This blog post was updated on September 8, 2020.

There’s more than one side to any island and some of the world’s bigger, more beautiful islands deserve to have all their sides explored in full. So, if you dream of a vacation that’s filled with discovering waterfalls, hiking mountains and rainforests, admiring scenic coastal views, and visiting far-flung beach communities – and don’t mind doing all that with your window rolled down while listening to your favorite road-trip playlist, then keep reading.

Here’s the ultimate list of island road trip ideas for driving enthusiasts who love the thought of spending some time in paradise, but prefer to keeping moving and not get stuck in one place.

Big Island of Hawaii

For some action-packed roadtrippin’, pack your bags and book some flights to Honolulu (or, you know, Kawaii, Oahu… or the many other spots) because the island of Hawaii, (aka the Big Island) is indeed just that: BIG! At 4,000 square miles, it’s not only the largest of the Hawaiian Islands but also the largest island in the entire U.S. Within all that square mileage is some of the most beautiful and fascinating scenery in the world. There’s the active volcano, Kilauea, which might be erupting when you visit. And if you’re lucky you even see the lava flow. There’s also Mauna Kea, the world’s tallest mountain, as long as you’re measuring from its seafloor base to its highest peak (the base of Mount Everest in the Himalayas is above sea level). During the winter months, Mauna Kea can sometimes be snowcapped. The island is home to rainforests and deserts, as well as white, black and even green sand beaches, remote hideaway coves, world-class resorts, farms and cattle ranches and all sorts of wonderful vistas to admire the majestic Pacific Ocean and the grandeur of this massive chunk of earth (and well-paved roads to drive on while there).

Vancouver Island, Canada

Part of the province of British Columbia on Canada’s west coast, Vancouver Island is about 300 miles long and 60 miles wide. A highlight for many travelers visiting the island is to tour it by car. The ultimate destination for the keenest adventurers is making it the tiny town, and year-round surfer’s outpost, of Tofino. Laidback Tofino sits on the far north of the island at the end of a peninsula in the Clayoquot Sound with pristine beaches, lakes, and ancient untouched rainforest surrounding it.

Flores, Indonesia

Fantastic Flores in the southeastern corner of the Indonesian archipelago has magnificent mountains, all sorts of hidden beaches, waterfalls, lakes, traditional villages and dozens of dive sites. Accessing all of that island wonder via the island’s 400-mile Trans-Flores Highway is the stuff of road trip dreams. Despite being a relatively underrated destination, this long narrow island in southeastern Indonesia has good infrastructure, an impressive range of accommodation options and plenty to see and do for all types of travelers. By the way, here there be dragons! Namely Komodo dragons and the best place to find the Komodo National Park, just a short boat ride away from the western end of Flores.


Is a cold-climate road trip idea more your thing? Well, luckily for you, Iceland is just that. For splendid isolation, desolate landscapes, windswept seascapes, geysers, surreal geothermal activity, volcanoes, massive waterfalls, and lots and lots of wide-open spaces (not to mention superbly paved roads, modern accommodation, and kindly salt-of-the-earth folks), Iceland is a superb place to be if you’re an island lover who also loves to road trips.

RELATED: The Dos and Don’ts of International Road Trips


Yep, we’re talking about the whole Emerald Isle with potential stops in both the Republic of Ireland to the south and Northern Ireland (part of the United Kingdom) to the north. See Galway Bay, tour the Ring of Kerry, explore historic towns and cities like Dublin, Cork, Limerick, and Belfast, kiss the Blarney Stone! Also make sure to park the car overnight for an evening in a pub, partaking in the local beer or whiskey and listening to traditional folk music.

Sicily, Italy

The largest island in the Mediterranean Sea, and a region of Italy that’s rich in natural beauty spots, historic sites, amazing weather, and delicious food – Sicily is a world unto itself with the ancient Greek settlement of Valle dei Templi, the ginormous (and sometimes smouldering) volcano, Mount Etna, romantic getaways like Taormina and Syracuse and more hidden gems that you could hope to see in a lifetime (but that’s not to say you shouldn’t start trying ASAP).

South Island, New Zealand

Big untapped wilderness with glaciers, expansive lakes, rugged coasts, massive mountains, exceedingly friendly folks living quaint cities and towns and some of the best cafe culture in the world – everything about New Zealand’s South Island is delightful. Taking an opportunity to explore by car (preferably a camper van) could end up being the most memorable trip of your life. Must-see stops for any itinerary should include Aoraki (Mount Cook), the adventure sports outpost of Queenstown located on Lake Wakatipu and the epically gorgeous Milford Sound in the stunning Fiordland region on the southwestern coast of the island.


For authentic Chinese culture from age-old traditional villages to the cutting edge contemporary city life in bustling Taipei, the island of Taiwan awaits keen travelers ready for a fascinating experience. Be sure stock up on snacks before hitting the road and to make sure there’s plenty of time to stop for meals while driving because Taiwan is the foodie-est of destinations. From bubble tea to fried chicken, if the Taiwanese didn’t invent it they at least made a yummier version of it. On the road, you’ll have coffee plantations, ancient temples, forests, beaches, and rice paddies to fill your itinerary.

Got a favorite island? We’d love it if you could share your tips on which islands you think are worth exploring

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About The Author

Chris Osburn is a freelance writer, photographer, consultant, curator, and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world. He's called London home since 2001.