The islands are tropical year-round, but there are some things the popular travel sites don’t mention. Hawaii thrives from tourism and is known to be a holiday vacation destination, so it makes sense that locals and travel sites never mention any shortcomings. After living in Maui for three weeks there are a few surprising downfalls and amazing rare excursions we had no idea about despite hours of research.

Most of the Hawaiian Islands have a rainy season from late December to March, sometimes earlier or later. The popular travel sites will tell you that it rarely rains in most parts of the islands, but this isn’t true! There are hundreds of micro-climates on each island. Different parts of the islands will have different amounts of rain so be sure to research annual rainfall in your preferred area before booking your accommodations.

In Maui the best place to stay is southern Lahaina because they receive little to no rain year-round. We are staying in West Maui and it rains nearly every day, but we also have the nicest beaches so it’s a trade-off. We find ourselves escaping the rain by driving 15-minutes south to Lahaina every evening for sunset.

Other than rain, you can expect ideal temperatures in Hawaii all year with highs in the low-80s and lows in the mid-60s on the coastlines. If you plan to stay in the rainforest or on a volcano prepare for colder and rainier weather with lows reaching the 30s. Hikes in winter are unpredictable. We were going to hike the top of a volcano, Haleakala, on a clear and cloudless day. By the time we reached the summit it was down pouring with zero visibility. Not to say that you won’t get lucky, but most mountainous hikes will include rain during the winter with partial views. The water temperature is warm all year so if you can stand room temperature water leave your wet suit at home.

Winter brings huge waves to the North Shore of every island. If you are an experienced surfer Hawaii in winter is the place to be! Rain, wind and storms typically follow the swell so those staying on any northern shore be prepared with a rain jacket in tow. Boat excursions can be canceled or rerouted during winter due to the swells as well. We booked a cruise to the small crater island of Molokini and were rerouted to a closer bay because of the large winter waves. For beginner surfers, Maui has a mix of large and beginner waves which is one of the main reasons we chose this island. We have been able to surf nearly every day!

Humpback whales and their babies visit the calm channels of Maui from November to March every year to escape the cold and breed. Whale watching is only available in winter, so you’ll be able to see breaching humpbacks if you are staying in Maui and other surrounding islands. This makes for a fun activity rain or shine! If you have a place overlooking the water you could see the whales from your room!

I am in heaven living in Hawaii for a couple of months and recommend a holiday here to anyone, but wish someone would have given me these tips before we booked our accommodations! Ideal temperatures, holidays, whale watching, and big swells make the islands a popular place to be in the winter so this will drive prices up. The best advice I have is to book everything in advance, including your car rental. Prices get steep closer to the holidays and inventory runs out! If you are planning on traveling to Hawaii during COVID read this blog first. Thanks for following our journey as we work remotely the rest of this year! I hope this helps you plan your winter Hawaiian vacation.