Hawaii Island Hopping Holiday • Freedom Destinations
H3 Highway, Oahu
Na Pali, Kauai
Haleakala National Park, Maui
Waikiki Beach, Honolulu
Na Pali, Hawaii

Hawaii Island Hopping

17 day Fly Drive Holiday - from £3299

With flights from £4449

Take in the highlights of the Hawaii on this island hopping holiday to O’ahu, Kauai, Big Island and Maui, with a hire car on each to explore at your own pace.


  • Enjoy four nights on each of Hawaii’s main islands
  • Relax on Waikiki’s famous beaches
  • Learn about the poignant history of Pearl Harbor
  • Drive the signature Road to Hana
  • Witness the spectacular views from Waimea Canyon lookout

Your Holiday Includes:

  • 4 nights on O’ahu
  • 4 nights on Kauai
  • 4 nights on Hawaii
  • 4 nights on Maui
  • Inter-island flights
  • Car hire on each island
  • Optional UK flights
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Your Itinerary

Day 1 - Honolulu

Arrive at the International Airport in Honolulu and immediately immerse yourself in the Hawaiian atmosphere. Collect your car and proceed to your hotel for the start of this wonderful journey.

Home to the State Capitol, Honolulu is the vibrant epicentre of Hawaii and the place where most of the people live. Here you’ll find everything from historic landmarks and treasured monuments to world-class shopping and a flourishing arts and culture scene. Be sure to explore the vibrant downtown district. Next to the skyscrapers of the island’s main business district, you’ll find important landmarks like the Iolani Palace, the King Kamehameha I statue, the Kawaiahao Church and the Aloha Tower.

Hotel: Waikiki Sand Villa Hotel or similar

Day 2 - O'ahu

The best beaches of O’ahu are undoubtedly in Waikiki. From Duke Kahanamoku Beach to Kaimana (San Souci) Beach, enjoy the best the ocean has to offer. Whether it’s surfing, a nice swim or just a lazy day at the beach, in Waikiki you can have it all. While in the area, shopaholics will find their heart’s desires at the Ala Moana Centre, the biggest open-air shopping mall in the United States.

For those who enjoy more active pursuits, make a trip to Diamond Head State Monument, a volcanic tuff cone, and one of the most iconic landmarks of O’ahu. You can hike from the trailhead to the summit, indulging in spectacular views along the way.

Hotel: Waikiki Sand Villa Hotel or similar

Day 3 - Pearl Harbor & Kualoa

A must-see is Pearl Harbor. Named for the pearl oysters that were once harvested there, it is the largest natural harbour in Hawaii, a National Monument and a United States naval base. Here you can visit the USS Arizona Memorial, USS Oklahoma Memorial, USS Utah Memorial, and parts of Ford Island and Battleship Row, and learn about the attack on Pearl Harbor, and the subsequent entry of the United States into World War II.

Just a 30 minute drive further east, is Kualoa; a private nature reserve, as well as a popular tourist attraction and filming location for movies such as Pearl Harbor, Godzilla, Jumanji and Jurassic Park. Tours are available at the park where movie buffs can learn about the filming locations as well as the stunning natural environment of Kualoa.

Hotel: Waikiki Sand Villa Hotel or similar

Day 4 - North Shore

Another day in paradise! Drive to the northern coast. Along the way, visit the famous Dole Pineapple Plantation before arriving in Haleiwa. This historic surf town, is the cultural hub of the North Shore and a dream for the surfers among us with cool surf shops, local restaurants, and plantation-era buildings.

Experienced surfers will want to hit the towering waves during the winter months, while beginners can enjoy the summer water conditions when waves are generally smaller. Another major draw of the North Shore is the magnificent hills, forests and waterfalls, with a choice of hiking trails to follow.

Hotel: Waikiki Sand Villa Hotel or similar

Day 5 - Kauai

Today, fly from O’ahu to Kauai, also known as “Garden Island” and collect your hire car. With approximately five million years of history, it is the oldest of the main islands in the Hawaiian archipelago, brimming with unspoilt natural beauty.

The tropical rainforests, amazing beaches and beautiful mountains quickly caught the attention of Hollywood, with more than seventy movies and television shows filmed on Kauai, including Jurassic Park, the 1976 version of King Kong, two Elvis Presley films and Pirates of The Caribbean.

Most of the locals live in Kapaa which is situated on the east side of the island. Lihue is the second largest town in Kauai and offers wonderful attractions such as museums and zip lining experiences. As for dining and nightlife, Garden Island is home to more traditional establishments, ideal for those who want to get a taste of real Hawaiian culture.

Hotel: Plantation Hale Suites or similar

Day 6 - Wailua Falls & Kalalau Trail

Today, explore the east side of Kauai. Visit the Wailua River State Park, located just north of Lihue and home to Wailua Falls, a 173 foot double waterfall, that featured in the opening credits of the television series Fantasy Island.

On the northern side of the island, you’ll find one of the most awe-inspiring trails in Kauai. The Kalalau Trail offers beautiful sights of waterfalls, valleys and much more. 11 miles (18km) long, it leads you from Ke’e Beach to Kalalau Beach. It is the only way to gain access to some parts of the rugged coast. It may be challenging for casual hikers, but it’s absolutely worth it. Since there’s only one road taking you up north, the drive itself is stunning and there are plenty of opportunities to stretch your legs and enjoy the view.

Hotel: Plantation Hale Suites or similar

Day 7 - Waimea Canyon

There are many options to relax on Kauai with beaches, bars and markets for shopping. But for the casual adventurer, it has an array of activities in store. One of the biggest highlights of the island is Waimea Canyon. Often referred to as the Grand Canyon of the Pacific, it was carved thousands of years ago by the Waimea River. The ten miles long and 3,500 ft deep canyon has three lookout spots from which you can view the canyon: the official Waimea Canyon lookout, the Puu Ka Pele lookout and Puu Hinahina lookout. Hiking trails will bring you to extraordinary places such as the Waipoo waterfall.

For those who don’t like hiking, it is also possible to drive up the Waimea Canyon or to join a tour with a professional guide. Along the way, visit Captain Cook’s landing, the location where in 1778, James Cook set foot on the island. This event would change Hawaii forever as they got introduced to the western world. Here, in Waimea, you can see the statue of James Cook, erected to remember his first contact with the Hawaiian Islands.

Hotel: Plantation Hale Suites or similar

Day 8 - Poipu Beach

For a relaxing day head to the beach. One of the best is Poipu Beach, located on the south shore of Kauai and loved by both visitors and locals. Popular activities are surfing, snorkelling, fishing or bodyboarding and the beach has convenient amenities like bathrooms, showers and sufficient parking space. Poipu Beach even has its own protected swimming area for families with young children. Enjoy your last night on the island with a traditional meal, accompanied with typical Hawaiian entertainment.

Hotel: Plantation Hale Suites or similar

Day 9 - Hawaii (Big Island)

Leave Kauai behind and fly to the Island of Hawaii, more commonly known as Big Island, as it is the largest of the Hawaiian archipelago. The Big Island also has various types of climate zones. This extraordinary feature guarantees a day of extreme variety; you can start your day at the Ka’u desert (home to dried lava remnants, volcanic ash, sand, and gravel desert) and end up in a tropical rainforest.

Most of the population live in West Hawaii and it is here that your Big Island adventure begins. Famous for sport fishing, snorkelling, sunsets and coffee, which is cultivated on the slopes of Mount Hualalai, there is plenty to do in Kailua-Kona, and because the mountains block the north easterly trade winds, Kona gets very little rain and enjoys more than 300 days of sunshine a year.

Hotel: Royal Kona Resort or similar

Day 10 - Kailua Kona & Saddle Road

Prepare for a day in Kailua-Kona with a cup of coffee, brewed with locally grown beans. Kailua Kona’s quiet beaches are perfect for sunbathing. As well as being a great spot to see turtles, the snorkelling is particularly good in this area. If you want to relax without getting your feet wet, then Ali’i Drive is the place to go. Here you can find shops selling souvenirs and t-shirts, fashion and convenience stores. There is more to see though as it is here you can also find Hulihe’e Palace, a museum that was once a vacation house for royalty or stop at Ahu’ena Heiau; a temple that is dedicated to the Hawaiian god, Lono. Remember to leave time to head out in to the beautiful landscape of Big Island. Take the Saddle Road; a scenic drive crossing the island, with breathtaking lookouts along the route.

Hotel: Royal Kona Resort or similar

Day 11 & 12 Mauna Kea & Volcanoes National Park

90 minutes east of Kailua-Kona is Mauna Kea. Measured from its base (at the sea floor) to the top, it is the tallest mountain in the world and is simply wondrous to experience. Some of the clearest skies on the planet can be found here, which means the star gazing at night is mind blowing. Take a tour and make a stop at the Onizuka Centre for International Astronomy to learn more and to get acclimated to the altitude.

If you can, a helicopter ride is highly recommended. These one-of-a-kind tours can show you the island in a whole day while you will be able to see amazing places that would otherwise be difficult to reach over land. Another way to get a whole new perspective is through ziplining, an activity offered all over the island. The longest zip line can be found in Hilo/Kona and is 2,400 feet long (731m).

A trip to the Big Island is not complete without a visit to Hawaii Volcanoes National Park, located in the southeast of the island. Founded in 1916, this park is home to two volcanoes including the most active volcano on earth; the Kilauea volcano. You will find hiking trails through volcanic craters, petroglyphs as well as a museum.

Hotel: Royal Kona Resort or similar

Day 13 - Maui

This morning fly to Maui, the second largest island of Hawaii, and collect another hire car. It is primarily known for its diverse natural landscapes; a result of a unique combination of geology, topography and climate. Maui flawlessly combines eco-tourism with resort-like vacationing and offers countless possibilities for both adventurers, families and those who just want to unwind. An oasis of majestic ocean hideaways, lush green mountains and picturesque beaches, the island of Maui epitomizes mythical wonder. Add to that the genuine Maui culture, which locals would love you to partake in. There are over 30 beaches and bays to snorkel at around the island and you’ll find even the locals hitting the waves to surf.

Hotel: Royal Lahaina Resort or similar

Day 14 - Road to Hana

The Road to Hana, is a curving route around mountains, passing by black sand beaches and waterfalls. It is one of Maui’s signature adventures. In the case of this adventure, it is just as much about the journey as it is the destination. Along the way, major attractions are the Seven Sacred Pools and waterfalls of Ohe’o Gulch. Although there are no big distances to travel on Maui, it is advised to use an entire day exploring the Road to Hana. With its many curves and lookouts, it does take some time to see it all.

Hotel: Royal Lahaina Resort or similar

Day 15 - Haleakala National Park

Visit the sprawling Haleakala National Park that encompasses the island’s highest peak, volcanic Haleakala, with the famous crater on the summit. The park is known for its unique volcanic features, rare endemic flora and fauna, its long scenic drive with numerous overlooks, and the unusually clear views of the night sky as well as amazing sunrises.

Hotel: Royal Lahaina Resort or similar

Day 16 - Lahaina

Head to Lahaina, one of the main attractions on the island with an entire street of shops and restaurants which leads to a wharf where many set out for a sunset cruise or whale watching journey.

Maui is the whale watching centre of the Hawaiian Islands due to humpback whales wintering in the sheltered ‘Au’au Channel. The whales migrate approximately 3,500 miles (5,600 km) from Alaskan waters each autumn and spend the winter months mating and birthing in the warm waters off Maui, with most leaving by the end of April.

Known locally as Lahainatown, it has a long and diverse history from its Hawaiian population beginnings to the arrival of travellers and settlers and its use as a significant whaling port. It’s definitely worth spending some time here and with beaches nearby, relaxing is just steps away. Enjoy your last night in Maui with a luau, a traditional Hawaiian party with local food, music and hula.

Hotel: Royal Lahaina Resort or similar

Day 17 - Farewell from Hawaii

Enjoy your last moments in Hawaii and depart for the airport at leisure. Why not add a stopover in Los Angeles or Las Vegas to break the flight home?

17 day Fly Drive Holiday - from £3299

With flights from £4449


  • Add extra nights on O’ahu, Kauai, Hawaii or Maui
  • Add a city stay in Los Angeles, San Francisco or Las Vegas
  • Pre-book a Maui helicopter flight or Waimea Canyon day tour
  • Choose to fly Economy, Premium, Business or First Class

Include this Fly Drive Holiday in an America holiday designed for you

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Prices are per person, based on two people sharing a double or twin room. Flights, hotels and tours are subject to availability and seasonal variations may apply.

Hawaii Island Hopping route map


Enjoy independent touring at its very best. You can book our self drive holidays as they are or add extra days in the places you choose.

Your self drive includes:

  • Well planned, easy to follow routes
  • 16 nights pre-booked hotel accommodation
  • Modern, air-conditioned car
  • Unlimited mileage
  • Roadside assistance
  • Car upgrades available upon request

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For advice or to start planning your holiday

talk to an America Expert on 0333 234 0922