Christmas vacation in Hawaii
[ Insider Tips ]

How to Plan a Christmas Vacation in Hawaii

Tired of freezing cold temps, whipping winds, and a foot of snow each Christmas? Me too. Each year there’s nothing I long for more than a Christmas vacation in Hawaii.

Who wouldn’t want to spend the holidays basking in the sun on a white sand beach as crystal clear waves crash on the shore? Just thinking about it feels like paradise!

Unfortunately, before escaping on a dream Christmas vacation in Hawaii, a bit of planning is required. Otherwise, you’ll waste thousands of dollars and scramble for reservations. That’s no way to spend the holidays.

To plan your perfect holiday in Hawaii, follow my guide.

Table of Contents:


Santa hat hangs off of a white hammock on a Hawaii beach

Setting Your Travel Budget

Before you get too deep in the planning process, you should know the winter months are a peak tourist season in Hawaii. Travelers come from all over the world to escape the cold winter weather, meaning transportation and accommodation rates are at their highest.

This is where a defined travel budget comes in handy. Knowing what you can afford to spend on a Christmas vacation in Hawaii ensures you plan out a trip you’re comfortable with.

When determining your budget, consider the following:

  • Flight and transportation costs, including gas
  • Hotel nightly rates
  • Activity costs
  • Expenses for dining out each meal
  • Shopping
  • Gratuity for waiters, tour guides, etc.

Figuring out a travel budget can be scary, but don’t worry! It’s possible to travel to Hawaii on a budget, even during the holiday season. The key is to be a little creative when organizing your travel plans.

It’s difficult to say what a typical travel budget would be for a trip to Hawaii, as it depends on factors ranging from your financial situation to the hotel you choose to say at. Fortunately, the next sections will help you devise your ideal budget.


Airplane right wing over a sun flare

Finding Flights

Sadly, flights to Hawaii are not the cheapest. However, if you do your research and possibly a bit of finagling, you will be able to find flights that fit your budget.

Buy Early

The sweet spot for buying flights is about 3.5 months or 3 weeks before your trip. This is when ticket prices tend to be at their lowest. Although, I would not recommend waiting until 3 weeks before your Christmas vacation in Hawaii to purchase plane tickets. Why leave it up to chance?

If possible, book your seats as far in advance as possible. Use a website with a price tracker to help you decide when to buy. Scott’s Cheap Flights is a great service to use if you have time to seek out the best deals.

Consider Trip Insurance

I live in New England which almost guarantees flight delays due to snow storms, ice, and freezing conditions. If you plan to depart from a similar location, consider purchasing trip insurance in case your flights get canceled due to weather issues.

Look at Other Airports and Times

If you have the option to depart from multiple airports, compare flights to Hawaii from each airport. Flight prices may fluctuate depending on your departure location.

Playing around with flight times can also reduce the overall cost of your tickets. Look for flight times that give you plenty of time on the island but won’t destroy your budget. A bit of compromise may need to be made. Would you rather save money on flights or spend more time in Hawaii?


Hawaiian island surrounded by deep blue ocean water

Choosing an Island

The hardest part about planning a Christmas vacation in Hawaii is choosing which island to visit. They’re all amazing! Ultimately, your decision will boil down to affordability and the activities on each island.

During the winter months, flights to Oahu and Maui tend to be the most affordable, but prices for rooms and activities on the islands will be high. In addition, since Oahu and Maui are considered to be the most “touristy” islands, they will also be the most crowded. Activities on Oahu and Maui range from captivating luaus to outdoor adventures, and historic museums to guided tours.

While flights to the Big Island and Kauai can be on the pricey side (although, not always!), the islands boast affordable accommodations and an abundance of free outdoor activities. Also, flights to these islands will include a few layovers, depending on your departure location.

Of course, if your travel budget permits it, island hopping is always an option, too!

After some research, pick the Hawaiian island that suits your travel preferences and start organizing the rest of your tropical Christmas getaway.


Sheraton Maui Resort exterior along the island coast

Booking a Hotel

From lavish condos to budget hotels, the Hawaiian islands have every type of accommodation you can think of. However, before you make your reservation, there are a few things to consider.

Hotel Amenities

When researching hotels, consider the amenities you need for your stay. Most travelers prefer to have amenities such as:

  • Free WiFi access
  • Complimentary breakfast
  • Ice makers
  • Parking
  • Swimming Pools
  • On-site dining

As you browse hotels, filter your search by amenities to ensure these conveniences are available before you book. And, since the winter season is a popular time for tourists, it’s in your best interest to book as soon as possible before all the rooms fill up!

Location, Location, Location

Also, factor in the hotel’s location. Accommodations near top destinations such as the beach or shopping village often boast hefty rates. Think about finding a hotel a short distance away from popular attractions or areas for lower nightly rates.

Seasonal Deals

To entice travelers to book a room, hotels may offer promotional discounts or deals during the winter months. To make your Christmas vacation in Hawaii more affordable, ask about available promotions before you book.

The Bundle it! promotion from Reserve Hawaii allows you to combine your hotel room with tickets to a luau, tour reservation, or other travel experience purchase for greater savings. Try it out and see how much you can save on a Christmas vacation in Hawaii!


Man in a red flannel T-shirt drives a car with black leather interior

Deciding on Ground Transportation

At first glance, you may believe you need a rental car while in Hawaii. However, this isn’t always true!

For instance, all of the islands have Uber and Lyft. These ride-sharing services can cut down on your travel time and expenses while exploring the islands. And, if you require a car for the day such as for a trip along the Road to Hana, services such as Turo are available for easy rentals. Plus, the bus system on certain islands, such as Oahu, is simple to navigate and super affordable.

However, if you do decide to rent a car for the duration of your trip, keep in mind that rental companies may restrict where your vehicle can go. This is due to the natural landscape of the island and for your safety as well. Always adhere to these restrictions!

The cost of a rental car will depend on the duration of your trip, the age of the renter, the size of the car, and the insurance package you select.


Two men carrying surf boards walk across the beach at sunset

Planning an Itinerary

Having an itinerary planned out ahead of time allows you more time to explore and enjoy the islands rather than figuring out what to do each day of your Christmas vacation in Hawaii.

Research the activities available on your island of choice and select those which interest you. A few of the top tourist activities and destinations include:

And, of course, this is only a handful of what’s waiting for you on each island! Best of all, each island is home to numerous free things to do. You can have a blast without blowing your budget.

If you know of a tour, activity, or luau you’d like to attend, book tickets ASAP. The earlier you reserve your spot, the better pricing you’ll receive. And, you won’t have to spend money on the spot once you’re on the island—it’ll already be part of your travel budget.


Sun hat, sunglasses, and miscellaneous beach items sit outside a blue suitcase

Packing Your Bags

Now that your trip is organized and booked, it’s time to pack!

While you should pack shorts and T-shirts for warm weather, keep in mind it’s still the winter. Although Hawaii doesn’t get piles upon piles of snow like we do up North, it can be chilly at night. If you’re one to think anything below 70℉ is cold, bring a light jacket and pants.

To simplify your packing process, use our Ultimate Hawaii Packing List. It’s got everything you’ll need, including reef safe sunscreen!


A palm tree is decorated with holiday lights for the season.

Enjoying the Hawaiian Holiday Celebrations

Once you’re on the island, kick back, relax, and enjoy your Christmas vacation in Hawaii! You’ve earned it.

While you’re there, take in some of Hawaii’s notable holiday celebrations including:

  • Honolulu City Lights
  • Lighting of the Banyan Tree in Lahaina
  • Waimea Christmas Lights Parade
  • Kauai Festival of Lights

These celebrations not only bring the Christmas spirit to each island, but they also educate visitors about Hawaiian holiday traditions.

Start Planning Your Christmas Vacation in Hawaii

Are you excited to spend the holidays in Hawaii? What are you still reading for? Go book your Hawaiian Christmas trip!

Oh, and Mele Kalikimaka!

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