Planning a Trip to Hawaii in 2027: 14 Essential Details

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If you’re planning a trip to Hawaii in 2027, you’re in for a treat. After living in Hawaii for five years and now making multiple trips back per year (we’re lucky enough to call it our job), we learned a thing or two about planning the perfect vacation.

Here are our fifteen essential details to help you plan your trip to Hawaii, whether it’s your first time or your 50th.

Hawaii Trip Planning At a Glance

Question	Our Answer
What island?	Oahu: Nightlife, great food, hiking Maui: Beaches, snorkeling, resorts Big Island: Volcanoes, adventure, wildlife  Kauai: Dramatic landscapes, lush forests, slower pace
Best time of year	September/October and April/May
How long?	7 days minimum; the 2026 average was 7.57 days.
Where should you stay?	A hotel for a resort experience: big pools, housekeeping, plush amenities. A vacation rental for groups, more space, and a kitchen.
Rental Car?	Yes, at least for part of your trip.
Cost?	About $8,400 for a couple and $12,000 for a family of four.
How far in advance should I book?	Six months.
How many islands?	One

1. What island should you visit?

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

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

Big Island if… volcanoes, adventure, and swimming with manta rays are on your bucket list.

Kauai if… you love jagged cliffs, lush landscapes, food trucks, and a quieter, slower pace.

The first and most crucial step in planning a trip to Hawaii is to pick the island or islands you want to visit. While the islands share similarities, they also differ enough that you should take time to decide 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.

If multiple islands are calling your name, our island-hopping guide will help you plan. You may also want to consider opting for a cruise; we have you covered there, too!

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

September/October and April/May are some of the best times of year to visit Hawaii.

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

Here’s how we came to that decision.

Weather in Hawaii

Hawaii is located in the tropics, so you will have warm weather year-round. But some months have much higher rainfall. If you want 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.

Most resorts and vacation rentals are on the leeward (dry side) of the islands.

Prices in Hawaii

A trip to Hawaii is expensive. And coming during a peak time, like between Christmas and New Year, can make your trip even more costly.

If you want your travel dollars to go further and get better deals on accommodations and flights, the best times to visit are May, September, October, and November.

During these months, you’ll find better deals on hotel rooms and vacation rental stays. Our full cost breakdown for a family of four to Oahu helps explain the costs.

If you want to know how we budget, book, and reduce the cost of our travel, check out our article on booking a trip to Hawaii.

Avoiding Crowds in Hawaii

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

Like most vacation destinations, Hawaii has clear busy and slow 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’ll be 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!)

3. How long should your trip to Hawaii be?

We recommend planning a trip to Hawaii for at least 1 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.

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 a few days in Hawaii will feel rushed and exhausting.

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:

• How many days do you need on Oahu?
• How many days do you need on Maui?
• How many days do you need on Kauai?
• How many days do you need on the Big Island?

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

Stay in a hotel if you want 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 prefer to cook instead of eating out every meal.

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

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 which 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

We have an article on Where to Stay in Hawaii covering the resort areas on each island. Plus! We have a full Where to Stay directory with our favorite hotel picks (from budget to luxury) and vacation rentals on each island.

5. 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 staying in Waikiki, there may be days when you never use your rental car. There’s a lot to do within that 2-mile strip, and Waikiki Beach is great!

You can save on expensive hotel parking fees by renting a car only on days you want to explore the rest of the island. Rental car companies have offices in Waikiki, making it easy to pick up a car and take it out for the day.

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, and here is an itinerary for Oahu without a rental car.

6. How much does a trip to Hawaii cost?

A trip for two to Hawaii in 2027 costs about $8,400, according to our research. That’s roughly $760 a day for two people, or $380 per person per day. This factors in about $1,064 for flights, $3,198 for a hotel, $1,057 for a rental car, $2,000 for food, and $1,056 for activities.  

If you’re bringing the kids, a trip to Hawaii for a family of four costs around $12,083 by our calculations.

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.

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 reads: 
What is the cheapest (and most expensive) island to visit?
How Much Does a Trip to Hawaii Cost for Two People?

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

We recommend booking your trip to Hawaii at least six months in advance.

Our travel tip, over and over: for the best vacation experience, book early. Don’t be disappointed by a lack of rental cars, sold-out tours and luaus, or no restaurant reservations.

To avoid disappointment, book these things early.

Rental Car

We recommend booking a rental car when you book a flight, about six months in advance. 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 booking your rental car early is essential, we always use and recommend Discount Hawaii Car Rental. They almost always have the best prices (seriously, we’ve saved thousands with them), book with national carriers, and let you pay at pickup. So you can check prices as often as you like, and if prices drop, you can cancel your reservation and book a new one.

Lodging

Right now, you may be seeing some low plane fares from the mainland to Hawaii, so people are snatching up seats before looking at the rest of their trip.

While plane tickets are cheap, lodging is absolutely not. You may be able to find some deals here and there, but we recommend looking at (or even better, booking!) lodging when you book that flight.

Tours and activities

If you know you want to do a specific tour or activity, consider booking it a few months in advance. Luau 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. We’ve taken over 152 tours since we started The Hawaii Vacation Guide. We enjoy testing these tour companies so we can recommend the best!

We have discounts with many of our favorite tour companies. Find all our Hawaii Vacation Guide Coupon Codes here.

Reservations Required

Several natural landmarks in Hawaii require a ticketed entry. The state is trying to protect natural resources and land by ensuring that each site doesn’t have too many visitors at once. 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:

• Hanauma Bay Nature Preserve: tickets may be reserved two days in advance of your visit. Book a Hanauma Bay reservation here.
• Haleakala Sunrise Entry: bookings can be made 60 days in advance (with additional tickets being released two days prior to the date you want to visit). Book sunrise reservations here. Also consider: should you go to Haleakala for sunrise or sunset?
• Haena State Park: Plan your visit to this park on the north shore of Kauai and book tickets 30 days in advance.

We lay out 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. 

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. Here are our favorite Wailea and Kihei restaurants, if you plan to go to Maui.

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. 

Leaving Maui right now (literally about to board) and we LOVED your wayfinder itinerary. Always had great places to see and yummy food to eat wherever we went!

Laura

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

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 a second island to visit, but know you will be moving around a bit more, and you probably won’t get to see everything on each island you hoped 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.

Of course, you can always ignore this sensible advice, like a few of our newsletter readers, and read up on visiting all 4 major Hawaiian islands in just 2 weeks.

Related read: Get all the details you need to know about island hopping in Hawaii. (and no, there is no ferry in Hawaii unless you’re heading out to Lana’i from Maui).

While You’re in Hawaii, Trip Planning Advice

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

9. Leeward vs Windward  

Geography on the islands matters because it affects the weather you experience and what you do while on vacation. One big thing to understand about 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 to visit are 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.

10. Eat local

One of the treats of visiting a new place is the opportunity to try local foods you might not eat back home. Eating local is one of nine ways to have an authentic Hawaiian experience.

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 pounded into a paste), laulau (meat wrapped in taro leaves and cooked), kalua pig (slow-roasted pork cooked in an underground oven), and poke (diced raw fish, wonderfully flavored).
• Shave ice: Not shaved ice. You may think that this is like a snow cone, 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. 

11. 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. And some of these can’t-miss activities can only be done in Hawaii.

Some things you might want to add to your list include:

• Night snorkeling or diving with Manta Rays on the Big Island
• Seeing the sunrise or sunset from Haleakala Crater on Maui
• Watching the big wave surfers on the North Shore of Oahu
• Viewing the stunning cliffs of the Na Pali Coast on Kauai
• Hanging out with humpback whales during their annual migration to Hawaii
• Hiking an active volcano in Hawaii Volcanoes National Park

This was just a taste, but there is so much more. To see the highlights of each island, check out our cheat sheets.

These island cheat sheets highlight the top 4 can’t-miss sights and activities on each island, plus 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!

For a full bucket list of everything you can enjoy in Hawaii, check out our list of the best things to do in Hawaii, organized by island. This list has some unexpected ideas!

12. Bring the right (reef-safe) sunscreen

Before you throw your favorite brand of sunscreen into your bag, stop. Hawaii has rules in place to protect the reef and sea life, and they matter. One of those rules is around the type of sunscreen you can use — you can only use reef-safe sunscreen in Hawaii. Sunscreens containing the 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.

13. Snorkel to see amazing sea life

Living here, we love spending our days in the ocean. Nothing beats diving into warm, tropical waters and being greeted by colorful fish, turtles, octopuses, and more. But if it’s your first time snorkeling in Hawaii, here are a few 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 and learn about ROPE, a condition that can be life-threatening.

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 essential to keep you safe.

Second, snorkeling is much more enjoyable in gear that fits well and is easy to use. This became clear when we tried 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, cheap gear adds to Hawaii’s already full landfills.

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 fits you. If it doesn’t work right, pop in and switch to a different rental set.

Go to the best places

Not all snorkeling spots are created equal. Some places on the island naturally have more vibrant reefs and are home to more fish and other 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.

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:

• Molokini Sunrise Snorkel with Kai Kanani: beat the crowds to Molokini with this special sunrise snorkeling tour leaving directly from the beach in Makena/Wailea.
• Beach loading snorkeling trip from Ka’anapali: if you’re staying in Ka’anapali, you can’t get more convenient than this tour!
• Na Pali Coast Snorkeling with Holo Holo Charters: Cruise up the coast of Kaua’i and off the island of Niihau for a full day of snorkeling.
• Power Raft snorkeling at Kealakekua Bay with Captain Zodiac: Head to Kealakekua Bay and the Captain Cook monument for the best snorkeling on the island.

Understand the rules protecting sea life

When you’re snorkeling and enjoying the crystal-clear water, it’s essential 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.

14. Learn about the culture of the islands

Hawaii is a unique US state for many reasons, but one important thing to understand is that it had a long, rich history before becoming part of the US. Learning a little about the culture and the history will enhance your stay and give you a 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 visiting the Bishop Museum and Iolani Palace. And make sure to brush up on some simple Hawaiian words like “mahalo” (thank you).

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.

This article covers how to have an authentic Hawaii vacation.

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 the island. Thousands of customers have loved them, whether they were planning a trip a year away or one 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.

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