It is tempting to fit several islands into one vacation. Every island looks beautiful, and travelers naturally want to see as much as possible.
For a seven-night trip, I usually begin by asking whether the extra airport day is worth the tradeoff. Checking out, driving to the airport, returning a rental car, flying, collecting luggage and starting over can take most of a day.
One island often creates the more relaxing vacation. Two islands can work well when the trip is longer and each island serves a clear purpose—for example, pairing Oʻahu’s culture and dining with Kauaʻi’s quieter natural scenery.
Planning note
Every trip is different. Recommendations should be matched to your dates, group, budget and priorities.