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How to Plan a Hawaii Trip: FAQs + 9 Tips for Planning the Vacay of Your Dreams

Planning a first-time trip to a new place is always equal parts exciting and intimidating. Figuring out the travel requirements, the best places to see, and the perfect time to go can be difficult. Make the place you’re visiting Hawaii, with all of its multifaceted and unique islands, and your decisions become that much more difficult. But don’t stress. We’re here to help make planning your trip to Hawaii easy. Read on to discover how to plan the ultimate Hawaii trip and get tips for making your Hawaiian getaway the vacation of your dreams.

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Frequently Asked Questions About Planning a Hawaii Vacation

Let’s jump right into it. The last thing you want to do when preparing for your Hawaii trip is to start planning before you’ve found answers to your burning questions. So, before we dive into the crystal-clear waters of Hawaii’s gorgeous beaches, let’s clear up some things.

How Much Does a Hawaii Trip Usually Cost?

Hawaii isn’t cheap, but it’s not so expensive as to be out of reach either. The average cost for a 10-day trip to Hawaii is about $10,000 for a family of four. However, that price can go up or down based on several factors.

  1. The island
  2. Travel style
  3. Where you stay
  4. How you get around
  5. What you eat

A luxury getaway to Maui will cost more than a budget vacation in Oahu, but it all boils down to how you plan your trip to Hawaii. Regardless of the island you choose to visit, there are always ways to shave off some expenses and rack up the savings.

How Do I Plan a Trip to Hawaii for the First Time?

Going on a trip to Hawaii for the first time is as easy as making a plan and breaking it down.

  1. Figure out the entry requirements
  2. Choose an island
  3. Figure out the best time to travel
  4. Book flights
  5. Select accommodations 
  6. Plan sightseeing
  7. Arrange transportation 
  8. Pack appropriately
  9. Learn common Hawaiian words

A little planning will go a long way towards helping you have your dream trip—and save you from any undue stress along the way. 

Should I Visit More Than One Island?

It may seem like a no-brainer. You’re already paying for the trip to Hawaii, accommodations, transportation, and food. So, you may as well get your money’s worth and see as many of the islands as possible. 

Normally, we’re all about getting the most from your budget. However, travelers should be wary of biting off more than they can chew here. 

Only visit more than one island if you have the time. 

Each island bursts with incredible sights and an infinite number of activities to keep your schedule busy. Unfortunately, packing in multiple islands on a seven-day trip is just as likely to stress your sanity as it is your budget. That’ll quickly remove any enjoyment you might find in exploring other islands.

Of course, if you plan to stick around for longer on a 10- or 14-day trip, then we fully support you on exploring more. Go island-hopping or even split your vacation between two islands. It’ll be an experience you won’t soon forget.

Where Should I Go in Hawaii for the First Time?

Oh, to be a first-timer on the shores of Hawaii. If you’re planning a trip to Hawaii for the first time, Oahu is a spectacular aloha. Easy to get to, the cheapest of all the islands, and endless fun in the sun make Oahu an ideal destination for first-timers.

You’ll find the perfect mix of affordability, adventure, surf, and sand. Suffice it to say, Oahu is called the Gathering Place for a reason; there’s truly nowhere else like it. And while you can’t go wrong with any island as your first choice, Oahu is a genuine standout for getting the most out of your first visit. 

How Long Should I Stay?

The minimum time you should shoot for to enjoy your Hawaiian vacation is seven days. This allows time to adjust and explore one island in-depth, discovering its leading attractions and hidden treasures. However, if you want to visit multiple islands, plan to spend ten or fourteen days.

Of course, work or other obligations might get in the way and force you to take a four or five-day vacation instead. And if it’s between four days or zero days spent on the islands, any number of days always gets our vote. 

But, keep in mind that for some, it’s a long way to go for a short trip. If possible, it’ll make more sense to reschedule for a better time than spend half your vacation adjusting to the time difference and only a day or two truly exploring.

9 Pro Tips for Planning Your Hawaii Vacation

So, you want to plan a trip to Hawaii? Then, let’s get into it. Here are nine helpful Hawaii travel tips for planning the perfect Hawaiian getaway.

1. Know the Entry Requirements

Domestic travelers flying to Hawaii will be pleased to know they don’t have to meet any travel requirements. 

As of March 25th, 2022, the Hawaii Safe Travels program ended, so visitors from the US no longer need to show proof of vaccination or a negative test. The statewide mask mandate also expired in March. However, some establishments may require you to wear a mask indoors; so come prepared and be respectful.

International travelers coming to the US have no additional requirements to travel to the Hawaiian Islands. No need for a negative COVID-19 test, but you do have show proof of vaccination for entry. 

2. Choose Your Hawaiian Island 

From getting romantic on Maui to hanging ten on Oahu and losing yourself in Kauai, you can’t go wrong with your choice of Hawaiian Islands. But depending on what your trip to Hawaii entails, there’s likely one island that’ll meet your needs more than any other. So, before you go, consider what you want out of your visit to Hawaii, and you’ll help yourself land feet first on the perfect shore.

Big Island 

If it’s an outdoor adventure you want, look no further than the Big Island. 

While the official name for this island of lava rocks and soaring cliffs is Hawaii Island, you’ll more often hear it called the Big Island by locals and visitors alike. Here, you’ll find the definition of going big or going home. The Big Island is the largest and youngest of the Hawaiian Islands. With five active volcanoes, it’s the place to see creation in action. Many early risers head to Hawaiʻi Volcanoes National Park to watch the fiery lava flow under a brightening dawn sky.

Learn about the sacred nature of the mauna (mountains) and stargaze from the tallest peak on the island at Mauna Kea.

Black sand beaches dot the coastline, and if your main goal is to sink your toes into as much black sand as possible, then the Big Island will be your destination of choice. Of course, it’s not all black sand here; you’ll find plenty of white sand beaches, golden coasts, and a rare green sand beach on the island’s south shore. 

Staggering sea cliffs, stunning valleys, and ever-changing landscapes make the Big Island a unique and rare sight, even among its sister isles.

Maui 

If you’re looking for an excellent sampler of all Hawaii has to offer, take your trip to Hawaii to the next level with a visit to Maui. The “Valley Isle” is an exhilarating blend of fun and romance, perfect for family vacations or intimate getaways. 

Visitors in love with technicolor beaches will delight in the painter’s palette of colors to be seen on Maui, from red sand to black and pristine white. And the beaches aren’t the only scenic views to be had. The Hana Highway in Maui is famed for its picturesque scenery and great stops, like the Maui Garden of Eden and the Hanawi Falls.

Learn to dance the hula from native Hawaiians, snorkel at the volcanic caldera Molokini, and wake early to catch the sunrise above the clouds at Haleakala. 

Whether planning the family adventure of a lifetime or looking to celebrate your romance with your next Hawaii trip, Maui bursts with fun, charm, and endless views. 

Oahu

As we mentioned earlier, Oahu is the “Gathering Place,” perfect for travelers planning their very first trip to Hawaii. Oahu combines an urban atmosphere with laid-back beachy vibes and a carefree, surf’s-up attitude. 

Honolulu is a prime example, offering a mecca of Hawaiian culture and history. The Bishop Museum, Pearl Harbor National Memorial, and Iolani Palace are all must-see spots in Honolulu, along with the two-mile stretch of sand making up Waikiki Beach. You’ll also find one of the most incredible foodie spots among all the islands in Honolulu. 

The city shines bright, but other treasures await outside city limits. Surfers will find themselves called to The Seven Mile Miracle along Oahu’s north shore. Meanwhile, the more leisure-focused visitors will find spots like Hanauma Bay to unveil a treasure trove of delights under the sea. Oahu takes fun in the sun and runs with it along 112 miles of gorgeous coastline.

Kauai 

Kauai is for escapists. Paradise seekers and jungle adventurers will find themselves at home on the “Garden Isle,” where peace and quiet await among the ever-green landscapes of Kauai. With no mega-resorts in sight, Kauai’s relaxed atmosphere presents the perfect place to lose yourself among lush cliffs and dense jungles and soak in more of the Hawaiian cultures and traditions that make the islands so unique.

Big towns feel small in Kauai, from beautiful Hanalei, hugged by mountains and the sea, to historic Koloa, with its old sugar cane mill. And, with so few people on the island, exploring gems like Waimea—also known as the Grand Canyon of the Pacific—with its cascading falls and ancient archeological sites, feels like a discovery. You’ll find no shortage of long, sandy stretches of beach either. With over 50 miles of sandy shores, the beaches feel endless.

More than any other Hawaiian island, Kauai is where natural beauty abounds, and dramatic views take your breath away.

Lanai 

Travelers looking for a remote destination will find it on Lanai. Affectionately called “Pineapple Isle,” Lanai was once home to the largest pineapple plantation in the world and provided three-quarters of the world’s pineapples. If you visit today, you won’t find acres upon acres of pineapple plantations, but endless rugged landscapes await. Off the beaten path takes on a very literal meaning here, where only 30 miles of paved road exist. The other 400 miles of rough trails await exploration. 

Treat your eyes to alien spectacles like the Garden of the Gods, or head to Shipwreck Beach, where a large wreck sits eerily just offshore. 

Whereas other islands see millions of visitors annually, Lanai sees less than a hundred thousand people. It gives you a sense of what all of Hawaii may have looked like before large cities and tourism took over: tight-knit communities, infinite stretches of beaches, and an island left to grow and thrive in its natural state.

Molokai

The “Friendly Isle” is the perfect place to set up camp for those interested in the complete opposite of resort living. Nature thrives on Molokai, with little in the way of development to stunt the island’s verdant growth or obstruct the gorgeous views.

And while beautiful is certainly a term to describe Molokai—and all of the islands, truthfully—Molokai’s authenticity and history make the argument for planning your next Hawaii trip here. 

Many native Hawaiians call Molokai home, and their dedication to preserving the island and their way of life helps keep it pristine. Discover history at the Kalaupapa National Historical Park or venture out to shores like Papohaku Beach, one of Hawaii’s largest white sand beaches, to find paradise.

3. Know the Best Time to Travel 

The Hawaiian Islands are a year-round destination. But, with so much to enjoy, that makes it all the more crucial to pick the perfect time for your visit, whether that means soaking up the most sun, nabbing the best deals, or making sure the timing is right to enjoy your favorite activities. 

Here are some of the best times to visit Hawaii, depending on what you’ll be doing.

Best Weather

Most visitors to Hawaii flock to the beaches for sun, sand, and the shimmering blue waters. The best months for soaking in the sun and enjoying Hawaii’s beaches are between March and September. These months see the warmest temperatures, averaging 85° F, and the least amount of rainfall. So, if you plan to fill your Hawaii itinerary with snorkeling, swimming, and surfing, the late spring to early fall is the perfect time to plan your trip.  

Best Deals

The best time of the year to visit Hawaii for low prices is during the shoulder season in late spring and early fall. April, May, September, and October typically see the cheapest flights and best deals on accommodations. As a bonus, you’ll also avoid the worst crowds, which show up around the holidays in November and December, and the summer months of July and August, always a popular time for family travel.

Pro-tip: Plan your trip in May or September for the perfect combination of low prices, small crowds, and classic Hawaii weather.

Surfing. For expert surfers, winter in Hawaii is the dream. Mid-November to early February promises big swells and surf competitions all along Oahu’s north shore. Rest assured, though, you can find great surfing on any of the islands, typically along the northern shores in the winter.

Whale watching. The peak season for whale watching is January to March, but you can generally spy humpback whales off the islands’ coasts anytime between December and May. For your best chance at catching a good look at these amazing creatures, check out the island of Maui or the Big Island’s Kohala Coast.

Sea Turtles. The best time to see Hawaiian Green Sea Turtles is during the summer and nesting season, between May to October. With calm waters and warm sands, you’ll catch turtles coming ashore from late morning to mid-afternoon, when the sun is at its hottest.

4. Book Your Flights

Flights can often be the most expensive part of your trip, especially if you’re planning a Hawaii vacation for the whole family. Though the islands have five major airports, the best places to fly to will be Honolulu International Airport on Oahu and Kahului Airport on Maui. These airports see the most traffic and the cheapest deals and put you right in the center of all the action.

While Hawaiian Airlines has direct flights from the US to Hawaii—and provides inter-island flights—it has a limited number of destinations on the mainland, most from the west coast. So, if you’re flying from anywhere else, you may want to compare the prices with other airlines, including Alaska, American, United, and Southwest Airlines. Currently, Southwest is the only budget carrier offering flights from the mainland to Hawaii. 

If you’re an east coaster in the middle of your Hawaii vacation planning, keep in mind flying direct isn’t the only way to get to the islands. One of the best Hawaii travel tips we have is to look for deals from west coast cities to Hawaii first, then cheap flights out to the west coast. It’ll involve a bit more coordinating, but you may be able to save yourself hundreds or even thousands of dollars getting to Hawaii. 

Want to save even more? Sign up for the Next Vacay newsletter to get the best deals to Hawaii delivered right to your inbox. 

5. Decide Where to Stay

Accommodations in Hawaii aren’t cheap, especially when staying at a hotel or resort. Thankfully, Hawaii has options for every budget. Between pampered resort stays, fancy hotels, comfy Airbnbs, and simple-living camping, Hawaii feels like a true choose-your-own-adventure experience.

Resorts/Hotels

The average nightly rate of a hotel room in 2021 was roughly $325. And recent numbers from the Hawaii Tourism Authority show those prices aren’t coming down anytime soon. In June 2022, the average daily rate for even mid-scale hotel rooms was $246, and that number soared to $949 for luxury resorts.

These high prices reflect the price hikes and demand of the summer season, but overall, resorts and hotels are definitely the more expensive option. If you’re planning to treat yourself, make your plans and book early, and don’t forget to use any hotel points/rewards to save money. 

Vacation Rentals

If you’re trying to plan a budget trip to Hawaii, avoid the hotel rooms and consider a vacation rental instead. Compared to the average daily rate of $414 for hotels in July, vacation rentals were just $301.

Families and big groups of friends can stay together with a vacation rental and enjoy more privacy and room to roam. And you don’t have to skip out on the resort-like amenities either. 

Some rentals on Airbnb and Vrbo offer up beachfront views and fancy pools. They also make it easier to cook your own meals and reduce food costs. 

Overall, vacation rentals are a more affordable but still comfortable option for making yourself at home in Hawaii. 

Camping

Five islands—Oahu, Kauai, Big Island, Maui, and Molokai—encompass over 50 parks, making camping the cheapest accommodation on the Hawaiian Islands. Camping permits range from as little as $18 to $30 for non-residents, and the island parks cover city campgrounds and plenty of beach campgrounds for amazing views during sunrise and sunset.

Pro-tip: Hawaii campgrounds are closed on Wednesdays and Thursdays, so you’ll have to find other accommodations if you’ll be in Hawaii on those days.

6. Plan Your Sightseeing 

It used to be that when you wanted to visit Hawaii, you could just pick up and go. But if there’s one lasting effect of the pandemic, it’s the realization of how harmful overtourism can be to the land and beaches so many love. So, to prevent overcrowding, some of the islands have implemented reservations for popular tourist hotspots.

All this means that you’ll want to do your research before you go. Check out which sights on your chosen Hawaiian Island require reservations and ensure your plans include the necessary bookings to visit these must-see places on your next trip to Hawaii.

Here are some of the biggest attractions in Hawaii that now require a reservation:

  • Hanauma Bay Nature Preserve in Honolulu, Oahu. The preserve is only open Wednesday through Sunday, with online reservations available two days in advance.
  • Waiʻānapanapa State Park in Hana, Maui. Reservations can be made up to 30 days in advance. 
  • Hāʻena State Park on the north shore of Kauai. The park offers three reservation systems: Shuttle + Entry ($35), Parking + Entry ($10 per car + $5 per passenger), and Entry Only ($5).
  • Haleakala National Park in Maui. Visitors only need to make a reservation for sunrise viewings.
  • Diamond Head in Honolulu, Oahu. Reservations are available 30 days in advance, with refunds allowed up to 15 days before reservation time and changes until midnight the day before.

Seeing the sunrise from Haleakala or gazing out over Honolulu from Diamond Head is still as easy as ever. In fact, making reservations for your top places to visit will help you plan your Hawaii trip itinerary all the more effectively. The end result is maximizing your fun and minimizing your worries on your trip.

7. Arrange Your Transportation

When you’re flying over the Hawaiian Islands, you’ll realize you want the freedom to explore wherever and whenever you want. The best way to do that is by getting a rental car. 

Anyone who visited Hawaii during and shortly after the pandemic likely remembers the all-out bloodbath that was securing a car rental. Travel all but ground to a halt during the pandemic, causing many rental car companies to sell off their fleets. When travel picked back up, there weren’t enough rental cars to go around. 

Thankfully, car rental companies are on the road to recovery, with more vehicles to meet the high customer demand. As such, car rentals have dropped from over $200 a day to a more manageable $75. However, that doesn’t mean you should wait until the last minute to book. Instead, book early, and use a service like Discount Hawaii Car Rental, so you don’t have to pre-pay your reservation. That way, you can keep an eye out for price drops and cancel your reservation if something better comes along. 

That said, car rentals may not be necessary for your entire trip. Oahu is a perfect example. If you’re staying in Honolulu, plan for a few days wandering the city attractions and the miles of Waikiki Beach on foot or by bus.

Buses are another possibility, but only on some of the Hawaiian Islands. Molokai and Lanai, for example, have no bus systems to speak of, while Maui, Kauai, and the Big Island offer limited routes. Oahu has the most extensive bus route, but remember to account for the longer travel times if you plan to use it. 

8. Know What to Pack

Packing lists. Some people hate ‘em, and some can’t live without ‘em. But whether you consider them a necessary evil or your sacred texts, plan to have one, or a few, on your trip to Hawaii.

Granted, you may need to pack a few extra things if you’re traveling with a baby or, as is the case for many people heading to Hawaii, planning an epic beach vacation. However, there are some fundamental essentials you won’t want to forget.

Hawaii Trip Packing List Essentials:

  • Shorts and t-shirts
  • Swimsuit 
  • An island-style outfit
  • Comfortable shoes
  • Sunglasses
  • Mineral-based sunscreen
  • Sun-protective clothing
  • Backpack
  • Beach bag
  • Reusable water bottle
  • Some warmer clothes 
  • Natural bug repellent

Mineral-based sunscreens will help keep your skin and coral reefs healthy, while comfortable shoes will cushion every step as you trek through jungles and across Hawaii’s picture-perfect shores.

9. Learn Common Hawaiian Words and Phrases

Flight and hotel booked, sightseeing reservations made, and bags packed—your plans are complete, and your trip to Hawaii is set. But before you hop on a plane and jet set around the country, or just off the coast, to your vacation destination, take a few moments to learn some Hawaiian words before you go. 

Don’t worry, Hawaii has plenty of English speakers; you won’t run into any trouble getting around. But, learning a few key phrases from the Hawaiian language will make it easier and show your respect for the amazing culture found on the island. 

Aloha (a-lo-ha) – hello, goodbye, or used to convey positive intentions and respect.

Ohana (o-ha-nah) – family

Keiki (kay-kee) – child

Mahalo (ma-hah-lo) – thanks 

Note: You can also say mahalo nui (mah-hah-loh noo-ee) or mahalo nui loa (mah-hah-loh noo-ee loh-wah) to say thank you very much and thank you so very much.

‘A‘ole pilikia (ah-oh-leh pee-lee-kee-yah) – you’re welcome

A ‘o ia (ah-oy-yah) – “you’ve got this!” or “there you have it!” 

Get the Best Deals to Your Island Paradise with Next Vacay

Visiting Hawaii doesn’t have to be impossible or even difficult. Getting to paradise is as simple as signing up for the Next Vacay newsletter. 

As part of the Next Vacay family, you’ll get deals delivered right to your inbox, with cheap flights to Honolulu, the Big Island, and more. Traveling to Hawaii has never been easier. So, even while costs continue going up, keep your travel expenses low by scoring a great deal.

Fly with Next Vacay, and you’ll be saying aloha to the Hawaiian Islands in no time.

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