Planning a Trip to Hawaii? Here’s Your Timeline…

Planning a trip to Hawaii

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You’re planning a trip to Hawaii…wahoo!! How exciting! But it can also be pretty overwhelming…I mean, how do you even know where to start? While you’ll find detailed posts on topics like choosing the best time to go, picking an island, booking accommodations and flights, etc., on my blog, this timeline will let you know exactly when you should be tackling each one of these tasks to insure that you have the most options available for the best prices.

12+ months

If you’re planning this trip over a year in advance, use this time to do preliminary research about when the best time to go will be (for your circumstances) and choosing an island (or two).

Read more about:

Which Hawaiian island to visit

When to go to Hawaii

6-12 months

Your accommodations should be the first thing you book. If you’re traveling during peak times, many places book up almost a year in advance. Of course, you’ll usually be able to find some place to stay if you wait until the last minute, but booking your accommodations in advance will insure that you have the most options available to you. This is especially relevant if you’re looking at condos or Airbnbs. The best properties (and best deals) will start to disappear if you wait too long.

Where you stay on the island will have the biggest impact on your vacation. First, you’ll have to decide what TYPE of place you’re going to stay at (and this will have a lot to do with your budget). Do you want a luxury beach resort? Looking for a condo? Are you open to staying in a vacation rental away from the beach? Are you determined to stay beachfront but need to stick to a specific budget? Depending on what type of accommodations you’re looking for, that may lead you towards staying on a particular part of the island.

Each island has its different resort areas. You’ll either end up finding the perfect place to stay and then by default end up setting up camp on that part of the island, or you’ll do research and know which part of the island you want to stay on and then look for a place to stay around there that works for your budget.

Wherever you decide to stay, I DO NOT recommend staying at a fabulous beach resort and NEVER LEAVING THE RESORT. Hawaii is too fabulous to go all that way and spend your whole trip lying under an umbrella at the beach. If you want that, go to Mexico. That doesn’t mean that Hawaii isn’t for beach bums though! For me, the perfect trip to Hawaii looks like this: get up early, have breakfast, go on some type of adventure, come back to the resort and bum around the pool and beach all afternoon, and then get cleaned up and go out to dinner. But to each their own. Find out what works for you, but please, get out there and SEE Hawaii!!

Check out my recommendations for where to stay on Maui, Kauai, Oahu, and the Big Island.

RELATED: How much does a trip to Hawaii cost?

How to save $1000 on a trip to Hawai

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

4-6 months

Four months out is the ideal time to book airfare, but I like to start monitoring it about 6 months out so I know when I’ve found a good deal.

For many people, this might be the most expensive plane ticket they ever buy and the longest flight they ever take. That’s kind of daunting. No worries, I’m going to make it simple for you!

When you’re looking for a flight to Hawaii, you’re either going to book it two ways.

The cheapest ticket possible or the most convenient flight possible. Obviously, your budget will determine which route you’ll go. If you’re searching for the cheapest flight possible, you’ll probably end up flying through LA and possibly through Honolulu before heading to your final destination (unless Oahu is your final destination!). From LA, flights to Hawaii are about 5-6 hours (depending in if you’re coming or going and catch a tail wind). From Oahu, flights to Kauai, Maui, and the Big Island are only about 40 minutes.

If you’re trying to go the most convenient route, you’re going to want to avoid LA like the plague. It’s a crazy big airport with a lot of terminals and for some reason when you’re flying to Hawaii, it seems like you usually have to switch terminals and recheck bags which is never any fun. Ideally, you’ll be able to book a direct flight from a major hub throughout the country (Dallas, Atlanta, Chicago, etc.) to your final destination (Oahu, Maui, Kauai, or the Big Island). These flights are usually more expensive (and longer!) but make the travel day MUCH easier.

Read more tips for saving money on airfare here, and tips for surviving the long flight to Hawaii here.

2-3 months

Reserve your rental car. Rental cars are finite on Hawaii so don’t wait around too long to reserve one or you may end up having to rent a more expensive category than you need. I always book through Discount Hawaii Car Rentals and am able to reserve without paying until I arrive.

I’m a big fan of renting a car when in Hawaii (remember above when I preached about not just sitting at your resort for the whole trip? Yeah). No matter which island you’re staying on, you’ve GOT to get out and explore it. Some of the resorts (especially those on Waikiki) do charge a fee to park it, but factor it into your budget and go with it). Your budget will depend on what kind of rental car you go with (read this) but the two most popular rental cars in Hawaii seem to be four door Jeeps and convertible Mustangs.

1-2 months

Start planning your daily itinerary and booking activities. Depending on your vacation style, you may want to just beach bum around and go with the flow or you may prefer to have a tentative schedule so you make sure you see and do everything you want. In the very least, I recommend booking activities that you’re set on well before your arrival. Popular luaus and activities (helicopter tours, snorkel trips, etc.) often book up months in advance so I prefer to make these reservations once I know my dates. While you’ll usually be able to book SOME luau or activity close to your departure or even once you arrive, it may not be the one you want. So don’t get caught paying a premium price for your second choice. Book activities in advance.

I would only recommend planning one major activity a day (i.e. snorkeling trip, surf lessons, etc.) and filling in the rest of your day with time exploring beaches, small surf towns, hiking, etc. If you’re planning a big daytrip (i.e. driving the Road to Hana, hiking Haleakala, touring Volcano National Park, or seeing the Waimea Canyon), I would recommend setting aside the entire day for it. If you have time for some extra fun at the beach, great! If you don’t, you won’t be disappointed.

The last thing I would plan out are any restaurants or dining experiences that are important to you. Luaus need to be booked in advance and if you have your eye on any fancy restaurants (I’m looking at you Mama’s Fish House!) sometimes those book up, especially during high season.

15 Things to Do on Maui

15 Things to Do on Kauai

15 Things to Do on Oahu

15 Things to Do on the Big Island


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!