If you’re starting to plan your Hawaiian vacation, woohoo!! I’m so excited for you. You’re going to LOVE Hawaii. But if you’ve never been to Hawaii before, I’m guessing you might also be feeling a bit overwhelmed. After all, it’s a big trip and that’s a lot of money to spend. I know you want everything to be perfect. Don’t worry! This post will walk you through everything you need to do to plan the perfect Hawaiian vacation in 6 easy steps.
And hey! I even made you a FREE handy dandy workbook that you can use to track all the details of your trip budget plus plan out an itinerary! Grab it by clicking on the picture below. And now, on with the main show!
1.Decide which island(s) to visit. There are four main Hawaiian Islands (Oahu, Maui, Kauai, and the Big Island).
Oahu: Oahu is the main island and attracts the most visitors. It’s where you’ll find Honolulu, Waikiki Beach, Pearl Harbor, Diamond Head, the Dole Plantation, gorgeous Lanikai Beach, the Polynesian Cultural Center, and the famed north shore. If you’re heading to Hawaii to see the famous sights, and have plenty to see and do, Oahu is probably your island.
Maui: Maui is the second most visited island and is known as the “honeymooner’s isle.” It’s slower, more laid back, and much more natural. Maui is famous for its beach resorts, golf, Road to Hana, Haleakala Crater, and snorkeling at Molokini Crater. If you want a relaxed vibe with still plenty to see and do (most of it natural), Maui is your spot.
Kauai: Thought to be Hawaii’s prettiest island by many (myself included), Kauai is the oldest island in the Hawaiian island chain and has probably the most “authentic” Hawaiian vibe you’ll find. It’s quiet, peaceful, pretty lazy, and gorgeous to the MAX. Kauai is famous for its Napali Coast, Waimea Canyon, and Hanalei Bay. If you’re looking for the stuff Jurassic Park is made of, this is your island.
Big Island: As you’ve probably guessed, the “Big Island” (also just called “Hawaii”) is the largest of the Hawaiian Islands and packed with plenty to keep you busy for weeks. The Big Island is home to Hawaii’s only active volcano, black (and green!) sand beaches, beautiful farmland, stunning valleys, and more waterfalls than you can count. The island is so large that it’s divided into two sides (Kona and Hilo), each with their own airport. The sheer size of this island makes planning a trip there daunting for many tourists, but it is BEAUTIFUL and home to some of the most unique features in the Hawaiian Islands.
Can’t decide which island to visit? Who says you have to choose?? Split up your trip and stay on more than one!
A word about island hopping though: the islands are farther apart than you might think so there are no ferries between the four main islands, meaning you’ll have to fly. You’ll most likely be flying Hawaiian Airlines interisland, which flies regional 747s (not small planes) but airfare isn’t super cheap. Expect to pay around $150/person round trip and even though flights are only about 40 minutes, you still have to go through the traditional check-in/TSA process (which recommends you arriving 1-1 ½ hours before your flight. This means daytrips between islands are both expensive and time consuming so I wouldn’t plan to be on each island for less than 3 days.
2.When to Go: Every other decision you make about your trip is going to hinge on this one. High season in Hawaii usually starts mid November and can run through April. High HIGH season is Christmas to New Years. Airfare and rooms during this time are ridiculously expensive and book out pretty far in advance. Winter is the most popular time of year to go to Hawaii because obviously people want to go somewhere warm when it’s cold at home. Keep in mind through that the seasons are the same in Hawaii as in the mainland US so winter at home is also winter in Hawaii. Although the temperatures are obviously much more mild, winter means rainy weather. And the upcountry areas of Maui and the Big Island have more pronounced seasons with cooler, cloudier, and rainier weather in the winter and everything blooming in the spring. You won’t notice this much at lower elevations (by the beaches) but the rain may put a damper on your vacation, especially if it’s a short trip.
If you want to see the humpback whales (especially around Maui), their migration usually begins in October and runs through May (the Pacific Whale Foundation guarantees sighting on their cruises from Nov 4-May 15th) with prime season being in February.
So when is the best time of year to go? I would either go in March or April (for whale spotting) or August through early November. There’s really no bad time of your for Hawaii, but those are my picks.
3.Booking Airfare: This is one of the most intimidating parts of the process for most people. 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. 1) The cheapest ticket possible, or 2) 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.
For example, living in Tulsa, Oklahoma, the cheapest way for me to get to Maui is usually Tulsa>Dallas>LA>Honolulu>Maui. Wow, that’s an exhausting day! And if you miss any one of those flights you might find your trip delayed by a day. On the other hand, the most expensive ticket to Maui is usually Tulsa>Dallas>Maui. Hallelujah! That 8-hour flight from Dallas to Maui is soooo worth it when it shortens my overall travel time by up to 8 hours. In the middle, I often end up traveling from Tulsa>Dallas>LA>Maui which is a happy medium and while it adds an extra stop, it usually also saves $300-400 off of my ticket. So booking airfare is all about finding that sweet spot between cheapest ticket and most convenient flight.
Feeling overwhelmed? Don’t freak out! Download the FREE handy dandy workbook that you can use to track all of your trip details plus plan out an itinerary! Grab it by clicking on the picture below.
4.Find a Place to Stay: 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.
For example, on Maui you’ll find two major resort areas: Wailea and Ka’anapali. If you want the best in high-end luxury, you’ll end up staying in Wailea at either the Four Seasons or the Grand Wailea. If you want a beachfront resort on more of a budget, you might end up on Ka’anapali at either the Westin or Sheraton. 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!!
If you’re planning a trip to Maui, check out these recommendations for where to stay.
5.Book a Rental Car: 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.
6.Plan Your Days and Book Activities: This is the fun part! Some people like to show up with no plans, see how the trip goes, and decide each morning what they’re going to do. I recommend at the very least sketching out a general itinerary of what you’ll do everyday, especially if you’re interested in doing any excursions with tour companies. If you’re planning on doing any sort of activity that’s ran through a tour provider, I would NOT wait until your arrive to book. Some of the more popular tours and excursions book up in advance and if you wait until you arrive on island, you may end up missing out or only being able to book a “less than great” company for the same price as the best tour company on the island. Do your research before you leave home and book with the company that looks best to you.
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.
Don’t forget to grab the FREE workbook that you can use to track all of your trip details plus plan out an itinerary! Grab that by clicking on the picture below.
Are you loving these tips? If you want a full step by step strategy for how to save $1000 on your trip to Hawaii, sign up for my online workshop, Hawaii Dreamin.’ You can sign up here or by clicking the image below. In this workshop, I teach the strategies that I use to dramatically cut the costs on my trips to Hawaii and cover every aspect of saving including airfare, accommodation, food and activities plus picking the absolute cheapest time of year to visit.