Hawaii Trips

What Inspires You?

Beaches  ▪  Family  ▪  Food  ▪  Haunted  ▪  Music  ▪  National Parks  ▪  Outdoor Adventures  ▪  Relaxation  ▪  Road Trips  ▪  Scenic Drives  ▪  Shopping  ▪   Space  ▪  Weekend Getaways

Destinations: Trips by State or Province  ▪  Northeast  ▪  South  ▪  Midwest  ▪  West  ▪  Canada  ▪  Mexico
Seasons: Spring  ▪  Summer  ▪  Fall  ▪  Winter

Pick any island in our 50th state, and you’ll travel to a paradise that boasts warm seas year-round, waterfalls dropping from steep cliffs, tropical jungles and vibrant flowers everywhere. Enterprise recommends renting a convertible, whether your road trip takes you to a quiet cove on Oahu, an historic whaling town on Maui or an active volcano on the Big Island.

A Mindful Journey in Maui

Hawaii’s natural beauty is the perfect setting to slow down.
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The Road to Hana

Challenging drive leads to beautiful vistas and simple food.
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On the Road — and the Beaches — in Maui with Friends

The Hawaiian island’s tropical embrace offers a memorable vacation in paradise.
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A Do-Over Honeymoon in Hawaii

A couple soaks up Oahu’s charm on a romantic getaway.
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5 Great Hawaiian Beaches

Oahu and Maui both offer beautiful stretches of sand.
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Get more Hawaii road trip ideas.