Hawaii in winter: whale season, big surf, and which side of the island to stay on

Hawaii doesn’t really have a bad season. But it does have different ones, and winter is the one that surprises people most, in good ways and a few not-so-good ones.

My Hawaii page covers which island fits which kind of trip and how to move between them. This is about what changes when you go in the winter months, and how to plan around it.

Whale season

Every winter, humpback whales travel from the North Pacific to Hawaii’s warm, shallow waters to breed and give birth. Their season runs roughly from December through April, and the peak is usually January through March.

During those months you can often see whales from shore, spouting and breaching offshore, without ever getting on a boat. Maui is the best known for it, because the channel between Maui and its neighboring islands is especially shallow and protected. But whales are seen around all the main islands.

If whale watching is a priority:

• Aim for January through March for the best odds.
• Choose a hotel with an ocean view facing the right way. Watching from your balcony with morning coffee is a big part of the magic.
• Book a whale-watching cruise early in the trip, so if the weather turns you still have time to try again.

Big surf on the north shores

Winter brings big swells to the north-facing shores of the islands. On Oahu, the North Shore becomes one of the most famous surf spots in the world, and watching the waves from the beach can be a highlight.

The flip side is that those same beaches can be dangerous for swimming in winter. The calmer water usually shifts to the south- and west-facing shores, so where you stay matters.

More rain on the windward sides

Each island has a windward side, facing the trade winds, and a leeward side, sheltered from them. In winter, the windward sides get more rain. That rain is what keeps them so green, but it can mean more showers during your stay.

The leeward sides, often the south and west shores, are usually drier and sunnier. That’s one reason so many resorts are on those coasts.

So which side should you stay on?

For most winter trips, the sunnier, calmer sides of the islands make the best main base, with the north shores as day trips for the views and the surf.

A few examples of how that plays out:

• Maui: the west and south shores are popular for winter, with calmer water and good whale watching from shore.
• Oahu: many people stay on the south shore and drive up to the North Shore for a day to watch the big waves.
• Kauai: the south shore tends to be sunnier in winter than the north, which is lush but often wetter.
• The Big Island: the west side, the Kona and Kohala coasts, is usually the drier side.

Every island has exceptions and microclimates, and I’ll match your hotel to what you want to do.

How to plan a winter trip

Winter is a popular time for Hawaii, especially around the holidays and over spring break, when prices and crowds go up. January after the holidays and early December can be good value.

A few tips:

• Book holiday weeks early. Christmas and New Year’s are among the busiest weeks of the year.
• Plan more than one island if you have ten nights or more. My Hawaii page explains how many islands fit comfortably.
• Pack a light rain jacket even if you’re staying on the sunny side.

If you’re picturing Hawaii this winter or next, tell me whether whales, surf or a quiet beach is the priority and how many nights you have. I’ll match the island and the side to it.