Hawaii Itineraries

Why Use Our Hawaii Itineraries to Plan?

Travel Guide's to help you plan for a visit to each Hawaii island

At some point in planning your vacation to Hawaii, it’s probably going to hit you, “Wow, this is a lot harder than I thought it’d be... there’s so much to do.”  Welcome to the state where the possibilities for activities and adventures are limitless, to where you’ll likely never find yourself bored unless you simply refuse to leave your hotel room. This portion of our website is here to help you find some focus in planning your trip and should allow you to organize what you want to do into simple itineraries.  Planning your vacation doesn’t have to be a chore, and hopefully, our recommendations will be of assistance in your own preparation.

For nearly 25 years now we’ve been visiting Hawaii and making detailed notes about what each island’s highlights are and what visitors like yourself simply must-see based on the limited time you’ve allocated for each Hawaiian Island. It is difficult and can even be overwhelming to start planning a trip to Hawaii. One quick look on this website and you’ll soon discover there are hundreds of possibilities per island; a variety of sights to see, a plethora of beautiful beaches to choose from, and a diverse set of incredible trails that criss-cross each of the unique Hawaiian islands. Honestly, you could spend months in Hawaii and not see and do it all. Having a reliable guide, that’s key.

Most visitors come to the islands for about a week and a half, but if you’re like the typical traveler to the Aloha state, you may want to split your trip up between islands. Each island has its own unique “personality” and unique feel, no two are exactly the same. We recommend most travelers visit at least two islands if you’ve got enough time to do so. Pre-pandemic, in 2019, the average visit in Hawaii between all islands was roughly 10 days (9.3 to be exact). As we mentioned, most visitors visited two or more islands during their visit, splitting their time according to their interests.

Average rounded length of stay per island:

• Maui: 8 days
• Kauai: 7 days
• Big Island: 7 days
• Oahu: 6-7 days

How to use our Hawaii itineraries for your trip

Hawaii 'Pack-and-Go' Wayfinder Guides for daily excursions

Ultimately, we’ve designed our itineraries around a set number of on-island days: offering one, two, three, four, five, six, seven, and in some cases, ten days for exploring the island, soaking in the best sights, and ensuring your precious time (and potentially money) on each island are well spent. We’ve tried to balance our itineraries between those who seek adventure and those who are looking to find a good beach and relax. Overall, we want your experience to be exactly what you’ve dreamed of when planning your Hawaii trip!

For each island, we’ve attempted to split up the itinerary days by sorting attractions according to their geographic proximity; i.e; on West Maui day, you’d explore the best of West Maui’s attractions, beaches, and activities.

Our itineraries are not meant to necessarily be followed consecutively, which would probably be exhausting, but instead as a grab-and-go resource for ‘mapping’ your trip - think of us as a Wayfinder’s guide to each Hawaiian Island. We always like to travel by making day-by-day plans, putting the most important attractions and activities (the must-see and do) upfront, and if the weather doesn’t cooperate one of those days we just switch that day with another. That way we always get to the important stuff first, and if we have to skip anything, it’s ideally the minor attractions only.

We’ve provided directions via Google Maps when possible, as Google Maps works on all platforms and across all devices. You should be able to pop the directions into your phone or tablet and go. To help you visualize each day’s itinerary, we’ve also provided overview maps that'll help you get your bearings.