Plan your island trip to Maui, Hawaii using these free, ready-to-go itineraries!

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Map It Out!

Plan your island trip to Maui to enjoy amazing food, fun cocktails, picturesque sunsets, stunning beaches, unique adventures, plenty of activities and more!

Working remote has its perks. And when we were looking to escape the Chicago winter, we looked pretty far! We spent two months in Maui so that you can enjoy 7-10 days of the BEST. No matter where you book your lodging, I’ve got you covered with three free, ready-to-go itineraries to choose from (above)!

Where to stay:

  • Northwest Maui (including Lahaina, Kaanapali and Kapalua) – great weather throughout the year, high number of beaches available, a variety of stores to shop, can be touristy and crowded, extremely high number of restaurants, rather far from the most adventurous activities, pretty developed area, mountain and ocean views
  • Southwest Maui (including Kihei and Wailea) – great weather throughout the year, sunniest part of the island, decent selection of beaches, small stores but no major shopping, a variety of restaurant options, rather far from most adventurous activities, small town followed by large resort community,  pretty developed area, vast ocean views

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 1-2 months out to ensure you are able to select your preferred dinner time.
  • We went to bed between 6pm-9pm every night. With jetlag (from central time zone), we always woke up between 5am-7am.
  • The dress code is generally casual. It is normal to see people at dinner in post-beach gear, athletic gear, shorts and tees or sundresses. The nicer restaurants ($-$) have light dress codes for men: no hats or open toed shoes. It is rare to see women in heels, so just pack one or two sundresses with sandals.
  • 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. ABC Stores is your spot!
  • Hawaii is expensive. Try to grocery shop for breakfast and pack lunches when possible. Eating out for every meal will add up. Or go during happy hours!
  • Get a top down car rental! It allows you to enjoy the beauty of the island and appreciate your drives more.
  • If you get seasick or car sick, consider asking your doctor some nausea patches.
  • 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!!

More resources made for you!

We encountered an issue when trying to get to Hawaii with Covid restrictions in place. There was a slight delay in our arrival due to shipping our test results back that could’ve been avoided! So I have outlined a step-by-step guide to help exempt you from a 10-day quarantine upon arrival to the islands. This blog post covers considerations when booking your trip, creating a Hawaii account, scheduling and taking your test, uploading requirements to your Hawaii account and then checking off final items before you leave. Click here to learn more!

Check out this carefully curated list, by none other than Matt himself, of must-try Mai Tais on Maui complete with ratings, descriptions and pictures. Many live at the best restaurants on Maui too! And if Mai Tais aren’t for you, I included my drink of choice as well. View the list here!

*as reviewed by Coffee to Cork* coming soon on the blog!

Plan your island trip to Maui, Hawaii using the free, ready-to-go itineraries above!

February 27, 2021