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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'

Discover the Itinerary

Scroll right to view the days

  • Day 1

    • TRAVELHome to Honolulu International Airport
      Honolulu International Airport (HNL), Rodgers Blvd, Honolulu, HI, USA
    • OTHERPick up hire car
    • ACTIVITYVisit Pearl Harbor
      Pearl Harbor National Memorial, Arizona Memorial Place, Honolulu, HI, USA
    • ACTIVITYHike the Kaiwa Ridge (Lanikai Pillbox) Trail
      Lanikai Pillbox, Kailua, HI, USA
  • Day 2

    • FOODCoffee/ Snack - Surfer's Coffee
      Surfers Coffee, South Kamehameha Highway, Wahiawa, HI, USA
    • ACTIVITYShark Cage Diving
      Hale‘iwa Boat Harbor, Haleiwa, HI, USA
    • ACTIVITYNorth Shore Marketplace
      North Shore Marketplace, Kamehameha Highway, Haleiwa, HI, USA
    • ACTIVITYHanauma Bay Nature Preserve
      Hanauma Bay Nature Preserve, Hanauma Bay Road, Honolulu, HI, USA
  • Day 3

    • ACTIVITYActivities at Kualoa Ranch
      Kualoa Ranch, Kamehameha Highway, Kaneohe, HI, USA
    • FOODGiovanni's Shrimp Truck
      Giovanni's Shrimp Truck, Kamehameha Highway, Haleiwa, HI, USA
    • ACTIVITYSunset Beach
      Sunset Beach, Pupukea, HI, USA
  • Day 4

    • ACTIVITYLanikai Beach
      Lanikai Beach, Kailua, HI, USA
    • ACTIVITYExplore Kalakaua Avenue
      Kalakaua Avenue, Honolulu, HI, USA
    • OTHERReturn hire car
    • TRAVELHonolulu International Airport to Lihue Airport
      Honolulu International Airport (HNL), Rodgers Blvd, Honolulu, HI, USA
    • OTHERPick up car hire
  • Day 5

    • ACTIVITYHelicopter tour over Waimea Canyon and Nāpali Coast (see notes)
    • ACTIVITYNāpali Coast State Wilderness Park
      Nāpali Coast State Wilderness Park, Kapaʻa, HI, USA
    • ACTIVITYExplore Hanalei Town
      Hanalei, HI, USA
  • Day 6

    • ACTIVITYWaimea Canyon Lookout
      Waimea Canyon Lookout, Waimea, HI, USA
    • ACTIVITYWaimea Canyon Hike
      Waimea Canyon State Park, Waimea Canyon Dr, Waimea, HI, USA
    • ACTIVITYSunset at Polihale Beach
      Polihale State Park, Lower Saki Mana Road, Waimea, HI, USA
  • Day 7

    • FOODCoffee/ Snack - Java Kai
      Java Kai, Kuhio Highway, Kapaʻa, HI, USA
    • ACTIVITYKayaking - Wailua River
      Wailua River, Wailua, HI, USA
    • FOODKoloa Fish Market
      Koloa Fish Market, Poipu Road, Koloa, HI, USA
    • ACTIVITYSpouting Horn Park
      Spouting Horn Park, Lawai Road, Koloa, HI, USA
    • ACTIVITYSunset Poipu Beach
      Poipu Beach, Koloa, HI, USA
  • Day 8

    • OTHERReturn hire car
    • TRAVELLihue Airport to Kona International Airport
      Lihue Airport (LIH), Mokulele Loop, Lihue, HI, USA
    • OTHERPick up car hire
    • ACTIVITYExplore Waipi‘o Valley
      Waipi'o Valley, Waipio Valley Road, Honokaa, HI, USA
    • ACTIVITYManta Ray Night Dive (see notes)
      Kona, HI, USA
  • Day 9

    • ACTIVITYDrive the Hāmākua Coast (Hamakua Heritage Corridor from Hilo to Waipio Valley Lookout)
      Hilo, HI, USA
    • ACTIVITYStargazing at Mauna Kea
      Mauna Kea Observatory, Hawaii, USA
  • Day 10

    • ACTIVITYHike- Nāhuku (Thurston Lava Tube)
      Nahuku - Thurston Lava Tube, Hawaii Volcanoes National Park, HI, USA
    • ACTIVITYHawaii Volcanoes National Park
      Hawaiʻi Volcanoes National Park, Hawaii Volcanoes National Park, HI, USA
    • ACTIVITYPunaluʻu Black Sand Beach
      Punaluu Black Sand Beach, Hawaii, USA
  • Day 11

    • OTHERReturn car hire
    • TRAVELKona International Airport to Kahului Airport
      Kona International Airport-KOA (KOA), Kupipi Street, Kalaoa, HI, USA
    • OTHERPick up car hire
    • ACTIVITYDrive the 'Road to Hana'
      Road To Hana, Hana Highway, Kula, HI, USA
    • ACTIVITYHana Lava Tube
      Hana Lava Tube, Ulaino Road, Hana, HI, USA
    • ACTIVITYWaiʻānapanapa State Park
      Waiʻānapanapa State Park, Waianapanapa, Hana, HI, USA
  • Day 12

    • ACTIVITYExplore Lahaina
      Lahaina, HI, USA
    • ACTIVITYWhalers Village (shopping)
      Whalers Village, Kaanapali Parkway, Lahaina, HI, USA
    • ACTIVITYHike or drive to Haleakalā summit for sunset
      Haleakalā National Park, Hawaii, USA
  • Day 13

    • ACTIVITYMakena Beach
      Makena Beach, Makena Alanui, Kihei, HI, USA
  • Day 14

    • ACTIVITYʻĪao Valley State Monument
      ʻĪao Needle State Monument, Wailuku, HI, USA
    • OTHERReturn car hire
    • TRAVELKahului Airport to Home
      Kahului Airport (OGG), Keolani Place, Kahului, HI, USA