10 Best Island Road Trips in the World, Ranked

The best island road trips are the loops and coastal runs where the road is hemmed in by the sea on almost every side: Iceland's Ring Road circles a whole country, Maui's Road to Hāna threads a jungle coastline, and Japan's Shimanami Kaidō actually hops six islands on six bridges. An island concentrates a drive. The water is never far, the light bounces off it, and the route almost plans itself because there is usually only one great road and it goes most of the way around.

This is a ranked list of ten island drives pulled straight from the catalog, with real distances, durations, and best-season windows so you can plan around ferries, monsoons, and snow. Every entry links to its full route guide, and because so many hug the shore, you can browse the wider set in our Scenic Coastal Drives hub.

The 10 best island road trips at a glance

Here is the ranked shortlist. Distances, durations, and seasons come straight from each route's page, so build your trip around the months the road is actually at its best.

If you only do one

Drive the Iceland Ring Road. No other island trip on this list wraps an entire country into one continuous 1,332 km loop, and none packs so much variety into nine days: the tectonic rift at Þingvellir, the Strokkur geyser firing every few minutes, Seljalandsfoss and the black-sand coast at Vík, the blue icebergs of Jökulsárlón, the volcanic weirdness of Mývatn, and whale watching out of Húsavík. It is at its best from June to September, when the whole circuit is reliably open and the daylight barely quits. A standard car handles Route 1 fine in summer, though the highland F-road shortcuts stay strictly 4WD only.

1. Iceland Ring Road, Iceland

The definitive island drive is a full lap of one. The Iceland Ring Road traces Route 1 clockwise from Reykjavík for 1,332 km through the south coast waterfalls, the East Fjords, the geothermal moonscape around Mývatn, and the northern capital of Akureyri before closing the loop through the west. Give it nine days, ideally from June to September, when the highland weather settles and the light stretches a driving day past midnight. It is rated moderate and an SUV is the sensible choice, but the paved ring itself is straightforward the whole way around.

2. Road to Hāna, United States

Maui's Road to Hāna is the tropical island drive distilled: 84 km of the Hāna Highway threading Maui's northeastern coast through 59 bridges and 620 curves, past bamboo forests, waterfalls tumbling into the sea, and the black-sand beach at Waiʻanapanapa State Park. It is short enough to be one long day, but it rewards two, with an overnight in sleepy Hana before the ʻOheʻo pools at Kīpahulu. The drive runs year-round, and because the highway is narrow and slow by design, the whole point is to stop often rather than push through.

3. Shimanami Kaidō, Japan

No drive makes island-hopping this literal. The Shimanami Kaidō links six islands across the Seto Inland Sea on six graceful bridges, arcing 70 km from Onomichi in Hiroshima to Imabari in Ehime. Along the way are lemon groves, the hilltop Suigun castle on Innoshima, the mosaic hillside of Kosanji Temple at Setoda, and the Kirosan Observatory on Oshima, where the whole bridge chain lays out below you. It is an easy one to two day drive, at its finest in the shoulder seasons of April to June and September to November, when the sea haze lifts and the light turns crisp.

4. Milford Sound Drive, New Zealand

Fiordland is New Zealand's wildest corner, and the Milford Sound Drive is the only road into it. From Te Anau it follows the inland fjord shores, crosses the golden Eglinton Valley, passes the still Mirror Lakes, then climbs to The Divide and bores through the 1.2 km Homer Tunnel before dropping steeply into mountain-rimmed Milford Sound. It is 240 km return, best spread over two days, and open reliably from November to April. Leave Te Anau early, because the tunnel runs one-way on a signal and the tour coaches stack up by mid-morning.

5. Cabot Trail, Canada

Cape Breton Island's Cabot Trail is one of the most scenic drives in North America, a 298 km loop that climbs over the Cape Breton Highlands, drops to sea-level fishing villages, and traces cliff edges with 300 m plunges into the Gulf of St. Lawrence. Base yourself in Baddeck, run the loop over three to four days, and pause in Cheticamp for Acadian music and Pleasant Bay for whale watching. Go from June to October, when the park is fully open. Late September and early October add the Maritimes' fierce autumn colour to the headlands.

6. Overseas Highway, United States

Few roads feel as much like driving on the sea as US-1 through the Florida Keys. The Overseas Highway runs 230 km over 42 bridges from the mainland to Key West, with turquoise flats on both sides, pelicans on the railings, and the famous Seven Mile Bridge out over open water. It is an easy one to two day run past Key Largo, Islamorada, and the beach at Bahia Honda, ending at the southernmost point of the continental United States. The dry season from November to April is the sweet spot, before summer heat and hurricane risk build.

7. Taiwan Island Loop, Taiwan

For a full circuit of a single island, the Taiwan Island Loop runs about 1,250 km clockwise from Taipei down the wild Pacific east coast to Hualien, through the East Rift Valley to Taitung, around the South Link to the Kenting Peninsula, then back up the west through Kaohsiung, the tea-terraced heights of Alishan, and Sun Moon Lake. Give it ten days. The comfortable windows are spring, March to May, and autumn, October to November, either side of the humid summer and its typhoons. The driving is moderate and the roads are good throughout.

8. Bali West and Highlands Loop, Indonesia

Most visitors never leave Bali's crowded south, which is exactly why the Bali West and Highlands Loop works. In about 340 km over five days it climbs from Ubud into the volcanic caldera country of Kintamani, drops to the black-sand calm of Lovina, reaches the coral and jungle of Pemuteran and Menjangan in the far west, then eases back for a Tanah Lot and Jimbaran finish. It is a moderate drive best in the dry season, April to October, when the mountain roads are clear and the rice terraces are greenest.

9. Hokkaido Flower Route, Japan

Japan's northern island turns technicolour for a few short summer weeks, and the Hokkaido Flower Route is built to catch it. The classic Asahikawa to Biei to Furano drive follows Route 237 and quiet country loops for about 130 km through patchwork hills, the striped flower fields of Shikisai-no-Oka, the surreal Shirogane Blue Pond, and the lavender rows at Farm Tomita. It is an easy three-day drive, and the season is tightly defined: late June to August, when the lavender and the wider flower patchwork are in full bloom before the northern summer fades.

10. Cuba Central Highway, Cuba

The Cuba Central Highway crosses the spine of the Caribbean's largest island, running 870 km along La Carretera Central from Havana to Santiago through colonial cities, tobacco country, and a rolling parade of vintage American cars. Over nine to twelve days it links the pastel streets of Trinidad, the bay at Cienfuegos, and the old quarter of Camagüey before reaching the music and revolutionary history of Santiago. It is a moderate cultural drive best in the dry season, November to April.

Frequently asked questions

What is the best island road trip in the world?

For range and scale, the Iceland Ring Road is hard to beat: it circles an entire country in 1,332 km and nine days, moving from waterfalls and black beaches to geothermal fields and whale-watching harbours. If you want something shorter and warmer, Maui's Road to Hāna and Japan's Shimanami Kaidō are the standouts, each drivable in a day or two.

Which island road trips can you do in a weekend?

Several here fit a long weekend. The Road to Hāna (84 km), the Shimanami Kaidō (70 km), and the Overseas Highway (230 km) are all one to two day drives, and Milford Sound works as a two-day return trip. The longer loops, Iceland, Taiwan, and Cuba, need a week or more.

Do you need a 4x4 for these island drives?

Mostly no. Almost every route on this list is paved and rated easy or moderate, so a normal car is fine. Iceland is the one to watch: the Ring Road itself is straightforward in summer, but the highland F-road shortcuts are strictly 4WD only and off-limits to standard cars.

When is the best time for a tropical island road trip?

Aim for the dry season. In the Florida Keys and Cuba that means November to April, and in Bali it means April to October. Hokkaido is the outlier, best in the short late-June to August flower window, while Maui's Road to Hāna is genuinely year-round.

Plan your island road trip

Pick an island, check the season, and let the coast do the routing. For the full stop-by-stop detail on the top pick, read our Iceland Ring Road guide, browse the complete Scenic Coastal Drives collection, or trace your own island loop on the interactive map.