11 Tips for Winter Travel to Hawaii

by Mariam Beard • Last Updated: December 2022

Disclosure: This post may contain affiliate links, which mean that we may receive a commission if you click through and make a purchase using these links – at no additional cost to you.

As a local resident of Hawaii, I have compiled 11 tips to help you make the most of your WINTER TRAVEL to the islands. From booking ahead to knowing where your activity is located, these tips will help you make the most of your time in Hawaii.

Tip 1: Holiday Hours and Weekend Hours are important to note.

December and January are typically the busiest months for Hawaii travel. It’s important to book your activities ahead of time. This is especially important if you’re traveling with a large group or family. A good example of this is the Old Lahaina Luau on Maui. It books up months in advance, so if the week you’re there the luau cancels due to rain, you won’t be able to get rescheduled unless there’s space.

Tip 2: Know That Sunset Times Vary

In December, January, and February Sunset time is earlier: 5:45/6:00/6:15pm

In Summer Months (July), sunset is later at 7:15pm

Keep the sunset time in mind if you are planning on dining at an oceanfront restaurant.

Tip 3: Know that Winter Season = Rainy Season

Plan ahead for any tours and activities as some outdoor activities can cancel.

December/January February is our rainy season.

Tip 4: Book ahead – especially with a large group

Book your activities ahead to get your 1st choice activity date and time.

Tip 5: Know there have been changes with reservations

As of May 2022, there is now a 100% online reservation system to hike DIAMOND HEAD CRATER. You go on the state’s website, pick the date you want to go, and it’ll show you a list of available times. You’ll pay the state $5 for entry or $10 for parking. From there, you’ll get a confirmation email and that’s what you show the box office at the arrival.

Link: https://dlnr.hawaii.gov/dsp/parks/oahu/diamond-head-state-monument/

Tip 6: Plan to Arrive Early for North Shore

If you’re trying to visit the North Shore, this advice is particularly useful if there’s a surf competition going on. If seeing the big wave surf is something that is important to you, make sure to give yourself a little bit of buffer time to actually find parking on the day that you want to go. Parking is often free AND limited.

Tip 7: Double Check and Know Where Your Activity or Tour Is in Advance

It’s always a good idea to double-check where your activity or tour is located. For example, if you’re doing a snorkel boat tour and your check-in point is at Kewalo Basin Harbor, it’s only about 4 miles (6.4 kilometers) or a 15 minute drive from Waikiki.

However, parking at that harbor is limited. If you’re doing an early morning tour or perhaps a sunset tour, give yourself a little bit of extra time to find parking just in case the main parking lot is full and you have to drive around a little bit to look for parking.

Tip 8: Give yourself ample time to get to/from your activities

It’s always a good idea to give yourself extra time to get to/from your activity in case you get lost (or take a wrong turn!) or get stuck in traffic. Traffic on Oahu is a very real thing and can be unpredictable.

Popular North Shore Activities:

Tip 9: Check to See If Your Activity Includes Transportation

Oftentimes, if transportation is available at a low cost, it’s typically going to be a lot cheaper than if you were to get a taxi, Uber, Lyft, or a rental car.

For example, the Polynesian Cultural Center’s own shuttle service only charges $25 per person round trip. If you’re a solo traveler or two people, paying $50 for round-trip shuttle service is going to be significantly less than having to rent a car, pay for gas, pay for insurance, pay for potentially the parking or valet at your hotel to keep the car overnight when you return, and all the time spent driving.

Tip 10: A Rental Car Can Often Be a Good Deal

If you’re traveling with a larger family or group, and you’re using your rental car not only as transportation to and from the activity but to do other things as well, a rental car might make the most sense.

For example, on the way to the North Shore zipline, you can also check out the Dole pineapple plantation, explore Haleiwa town, go into Waimea Valley botanical garden, and of course check out the rest of the North Shore.

Tip 11: Always Have Backup Transportation

Uber and Lyft are pretty reliable in the Waikiki area and downtown Honolulu. However, keep in mind that Uber and Lyft are people just like you or I, so if there aren’t any drivers in that specific area where you are – you’re kind of stuck. The same can be said for specific times.

For example, over Halloween there was an event called Hallabaloo in Chinatown. For this specific event, Uber and Lyft would normally cost about $20 to get from Chinatown to Waikiki. However, for this specific event, because of surge pricing and less drivers more demand, it would have cost $60 to go just about 5-miles.

If you’re staying at a hotel instead of an Airbnb, I would also recommend chatting with the bell desk to get the phone numbers for taxi services that your hotel’s bell desk recommends. It’s always best to have a couple taxi phone numbers in your phone saved just in case Uber and Lyft does not go through. 9 out of 10 times, it’ll be easy to get an Uber or Lyft, however it takes an extra two minutes to just get those extra taxi phone numbers and having them in your phone can give you peace of mind – especially if you’re going outside of Waikiki or if you’re concerned on getting a ride back into Waikiki.


Hawaii is an amazing place to visit and I hope these tips help you make the most of your time here. From booking ahead to knowing where your activity is located, these tips will help you make the most of your time in Hawaii. Have a great trip!

Related Posts:


2 responses to “11 Tips for Winter Travel to Hawaii”

Leave a Reply

Aloha! I'm Mariam.

I'm an Oahu resident sharing my adventures here in Hawaii to help take the guesswork out of planning your trip to Hawaii.

I've worked full-time as a concierge for a decade and have planned thousands of itineraries for travelers like you!


Blog at WordPress.com.