How to Plan a Travel Itinerary Like a Pro

Whether you’re planning a trip to Hawaii, or another exciting destination, here are my best tips (and my process) for how to plan a travel itinerary: 

Know Your Vacation Style

How you like to vacation will have a huge impact on how you plan your trip and how much you’ll be able to see and do. So what exactly is a “vacation style?” Well, simply put, it’s how you like to spend your vacation!

Are you the type that’s up with the sun and out about adventuring all day only to return to your room to shower and sleep? Are you the type who enjoys spending the majority of your time hanging out at your beach resort? Or do you like a bit of both?

Everyone has a different idea of vacation so the first thing you’ll have to do is decide which suits you best. Are you always on the go, do you spend most of your time beach bumming, or do you do a combo of both? Part of your decision will be based on your personality and likely part will be based on where you’re staying.

For me personally, when I’m staying in a condo or budget hotel, I’m more likely to be out and about everyday, but when I’m staying at a nice beach resort, I’m more inclined to spend time lounging by the pool or on the beach. If you’re the type who’s always on the go, you’ll be able to see a lot of the island. If you want beach time too, I recommend renting beach gear (chairs, umbrella, snorkels, cooler, etc.) for the length of your stay and throwing them in the car so you’ll have them wherever you end up. If you’re staying at a nice beach resort, I would suggest planning a different activity each morning and spending each afternoon at the resort. You may need to set aside an entire day for certain adventures like driving the road to Hana. Or you may decide to split your trip up like I mentioned earlier and do the bulk of your exploring while you’re staying in a condo or vacation rental and then move to a nice beach resort when you’re ready to just relax. 

Come up with a Game Plan, but Don’t Overplan! 

If I could only give you one piece of advice about planning your trip to Hawaii, this would be it. I know…it costs a lot of money to get to Hawaii (and it’s so far away). For a lot of people, it’s a once in a lifetime trip and of course you want to see absolutely EVERYTHING. But trying to cram it all into one trip will likely leave you feeling like you spent your whole trip in the car (or in airports) and now need a rest from your vacation upon returning home. 

Here’s how I always lay out my trips:

As I’m researching my destination (yes, I do a LOT of research), I keep a running list of things I want to do, places I want to visit, restaurants I want to eat at, shops I want to go to, etc. From my main list, I break it down into three categories:

A “don’t miss” list: This could be anything from seeing sunset at Haleakala to driving the Road to Hana. These are the things that you ABSOLUTELY have to see/do or you’ll return home heartbroken. Okay, that’s a little dramatic, but you get my point. 

A “nice to see” list: These are things that you really want to see and experience, but they might be a little more minor. For example, seeing the sea turtles at Ho’okipa beach or snorkeling at Black Rock. These are just examples, obviously, what might be a “nice to see” for somebody may be a “don’t miss” for you.

An “if there’s time” list: I think you can guess what this list is for. Things that you’d like to see or do if there’s time, but won’t be upset about if you miss.

As you lay out each day, plan ONE thing from your “don’t miss” list each day. Combine it with one or two things from your “nice to see” list, and a smattering of things from your “if there’s time” list. Prioritize your “don’t miss” item every day (whether it’s doing it first thing or making sure you have a reservation for it) and fill in the rest of the day with things from the other categories.

Get Familiar with Google Maps

Once you have your lists of activities and things to do, the best way to sort them into days is by their location on the island. Many people underestimate how big Maui is and due to a lack of direct roads (plus traffic) it can take quite a while to get around. So don’t waste time crisscrossing all over the island, and try to plan each day’s activities on one part of the island.

My favorite way to start sorting activities and sites into days is by using a Google Maps. Plot all of your locations on a Google Map and then you’ll be able to see which ones are near each other and start planning your days that way. Of course, this can also be done on a paper map, but on a Google Map, you can create layers for different days or different types of activities and sites and organize things that way.

While generally speaking, focusing your day on only one part of the island is the most efficient strategy, there are some times when this doesn’t make sense. The major scenario where this doesn’t work is when you’re staying at a nice beach resort that you want to spend a lot of time at. In this case, I would plan a morning’s worth of activities on one part of the island, return to your resort for an afternoon of playing on the beach or at the pool, and then don’t be afraid to venture back out somewhere for dinner.

Be Flexible

I think this tip is the secret to making a good vacation great!  It’s so simple, yet key to really having the best experience in Hawaii. I think that a good plan is essential, but you have to know when it’s time to go to plan B. Or do something else entirely.

The major thing you’ll have to be flexible about in Hawaii is the weather. While the temperature is always pretty balmy (unless you’re in the upcountry area of Maui), a good rainstorm can change your plans pretty quick! A word of warning: it’s not unusual for a 10-14 day forecast to predict rain everyday in Hawaii so don’t panic and think your trip is going to be a total wash! It’ll likely just be quick storms that roll in and roll out. But for days where the local forecast truly is predicting rain, you might have to mix things up! One good thing about the Hawaiian Islands is that they’re pretty large so except in the case of a major storm system, the weather will likely be different on different sides of the island. Check the weather forecast the night before (or morning of) and you may decide to rearrange your days based on the weather. Obviously this may not work if you have activities or tours booked, but otherwise, don’t be afraid to swap out days in your itinerary to go chasing the sunshine!

P.S. Thanks for sticking around and reading this whole post! If you have ANY questions about planning your trip to Hawaii, you can join my free Facebook group here. I’m there answering questions every day and there are 7500+ other friends who have a ton of Hawaii information to share!

Also, if you want to follow along on my travel adventures in real time, you can follow me on Instagram (@caitylincoln). My post captions are full of travel tips and I have a ton of story highlights and videos with great info. And please share my account with your friends that are headed to Hawaii! Your support really helps me keep this blog running!