DAY ONE // Friday
5 p.m. Arrive at the open-air Lihue airport and pick up your rental car. Kauai is roughly circular, and for your first night, you’ll head to the southern, sunnier coast, before moving up to the more verdant north shore for the following nights.
5:30 p.m. After driving 30 minutes south, check into Koa Kea Hotel and Resort, an intimate, beachfront property tucked among the bigger tourist operations in the Poipu area. All rooms have their own lanai (balconies); some have ocean views. The sunset over the sea should help you shift swiftly into tropical-vacation mode: toast your new mind-set with a glass of wine (a bottle is included with the room) or a cocktail by the pool bar. The nearby fire pits and hot tub ooze warmth. From about $429 a night, meritagecollection.com/koakea