ll often find cooler weather and more rain.

Beautiful landscape of a lighthouse in Lahaina

Whether it’s a family-focused vacation or a romantic couple’s getaway, it’s always a good idea to cruise to Hawaii. Start planning your next cruise by browsing our itineraries.

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Free Vacation Planning Services