Hawaii, by land —
twenty years ago

This is the oldest trip on this site. April 2005, twelve days, four Hawaiian islands by land — flights between them, hotels on each, rental cars, and the kind of paper itineraries you used to fold up in your back pocket. We didn't know it at the time, but this was the trip that turned us into people who travel, take photos of every meal, and come home already planning the next one. Twenty years later, when someone asks us about Hawaii, this is the trip we still pull from. The cruise we did in 2016 added new perspectives — but our Hawaii knowledge starts here.

So here's the journal, twenty years late. The photos look like 2005 (the digital cameras we had then had a different soul). The places mostly haven't changed.

Land tour vs. cruise —

We've now done Hawaii both ways. The 16-night cruise on Carnival Miracle in 2016 was a completely different experience: more relaxing, less planning, you wake up at a new island every morning. The 2005 land tour was the opposite: more logistics, more rental cars, but more time on each island and more flexibility on the schedule. Neither version is better — they're different trips with different strengths. If you want a sampler, do the cruise. Five sea days each way, four islands in port days, an easy and beautiful trip. If you want to actually know an island — drive the Road to Hana, hike a volcano, eat at the same little restaurant three nights in a row — do the land tour. Or do both, twenty years apart, like us.

We were in our twenties, with cheap digital cameras and a folded-up Pleasant Holidays itinerary in the back of a rental car. We've never stopped chasing this feeling. — Greg, looking back

The four islands —

Oʻahu. We started in Honolulu — Pearl Harbor, Waikiki Beach, the North Shore for the day. Oʻahu is the most logistical island (most traffic, most tourists) but it's also the one with the most history and the most variety in a small space. We'd recommend three full days for first-timers.

Maui. The big middle stop. We drove the Road to Hana (do it; bring snacks; don't try to do it in a half-day) and spent an afternoon at Iao Valley. We did not snorkel at Molokini. We regret not snorkeling at Molokini. Plan for at least three days.

Big Island (Kona & Hilo). Volcanoes National Park on the Hilo side is the headline — earth that's literally still being made. The Kona side is sunshine, beach, and coffee farms. Plan for four days minimum and you'll still be cutting it close.

Kauai. The quiet, green one. Waimea Canyon. Na Pali Coast (you can't drive it; you have to hike, boat, or fly). Princeville. Hanalei Bay. We had two days on Kauai and have been telling people for twenty years to give it four.

See all 440 photos from this trip →

What we'd do differently — twenty years on —

1. Pick fewer islands, more days each. Four islands in twelve days felt like a lot at the time. Looking back, three islands in twelve days would have been better — Maui, Big Island, Kauai, four days each. Oʻahu can be its own trip later.

2. Stay at one or two places, not five. Inter-island flights and hotel changes eat days. If we did this trip again, we'd pick one or two anchor islands and explore from each one rather than hopping every two nights.

3. Eat where the locals eat. The hotel restaurants are fine. The local plate-lunch spots and shave-ice stands are the trip. We figured this out by day five and have been correcting for it ever since.

Want to plan one? —

Inter-island Hawaii land tours are one of our favorite trips to plan — every traveler wants something slightly different, the flight logistics are real, and the hotel choice on each island can make or break the experience. We have personal preferred-supplier relationships with all the major Hawaii hotel groups (Outrigger, Aulani, Halepuna, Four Seasons Hualālai, Grand Hyatt Kauai) and can pair flights, transfers, and rentals into a clean single booking.

Plan my Hawaii trip

Read the Hawaii cruise version: Sixteen days, four islands, one Pacific (Carnival Miracle, October 2016)