Planning Your First Hawaii Trip

Lost in Hawaii

This post may contain affiliate links, which means I'll earn a small commission if you purchase something through these links. You won't pay any extra; instead, you'll be helping Aloha With Love to thrive. Thank you! Learn more.


Planning a trip to Hawaii can be daunting. Many island visitors are coming for their wedding or honeymoon, which means everything must be absolutely perfect. For others, Hawaii is that once-in-a-lifetime trip that won’t ever happen again.

A common question I’ve been asked by friends and planners alike is which island they should go to first? Each island has its own atmosphere, environment and people that make it unique. Not every island has waterfalls, volcanos or even snow! In fact, some islands are pricier to vacation at!

I hope this helps you narrow it down!

Aloha with love,

Planning your first trip to Hawaii
Lumahai beach on Kauai.

The Island For You


Undisputed champion for most visits by Hawaii vacationers. Waikiki is tourist central and the strip is packed with hotels lining the beautiful Waikiki beach. Despite the number of people, there is plenty of space at the beach and an endless choice of restaurants, free activities, entertainment, festivals and tours. Outside of Waikiki, you’ll find less traffic and less people while touring the rest of the island – particularly the famous North Shore and Windward side of the island.

Local Tip: Avoid rush hour traffic by not driving between 3 PM – 6 PM in Honolulu.

If you’ve never been to Hawaii or any other tropical island before, Oahu is a great place to choose. It mixes city life with country life well and you’ll have hundreds of choices to choose from for entertainment. There are plenty of activities will take you way out of Waikiki like the popular Paradise Cove Luau and will even pick you up.


Recently, more people are choosing Maui over Oahu for their first trip. In a few years, I expect Maui to resemble a mini Oahu and even now many people are already saying it’s too crowded. As an Oahu girl, Maui has more of a country feel to me because it’s still missing the towering buildings that populate Oahu. The two biggest attractions there are Haleakala and the Road to Hana (both are amazing!).

If your last visit to Hawaii was Oahu, Maui will make a fantastic second trip to Hawaii. Or, if you’ve been to a tropical island before and know you want less people and more nature, you’ll want to head here or any of the other islands listed below.

Big Island

Hawaii may be small, but the Big Island feels huge. You’ll do a lot of driving here since everything is spread apart. But the amazing thing to see is Hawaii Volcanoes National Park.

The Big Island is split into two very different areas: Kona and Hilo. Many visitors like to spend most of their time in Kona and one or two nights in Hilo (for lava viewing). Check out my lava tube list for the Big Island since these are unique to the island.

Extra Tip: In order to do the Big Island justice, I’d recommend staying for about a week.


For me, complete rest and relaxation can be achieved on Kauai. Life is slow here and you’ll find yourself changing your speed to match island time. The views are amazing because the island is so much older than the other islands. It’s had time to create large canyons and sweeping cliffs. One of the best Kauai activities is river tubing – something you can’t do on any other island.

Local Tip: Many monk seals call Kauai home. Bring your camera on beach walks and don’t stray too close.


98% of Lanai is owned by Larry Ellison who purchased it a few years back and it is marketed as a resort for the wealthy. Vacationing in Lanai may put you back a few pennies, but it’s still possible to find acceptable accommodation if you’re on a budget. Despite the higher prices, Lanai has a number of visitors who are attracted to its unexplored atmosphere.

Local Tip: Make a stop at Shipwreck Beach.


You won’t find any huge resorts, five-star dining or shopping malls here. Most beaches will be empty and the landscape has remained unchanged for the past several years and will likely remain so for many more years to come. The beachfront accommodations are more simple than luxurious and the snorkeling here is a thumbs up.

Local Tip: Give Philip Kikukawa at Molokai Bicycle (my Dad’s friend!) a call to discover Molokai.

Kahoolawe and Niihau

Unless you join the Kahoolawe restoration volunteer group or are invited to come to Niihau by a resident, you probably won’t have a chance to visit either of these islands. However, you can snorkel there!

Recommended Links For Planning Your First Trip To Hawaii

  • I’ve got a week-long budget itinerary for folks staying on Oahu. If you know me, I have you visiting local eats and doing fun, cheap and free activities.
  • The best place for Big Island information is the Love Big Island vacation guide. Fantastic place for up-to-date info.
  • If you’re into exploring the wild side of Hawaii, give Unreal Hawaii a try. Super descriptive posts about what to expect when you explore the Hawaii landscape.

My Funny Story

During summer break while in college, I worked as a cashier at Dole Plantation. I was often asked how far the drive was to the North Shore or Polynesian Cultural Center or even the drive back to Waikiki. But the strangest question I ever got was when a couple asked me to point out where they were on the map. The handed over a very well-used map with folds and creases everywhere – which is normal. The strange part was that it was a map of the Big Island and not Oahu! Apparently, they had been driving around Oahu for more than a few days using this Big Island map. Literally, lost in Hawaii!

Your subscription could not be saved. Please try again.
Your subscription has been successful.

Get Emails From Hawaii!

I travel, explore, work and enjoy life in Hawaii. Get email updates and join me on my adventures.

By browsing this website, you agree to our use of cookies. We will never sell your personal information.