Flying solo? Make your home base Kauai’s Hanalei Town on the island’s North Shore. The small town is famous for its crescent-shaped beach and has a friendly, laid-back vibe, where travelers and locals come for the excellent surfing and on-point restaurants. Start the day with a surf lesson from Hawaiian Surfing Adventures, which will get even the biggest rookies riding waves. When hunger strikes, head to Hanalei Taro & Juice Co.’s food truck for farm-to-table Hawaiian fare like kalua pig, poi, lomi salmon, and smoothies made from taro ⎯ a local, heart-shaped root vegetable sourced from Hanalei’s misty green mountains.

Spend the afternoon lounging on Hanalei Bay’s white sand beach, browsing local artists’ work at the town’s art galleries, exploring the flora and fauna at Limahuli Garden and Preserve, or kayaking the Hanalei River. Come evening, head to Tahiti Nui for a dinner of fresh Ahi paired with live music.

You’ll feel like you’re on your own private island when visiting Lanai. There are no traffic lights, and 18 miles of pristine sand make it easy to find a secluded spot by the water. Rent a four-wheel-drive to access out-of-the-way places like the Garden of the Gods, a hiking destination with otherworldly rock formations and breathtaking views of neighboring islands. Plan on a visit to Puu Pehe (Sweetheart Rock) ⎯ the sunset is spectacular and spinner dolphins can often be spotted playing in the water.

Food and cultural festivals are everywhere on the Big Island. The Kona region is known for its coffee production, and celebrates the history behind the bean during the annual Kona Coffee Cultural Festival. This event typically takes place in November and includes coffee farm tours, coffee and tea pairing events, and the Holualoa Village Coffee & Art Stroll, which takes visitors through the art enclave of Holualoa. The island also hosts the Merrie Monarch Festival in spring, when hula schools from every island come together to perform. In the fall, the Hawaii Food and Wine Festival draws top chefs from around the world for a week full of drinking and dining. To stay up to date, be sure to check festival websites for any schedule changes or updates that may impact your plans.