If you’re planning a trip to Hawaii in 2022, you’re in for a treat. With sparkling waters, stunning sand beaches, waterfalls, volcanoes, and more, Hawaii is an amazing vacation destination. After living here for over four years (and visiting dozens of times before making the move), we have learned a thing or two about planning the perfect vacation.

Here are the best tips that you need to know to help you have an amazing trip, whether it’s your first time or your 50th:

What to know before your trip to Hawaii:

1. What are the COVID restrictions?

Through March 25, 2022, visitors to Hawaii will need to know what COVID restrictions are in place before visiting Hawaii. There are two types of requirements: requirements to enter Hawaii and then requirements to know once you arrive. Beginning March 26, 2022, there are no restrictions for entering Hawaii. You do not need to show a negative COVID test or proof of vaccine.

The mask mandate for Hawaii has also expired, so there is no state level requirement to wear masks indoors or out.

This official Hawaii State site has all the latest and greatest information you need to know.

2. What island should you visit?

The first and most important step in planning a trip to Hawaii is to pick the island or islands you want to visit. While the islands do share similarities, there are enough differences that it’s important to spend time deciding which island is right for you.

This video we made will help you pick the perfect island for your trip. But if you’re short on time, and can’t watch it just yet we have a quick quiz to help you narrow down your options.

Head to Oahu if: you enjoy nightlife, great food, and a cosmopolitan vacation. It’s also the best island in Hawaii for hiking.

Fly to Maui if: beaches, snorkeling, and great resorts are your thing. It’s also the best Hawaiian island for snorkeling.

Pack your bags for the Big Island if: volcanoes, adventure, and swimming with manta rays is on your bucket list.

Kick your feet up in Kauai if: you love jagged cliffs, lush landscapes, and a quieter, slower pace.

3. What’s the best time of year to visit Hawaii?

There is truly no bad time to visit Hawaii, but there are some factors that make certain times of the year more optimal than others. When we think of the best time of year to visit Hawaii (or the worst) we like to break down when to visit based on the best weather, the best cost, and the fewest crowds.

In general, we think that the best time to visit any Hawaiian island is during the shoulder season: September/October and April/May. 

Here’s how we came to that decision:

Hawaii trip planning weather


Hawaii is located in the tropics, which means that you will have warm weather year-round. But there are definitely months of higher rainfall. And if you want to have the best chance of avoiding rain on your trip, you shouldn’t visit during those months.

The chart below breaks down the average rainfall by month for each island. Note, rain varies on different sides of each island — we are showing average rainfall for one popular visitor destination on each island.

planning a trip to Hawaii


A trip to Hawaii is expensive. And coming during a peak time, like between Christmas and New Years, can make your trip even more expensive. If you want your travel dollars to go further and get better deals on accommodations and flights, the best time to visit is during May, September, October, and November. During these months you’ll find better deals on hotel rooms and vacation rental stays.


Avoiding the crowds can mean the difference between getting on the boat tour that you’re excited about or staying on shore. Or finding parking at the beach that you want to visit.

Just like most vacation destinations, Hawaii has very clear busy periods and slower periods. The Hawaii Tourism Authority does a great job of tracking visitor arrivals to Hawaii and it’s clear that if you want to avoid crowds, February, April, May, September, and October are the months to visit.

That said, if you’re coming to Hawaii for something very specific, like whale watching, you’re going to be a little less flexible with your timing. Whale season runs from mid-December through mid-April, so showing up outside of those months would be a disappointment.

Related read: This is the worst time to visit Hawaii (we really try to avoid this period if possible!)

Hawaii Trip Planning

4. How long should your trip to Hawaii be?

Getting away for a vacation can be difficult, but you want to stay long enough to make it worth your while. Hawaii is not a quick trip, even from the west coast. Plan on a 5 hour plane ride and a few hours time difference. So heading to Hawaii for just a few days will make your trip feel rushed and exhausting.

We think that the minimum amount of time you should plan for a trip to Hawaii is one week. During that week you’ll be able to stay on one island and explore a few different areas. You can make the most of your time by using one of our step-by-step itineraries.

If you can, stay longer and see more. And if you plan to island hop, your trip needs to be much longer than one week.

If you know what island you’re planning to head to, you can dive into more of our advice with these articles:

5. Where should you stay? Hotel or vacation rental?

Once you know what island you’re visiting, it’s time to book your accommodations. The first big decision comes down to booking a hotel or a vacation rental.

Stay in a hotel if you’re looking for a resort experience: big pools, great service, and daily housekeeping. Book a vacation rental if you are traveling with a group, want more space, and would prefer to have a kitchen instead of eating out every meal.

Still on the fence? You can read our full breakdown of whether you should choose a hotel or vacation rental for your Hawaii vacation.

If you know what island you’re visiting, we have specific advice on where to stay on each island — locations, hotels, and vacation rentals. Check out our island-specific travel guides:

Oahu Travel Guide

Maui Travel Guide

Big Island Travel Guide

Kauai Travel Guide

6. Do you need a rental car?

To fully enjoy your vacation, you probably need to rent a car. But that doesn’t necessarily mean you need to rent it for the entire duration of your stay, especially if you’re staying in Waikiki.

If you’re planning a trip to Oahu and you’re staying in Waikiki, there may be days where your rental car is never used. There’s a lot to do within that 2-mile strip! You can save on expensive hotel parking fees by just renting a car on days that you want to explore the rest of the island. Rental car companies have offices in Waikiki which makes it convenient to pick up a car and take it out for the day.

There is also a car share company, Drive Hui, that is available in Waikiki.

On the other islands, it’s a bit trickier to go without a car. To see and explore, you’ll probably want to book one. We love using Discount Hawaii Car Rental to help us get the best price for a rental car on each island.

Set on not getting a car for your entire trip? Here are some creative ways to visit Maui without a rental car.

7. How much does a trip to Hawaii cost?

Let’s be blunt: a trip to Hawaii is never cheap. There are definitely ways to save money, but it’s still an expensive destination to visit.

To help you get an idea of how much you should plan on spending (or how much you’ll need to save up), we calculated the cost for a family of 4. We estimate that an average trip cost for a family of four for 10 days is approximately $12,000. You can read all about how we got that Hawaii trip cost estimate here. But remember this is an initial estimate. Your trip cost will vary based on when you go, what island you visit, and how you want to spend or save your money.

Related read: What is the cheapest (and most expensive) island to visit?

Hawaii trip planning Maui

8. How far in advance should you book your trip to Hawaii?

The summer of 2021 taught us one big lesson: for the best vacation experience, book early. Visitors were disappointed with the lack of availability of rental cars, completely sold-out tours and luaus, and no restaurant reservation availability.

To avoid disappointment, book these things early:

Rental Cars

We recommend booking a rental car when you book a flight. That way you know you have something reserved for you and you won’t be stuck with a 2 door coupe for $500/day for your family of five.

Because it’s important to book your rental car early, we always use and recommend Discount Hawaii Car Rental. They almost always have the best prices (seriously we’ve saved thousands with them), they book with national carriers, and you don’t have to pre-pay your reservation. So you’re welcome to check prices as often as possible and if you find that prices have dropped, you can cancel your reservation and just make a new one.

Hawaii Trip Planning Tours and Activities

Tours and activities

If there is a specific tour or activity that you know you want to do, consider booking it a few months in advance. Luaus and popular tours book up very early, especially during the busier months.

We’ve put together a list of our favorite tours on each island, to help you get started planning. It took us 18 months and a lot of testing out tours, but we have a list of tours for each island that we’re excited to share.

Entry tickets

There are a number of natural landmarks in Hawaii that require a ticketed entry. The state is trying to protect the natural resources and land by making sure that each spot doesn’t have too many visitors at one time. But with some advanced planning, you can secure your ticketed entry to some of these beautiful locations.

A few popular spots that require ticketed entry include:

We layout all the necessary reservation timelines in our island itineraries. They make your planning so much easier.

“So excited. We have been loving your itinerary!!! We would have paid triple the price for this. It’s so valuable!” – Sara C. 

Hawaii Trip Planning restaurants


If you are hoping to hit up the most popular restaurants in Hawaii, planning ahead is crucial. But how far in advance they accept reservations varies. For example, Mama’s Fish House on Maui accepts reservations 6 months in advance. But Merriman’s on Maui only accepts reservations 30 days in advance.

Don’t forget: all of our island itineraries have specific instructions on when and how to make reservations for restaurants, activities, and sights on your trip. 

9. How many islands should you visit on your trip to Hawaii?

You’re making a big trip to Hawaii and you want to see as much as possible, but do you have enough time to visit more than one island? We recommend that if you’re taking a one week trip, you stick to one island. There is a lot to see on each island and you could stay as busy as you’d like to for more than a week, easily. If your trip is 10+ days, you could add on a second island to visit, but know that you will be moving around a bit more and you probably won’t get to see everything on each island that you were hoping to see.

While the islands in Hawaii are close together and just a quick 30-45 minute flight, your island hopping travel day will still cut into your vacation. Between packing up, the airport process, and checking into accommodations on your new island, this can easily take up half a day of your vacation.

Related read: Get all the details you need to know about island hopping in Hawaii. 

Hawaii Trip Planning Maui

While you’re in Hawaii:

Once you’ve landed in Hawaii, congratulations! Soak up that sunshine and start living that epic vacation life. Here are some important details to know now that you’re on island time.

10. Understand the geography  

Geography on the islands is important because it will affect the weather you experience and what you do while on vacation. One big thing to understand about the geography is that each island has a windward and a leeward side.

The windward side of each island faces the tradewinds. Here you’ll get more rain and wind, but you’ll also get lush landscapes (thanks to all of that rain!). The leeward side of each island is more protected from the wind and rain and you will have drier, sunnier weather. Most of the famously beautiful beaches you plan on visiting are located on the leeward side of the island.

For example, on Maui, the leeward side of the island includes some great beaches, like Wailea Beach and Ka’anapali Beach. The windward side of the island is home to the Road to Hana and a lot of beautiful waterfalls.

When you understand the island’s geography, you can better prepare for what to expect. If you’re looking for a lush, jungle experience, with waterfalls and greenery head east to the windward side. If you’re looking to beat the rain and get some sun, the west or leeward side is your best bet.

11. Eat local

One of the treats about visiting a new place is the opportunity to try new, local foods that you might not eat back home. There are a few things you should consider trying while you’re here:

  • Fresh, locally caught fish: If you’re a seafood fan, don’t miss out on the fresh fish. You can enjoy it at either a restaurant or from a fish market. You’ll see options like Mahi Mahi, Ono, Opah, Ahi, and more.
  • Locally grown produce: Enjoy dragon fruit, coconut, lilikoi, pineapples, locally produced honey and more. We love doing farm tours, but if that’s not part of your vacation itinerary, try a farm-to-table restaurant. You’ll get to sample some island flavors while supporting the agriculture industry here.
  • Traditional Hawaiian food: You don’t need to go to a luau to sample some traditional Hawaiian dishes. Look for dishes like poi (taro that has been pounded into a paste), laulau (meat wrapped and cooked in taro leaves), kalua pig (slow-roasted pork cooked in an underground oven), and poke (diced, raw fish that is wonderfully flavored).
  • Shave ice: Not shaved ice. You may think that this is like a snowcone, but it couldn’t be further from it. Soft fluffy ice shavings that are flavored with different syrups and creative flavor combinations. You might also have the add-on of fruit and ice cream. It’s so, so good. Don’t forget to check out our five favorite shave ice spots on Kauai

Sample straight from the ground. Check out our favorite farm tours on Maui. 

Hawaii trip planning whale watching maui

12. See the can’t miss sights

The beaches in Hawaii are incredible. But there’s a lot more to explore on each of the islands. Some things you might want to add to your list include:

This was just a taste, but there is so much more. If you want to view the highlights of each island, check out our cheat sheets.

Not only do these island cheat sheets highlight the top 4 can’t miss sights and activities on each island, you’ll also get tips on where to stay, a map of the island with the main sights, towns, and airport locations, the top places for food on each island, and more.

They’re designed to make kicking off your trip planning even easier. Grab them for free and start planning!

13. Bring the right (reef-safe) sunscreen

Before you throw your favorite brand of sunscreen into your bag, stop. Hawaii has rules in place to help protect the reef and sea life that are so important. One of those rules is around the type of sunscreen you can use. Sunscreens containing chemicals oxybenzone and octinoxate are no longer sold in Hawaii. These chemicals have been found to contribute to coral reef bleaching.

You can check out a full list of our favorite reef-safe sunscreens and make sure you’re only using legal sunscreen in Hawaii.

Hawaii trip planning snorkeling

14. Snorkel to see amazing sea-life

Living here, we love spending our days in the ocean. There is nothing like diving into the warm, tropical waters and being greeted by colorful fish, turtles, octopi, and more. But if it’s your first time snorkeling in Hawaii, there are some essential details you should know.

Understand safety risks

Snorkeling may look easy, but water conditions, physical conditions, and more come into play. It’s not always as safe as it looks — drowning is the number one cause of visitor death in Hawaii. Before you go out, review the safety tips to make sure you’re doing what you can to keep yourself safe.

Use good gear

Hear me out on this one. You’ll find a number of blogs telling you to pick up a cheap set of fins and a mask from an ABC store or Target once you arrive. There are a few reasons we don’t suggest that.

First, safety. Well fitting gear (fins that stay on and a mask that doesn’t leak) is important to keep you safe.

Second, it’s a significantly more enjoyable experience to snorkel in gear that fits well and is easy to use. This was apparent when we were trying to teach our preschooler to snorkel. The cheap gear didn’t cut it but once we got him in a good mask, he was off!

Third, buying cheap gear just adds to the already full landfill here.

That’s not to say you need to shell out and buy expensive gear. If you plan to snorkel many times, even after this trip to Hawaii, it’s worth it to buy good snorkeling gear. We have sets listed on our recommendations page.

Otherwise, renting snorkeling gear is a great option. The shop staff can help you find gear that is the right fit for you. And if you find that it doesn’t work right, pop in and switch it out for a different rental set.

Go to the best places

All snorkeling spots are not created equal. Some spots on the island naturally have a more vibrant reef and are home to more fish and sea life. Other spots may be more affected by ocean swells at various times of the year.

On our guide pages we list out the best snorkeling spots on each island. You’ll want to check these pages out before hopping in the water:

Oahu Travel Guide

Maui Travel Guide

Big Island Travel Guide

Kauai Travel Guide

And if you’re looking for the best snorkeling spots in Hawaii by month, we have you covered.

Hawaii trip planning turtles

Take a snorkeling tour

While we love snorkeling from the beach and we do it often, going on a snorkeling tour is a really special experience. On a good snorkeling tour, you’ll learn about the ocean, the sea life, and be taken to some cool spots that aren’t easily accessible from the beach. Plus, you’ll be able to see the islands from the water, giving you a different perspective and appreciation for their beauty.

We have a full list of our favorite activity providers and tours on each island, but here are a few that are incredibly special:

Hawaii trip planning spinner dolphins

Spinner dolphins off the coast of Lana’i

Understand the rules protecting sea life

When you’re snorkeling and enjoying the crystal clear water, it’s important to keep in mind that you want to make as little impact on the sea life as possible. Stay at least 10 feet away from turtles while snorkeling. You’re required to stay at least 50 feet away from Monk Seals. And if you see spinner dolphins, you’ll need to give them 50 yards of space.

15. Learn about the culture of the islands

Hawaii is a unique US state for many reasons but one thing that is important to understand is that Hawaii had a long and rich history before becoming part of the US. Learning a little about the culture and the history will enhance your stay and give you new appreciation for these amazing islands.

There are plenty of ways to learn more about Hawai’i while you’re here. Consider visiting museums. On Oahu we love visitng the Bishop Museum and Iolani Palace.

You can also visit heritage sites like Puuhonua o Honaunau National Historical Park on the Big Island. You can find a list of heritage sites to visit on the Hawaii Tourism Authority website.

Make your trip planning so much easier

If you’re planning a trip to Hawaii, we’ve got you covered. Our island itineraries help you navigate the planning process and make your trip smooth once you’re on-island. Thousands of customers have loved them, whether they were planning for a trip that was a year away or a trip that was a day away.

This is not a question but simply a “thank you”.  Our original European vacation plans fell through last minute.  So we had 2 weeks to plan something else…your Vacation Guide was a LIFE SAVER.  We had no idea how to begin planning, which island, where to stay, what to do.  Your honest reviews of the islands led us to Maui for 8 days….Mahalo!!.  You guys are awesome!!” – Eva M.

Hawaii itineraries