Hawaii Itineraries

Let us take the guesswork out of planning your next trip to Hawaii. Here are our most popular sample itineraries for the main Hawaiian Islands.

hawaii itineraries

Our All-Around Best Itineraries

Planning a trip to Hawaii in 2022 and beyond is overwhelming. The internet is full of outdated information. Stop piecing together your trip and grab one of our island itineraries. They’re the best grab-and-go itineraries plus so much more.

First-Time in Hawaii Itinerary 10-days

Your First-Time in Hawaii Itinerary (10-Days)

You want to plan the right Hawaii vacation for you, your partner, or your family. Hawaii is an expensive place to visit and a long way to travel, you want to do the trip right. This first-time Hawaii itinerary is how you do your trip right.


Maui itinerary with toddler

The Best One Week Maui Itinerary…With a Toddler in Tow

When we moved to Maui we were eager to explore the island as much as possible. After we settled in we took a couple of weeks off work to explore and feel like we were on vacation. Well, as much as you can feel like you’re on vacation with a toddler in tow. 

We prepped, planned, and had the best time. And from that, we came up with our no-fail, perfect Maui itinerary with a toddler. 

Maui Honeymoon Guide Itinerary

The Perfect Maui Honeymoon Guide and Itinerary (with can’t miss tips)

You’ve made the great decision to head to Maui for your honeymoon (our favorite Hawaiian island for a honeymoon). Now, you need to figure out what exactly you should do. 

Don’t worry, we’ve got you covered with this detailed and picture-perfect eight-day Maui honeymoon itinerary.


Best 5 Day Oahu Itinerary

Best 5 Day Oahu Itinerary

Whether it’s your first time to Oahu or your tenth, visiting this Hawaiian island is special. We know, we’ve vacationed there and lived there, and love going back time and again.

After living on Oahu for two years, we developed the perfect itinerary for our friends and family who would come out to visit. It mixes adventure, culture, and just the right amount of down-time.

Oahu Hawaii Itinerary No Rental Car seven day itinerary hawaii

7-Day Oahu Itinerary Without a Rental Car

Oahu is the best Hawaiian Island to visit without a rental car. Traveling around the island is cost-effective with a mix of Ubers or taxis, guided tours, and staying in Waikiki. Avoid traffic, parking fees, and the hassle of a rental car with this seven-day Oahu itinerary.


3-day kauai itinerary

3-Day Kauai Itinerary: How to Make 3-Days Enough on Kauai

A visit to Kauai is a trip of a lifetime where you can explore the rugged shore, view stunning waterfalls, and feel like you’ve taken a step onto the set of Jurrasic Park. And while there is so much to explore, your visit will probably be limited in time. 

That’s why we’ve put together the perfect three-day Kauai itinerary. Whether you’re staying for three days or three weeks, this perfect itinerary will help you enjoy three action-packed days on the Garden Isle. 

Hawaii (Big Island)

What Can You Do in Hilo for the Day

1 Perfect Day in Hilo: Things to Do in Hilo for the Day

My first trip to Hilo made me not want to return. It rained the whole time. Even our hotel sheets felt damp. So when we were driving to Volcano National Park last month, I debated stopping in Hilo for the day. I’m glad we did. 

Hilo, Hawaii is worth a trip. If even for a day. Rain or shine, you can fill your day-long itinerary with things to do in Hilo.