Itinerary for Hawaii (3 Epic Islands and Budget Tips)

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Looking for the Best Itinerary for Hawaii? This post covers a few excellent options for your vacation!

Planning a trip to Hawaii this year? There is so much to see and do! Whether you enjoy relaxing on tranquil beaches, hiking through rainforests, climbing volcanoes, snorkeling, or exploring busy cities, there’s a little bit of everything.

This Itinerary for Hawaii guide will show you three excellent itineraries for Oahu, Kauai, and Maui. No matter which island is calling your name, you’ll find a handy and comprehensive itinerary for a 5 day visit. I know how overwhelming it can be planning a trip to Hawaii, so that’s why I created this guide!

So, ready to check out the best of what Hawaii has to offer? Keep reading to find out more…

Itinerary for Hawaii (3 Excellent Options)

Itinerary for Hawaii – 5 Days on Oahu:

Why visit Oahu: If you enjoy bustling cityscapes, historical sites, plentiful beaches, shopping opportunities, and tasty food of multiple cuisines from around Asia and the Pacific.

Day #1: Fly into Oahu

Your first day in Oahu is about flying in, getting to your hotel or accommodation in Waikiki, and getting settled in. Depending on how early you arrive, or how ambitious you are, may determine how much you want to do this day.

For a tasty and hearty dinner after the long flight, head to Royal Hawaiian Shopping Center which has tasty and affordable American, Vietnamese, Japanese, Chinese, and other cuisines available.

Day #2: Pearl Harbor and Waikiki

Spend the late morning / afternoon visiting Pearl Harbor. Pearl Harbor is one of those places you just can’t miss on a visit to Oahu. See where history was made on December 7, 1941, when a preemptive Japanese bombing raid on the US Naval base would cause the country to enter into the Second World War. You can easily take the bus from Waikiki to Pearl Harbor; and it’s much cheaper than renting a car or taking an Uber.

Later, spend the late afternoon and evening exploring Waikiki. This iconic and bustling beach is popular with surfers, swimmers, tourists, and just about everyone. No matter what your interests are, there is something to do in Waikiki. Head to Maguro Spot for for excellent Japanese and Hawaiian food, and Lahaina Shave Ice for a refreshing and tasty dessert.

Day #3: North Shore + Sunset Beach + Matsumoto Shave Ice

For Day #3, you may want to rent a car, even if only for one day. From Waikiki, take any of the cross-island highways towards Kaneohe, before continuing up Highway 83 around the North Shore. Be prepared to be met with deep blue ocean views, sandy beaches, towering lush cliffs, and more along the way!

Spend the afternoon at Sunset Beach, and hit up Matsumoto Shave Ice a few miles down the road for dessert.

Day #4: Koko Head and Hanauma Bay

For Day #4, you’ll head east to Honolulu’s upscale Hawaii Kai neighborhood. You can take the bus from Waikiki to the Koko Marina Shopping Mall, then walk another 15-20 minutes to Koko Crater and Hanauma Bay.

Koko Head Crater is by far one of the most fun hikes I’ve ever done, and highly recommend it. You’ll climb 1,000 feet straight up a railroad track that was used by the US Army and later Air Force as a radar station during and after WWII. At the top, you’ll get excellent views in all directions, including over Moloka’i, Lanai, and Maui.

Hanauma Bay on the other hand is a collapsed crater-turned beach. There are excellent opportunities for snorkeling, or just relaxing on the beach. Beware; there is a bit of a pricey entrance fee, but overall it’s definitely worth it!

Day #5: Manoa Falls, Diamond Head, Leonard’s Donuts

For your fifth day on Oahu, you’ll want to get an early start! Begin by taking the bus from Waikiki up to the Manoa Falls Trailhead. This fun junge hike is only 1.7 miles out and back, and will take you to the base of the 150′ waterfall.

After, take the bus down to Diamond Head Crater, perhaps the most iconic site on Oahu. Climb up through the old WWII era batteries and fortifications to the top, where you’ll be met with sweeping views over Waikiki and the rest of Oahu.

After a day of hiking, take the bus up to Leonard’s Bakery, and pick up some tasty and affordable malasadas, which are Portuguese-style donuts. Take your box of malasadas back down to Waikiki for sunset.

Itinerary for Hawaii – 5 Days on Kauai:

Why choose Kauai: If you enjoy a slow-paced lifestyle, sandy beaches, jungles, and canyons.

Please understand that unlike Oahu, you’ll definitely need a rental car for Kauai. The public transit is lacking on Kauai – that’s the trade off for visiting the quieter island!

Day #1: Fly into Kauai

Your first day in Kauai is about flying in, getting to your hotel or accommodation, and getting settled in. Depending on how early you arrive, or how ambitious you are, may determine how much you want to do this day.

For Kauai, I’d recommend staying in the East Side of the Island, especially in Kapa’a or Wailua. These towns are quiet, have accessible beaches, and are a central launching point for exploring both the North and South shores of Kauai.

Day #2: Waimea Canyon and Koke’e State Park

Once dubbed “The Grand Canyon on the Pacific”, Waimea Canyon is a must-visit for any visitor to the island. Over 10 miles long, 1 mile wide, 3,000 feet deep, with vibrant colorful cliffs, thundering waterfalls, and draped with lush vegetation, it’s quite easy to see where it got its nickname!

Then, just north of Waimea Canyon lies arguably the most breathtaking point on Kauai, if not in all of Hawaii. Koke’e State Park protects the land above the Nā Pali Coast, with views over the lush towering cliffs which seemingly drop into the azure Pacific Ocean.

Day #3: Hanauma Bay + North Shore

For day three, you’ll head up to Kauai’s scenic north shore, home to epic beaches, lush mountains, and scenic trails.

Hanalei’s Waioli Beach is in one word… breathtaking. The warm water of the shallow Hanalei Bay, backed by the quaint town with towering green mountains and thundering waterfalls in the background creates a surreal scene, like you’re in a book or movie.

Continue up to Tunnels Beach or Kalalau Trail to finish up your day.

Day #4: Waterfalls + Luau

Wailua Falls is a few miles inland, but you should definitely drive up there is you have a rental car. Laced with verdant vegetation, this 173-foot twin falls were all around my favorite waterfall on the island!

This double-waterfall is conveniently just 2 miles up Kuamoo Road from the Kuhio Highway, making it an easy stop if you’re driving past. Over 150 feet tall, the falls pour over a volcanic rock face creating a dramatic sight. Plus, it’s free to visit!

Located just south of Kapa’a and the Wailua River, this beautiful state park boasts a beautiful stretch of beach and picnic tables with great views. There are actually jetty-enclosed swimming areas here too. Plus, wild chickens. Lots and lots of wild chickens. Get ready to see many more of these on Kauai!

Day #5: South Shore Beaches

Day five is all about relaxation! There are three excellent beaches on the South Shore of Kauai. These include Poipu Beach, which is popular and a bit crowded. Then there’s Salt Pond Beach Park, and finally Kekaha Beach, a large, windy beach with very few crowds. Any three are excellent!

Itinerary for Hawaii – 5 Days on Maui:

Why choose Maui: If you like a slow-paced lifestyle, drier climate, volcano hiking, and scenic drives.

Day #1: Fly in

Just like in Kauai, you’ll definitely want to rent a car in Maui. There is a tourist bus system, but it’s nowhere nearly as extensive as the public transit in Oahu. Also, renting a car opens up the door to some pretty cool activities you couldn’t otherwise do, like on Day #2…

Day #2: Road to Hana

In just 65 miles, you’ll cross 54 bridges and navigate 600 turns. When you reach the sleepy town of Hana, you’ll have more to explore in the nearby Wai’ānapanapa State Park and the Kīpahulu District of Haleakala National Park. Along the drive, you’ll be constantly rewarded with jaw-dropping ocean views, thundering waterfalls, bamboo forests, and one thrilling drive!

Day #3: Lahaina, Iao Needle

Strolling the streets of Lahaina is a great way to spend an afternoon or evening. The former capital of Hawaii, this quaint town is home to the famous Banyon Tree, which takes up an entire city block.

Eating in a window seat at Cheeseburger in Paradise is always a relaxing experience, hearing the waves crash below you, and watching the sunset over the harbor is breathtaking!

Located in a lush mountain valley, it’s no wonder why towering Iao Needle is one of Maui’s most famous landmarks. The proximity to Kahului can’t be beat, and the sheer awesomeness makes this place a great addition to any Maui itinerary!

Day #4: Haleakala

To reach the Crater distract of Haleakala, you’ll need to drive up the ‘Haleakala Highway’, which ascends over 10,000 feet in 37 miles. (the highway holds the record for climbing the most elevation in the shortest amount of time!)

At the top you’ll have great view over the massive volcano crater, and can even hike down in!

You can spend the evening at the beach, in Kihei or the North Shore.

Day #5: Kihei/Wailea Beaches

The last day of your trip to Maui is all about relaxing on the South Shore. Check out the stunningly beautiful sandy beaches in Kihei and Wailea, and go shopping if that’s your thing.

How to Get Free Airfare to Hawaii:

When flying to Hawaii, why pay when you can score FREE airfare? When you use Swagbucks, you can get free gift cards for Southwest Airlines and Delta, which both fly into Oahu, Kauai, and Maui. Overall, this is the the best way to reduce the cost of your airfare to Hawaii. I’ve been a member of Swagbucks for about 10 years now, and it’s still one of my favorite ways to earn Free airline gift cards!

Here’s how it works:

Sign up with Swagbucks
Then start earning Swagbucks SB Points. There are so many EASY ways to earn Swagbucks! You can earn by Searching the Web {just like you would using Google}, Taking Surveys, Using Coupons, Shopping Online, Watching Videos, etc. I typically earn an easy $25 each month on Swagbucks!
Cash in your Swagbucks SB Points for Free Southwest Airlines Gift Cards and Free Delta Gift Cards!

What to Bring to Hawaii – Hawaii Packing List

When it comes to packing for Hawaii, think about the activities you want to do, and plan around that. Most visitors around naturally going to visit the beach, so a swimsuit is a must for them. If you want to take advantage of Hawaii’s excellent hiking, you’ll want to pack along some old comfortable clothes and hiking boots, for instance.

Normally, I’d recommend the following:

Swimsuit

Casual outfits for beach days

Casual or dressier outfits for shopping/luau/Pearl Harbor etc.

Hiking shirts, shorts, and shoes.

Saving Money on Groceries and Food in Hawaii:

Are you ready to slash your travel budget? Why not visit the grocery stores instead of restaurants? You’ll save so much money, especially if you decide to visit for a week or more. You can buy healthier foods like fruits, vegetables, and meats, rather than rely on cheap-but-questionable fast food. Overall, I usually end up going to grocery stores for breakfast, lunch, and snack food, even for weekend trips.

Saving money on groceries is an excellent way to eat healthier while saving money!

So, looking for even more Hawaii and Itinerary travel guides? Go check these out below…

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Itinerary for Hawaii (3 Epic Islands and Budget Tips)

Itinerary for Hawaii (3 Excellent Options)