California, Napa, Hawaii's Three Islands, and Chicago in One Trip

An ambitious way to see the American West

Some trips are built around one region done thoroughly; this one, in May 2022, was built around stacking as many genuinely different American landscapes into a single itinerary as we could reasonably manage. We moved from San Francisco to Napa Valley to Los Angeles, then island-hopped across three separate stops in Hawaii — Maui, Oahu, and Kauai — before closing the whole trip out in Chicago on the way home. It’s a lot of ground, and we knew that going in, but each leg was different enough from the last that it never felt repetitive.

San Francisco and a Napa detour

We started at the Hilton San Francisco Financial District, using the city as our base for a few days before a short detour into wine country at the Bel Abri Napa Valley Inn in Napa Valley. Pairing a genuine city stay with a wine-country detour is a well-worn combination for good reason — San Francisco gives you the hills, the bay, and a serious food scene, while Napa is close enough for an easy day-trip-or-overnight change of pace built around vineyards, tasting rooms, and a noticeably slower rhythm than the city.

Los Angeles as a connecting point

From Napa we moved down to Los Angeles, staying at the H Hotel Los Angeles, which functioned in this trip mostly as a stepping stone toward Hawaii rather than a destination we lingered over. LAX has strong connectivity to the Hawaiian islands, and using LA as the jumping-off point for the Pacific leg of the trip made more sense than routing through a smaller West Coast airport.

Three islands, three different characters

The Hawaii stretch was the heart of the trip, and deliberately split across three islands rather than one, since each has a genuinely distinct personality.

On Maui, we stayed at the Grand Wailea, A Waldorf Astoria Resort — a resort-heavy stretch built around beach time, pools, and the kind of full-service amenities that make Maui a popular choice for travelers who want the island experience without giving up much comfort. On Oahu, we based ourselves at the Hilton Hawaiian Village Waikiki Beach Resort, right in Waikiki, which is the classic pairing of beach and city that most people picture when they think of Hawaii — surf, a lively beachfront strip, and Honolulu’s city energy all within walking distance of each other. Kauai, where we stayed at the Hilton Garden Inn Kauai Wailua Bay, was the quietest and greenest of the three by a wide margin — it’s nicknamed the Garden Isle for good reason, with dramatic, jungle-covered terrain and a noticeably slower, less developed feel than either Maui or Oahu.

Inter-island logistics take real planning

Hopping between three Hawaiian islands sounds simple on a map, but it isn’t quite as casual as it looks. Inter-island flights are short — often under an hour in the air — but they add up quickly in both cost and time once you factor in airport transfers and security on each end, and a three-island trip like ours means going through that process multiple times rather than once. This is very much a leg of the trip that rewards booking ahead rather than assuming you can figure out flights once you’re already on the ground.

Chicago as a soft landing before home

Rather than flying directly home from Hawaii, we broke up the return journey with a stop in Chicago, staying at the LondonHouse Chicago, Curio Collection by Hilton. Using a Midwest hub like Chicago as a stopover before an international flight home is a practical way to soften what would otherwise be a brutal single push across that many time zones, and it gave the trip one more genuinely different American city to end on before heading back to Europe.

Why we’d do a trip shaped like this again

Looking back, the thing that made this trip work wasn’t any single stop — it was the range. City, wine country, another city, three islands with three distinct moods, and a Midwest city to close it out. It asked for more advance planning than a single-destination trip would have, especially around those inter-island hops, but the payoff was a single trip that covered more genuinely different kinds of American travel than we’d normally fit into one visit.

[Editor’s note: add what stood out most across these seven stops, and swap in your own photos when ready.]