Beginner’s Hawaii

First Time to Hawaii? Start Here

Where to begin, when you don’t know where to begin.

Hi there traveler!

If you’re thinking about a trip to Hawaii, it’s important to know that Hawaii is really six distinct destinations. Each island has its own unique landscape and personality.

A good starting point is to decide what you and your group are looking to get out of the vacation. Is it beaches and watersports? Golfing and spa days? Culture, art, and cuisine?

It can be a mix of any and all of these things, but it’s a good idea to have some thoughts because otherwise Hawaii research becomes overwhelming fast!

There are six islands open to tourism: Oahu, Maui, Kauai, Hawaii (the Big Island), Lanai, and Molokai. Each definitely has its own vibe. And they’re all great for different reasons.

Questions to ask yourself at the beginning of planning are things like, “How long can we stay?” “What’s our budget?” “How many islands do we want to visit during our trip?”  You can absolutely visit more than one island on your trip, but not all, so you need to get clear on your goals.

First let’s take a look at each island more closely…

Best welcome sign ever

Oahu has the largest population of all the islands as well as the best nightlife and is the most urban. So if you’re looking for the vibrancy of a busy metropolis, then Honolulu is the place for you.

This is where you’ll find world-class shopping and cuisine.

Waikiki is arguably the most well-known beach in Hawaii, and it is located right in Honolulu surrounded by many many hotels. Here you should have no trouble finding a hotel to fit your budget. They range from economy to luxury. Just be aware that the cheaper rates will land you farther from the beach.

Diamond head is a volcanic cone that you can hike up for amazing views of the Pacific Ocean and Honolulu. It is one of 50 state parks in Hawaii and has cultural and historical significance. So it’s a great destination for outdoorsy people and culture seekers alike.

Another popular beach is Oahu’s North Shore. This is a great surfing destination. Surfers flock there every winter to experience some of the best waves in the world. The summer and fall there are calmer which make it better for swimming and snorkeling.

A few other big draws to Oahu are Pearl Harbor, Iolani Palace, and the Polynesian Cultural Center. These are all places for history and culture buffs as well as families.

Pearl Harbor, Hawaii
Pearl Harbor

Maui is the second biggest island of the chain. This island is much slower paced than the hustle and bustle you’ll find in Honolulu. What it lacks in nightlife, it more than makes up for in beaches and natural landscapes. Although that’s not to say that there is no nightlife whatsoever. Small beach towns are scattered throughout the island that offer a variety of food, drinks, and entertainment.

Maui is known for its high-end luxury resorts and popular tourist attractions like its variety of beaches and Haleakala, the island’s largest volcano.

Haleakala National Park is a great place for hiking and biking. Many activities throughout this island are a dream for outdoor enthusiasts and families alike.

If you visit during the winter and early spring months, you’ll want to consider booking a whale watching tour. From December to April, Maui is one of the best destinations in the world to see humpback whales. During this time the whales migrate from Alaska to give birth, and you’re very likely to see several on your tour.

There are many great tour companies out there. Make sure to research them before booking so that you pick the right one for your tastes and needs.

Whale watching is an event

Kauai has more beaches per mile than any other Hawaiian island.  It’s known as the Garden Isle, and for good reason.

This island is un-spoiled and un-crowded. It’s one of the sleepier destinations of Hawaii and it’s a popular one for honeymooners.

Families can find some great beaches here as well. Poipu beach is very kid friendly because of its soft sands and light waves.

Kauai is great for hiking, taking helicopter tours (many movies have been shot here), and snorkeling and diving.

With regard to budget, you can go high or low. There are plenty of luxury resorts, but if you’re on a budget and love nature, camping is a real option.

If you’re looking for some of the finer things in life, head to Princeville for resorts, dining, and golf.

If this doesn’t make you want to go on hike, I don’t what will!

The Big Island of Hawaii is, well, just that…BIG. This one’s a lot more rugged and has so many cool things to do.

You can hike through the volcano tubes and throughout Volcanoes National Park. Stargazing on MaunaKea is excellent for all ages.

There are many amazing and unique beaches here. There are white sand beaches, black sand, and even green sand beaches.

The variety of nature on this island is amazing. And there is something for everyone, from horse-back riding to snorkeling and diving.

Nature lovers and budget travelers can find camping sites. And those with an affinity for luxury can find top resorts.

black sand beach
Black sands beach on the Big Island

Lanai and Molokai are two of the smaller islands in the chain. They are lesser known to visitors and lesser developed.

Lanai is known for luxury resorts, but anyone can take a ferry over for a day trip to enjoy the beaches and some snorkeling.

Molokai is more rugged and rural. There is so little traffic that there is not one single traffic light on this island.

There are B&B’s here and condo rentals if you wish to stay on Molokai.  If your goal is to truly live like a local, this is the island for you.

hawaiian islands from above
The chain of islands

Once you’ve learned more about each island, you can start to narrow down which ones you’d like to visit.

Make a list of what activities you want to do and that will help you decide where to go.

Many activities on each island do overlap, so it’s a good idea to think about your budget and the type of accommodations you’re looking for.

Keeping budget and accommodations in mind, don’t forget about population. Do you want a sleepy little village? A laid back luxury oasis? Or a busy, urban environment?

Taking these simple actions will get you well on your way to enjoying your first Hawaiian vacation.

It CAN be overwhelming. People’s biggest mistake is digging too deep on all the islands and getting lost on information overload.

Here’s a little secret: they’re ALL beautiful islands! They ALL have beautiful beaches. And there are friendly locals, great food, and great experiences on EVERY island.

Trust your gut and don’t expect to do it all in one trip.

Happy vacationing!