← Back to results
🇺🇸United States of America

Hawaii : Whistle-stop Tour
14 day travel itinerary

by TripMapper

Hawaii has become synonymous with paradise and it certainly lives up to the hype.

14 Days
Road Trip
Image by Jelle De Gier on Unsplash
Image by Jeremy Bishop on Unsplash
Image by Tatonomusic on Unsplash
Image by Brandon Cormier on Unsplash

There are so many phenomenal activities to do on the Hawaiian islands, and that’s why this state stands out from the crowd.

Each of Hawaii's islands has its own distinct personality, activities and sights. Whether you want to uncover local culture and cuisine, surf some of the world's wildest waves, watch a spectacular sunset from a volcanic landscape, or snorkel with manta rays, there's an island that will deliver:

The island of Kauai is known as the ‘Garden Island’ for a reason. It is draped in lush green valleys, jagged cliffs, cascading waterfalls and tropical rainforest. 

The Big Island's biggest draw is Hawaii Volcanoes National Park, home to one of the world's most active volcanoes. Seeing the solidified lava flows stretch out for miles in a stark, rocky landscape, reminds you that the volcano is very much alive.

Maui is beloved for its world-famous beaches, the dramatic, scenic drive on the 'Road to Hana' and the magnificent sunrise and sunset from Haleakala National Park. 

Oahu, 'The Gathering Place', is home to Honolulu and so much more. From bustling city life to laidback surf towns, there is plenty to explore.

Molokai remains true to its island roots with a high percentage of its population being of Native Hawaiian ancestry. 

Lanai is the smallest inhabited island. If you are looking for otherworldly landscapes and luxury resorts, Lanai is the island for you.

Use TripMapper to plan your trip and for staying in control of your travel budget. If you are in need of a little inspiration to get you started click 'Customise' to use our interactive Hawaii itinerary (below) for the best things to see and do in Hawaii - then customise to make your own!

By combining both a trip itinerary app and a travel budget app, TripMapper is the best all-in-one travel itinerary app to help you craft your perfect trip!

* Please check all relevant government guidance prior to, and during, your travels. Please also check any opening & closing times for all establishments contained within our itinerary. Find our Terms of Service here.

Itinerary Highlights

  • Take in the jaw-dropping views of the Napali Coast and Waimea Canyon
  • Go hiking across ancient lava flows in Hawaii Volcanoes National Park
  • Snorkel with giant manta rays and sea turtles
  • Watch a spectacular sunset at the summit of Haleakala
  • Surf some of the world's wildest waves
  • Chill out on Hawaii's white and black sand beaches
  • Explore lush valleys and waterfalls on the 'Road to Hana'