Planning a Hawaii vacation can sometimes feel overwhelming. Where do you start? What do you do? Which island should you visit? What should you eat and where should you stay? And when is the best time to go? 

First off, take a deep breath. 🙂 

Planning a Hawaii vacation doesn’t have to be stressful—in fact, it can be a lot of fun!

When my husband and I got married 2.5 years ago (at the time I’m writing this post), we decided that we wanted to visit Hawaii almost every year. That is to say, we wanted to visit during the winter months at least once. After a few trips, I can happily say I enjoy planning a Hawaii vacation. 

It’s really fun and does take a little bit of legwork. So if this is your once-in-a-lifetime trip, or one of many trips to Hawaii, then follow these simple steps to plan the perfect trip to Hawaii! 

1. Choose dates for your vacation to Hawaii

Did you know that there are busy seasons in Hawaii? Most people like to visit Hawaii when their own weather at home isn’t so great. Usually December to beginning of April are Hawaii’s busiest times. 

People just want to get out of the cold, like me. 😛 

But don’t let that deter you from choosing dates in the winter months. Hawaii is generally crowded all the time. These dates might just make it a little more difficult to book hotels, flights, and cars. And, unfortunately, some companies may raise prices during these times because they’re known to be so busy. 

Personally, I plan for a time that works with my husband’s work schedule. And maybe you have to schedule around children’s school, activities, and so forth. 

I find that choosing a date comes down to asking myself these questions: 

-What is most convenient for me? What works with my schedule? and 

-Do the prices look reasonable at this time? (Sometimes you WILL find that sweet price that works just perfectly for you and your family). 

To sum up, here are some things to think about when choosing your dates: 

• November is one of the wettest months in Hilo on the Big Island (I know because I lived there).
• November to May is when the whales migrate, with January-March considered the peak whale-watching season. These are great times to visit Maui. 
• Good travel deals usually occur in April, May, September, and October. 
• The Hawaii Vacation Guide says that December is the worst month to visit Hawaii. 

2. How many days should I plan for my Hawaii vacation?  

Long answer: I lived in Hawaii for most of my life. Family members and friends have visited many times. After my own trips to Hawaii, I came to the conclusion that 5-7 days is the perfect amount of time.

It gives you enough time to relax on the beach, explore sites, and do other fun activities like snorkeling, whale-watching, hiking, attending a luau, and so forth. 

Short answer: 5-7 days are the perfect amount for a trip to Hawaii. 

3. Which island should I visit? 

When planning a Hawaii vacation, you should know that there are 8 Hawaiian islands. However, only 4 of the 8 islands are the main attractions: Kauai, Oahu, Maui, and Big Island. 

If you are a first-timer to Hawaii, I suggest starting with Oahu or Maui, as they contain most of Hawaii’s iconic attractions. 

Kauai and Big Island are much slower, with a greater diversity of eco systems and natural beauties. They are, in my opinion, less crowded too. 

Check out my article: 10 iconic things to do on any Hawaiian island 

Here is the list of ideas that you can do on each island: 

Kauai: Enjoy beautiful and lush scenery, relax on white sand beaches, visit the “Grand Canyon of the Pacific,” take a boat out to see the Napali coast, see the beautiful Waipi’o falls, and go snorkeling at Tunnel’s Beach. This island is the honeymooner’s island, a perfect romantic getaway for couples. But there are plenty of family-friendly activities too! 

Oahu: Home to Waikiki, North Shore, and plenty of family-friendly hikes and activities, Oahu is Hawaii’s picture icon. There’s a lot of history, hikes, sites, and iconic Hawaiian food in town (Waikiki) and across the island. With so many things to do, this is a great spot for families!

Maui: Visit Haleakala National Park with its wide variety of species and landscapes, go whale-watching along the coast, snorkel at Molokini crater, and hold on tight as you drive the road to Hana. 

Big Island: Visit Hawaii Volcano National Park and admire the unique species of the island, see lava pour into the ocean, relax on a black sand beach, hike to a green sand beach, jump off the southern-tip of the United States, and see the snow on Mauna Kea. 

To make it simpler, I created the ultimate bucket lists for all four main islands.

Get instant access to these beautiful lists FREE when you sign up with your email. 🙂 

4. When planning a Hawaii vacation, how much money should I expect to spend?

This depends for every person, and I’ll show you how I organize the budget:

First, I write down the following categories on a piece of paper: flights, hotel, car, and food.

Second, I calculate how much it will be per person per day. 

Finally, times that number (from the following step) by how many people and how many days. That should give you a rough estimate to budget for your trip.

I’m sorry I don’t have exact numbers, but I give my best estimates below. 

Here is a little breakdown. 

Flights: 

My husband and I actually don’t pay for our flights besides about $20 dollars in taxes and fees, so check it out here:

How to Easily Budget for a Hawaii Vacation

Usually flights from the continental U.S. range anywhere from $500-$1200 round trip. 

The easiest way to know the average price of your flight to Hawaii is to do a search on Kayak, inserting your dates and then checking the box that says “flexible dates.” Kayak will highlight the cheapest rates for you. 

Hotel/stay: 

Hotels in Hawaii are expensive, with the starting price usually at around $100 a night. Because hotels can get pricey, Airbnbs and VRBO are budget-friendly options but carefully read reviews and watch out for scams. 

Unfortunately, bugs (cockroaches, mosquitoes, centipedes, etc) are a thing in Hawaii. And it’s the huge thumbs down for me, so just be careful when picking airbnbs or vrbo rentals. 

I don’t “pay” for hotel stays besides taxes and fees, and I’ll write an article how to do that soon! I will update this post as soon as I write that. 🙂

Car: 

When you book your flight, try to do a package deal with hotels and cars. There is usually a “package deal” option on most airline company websites for flights + car. I’ve found those to be some of the cheapest rates. 

Sometimes you can find even better rates with the flight + hotel + car packages. 

I don’t go through third party vendors anymore (like Priceline, Expedia, etc) because it’s so difficult to cancel or get help if something goes wrong. However, I have heard success stories of people getting amazing deals through third party vendors. I just like to keep things simple and work directly with companies, but if it works for you, then go for it! 🙂 

If you can’t get a good deal through a travel package, you can rent a car through any of the car rental companies on the islands. There are plenty to choose from, with rates as low as around $20 a day. 

Another great option is to use Turo. This is like airbnb for cars. So people put their cars on the Turo app for others to rent. Most times they’ll even pick you up from the airport without a fee, which is very convenient. No long lines at the rental car place, just one person working with another. 🙂 

Another amazing benefit is that you can rent a car via Turo for as low as $15 a day! The prices are very reasonable. Even luxury vehicles are seriously discounted in comparison to rental car companies. 

Food: 

If you plan to eat out for breakfast, lunch, and dinner I would estimate this for the cost: 

• $10 for breakfast
• $15 for lunch
• Anywhere from $18-$25 (or more) for dinner 

You can really cut costs down by buying stuff at the grocery stores or Costco to make your own meals, like breakfast foods, sandwiches, snacks at the beach, etc. 

However, I do encourage you to support the businesses in Hawaii by eating at local restaurants, food trucks, and farmers markets some of the meals. These businesses rely on the tourism industry.  

Also, I’m a firm believer that “tasting” a place makes travel that much more experiential, inspiring, and fun. 

Activities: 

You can spend hundreds of dollars on activities or nothing at all! There are plenty of free experiences on the islands to check out and enjoy. 

But just so you can get an idea, here are some examples of activities and price ranges: 

• Renting a surfboard: about $20/day
• Surfing lessons: about $100/person
• Whale watching tour: about $150/person
• Luau event: about $120/person
• Private tour (horseback riding, whale watching, hike, etc): about $500-$700/person
• Helicopter ride: $300-$600/person 

And here are some free activity ideas: 

• Relaxing on the beach
• Hiking (to a waterfall, mountaintop, beach, etc)
• Historic sites
• Free night shows at specific hotels (like in Waikiki) 
• Botanical gardens 
• Snorkeling (bring your own gear) 

Check out my ultimate Hawaii bucket list for more ideas! 

5. Booking flights, hotels, and car

I talked about the budgeting part of booking flights, hotels, and the car, but what about actually booking them? 

As I mentioned before, I recommend going directly through companies, but third-party vendors can sometimes have better deals. The reason I go directly through companies is the security and ease of communication if I run into any problems. 

Especially when Covid hit, I felt really grateful I could cancel flights, hotels, and cars quickly and easily through the company’s websites. 

6. Should I visit more than one Hawaiian island during my trip? 

When planning a Hawaii vacation, my short answer to this is no. 

There are two exceptions:

Exception #1: If you catch your inter-island flight in the evening, that allows you a whole day on the island. 

For example, you spend 3 full days on Oahu, and the third night you fly out to Maui. If you fly out in the night, you’ll be able to pick up your rental car and get situated at your hotel in Maui without wasting precious daylight hours. 

From observing friends and family plan their trips to Hawaii, I’ve noticed that so much time in Hawaii is wasted at airports, catching a flight to the neighbor island, only to cram in a day or two there. 

It’s really difficult to explore and enjoy the island, especially if it’s your first time there, in only a day or two. 

Ask yourself: Is it worth my time to travel to another island? Do I have enough time to really do what I want? 

I suggest visiting one island at a time. If this really is your once-in-a-lifetime trip to Hawaii and you can fit in more than one island, I recommend a max of visiting two islands. 

So many of my friends and family have made the mistake of visiting two islands, only to feel frustrated that they spent half the day at the airport, waiting in line at the rental car company, and checking in at the hotel. 

Don’t waste your precious time in Hawaii. 

Exception #2: You’re planning a Hawaii vacation for a long time.

Let’s say you’re going to Hawaii for 10 days. You can spend 5 days on one island, and 5 days on the other, giving you plenty of time to explore and really enjoy each island. 

Again, this is just my opinion but I highly recommend doing one island on your visit, unless you plan to spend a longer amount of time in Hawaii. 

To recap, my top tips if you want to do two islands in one vacation are: 

-Travel in the evening/night time so you’re not wasting your day at the airport, picking up the rental car, and checking in at the hotel. 

-Give yourself plenty of time to explore both islands. 

7. What activities should I do on my Hawaii vacation? 

This is just a starting list, and doesn’t even begin to include everything! 

• Relax on the beach, obviously 🙂 
• Go surfing, boogie boarding, body surfing, SUP, snorkeling, or scuba diving 
• Take a whale-watching tour
• Eat shave ice
• Try local cuisine 
• Attend a luau
• Visit historic sites like the Iolani Palace, Pearl Harbor Memorial, etc 
• Hike to beautiful waterfalls and mountain tops 

I recommend checking out these pages on my blog for more ideas: 

Go here and click on which island you’d like to visit

8. Preparation is key: What to know before you go to Hawaii

Hawaii is a unique place, with a halo-halo (mix) of cultures, eco-systems, and people. So it’s important to respect the people and the land, a concept called malama. 

Simple preparation like learning simple Hawaiian words, knowing what to wear, and being aware of the environment will help you feel more like a part of the island. 

Check out these articles to help you prepare for your trip: 

What to Pack for Hawaii

The Best Reef Safe Sunscreen

Hawaiian Words to Know Before you Go

13 Best Tips for First Time Visitors to Hawaii

9. Get Covid testing, if needed 

I’ve updated this article since I published it, and Hawaii is always changing its guidelines. Be sure to check out their website for the latest on covid testing and travel to Hawaii.

We had to get tested for covid so we went to Walgreens. I suggest going to your local local Costco and Walgreens. Try to plan ahead because the testing slots can fill up quickly. 🙁 And don’t forget to upload the results onto the Hawaii Safe Travels website before you leave!

Here is the list of certified places to get tested: Hawaii’s Pre-Travel Testing Program

10. Go on vacation to Hawaii and have fun!!! 

*Whew* Let’s take a deep breath because you’re finally going to Hawaii. You’re done planning a Hawaii vacation and it’s time to go! This is exciting and your experience will be unforgettable! 

Don’t forget to take pictures, malama the ‘aina, and HAVE FUN! 

Love,

Lei

Let’s hear it from you! 

Was this guide helpful? Do you have any more questions about planning your trip? Please let me know in the comments and mahalo for your kokua!

Save this for later!

Don’t forget to pin this so you can come back to it. 🙂 

Share the aloha!