71.5 F
Amy Fujimotohttps://alohawithlove.com
I grew up in Hawaii and when I'm not traveling the islands, I write down my Mom's recipes, hike with Daisy the waddling rescue, work on my 200+ gallon aquaponics system, and dream about my future van conversion so I can do some more traveling.

This post may contain affiliate links. If you click these links to buy something I may earn a commission with no additional cost to you. This helps keep Aloha With Love running, thank you! Learn More.

Aloha Hawaii Newbies,

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 signature
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!).

Local Tip: Every Friday, Maui has a party at a different town each time. I’ve included these in my Hawaiian Vacation Travel Calendar, which you can access by subscribing to this blog or by joining the Hawaii Travelers Facebook group.

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 here are the volcanos – I recommend reserving some time to view the lava in the dark.

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. If you’re looking for more ideas, my Dad grew up on Molokai and it holds a special place in his heart.

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!


Weather In Hawaii In April: Travel, Events And The Best Time To Go

Despite what you may think, Hawaii in April is not the rainiest month to visit Hawaii. By the time April hits, the rainy season is at the end of its run and the warmer days of May are already...

Hawaii In May: Weather, Travel, Events And The Best Time To Visit

Hawaii in May is one of the best times to visit the islands. The weather in Hawaii in May is fantastic, ticket prices and hotel prices are down, and there are typically less tourists this time of year since...

Hawaii In July: Best Time To Visit Hawaii

Hawaii in July is a beautiful time to visit the islands. The days are hot and sunny and spending your Hawaii vacation at the beach snorkeling, swimming, and learning to surf sounds like a really great idea. The July...

Best Hawaiian Island To Visit And The Best Time To Go

Choosing the best Hawaiian Island to visit is so difficult, isn't it? It's tough for me, too...and I live here! I know you want an easy answer so you can start booking your tickets, but the honest answer is...

20+ Things To Do In Oahu’s North Shore: The Best Of North Shore

I've got you covered if you're looking for the best things to do in Oahu's North Shore. As one of Oahu's biggest attractions, the North Shore of Oahu has something for everyone. Gorgeous beaches, Oahu's best snorkeling spots, amazing...

Where To Swim With Turtles In Hawaii And How To Find Them

Swimming with turtles in Hawaii is amazing! My heartbeat kicks up but at the same time I feel so calm. There's a sense of peace in me when I see them drift from rock to rock, relying on the...

Real. Local. Non-touristy.

My emails will make you smile!

I'm all about living life in Hawaii with passion, honesty, and respect. So if you like legal hikes, authentic experiences, and a kind and humble personality, I'm your local girl!

You'll love reading my fun and down-to-earth emails from a local perspective. I'll send you my personal tips, travel suggestions, and DIY project ideas that are perfect for Hawaii living.

Sign up below and you'll be added to my email list!

Aloha with love, Amy

Planning Your First Hawaii Trip