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Iconic Hawaiian Road Trips: Point of Interest Map
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Iconic Hawaiian Road Trips Vacation Packages


The stunning sun-soaked Hawaiian Islands boast some of the most beautiful beaches in the world, there is so much to do off the sand. Enjoy unforgettable scenic drives that await to be explored, the curvy Hana Highway snakes along Maui`s northeast coast, passing verdant green cliffs laced with waterfalls plunging to gold, black and red sand beaches. The North Shore of Kauai leads through dreamy Hanalei with a local authentic atmosphere and Hawaii Big Island where you can drive along the Craters Road through Hawaii Volcanoes National Park on a captivating and fascinating journey.

Best Vacation Packages:

Main Islands

More to Explore

  • Honeymoon in Hawaii

    Honeymooning in Hawaii is a once in a lifetime experience with five main islands to choose from each one boasting its own uniqueness. The astonishing sun-drenched islands offer miles of white sandy beaches, sparkling blue waters, soaring mountains, gargantuan volcanoes, and lush verdant rainforests.

  • Hawaii and Beyond

    Two vibrant countries in just one trip!... In your way to Auckland enjoy a Hawaii stopover and visit Oahu, known as a place of breathtaking natural beauty. From glorious sunrises to dramatic sunsets and beyond, there is so much to do and enjoy in Hawaii.

Experiences and Adventures

  • Volcanoes National Park

    Watch Hawaii in a different way! Visit Hawaii Volcanoes National Park. Located 30 miles southwest of Hilo this is the home of Kilauea volcano, one of the most active volcanoes on earth. This sacred place is one of the most popular visitor attractions in Hawaii.

SUGGESTED ITINERARIES

  • Runway to Road: Maui and Kauai
    6 nights from $2,627*
  • Hawaii exchanting islands!. Steel away in Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales; farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala), and finally, visit Kauai (-the garden island-, thanks to the tropical rainforest covering much of its surface. It is home to one of the wettest places on earth. The Waimea Canyon and the Nounou Trails traversing the Sleeping Giant mountain ridge are hiking destinations). Take advantage of the Rental Car to discover each destination.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Maui and out of Kauai
    • Rental Car for 4 days
    • Hotel in Maui for 3 nights
    • Flight from Maui to Kauai
    • Rental Car for 4 days
    • Hotel in Kauai for 3 nights


  • Runway to Road: Oahu - Maui - Kauai
    9 nights from $2,765*
  • This once in a life time get away is at your grasp in Hawaii!. Begin in Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach). Next, steel away in Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales; farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala), and finally, visit Kauai (-the garden island-, thanks to the tropical rainforest covering much of its surface. It is home to one of the wettest places on earth. The Waimea Canyon and the Nounou Trails traversing the Sleeping Giant mountain ridge are hiking destinations). Take advantage of the Rental Car to discover each destination.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Oahu (Honolulu) and out of Kauai
    • Hotel for 3 nights in Oahu (Honolulu)
    • Rental Car for 4 days
    • Flight from Oahu (Honolulu) to Maui
    • Hotel for 3 nights in Maui
    • Rental Car for 4 days
    • Flight from Maui to Kauai
    • Hotel for 3 nights in Kauai
    • Rental Car for 4 days


  • Runway to Road: Oahu and Maui
    6 nights from $2,316*
  • Hawaii`s Success destinations by car!. Visit: The Gathering Place; Oahu (the third largest island and most visited of the Hawaiian Chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach. This vibrant island offers the best of both worlds-tropical verdure and a lively night scene). After spending wonderful days under the sun, catch a flight to Maui (beauty atmosphere, history, and its never-ending supply of pristine beaches, waterfalls and gardens. The island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales and the magnificent sunrise and sunset from Haleakala -East Maui Volcano-). A Rental Car allows to discover these two islands at your own time!.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Oahu (Honolulu) and out of Maui
    • Rental Car for 4 days
    • Hotel for 3 nights in Oahu (Honolulu)
    • Flight from Oahu (Honolulu) to Maui
    • Rental Car for 4 days
    • Hotel for 3 nights in Maui


  • Runway to Road: Hawaii Big Island (Kona) - Oahu - Maui
    9 nights from $1,847*
  • See beautiful Hawaii through popular destinations!. Visit Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand beaches that are perfect for sunbathing, snorkeling and swimming), Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach-where surfing was born-); and finally, Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales (during winter months, farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala).

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Hawaii Big Island (Kona) and out of Maui
    • Hotel for 3 nights in Hawaii Big Island (Kona)
    • Rental Car for 4 days
    • Flight from Hawaii Big Island (Kona) to Oahu (Honolulu)
    • Hotel for 3 nights in Oahu (Honolulu)
    • Rental Car for 4 days
    • Flight from Oahu (Honolulu) to Maui
    • Hotel for 3 nights in Maui
    • Rental Car for 4 days


  • Runway to Road: Hawaii Big Island (Kona) and Maui
    6 nights from $1,816*
  • Enjoy this Rental Car Package to venture through these amazing Hawaii Islands. Start your adventure in Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand beaches that are perfect for sunbathing, snorkeling and swimming) and after that, have a pleasant stay in Maui (the island beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales; farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala).

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Hawaii Big Island (Kona) and out of Maui
    • Hotel for 3 nights in Hawaii Big Island (Kona)
    • Rental Car for 4 days
    • Flight from Hawaii Big Island (Kona) to Maui
    • Hotel for 3 nights in Maui
    • Rental Car for 4 days


  • Runway to Road: Hawaii Big Island (Kona) and Kauai
    6 nights from $2,331*
  • What better combination for your vacation than the beauty of Hawaii! with a Rental Car. This adventure combine Kona-Kailua (often referred to as Kona by locals, is a sunny seaside town located in the heart of the Kona district on the western coast of the Hawaii`s Big Island. The weather on this side of the island is almost always dry and sunny and there are many white sand beaches that are perfect for sunbathing, snorkeling and swimming) and Kauai (-the garden island-, thanks to the tropical rainforest covering much of its surface. It is home to one of the wettest places on earth. The Waimea Canyon and the Nounou Trails traversing the Sleeping Giant mountain ridge are hiking destinations). Take advantage of the Rental Car to discover each destination.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Hawaii Big Island (Kona) and out of Kauai
    • Hotel for 3 nights in Hawaii Big Island (Kona)
    • Rental Car for 4 days
    • Flight from Hawaii Big Island (Kona) to Kauai
    • Hotel for 3 nights in Kauai
    • Rental Car for 4 days


  • Hawaii Big Island (Self Drive)
    6 nights from $1,993*
  • A Big Island Experience in Hawai!. Drive through Hilo-Hawaii Big Island and enjoy all this unique place has to offer. From stunning waterfalls, active and dormant volcanoes, snow-capped mountains, lush vegetation and marvelous beaches to the most exciting activities, such as ziplining or snorkeling with manta rays. It is famous for its incredible natural attractions, particularly the volcanoes, which have shaped and continue to shape the landscape.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into and out of Hilo
    • Rental Car for 7 days
    • Hotel for 6 nights in Hawaii Big Island (Hilo)
    • Hotel Hawaii taxes
    • Plus a wide range of optional activities to add and book with instant confirmation.

    • Do not forget to arrange transfer to/from Airport or Rental Car service to have all services confirmed before traveling



  • Maui Escape (Self Drive)
    5 nights from $1,513*
  • Say Aloha in Maui. Discover this fantastic and the second largest Hawaiian island; beloved for its world-famous beaches, the sacred Iao Valley, views of migrating humpback whales, during winter months, farm-to-table cuisine and the magnificent sunrise and sunset from Haleakala; with a Rental Car.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into and out of Maui
    • Rental Car for 6 days
    • Hotel for 5 nights in Maui


  • Runway to Road: Oahu and Kauai
    6 nights from $2,368*
  • A Road Trip Adventure in these Hawaiian Islands!. Enjoy a fantastic holiday visiting: Oahu (the third largest island and most visited of the Hawaiian chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach) and Kauai (-the garden island-, thanks to the tropical rainforest covering much of its surface. It is home to one of the wettest places on earth. The Waimea Canyon and the Nounou Trails traversing the Sleeping Giant mountain ridge are hiking destinations). Connects with a flight and a Rental Car these destinations.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into Oahu (Honolulu) and out of Kauai
    • Rental Car for 4 days
    • Hotel for 3 nights in Oahu (Honolulu)
    • Flight from Oahu (Honolulu) to Kauai
    • Rental Car for 4 days
    • Hotel for 3 nights in Kauai


  • Oahu Escape (Self Drive)
    More details
  • ALOHA in Hawaii!... There is so much to do in Oahu with this Self-Drive Package!. It is the third largest island and most visited of the Hawaiian Chain. The Island is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach. These areas host thousands of tourists daily. This Island is special for romantic escapades or adventure full of adrenaline. Make plans for surf lesson in world-wide-known beaches or a fun night out to dance and drink, a place with perfect sunsets and spectacular sunrises. Discover the Island with a Rental Car!.

    What Makes Tripmasters Vacation Packages Different?
    Unique, fully custom approach to vacation planning
    Choose your preferred flight cabin class
    Select up to 14 nights in each city during your stay
    Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
    Add transfers, activities and experiences, and more services to enhance your vacation
    Live phone and chat support
    Included:
    • Flight into and out of (Honolulu)
    • Rental Car for 5 days
    • Hotel for 6 nights in Oahu (Honolulu)


Build Your Own Itinerary

Travel Guide

  • Hawaii Island Hopping

    Hawaii is not just one destination, it’s an entire archipelago of unique islands, each with its own landscapes, culture, and unforgettable experiences. From volcanic craters and lush rainforests to golden beaches and historic towns, the best way to truly experience the Aloha State is through a Hawaii island hopping vacation.

CUSTOMER REVIEWS

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Map of Hawaii

Iconic Hawaiian Road Trips

Orientation

Cities in Hawaii

  • Honolulu (Oahu)  
  • Kauai  
  • Maui  
  • more cities

Hawaii & Beyond