Hawai'i Planning Guide: 8 Frequently Asked Questions

Hey there!¬†ūü•į¬†

What Hawaiian Islands can you visit? What is the bet time to travel to Hawai'i? What island is the most beautiful? How long should a Hawai'i vacation be? How many islands should you visit? How much time should you spend on each island? What are the things to do in Hawai'i? What does a Hawai'i vacation cost?


A dear friend of mine planned a Hawai'i vacation last year and she turned to me for advice, since I've already planned a 4-week Hawai'i vacation myself. In fact, she asked me some of the questions I also pondered during my preparation.

Then I went online, scanned threads and blog posts, and found out that the majority of the people who want to travel to Hawai'i have the exact same questions.

I hope this Hawai'i planning guide answers these questions and helps you to create the Hawai'i vacation you're longing for.

These are the top 8 frequenly asked questions people have when planning a Hawai'i vacation:

  1. What Hawaiian Islands can you visit?
  2. What is the bet time to travel to Hawai'i?
  3. What island is the most beautiful?
  4. How long should a Hawai'i vacation be?
  5. How many islands should you visit?
  6. How much time should you spend on each island?
  7. What are the things to do in Hawai'i?
  8. What does a Hawai'i vacation cost?

So without further ado, let's dive right into it:

1. What Hawaiian Islands can you visit?

The Hawaiian Archipelago consists of 132 islands, 8 of which belong to the main islands: Kaua'i, O'ahu, Moloka'i, LńĀna Ľi, Maui, the Island of Hawai'i, also called the Big Island, as well as Ni'ihau and Kaho'olawe. You can visit all but¬†2 of those 8 major islands. Ni'ihau and Kaho'olawe are not open for tourists.

You can visit:

  • Kaua'i
  • O'ahu
  • Moloka'i
  • LńĀna Ľi
  • Maui
  • Big Island (aka Island of Hawai'i)


2. What is the best time to travel to Hawai'i?

In regards to climate and weather, you can't really do anything wrong here. The climate is tropical, this means that¬†the average anual temperature is 25¬įC or 77¬įF.

Hawai'i only has two seasons: summer and winter. 

Summer lasts from May to September.

In the summer, temperatures range from approximately 21¬įC or 70¬įF at night to 32¬įC or 90¬įF at daytime.

Winter lasts from October to April.

In the winter, temperatures are a little cooler, ranging from 18¬įC or 64¬įF at night to 26¬įC or 79¬įF during the day. In the winter, rain occurs more often.

Of course, these are only statistical data and the real temperature can vary. 

Owing to Hawaii’s proximity to the equator, hours of sunshine per day are almost stable throughout the year and day-night temperature differences are minimal. The sun rises and sets fairly quickly.

As you can see, there is little variation in climate. It might rain a little more during the winter and waves will be higher, but altogether the climate is pleasant throughout the year.

There is another thing I want you to know about:

There are several micro-climate zones in Hawai'i. This means that the weather in specific regions is different from the main tropical Hawaiian climate. E.g. mountain tops are cooler and perhaps snowy/icy, (lava) desserts are hotter and drier and on beaches it's warmer.


3. What island is the most beautiful?

Mirror, mirror, on the wall, who's the fairest of them all? 

The answer to this question is as subjective as the question "What is the most beautiful color in the world?". There is no right answer, as the answer depends on the person answering the question. For some, the most beautiful island is Maui, for some it's Kaua'i. Others love O'ahu - and so on.

There simply is no answer to this question I can give you. You have to find out yourself. The only thing you can do is to learn as much as you can about each island beforehand and find out what island speaks to you the most. 

You will soon understand that Hawai'i's true beauty doesn't lie in the number of pristine beaches or sublime waterfalls, but in the vibes and character of each island.

It would do all other islands injustice to say that one specific island is the most beautiful. Each island is unique and has its own beauty. Each island is magical. 

4. How long should a Hawai'i vacation be?

When answering this question I assume one thing: You're a person who likes to explore their travel destination. This means you don't only travel to Hawai'i to spend the entire day sitting on the beach and tanning. I also assume you're not a surfer (I believe in that case my recommendations are not fitting).

The answer to this question strongly depends on the money available to you.

Let's consider two cases:

Case #1: You are affluent and money isn't really an issue

You could stay as long as you want. You have to decide how long you want to stay in Hawai'i and how many islands you want to visit. For this, please see questions 5 and 6.

Case #2: You only have a certain amount of money available

Obviously, the length of your stay depends on your budget. The more money you have available for this trip, the longer you can stay. Then, several factors determine the length of your stay. Ask yourself these questions:

  • What and how many islands do you want to visit?
  • How long do you want to stay there?
  • What kind of accommodation do you choose (hotel, apartment, hostel)?
  • Will you self-cater or eat out most of the time?¬†
  • What activities do you plan on doing? Are they rather expensive or cheap?
  • Do you need a rental car?
  • Will you do a roundtrip, island-hopping or stay at a specific place the whole time?
  • For more ideas refer to questions 8 which goes hand in hand with this question

In case you want to first determine the length of your stay and then start saving money accordingly and to give you a general idea, here's my personal recommendation for the duration of Hawai'i vacation: 

In order to get the most out of your Hawai'i stay that allows you to really feel the islands, to get to know the culture, explore each island you chose to visit, to zoom out and get back in touch with nature:

  • stay at least two weeks
  • better yet 3-4 weeks

For each island you visit you can rougly plan 7 days and shorten or lenghten your stay accordingly, depending on your personal interests.

If you only want to vacation, as in: relax, tan, do nothing, then 1 week probably is enough.

BUT - I highly encourage you to NOT simply hang out, tan, do nothing. :) Hawai'i is incredibly unique and very exceptional in basically every respect: nature, landscapes, climate, geology, wildlife, marine life and flora. It would be a shame if you missed all these magical aspects. 

5. How many islands should you visit?

This depends on the length of your stay. Here are some suggestions:

If you stay 2 weeks, you could visit 2-3 islands.

If you stay 3 weeks, you could visit 3-4 islands.

If you stay 4 weeks, you could visit 4-5 islands. 

6. How much time should you spend on each island?

Here's a general rule of thumb: For each island you visit you can rougly plan 7 days and shorten or lenghten your stay accordingly, depending on your personal interests.

This was my personal itinerary for 4 weeks, perhaps it inspires you:

Arrival at Lihu'e airport on Kaua'i
10 days Kaua'i 
5 days Big Island
10 days Mau'i
5 days O'ahu
Departure from Honolulu airport on O'ahu

The next time I will travel to Hawai'i for 4 weeks, I would choose this route:

Arrival at Lihu'e airport on Kaua'i
8 days Kaua'i 
5 days Moloka'i
5¬†days LńĀna'i
5 days Maui
8 days Big Island
Departure from Kailua-Kona airport on the Big Island

As you can see, I left out O'ahu entirely and added two new islands: Moloka'i and LńĀna'i. The reason is simple: I enjoyed O'ahu, but it was a tat too urban for me. And I'd love to see Moloka'i and LńĀna'i, as they are supposed to be rural, calm and majestic.

Here are some recommendations for shorter travel times:

  • 1 week:¬† ¬†7 days Kaua'i
  • 1 week:¬† ¬†2 days Maui - 5 days Kaua'i if you want to visit 2 islands
  • 2 weeks: 3 days Maui - 6 days Kaua'i - 5 days Big Island
  • 3 weeks: 4 days Maui - 7 days Kaua'i - 6 days Big Island - 3 days O'ahu

General rule of thumb:

1 week per island, adjust accordingly

7. What are the things to do in Hawai'i?

If you believed that hitting the beach, doing a helicopter ride, learning to surf and visiting a LŇę Ľau with Hula Show is all that you can do, I'm here to proof you wrong! :)

There's so much that Hawai'i has to offer.

When doing I research for the Hawaiian Islands: Island & Landscape Formation and Nature online course, I've stumbled upon many great websites and information that wasn't suitable for the online course, but that I didn't want to deprive you of. So I created this simple guide to share with you:

Your Guide to Hawai'i Paradise

It's an 18-page PDF document with more than 130 tips, links and information on each of the 6 largest Hawaiian Islands that guides you towards the really important and worthy-to-watch attractions and sights. It includes a list of all towns, beaches, points of interest and cultural highlights for each island. This should help you to structure the islands better in your head, to prevent overwhelm and give you loads of ideas of what you can do in Hawai'i.

You get it as a free bonus if you enroll in the Hawaiian Islands: Island & Landscape Formation and Nature online course.


8. What does a Hawai'i vacation cost?

A trip to Hawaii can be expensive, but it doesn't have to cost a fortune. The question "How much does a Hawaii vacation cost?" is rather vague. You have to ask yourself the question: "How much does a Hawai'i vacation cost for me?"

Here are some factors that will determine your personal costs:

  • flights
  • choice of accommodation
  • choice of food
  • activities
  • rental car
  • gas
  • public transportation
  • entrance fees
  • insurances
  • souvenirs
  • miscellaneous (read below for ideas)

Certainly, the flights will be impactful, depending on your departure airport. But also think of all inter-island flights (island hopping). 

Next, as we discussed before already, it depends on the level of luxury you want to treat yourself to in regards to accommodation and food. 

What kinds of activities do you plan to do? How expensive will be they? 

Will you rent snorkel gear, surf boards, paddle boards etc.?

Do you have to pay fees to enter certain parks, hiking trails, museums, botanical gardens, ocean centers etc.?

What other expenses can you think of that have to be calculated? Perhaps: sunscreen, postcards, shave ice, tips, travel guides, laundry, visas, credit card fees, parking, getting to and from the airport etc.

But since you're here, I don't want to leave you hanging and give you a specific number that should help you get a good idea of what to expect in terms of the costs of a Hawaii vacation.

  • 3 weeks: 3.000-5.000 US $ / ‚ā¨
  • 4 weeks: 4.000-6.000 US $ / ‚ā¨

And here is an easy to remember rule of thumb:

Costs for a Hawaii vacation: 1 week ~ 1.000 $

Please be aware that it's only meant to give you a slight idea of what to expect. Your individual costs can be lower, higher or much higher than suggested.

If you need help calculating your budget or need a template that you can just fill out, the Vacation Planner for Finances Excel Sheet might be useful to you. It's included as a bonus in the Hawaiian Islands: Island & Landscape Formation and Nature online course.


Before you go, please read this

Before you go you need to hear one more thing: The Hawaiian Islands are magical.
The culture, language, history and the Aloha spirit are precious. The people are so friendly. The nature, geology and landscapes are outstanding.
It's imperative to me to make you aware of Hawai'i's true beauty, the wild and raw Hawai'i, to show you how the geology, mythology, nature, culture, language and climate are interrelated.
To help you see the bigger picture. By doing this, both you and I can contribute to more sustainable, friendly, respectful, responsible, sustainable and conscious travelling. 
Together, we can protect Hawai'i's nature, culture and language and help revive it. We will listen to their ancient stories and appreciate, acknowledge, their culture. As tourists entering a foreign land, we owe it to the Hawaiian residents and their land, their ocean, their heritage.


Be kind and love nature ūüĆĶ,



PS: There even is a¬†free course about Hawai'i¬†that will set you up for a meaningful Hawai'i experience.¬†And if there are any questions that you missed and need to have answered pop them in the comment box below and I'll be sure to reply. Don't hesitate! Chances are others have the same question as you and you'll do them a favor asking it.¬†ūüĆě



About the author

Daniela is convinced that by gaining deep insights into planet Earth and travel destinations you’ll create meaningful, grounding and memorable life and travel experiences. She explains fundamental geological processes that form and shape landscapes and combines these insights with philosophical and philanthropical views in her online courses, articles, and newsletter. She holds two bachelor's degrees in geosciences (B.Sc.) and business administration with tourism (B.A.). She is the owner and founder of EarthyMe, EarthyUniversity and the Science of Travel blog and the Stories of Earth newsletter.





Image Credit:¬†Photo by Seth Cottle¬†/¬† ĽAkaka Falls, Honomu, Island of Hawai'i, United States

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