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Plan a trip to Hawaii using this free, ready-to-go itinerary for Maui & Kauai! You’ll find paradise, adventure and peace on these islands. Hawaii had been my number one place to go ever since my Mom and Dad went for the Ironman and did not bring us kids. RUDE! But now being an adult, I get it. When Southwest came out with flights to Hawaii the same year that we had the Southwest Companion Pass, we HAD to go. Maui and Kauai were magical in their own ways.

Maui was activity filled for us. And it turned out to be even more exciting… We got engaged! (I may need to do a Chicago wedding planning inspiration post!)! We had memorable experiences at Maui Nui Golf Club, Ho’okipa Beach Park and on the Road to Hana. Plus we had amazing meals at Ferraro’s Bar e Ristorante, Mama’s Fish House and Paia Fish Market. Just a perfect island.

Kauai brought about a relaxed vibe. From coffee-filled mornings to lounging at the resort pool to massages, we embraced the chill. Yet, we also did some exploring. We added in a two-mile hike up Sleeping Giant, checked out Hanalei Bay Beach at Waioli Beach Park and toured the Princeville Makai Golf Club during sunset on a golf cart. Just another perfect island.

My itineraries are made with a focus on doing, eating & drinking, which leads to seeing! Make plans easier. The editable templates allow you to add in your own personality, interests and adventures. Or simply download the PDF for a ready to go version. Enjoy!

Notes for consideration:

  • Book your dinner reservations a few months out to ensure you are able to select an early dinner time.
  • We went to bed between 6pm-9pm every night. With jetlag, we always woke up between 5am-7am.
  • Buy your sunscreen when you get to Hawaii, as they have specific rules about the contents of the sunscreen so it doesn’t hurt the reefs.
  • Hawaii is expensive! Try to grocery shop for breakfast and pack lunches when possible. Eating out for every meal will add up.
  • Get a top down car rental! It allows you to enjoy the beauty of the island and enjoy your drives.
  • If you get seasick or car sick, consider asking your doctor some nausea patches. These helped me a TON when doing the Road to Hana.
  • I recommend splurging for a direct flight on the way home. It was pretty tough waiting in California for our connecting flight home. At that point, you just want your bed!!

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October 30, 2019