How to Plan a Trip to Hawaii: Step-by-step Guide! [2023]

Perched in the picturesque Pacific Ocean, Hawaii is home to an idyllic landscape like no other. Whichever island you go to, you'll find active volcanos, lush jungles, and killer waves. Top this all off with delectable cuisine and thriving culture—you'll never want to leave!

When planning your Hawaii itinerary, you should think about a handful of things. Factors like when you visit, what regions you travel to, and how you want to get around are all important. 

This guide will help you compile all of the essential information for planning a trip to Hawaii, plus the best tours and activities so that you can have an unforgettable vacation.

Whether you're seeking a sun-filled beach holiday, an adrenaline-packed experience, or a culture-packed trip to Hawaii, there's a lot on offer. This comprehensive planning guide will share with you some of the best tips and tricks on how to plan a trip to Hawaii successfully. 

So, let's turn your dreams into reality, step by step!

Step 1: Think about the best time to go to Hawaii 

Planning a trip to Hawaii can be done at any time of the year, as this destination offers sublime sights all year around. You'll need to figure out which season best suits you and what you want to get out of this trip.

Do you want to spend a hot summer's day sipping cocktails by the beach, or would you prefer to hike through the lush jungle in the wintertime?

Based on your preferences, here's what you should know about the seasons in Hawaii:

• Hawaiin summer: Between May to October, offering more sun and slightly hotter
• Hawaiin winter: Between November and April, when it's a bit wetter and the temperature is cooler

Overall, there aren't huge gaps in the climate, and it is relatively consistent. 

In the summer, this magnificent landscape poses perfect beach-friendly and watersports activities, making it the perfect season for those who want a taste of what Hawaii offers. 

For budget travelers, April to June or September to November is the best time to visit Hawaii, considering the more affordable prices.

December to March is the busiest period, so you can expect higher prices on flights and accommodation, along with bigger crowds.

Step 2: Determine your ideal travel budget 

Your ideal budget can vary, and it all comes down to your travel style. When planning a trip to Hawaii, you'll need to set up a budget that includes flights, accommodation, transport, attractions, and meals.

Once you've tallied out an average, think about the maximum amount you'd like to spend each day. If you're wondering how much money you'll need for your trip to Hawaii, the standard daily budget sits around US$250 per person.

Suppose you're a backpacker or budget traveler. In that case, you can find free activities and budget-conscious alternatives to help bring that average cost down. But to do so, you'll need to plan ahead. 

Don't skip a beat with these budget travel tips!

Step 3: Decide on which island(s) you're visiting 

Hawaii is home to eight enticing islands, each with its own history, culture, adventure, and lush landscapes. The six major islands are Kaua'i, O'ahu, Moloka'i, Lāna'i, Maui, and the island of Hawai'i (the big island). 

When planning a trip to Hawaii, pick the place that gets your attention and are geared towards the style of travel you enjoy. Although it's hard to go over all the differences here, I'll go over a few, so you get an idea!

• Kaua'i: With lush foliage, valleys, and jungles, this is the island to go to if you love wild, undeveloped nature
• O'ahu: Most of the Hawaiian residents live here, and it's most similar to a big metropolis on the mainland, being home to Honolulu (the state's capital)
• Moloka'i: A more rural island in the Hawaii bunch, Moloka'i is where you want to go if you're looking for history and you love beaches since it's home to one the largest white-sand beaches
• Lāna'i: One of the smallest islands, so come here if you're looking for luxury and privacy
• Maui: One of the more expensive islands, Maui is a good mix between nature attractions and dotted towns—consider renting a car here if you want to see everything
• Island of Hawai'i (the Big Island): Not to be mistaken with O'ahu, the Big Island may be the largest, but it's definitely not the most populated

Do you want to hike a bubbling volcano in Oahu, swim with wildlife in Maui, or trek through the lush tropical rainforests in Kauai? Would you prefer to soak up rural life on the big island, kick back in a resort in Lanai, or get immersed in local living in Molokai?

Whatever your desires, there's a destination in Hawaii for you!

Step 4: Think about how you'll get around 

Planning a trip to Hawaii can involve a lot of time and effort, but it's worth it. And when there's so much to do, you might be left thinking about how you'll get around. Before you fly to Hawaii, look at all the various transport options.

Hawaii is home to a well-developed transportation system, with trains, buses, and flights functioning. The most popular way to get around Hawaii is via shuttle, taxi, and ride-sharing apps. 

Alternatively, consider renting a car if you'd like to get off the beaten track. If you want to travel between the islands, you'll need to organize inter-island transportation ahead of time.

Step 5: Book your accommodation 

Hawaii is a vacationer's paradise, with literally every single accommodation option on the map. Considering your travel budget and preferences, you can choose between Couchsurfing, Airbnb, hostels, sharehouses, resorts, and hotels.

Unfortunately, some places in Hawaii aren't budget options for places to stay. Expect to pay more if you visit an island like Maui, for instance. Also, be sure to inquire about the extra taxes most accommodations charge as per government regulations. 

Suppose you're looking to stay in a hotel or resort or searching for an all-inclusive stay. Sites like Hotels.com can help you review various hotel deals. 

If you're planning a last-minute trip to Hawaii, you can adjust the filter to your price, dates, and other factors.

Step 6. Decide on sites & experiences

Before you near the end of the planning process, you'll need to source out your attractions and activities. Hawaii is notorious for its network of cultural experiences, beautiful beaches, and lush tropical adventures. So, what appeals to you? 

Here are some things you could add to your Hawaii itinerary:

• Chase waterfalls on the big island
• Trek through the Hawaii Volcanoes National Park
• Get a dose of island life at the Polynesian Cultural Center
• Sunbake on Waikiki Beach
• Learn about history at the Pearl Harbor National Memorial
• Get some greenery in the Ho-Omaluhia Botanical Garden
• Stroll along the teeming trails in the Nā Pali Coast State Wilderness Trail
• Go on a coffee-tasting or chocolate tour at one of the many plantations
• Pick up a piece of glass sand at the beach in Kauai

Step 7: Get your documentation organized

Now that you know how to plan a trip to Hawaii, it's time to get down to business. Make sure you've got a travel visa and purchase travel insurance. If you need clarification on what's right for you, look at this guide on the best travel insurance options.

Step 8: Learn to pack like a pro 

As you near closer to your departure date, the excitement can begin to take over. And those fluttery feelings can sometimes be a few nerves too. Packing is easy once you've got the hang of it. 

Packing for Hawaii might not be as simple as it sounds. Let us walk you through, step-by-step, how to pack for a trip to Hawaii!

If it's your first time visiting Hawaii, you may be feeling a bit jittery about the packing process.

Depending on the season you'll be traveling in, plus the kind of trip you're planning, your packing list can look very different. Comfortable walking shoes and lightweight clothing are always a good idea, alongside a sturdy backpack and luggage.

If you tend to overpack and later forget something important, like your passport or ID, I've got you covered. Take advantage of all essential travel items with this complete vacation packing list!

Lovely landscapes and beyond!

Now you know how to plan a trip to Hawaii, it's time to shred the stress and start getting excited! You've got your essentials down, but maybe something is missing.

That's where Pilot can be your savior!