Must-Read Guide To Visiting Hawaii For The First Time

I am so jealous. I wish I could visit Hawaii again for the first time! It’s truly one of the most beautiful places in the world and I’ll never forget the feeling of flying over the island and seeing its lush green mountains and crystal blue waters for the first time—absolute magic!

But enough about me, let’s talk about you. You’re planning your dream vacation to Hawaii and we’re here to help make it as amazing and smooth as possible. Whether you’re a beach bum, an adventure seeker, or craving some of the freshest poke of your life, this guide to visiting Hawaii for the first time has everything you need to know before you board your plane and saying aloha to paradise.

Visiting Hawaii For The First Time

The anticipation of a new destination is one we always crave, and if you’re like us and have been dreaming of visiting Hawaii then you get the feeling.

But along with the anticipation comes about 1,000 questions “December or April?” “Should we stay in Kauai instead of Maui?” or “Do I have enough time to see both islands?”. As a first-time visitor to Hawaii, it’s natural to have these kinds of doubts and questions.

And to help take that stress away we’ve created this ultimate guide for first-time visitors to Hawaii. From tips on where to go, the best time of year to visit, and even ways to save money, this guide has it all!

Flight Schedules

If you’ve started researching flights to Hawaii, you may have discovered that the islands offer a variety of airports. Some islands have more than one airport, and while one may seem more convenient at a glance, it might not be that way in reality. 

The most convenient route to get to Hawaii is by flying into Honolulu International Airport (HNL) on the island of Oahu. From there, you can easily connect flights or take a short flight to any other island in Hawaii.

Be aware though, that flying to the smaller islands can often involve small, propeller planes. 

When booking your flights, it’s important to consider which islands you want to visit and if they are connected by direct flights. Some islands like Kauai or Maui have direct flights from major cities, while others typically require a layover on Oahu.

If you’re unsure of which island you want to visit, you can check out our guide to the best island in Hawaii to visit for first-timers. This will give you some in-depth information on the different islands and why one might be more your style than another.

If flying isn’t your first choice, you can also opt for a cruise to Hawaii. These typically depart from the West Coast of the United States and take about two weeks to complete a round-trip journey around the Hawaiian islands. This is a great option if you want to see multiple islands without having to deal with inter-island flights.

Activities You Want To Do

Once you’ve sorted out your flights, it’s time to start planning the fun part—activities! Hawaii literally has SO much to do and so much variety. Whether you’re looking for adventure, relaxation, or cultural experiences, there is something for everyone.

If you love the outdoors, Hawaii is about to spoil you rotten with tons of options like hiking, surfing, snorkeling, and even volcano tours. And if you’re after a more chill vacation, you’ll find plenty of beaches to relax on and spas to treat yourself at.

If you want to experience Hawaiian culture, definitely check out a traditional luau for some great music, dancing, and tasty local food. You can also swing by historical spots like Pearl Harbor or the Polynesian Cultural Center to dive into the islands’ rich history and heritage.

Other popular activities include whale watching, golfing on some of the most gorgeous courses, and visiting waterfalls. And for those looking to splurge, there are luxury yacht cruises and helicopter tours to see the islands from a different perspective.

On your first trip to Hawaii, it might be tempting to just go wherever the wind takes you, but if you really want to make the most of your time on the islands, it’s a good idea to do some research and plan ahead when booking things to do in Hawaii.

One piece of handy advice is to schedule your most important activities early on. A lot of things to do in Hawaii are weather-dependent and may have to be postponed as a result. By planning these early on in your vacation, you can always reschedule if needed. You don’t want to run out of time to reschedule that must-see experience you had your heart set on. 

Booking ahead wherever possible is also highly recommended, especially if you’re visiting Hawaii for the first time in the busiest period. Not only does this ensure you won’t miss out, but it saves you from frittering away your precious vacation time waiting in long queues.

Suggested Activities To Try In Hawaii

• Ma’alaea Harbor: Whale Watching Catamaran Cruise – Enjoy a catamaran cruise along Maui’s coast while seeing whales in their natural habitat.
• Kauai: Hughes 500 4-Passenger Doors-Off Helicopter Flight – Take in the stunning sights of Kauai from a doors-off helicopter!
• Oahu: Shark Cage Dive on the North Shore – Experience action up-close of the sharks in Oahu!
• Waikiki: Turtles and Snorkeling Tour on Hawea Catamaran – Snorkel with turtles and lots of other marine life.

Best Time To Visit Hawaii

Truthfully, there’s never a bad time to visit Hawaii. That said, depending on the experience you wish to have, certain times of the year can be better than others. When planning your first visit to Hawaii, you want to research the weather and busiest seasons so you can plan accordingly.

Peak Season

Hawaii’s peak season runs from mid-December to March, right around the winter holidays. This is when the islands fill up with tourists from all over, so expect it to be busy and crowded. If you’re thinking of visiting during this time, make sure to book your accommodations and activities WAY ahead of time!

Off-Peak Season

The best time to snag awesome deals on flights and places to stay in Hawaii is during the off-peak season, which is usually from April to June or September to November—the sweet spot, we like to call it. The weather might not be as sunny as in peak season, but it’s still warm enough for outdoor fun making it one of the best times to visit Hawaii. Plus, you’ll enjoy more space and fewer crowds!

Weather In Hawaii

Hawaii has a tropical climate, so it’s warm and humid all year round. But depending on which island you hit up, the weather can change a bit. Oahu and Maui are usually drier, while Kauai is famous for its lush greenery thanks to more rainfall. The Big Island can be a little unpredictable with its weather, but it’s usually sunny and warm.

Surf Season

Hawaii is known for its world-class surfing, and the best time to catch some gnarly waves is during the winter months from November to February. This is when the big swells come in, making it ideal for experienced surfers. If you’re a beginner, no worries—summer (May to September) offers calmer waters so you can learn how to hang ten!

Whales Galore

If whale watching is on your bucket list, be sure to visit between December and April when humpback whales migrate from Alaska to Hawaii’s warm waters. You may even see them breach right off of Oahu’s beaches!

Cheapest Month To Visit Hawaii

If you’re visiting Hawaii for the first time on a budget, you’ll be looking for the most affordable time to visit. And Hawaii isn’t the cheapest destination, but if you plan strategically, you can save some serious cash.

The cheapest month overall to visit is usually April, followed closely by May and September. These months fall during the off-peak season, so flights and accommodations tend to be more affordable.

And while in most destinations, the off-season means rain, in Hawaii, it just means fewer crowds. Maybe you experience some afternoon or morning showers but usually the sun comes back out quickly. So you’ll still get to enjoy the warm weather and beautiful beaches—just with more space, fewer tourists, and money still in your bank account, ha!

How Long Should You Visit Hawaii?

Well, the answer is as much time as you can afford!

But seriously, this really depends on what you want to do and see. If you’re just looking for a quick tropical getaway—maybe five days will suffice. But if you want to island-hop and explore multiple islands or enjoy multiple activities like hiking, snorkeling, or surfing—you’ll need more time.

A good rule of thumb is 4-7 days per island (if visiting multiple islands) and at least 10 days in Hawaii overall. This gives you enough time to explore each island’s unique culture and natural wonders while still allowing some downtime.

And let’s be real—even after two weeks, you’ll be reluctant to leave Hawaii’s paradise behind and head back to reality. So if you can afford it, stay as long as you can and make the most out of your trip!

Which Hawaiian Island Has The Best Beaches

We’re not just being dramatic, this is such a hard question because each Hawaiian island has its own unique and beautiful beaches. However, there are a few standouts that are worth mentioning.

On Maui, Kaanapali Beach is known for its long stretch of white sand and crystal clear waters—perfect for swimming and sunbathing. Wailea Beach on the same island also offers stunning views and calm waters perfect for snorkeling.

If you’re headed to Oahu, Waikiki Beach is a must-visit with its iconic views of Diamond Head and plenty of activities like surfing and paddle boarding. For a quieter beach experience, Lanikai Beach on the Windward side of the island has some of the most pristine blue waters ideal for kayaking and snorkeling. You can also visit North Shore and Hanauma Bay.

Kauai’s Poipu Beach is a popular spot for families with its calm, shallow waters and soft sands. It’s never too crowded but there is enough going on to keep everyone entertained. It’s a great all-rounder!

On the Big Island, Hapuna Beach State Park is often ranked as one of the best beaches in the world with its wide stretch of white sand, perfect for swimming and sunbathing.

Ultimately, the best beach for you will depend on your personal preferences and what activities you’re looking to do. But if we could only choose one Hawaiian island for its beaches, we would have to go with Oahu. With more protected reefs than any other Hawaiian island, the waters are calmer and clearer, making for an ideal beach experience.

Which Is The Cheapest Island In Hawaii To Visit

Hawaii can be an expensive destination, but there are ways to visit the islands on a budget. Generally, the cheapest island to visit in Hawaii is Oahu. This is because it has a wider range of accommodations, from budget-friendly hostels to luxury hotels. It also has more dining options, activities, and bookable tours that cater to different budgets.

In addition, Oahu offers excellent public transport to save you on car rental fees too. 

Another budget-friendly choice is the Big Island, where you can enjoy a diverse landscape and tons of outdoor activities that are low-cost or even free, like hiking and visiting waterfalls.

Renting A Car In Hawaii

While most islands in Hawaii offer some form of public transport, you may find yourself needing to hire a car for part of your vacation. Hello, road to Hana! While Oahu has a great public transport system which makes getting around a breeze, other islands are best explored in a rental car, like Maui, Big Island and Molokai. 

Generally, renting a car in Hawaii is relatively inexpensive, with 4x4s costing slightly more. Be prepared for slightly higher gas prices in Hawaii than on the mainland, with some islands having even higher gas prices. Molokai and Lanai have the highest gas prices. 

If you’re considering renting a car on your first visit to Hawaii, it’s best to book in advance. Especially if you’re visiting in the busy season when the demand is high and rental agents often sell out. 

Overview Of Each Hawaiian Island

Can’t decide which islands to include when visiting Hawaii for the first time? We’ve summarized each island below to give you an idea of what to expect to help you plan which island to visit in Hawaii.

Oahu

Oahu is perfect for travelers who want a mix of city life and stunning beaches. The most populous island in the Hawaiian chain, Oahu has something for everyone. 

Sometimes referred to as ‘The Gathering Place’, Oahu is the third-largest island and one of the most visited in Hawaii. It’s home to the capital city of Honolulu, where you’ll find popular attractions such as Waikiki Beach, Diamond Head State Monument, and Pearl Harbor.

Foodies will be in heaven in Oahu, with the most variety of Hawaiian food options and delicious mom and pop shops everywhere, you’ll get your fill of kalua pig, shaved ice, and Loco Moco!

Personally, we think Oahu is the best island for those who are visiting Hawaii for the first time. It’s as straightforward as they come, with the international airport, Honolulu International Airport (HNL), located on the island, you won’t have to do any island-hopping to get there.

It’s also home to many hotels and resorts, which makes it easy to find accommodation options at various price points. It’s the perfect Hawaiian island for just about anyone, whether you’re a solo traveler or traveling with family.

And just because it’s the big city, don’t discount how green it is on the island with the best trails near Honolulu and waterfalls you can hike to.

Maui

Maui is also known as the ‘Valley Isle’ and is known for the sacred Iao Valley, incredible postcard-perfect beaches (some offering great snorkeling sites), and amazing whale watching. 

It’s also often considered the most romantic of all the Hawaiian islands, making it a popular destination for honeymooners and couples thanks to its beautiful beaches, luxurious resorts, and stunning sunsets.

But don’t let that fool you into thinking Maui is only for lovebirds—there are tons of activities and attractions that families or friend groups will love too.

One of the highlights of Maui is the Road to Hana, a scenic drive along the island’s rugged northeastern coast. This road takes you through lush rainforests, past waterfalls, and offers breathtaking views of the ocean. This is definitely a highlight of visiting Maui.

For those looking for some adventure, you can watch the sunrise at Haleakala National Park and explore bamboo forests, waterfalls, volcanic craters, and iconic red and black sand beaches.

As the second most visited island, there’s a wide range of accommodation, shopping, dining, and activities in Maui to choose from. 

Kauai

Kauai is a big time favorite of ours, but we’re not sure it’s the best choice for a first-timer to Hawaii. It’s still pretty underdeveloped, which is great for staying away from crowds, but it also means there is a lot more research and roughing it to get the same experience as Maui or Oahu.

Kauai, also known as the “Garden Isle”, is a lush and beautiful island that offers a more laid-back and secluded experience compared to its neighboring islands. So if you’re into a more local vibe and have done quite a bit of traveling in your life, this is the perfect spot for you.

It has some of the most beautiful and rugged landscapes in all of Hawaii, with stunning waterfalls, dramatic cliffs, and incredible beaches including the famous Na Pali Coast. With less development, there are also plenty of opportunities for outdoor adventures such as hiking and kayaking.

Kokee State Park is a must-visit for nature lovers, with miles of hiking trails and stunning views of Waimea Canyon. For a more chilled day, head to Hanalei Bay on the north shore where you can swim, snorkel, or just soak up the sun on its beautiful beach.

Big Island

The youngest and largest island in Hawaii, known as the Big Island, really stands out compared to its greener neighbors. While other islands are filled with lush rainforests and green plants, the Big Island shows off some cool lava landscapes created by its volcanic activity.

If you like your destinations to be diverse and different, then the Big Island is a must-visit. It’s home to 11 of the world’s 13 climate zones, meaning you can experience everything from lush green valleys to snow-capped mountains in one day.

One of the most popular spots on the island is Hawaii Volcanoes National Park, where you can see active volcanoes and learn about their geological history. The island also has some great beaches for snorkeling.

The Big Island is also famous for its coffee plantations, so be sure to stop by one and try some of the world-renowned Kona coffee. You can also visit Hilo, a charming town on the east side of the island known for its farmers’ markets and waterfalls.

I mean—coffee, volcanoes, snorkeling, and farmers markets? What more could you want for your first time in Hawaii?

Lanai

Lanai is known as the “Private Island” because it’s mostly owned by billionaire Larry Ellison. While there are a few luxury resorts on the island, there isn’t much else to do besides relax and enjoy the secluded beaches—which is lovely, don’t get me wrong. But it’s also quite expensive, and with all the other amazing things to do in Hawaii, it may not be worth the extra cost for a first-time visitor.

If you’re looking for a luxurious and exclusive vacation, Lanai may be perfect for you. There are ferries and flights available from Honolulu and Maui to get you there, so it’s not inaccessible, but we recommend saving it for a future trip when you’ve already experienced the other islands.

Molokai

If you’re one of those travelers who loves, even thrives, off the authenticity of a place, then Molokai may be right up your alley. It’s considered the most traditional and least developed island in Hawaii, with no traffic lights, just a handful of hotels, and limited tourist activities.

However, this also means that there isn’t much to do for tourists on the island. The main draw is the Kalaupapa National Historical Park, which has a tragic but fascinating history as a former leper colony.

If you’re interested in visiting Molokai, we recommend doing a day trip from Maui or taking a guided tour to learn about its history and culture. But like Lanai, it may not be worth dedicating an entire trip to this island alone.

What To Pack For Hawaii

No matter which island you pick there are a few essentials worth bringing with you. These are just a few things we never travel without:

• Daypack: Keep all your supplies secure, collapsible backpacks like the New Outlander are great but if you want something studier for camera gear the Shimoda Action X50 V2 or Shimoda Urban Explore are great options, just less portable.
• Packing cubes: If you haven’t yet started using packing cubes, where have you been?! You can fit several items of clothing into a Eagle Creek Pack-It Specter Cube and it keeps everything nice and tidy.
• Shell jacket: Depending on the season you’re going to need a waterproof and it doesn’t make a lot of sense to bring an umbrella when you can bring a waterproof shell jacket. This will also double as an additional layer. Shells like this are perfect for travelling because they’re versatile, light and easily rollable.
• Pocket cap: The Outdoor Research Radar Pocket Cap is a great travel hat simply because you can fold the brim. This makes it incredibly easy to pack and I can easily stick the cap in my back pocket if I want to take it off but not go through the trouble of putting it into my daypack.
• Comfortable sandal: I have reviewed the Rainbow Sandals, Double Layer Leather Sandal extensively before but I can’t go on a summer trip without them. They’re just so damn comfortable and great for extended periods of walking. Another sandal I love it the KEEN H2 Newport Sandal, I have reviewed them as one of the best sandals on the market, they’re just so versatile in summer conditions. Amphibious is the word that comes to mind.
• Travel toiletries case: I’ve been very happy with this Muji toiletries organizer because of it’s simplicity in design and comprehensiveness in terms of pockets, zippers and elastic holders.  The must-have feature for any toiletries organizer is the hook. Hanging your bag is always a better option than letting it sit on the sink especially if you’re using communal hostel washrooms.
• Insect repellant: Beach destinations and mosquitoes often go hand in hand. Pack the Off Mosquito Repellent to be prepared.
• Packable Towel: Hotels don’t like it if you bring their towels to the beach so pack your own. This one is great because it’s large (XL in fact), packs into a small form factor, and dries quickly. No risk of drying yourself with something the size of a hand towel.

First Time In Hawaii, But Definitely Not The Last

Planning your first trip to Hawaii is gonna come with so many questions and possibilities.  It’s difficult to decide between all the islands and activities, but don’t worry because no matter what you choose, it’s going to be an amazing experience. And chances are, once you visit one island, you’ll want to come back and explore the others too—at least that’s what happened to me.

And if you leave this article with just one piece of advice, let it be this—BOOK THINGS EARLY!  Flights, accommodations, and popular activities fill up quickly, especially during peak tourist season. So don’t wait until the last minute to plan your trip or you may end up missing out on some must-do experiences.

Frequently Asked Questions