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Planning a Trip to Hawaii


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Planning a Trip to Hawaii- Diamond Head Waikiki

It’s no secret that Hawaii is one of the most popular vacation destinations in the world. With its stunning beaches, lush rainforests, and dynamic cities, there’s something for everyone in paradise.

So how do I plan a trip to Hawaii? Well, this blog post is for you! There are many things to consider, from when to visit and where to stay. This post will give you Hawaii travel tips and information to start planning your future Hawaii trip.

Choose Which Island You Want to Visit 

You can visit six major islands in Hawaii- Oahu, Kauai, Maui, Lanai, Molokai, and the Island of Hawaii. Each Hawaii island offers a different type of experience. No matter which Hawaiian island you visit, you will have a fantastic time in Hawaii. Here are the islands and some of their must-visit attractions. 

1. Oahu

If you plan on visiting Hawaii, you can’t miss Oahu. Oahu, a.k.a. The Gathering Place, is one of the most visited islands in Hawaii. It’s home to Honolulu – the state’s largest city – and Waikiki Beach, one of the most popular beaches in the world. There’s plenty to do on Oahu, from exploring its natural beauty to checking out its vibrant nightlife scene.

Must-Visit Attractions

  • Kailua Beach Park
  • Kaneohe Sandbar
  • Diamond Head
  • North Shore
  • Lanikai Beach

2. Kauai

Kauai is the second-oldest and northernmost of the main Hawaiian Islands. This Hawaiian island is known for its rugged coastline, Opaeka’a Falls, and Waimea Canyon. The island, also known as the “Garden Isle,” is also home to dozens of beaches, including Hanalei Bay Beach, one of the most beautiful beaches in the world.

Must-Visit Attractions

  • Waimea Canyon State Park 
  • Na Pali Coast State Park
  • Poipu Beach Park
  • Spouting Horn
  • Wailua Falls

3. Maui

Maui, or the “Valley Isle,” is one of the most popular islands in Hawaii. With its stunning beaches, gorgeous scenery, and an array of activities, Maui is a favorite destination for visitors. There are plenty of activities to experience on Maui, from snorkeling to hiking to zip lining. In addition, Maui is also home to some of the best restaurants in Hawaii. If you’re looking for a Hawaiian vacation that has it all, Maui is the island for you.

Must Visit Attractions

  • Hana Highway
  • Ka’anapali Beach
  • Whale Watching 
  • Haleakala Crater
  • Wai’anapanapa State Park

4. Molokai

Planning a Trip to Hawaii- Molokai

Molokai is the fourth largest island in Hawaii, known as the “Friendly Isle.” It’s one of the most beautiful islands, with lush valleys, pristine white-sand beaches, and towering waterfalls. Molokai is worth a visit if you’re looking for a quiet, uncrowded getaway.

Must Visit Attractions

  • Halawa Valley
  • Kalaupapa National Historical Park
  • Papohaku Beach Park
  • Kaunakakai 
  • Pala’au State Park

5. Lanai

Consider Lanai if you’re looking for a getaway off the beaten path. Lanai is the smallest of the major Hawaiian Islands but still offers plenty of things to do. This small island, known as the “Pineapple Isle,” is located just off the coast of Maui and is known for its rugged beauty and secluded beaches. Lanai is a great place to unplug and relax. There are plenty of outdoor activities, from hiking and biking to snorkeling and diving.

Must Visit

  • Hulopoe Beach
  • Garden of the Gods
  • Shipwreck Beach
  • Lanai Cat Sanctuary
  • Lanai Culture & Heritage Center

6. Big Island

The Big Island is the largest of all the Hawaiian islands, hence the nickname Big Island. It’s known for its active volcanoes and lush rainforests. It’s also one of the most diverse islands, known for its active volcanoes and lush rainforests. Whether you’re looking for adventure or relaxation, you can find it on the Big Island.

Must Visit

  • Mauna Kea Summit
  • Akaka Falls State Park
  • Pololu Valley Lookout
  • Hawaii Volcanoes National Park
  • Waipi’o Valley
  • Punaluʻu Beach (one of the Black Sand Beaches)

Each Hawaiian island has something different to offer visitors, so choosing which island to visit depends on what you’re looking for in a vacation.

If you want to explore the history and culture of Hawaii, then Oahu or Kauai might be a better choice. Maui or the Big Island might be a better option if you’re looking for stunning beaches and natural beauty. Molokai and Lanai are great options if you’re looking for a more rural and authentic Hawaiian experience.

Note: There are direct flights to Oahu, Kauai, and Maui islands from the U.S. mainland. You’ll have to get on an inter-island flight to visit the Big Island, Molokai, and Lanai.

Should I Visit More Than One Hawaiian Island?

If you’re planning a trip to Hawaii, it’s worth considering whether you should visit more than one island. The Hawaiian Islands are an incredible place to visit, with each Hawaiian island offering its own unique experiences.

When deciding how many islands to visit, you must consider how long you’ll stay on each island. It’ll be challenging to visit all the islands in one trip. There are no ferries or roads that connect all of the Hawaiian islands. You’ll have to take inter-island flights to island hop.

If you’re only visiting one island, you can stay for as long as you’d like. However, if you plan to visit multiple islands, stay for more than one week per island. This will give you plenty of time to explore what each island offers. Also, be sure to take into consideration airport transportation time and flight duration if you’re traveling to other islands.

Decide How Long to Stay

Planning a Trip to Hawaii- Oahu Beach

How long to stay depends on what you want to do and see while you’re there. If you’re looking to just relax on the beach, then a few days may be all you need. But if you want to explore the islands and do some sightseeing, you’ll probably want to stay for a week or two.

I recommend planning to stay at least for a week if you’re visiting just one island, considering the time zone change. The longer, the better. Depending on where you live, it can take a whole day to get to Hawaii. It takes approximately 6 hours from the west coast (Los Angeles International Airport) to Honolulu International Airport. As mentioned earlier, schedule one week per island you plan on visiting if you’re visiting more than one island.

When is the Best Time to Visit? 

Planning a Trip to Hawaii- Aloha sign visit Hawaii

Hawaii is a great destination to visit any time of year. The temperatures are mild all year round, so you can travel anytime without feeling too hot or cold.

When to visit will significantly depend on when you can schedule a vacation. The peak season, such as summer break and the holiday season, will be more crowded and expensive. You’ll find it less crowded during the shoulder season, from March to May and September to October. However, suppose you’re looking for the best deals on airfare and hotel rooms. In that case, it’s best to visit during the off-season, from January to March.

Are you planning on whale watching?

Hawaii is a great place to whale watch all year round, but the best time to go is in January or February when the humpback whales are migrating. Numerous tour operators offer whale-watching tours, so it’s easy to find one that fits your schedule and budget. Make sure to dress warmly, as the weather can be chilly on the open water.

Book Flight 

Planning a Trip to Hawaii- airplane  Hawaiian Airline

When planning a trip to Hawaii, booking your flight is one of the most important steps. You’ll want to find a flight that fits your schedule and budget. Many different airlines offer flights to Hawaii, so do your research and compare prices. I like to use Google Flights to compare airline prices.

If you’re already a mileage member of a particular airline, choose that airline and book a flight!

Airport Parking

Are you getting to the airport from home by car? Don’t forget to reserve airport parking! You don’t want to miss your flight looking for somewhere to park your vehicle. 

My favorite place to reserve airport parking is ParkSleepFly. This site compares prices from several parking services! Select a service and reserve parking.

Book Hotel, Resort, or Vacation Rental

There are many options you can choose from when it comes to accommodation. You can stay in a luxurious resort, hotel, or vacation rental! Hotels offer a more traditional hotel experience, while resorts provide a more luxurious and all-inclusive experience. No matter your budget or style, there’s undoubtedly an accommodation option perfect for you in Hawaii.


Planning a Trip to Hawaii- Aulani Resort

Are you considering a luxury Hawaii vacation? Look into resorts! Resorts offer a variety of amenities that can make your vacation more enjoyable.

Luxury resorts typically include several on-site restaurants, bars, a spa, and a large pool area.

Additionally, resorts often offer activities like yoga classes, snorkeling tours, and meditation sessions that can help you make the most of your time in Hawaii.

Some resorts may even offer culture classes like lei-making, programs for kids, and luau shows. 

I recommend staying at a resort if you plan to use these amenities or sign up for activities.

By staying at a resort, you’ll be able to relax and enjoy all that Hawaii has to offer without having to worry about where you’re going to eat or what you’re going to do next.


Planning a Trip to Hawaii- Waikiki Hotel

If you plan to sightsee and sign up for off-site activities, consider staying at a hotel.

Hotels are typically more affordable than resorts. You’ll still get the basic amenities and services like a regular hotel.

If you’re planning on traveling with kids, you might want to see if they have a pool area. 

I love to book hotels/resorts for my trip from Priceline. Search on Priceline to see a list of amenities, reviews, and photos of hotels and resorts. 

The best part about Priceline is that they have the best price guarantee. They’ll refund the difference if you find a better deal elsewhere. You can become a Priceline VIP member just by signing up. (It’s free!) The more you book with Priceline, the higher the VIP level you qualify for! Check the Priceline website for more information about Priceline VIP and its perks. 

Vacation Rental

Vacation rentals come in all shapes and sizes, from small condos to large villas. Choose whichever fits your budget.

They also offer a variety of amenities, such as laundry facilities, which can save you money on your trip. Most vacation rentals will include a kitchen allowing you to prepare your own meals, saving you a lot of money! Reserve through sites such as Vrbo.

Another advantage of staying in a vacation rental is that you will have more space than you would in a hotel room. This is especially important if you are traveling with family or friends. You will also have more privacy than you would in a hotel.

Finally, by staying in a vacation rental, you will get to know the local community better. I like to stay in rentals as they can feel like you’re a Hawaii resident. You can explore all the little neighborhoods and find the best places to eat and shop.

Tip: Stay in the area where you’ll most likely spend the most time. Take into account the locations of any attractions you want to visit or activities you plan on doing. 

How to Get Around the Island

Planning a Trip to Hawaii- Rental Cars

I highly recommend renting a car when visiting Hawaii unless you’re staying in Waikiki. A rental car will make transportation so much easier. 

Make a reservation ASAP. I have friends who couldn’t find a rental car for their Hawaii trip. They eventually had to cancel all their activity reservations because they couldn’t drive to the meet-up location. 

Discover Cars is my go-to when it comes to a rental car. The website compares rental car prices for different car rental brands. All you have to do is to select a car and reserve it. 

Note: Some places/activities require a 4WD such as Mauna Kea Summit. Check if there are any requirements for the attractions you plan to explore. 

Waikiki Area Transportation:

Many locations in Waikiki are within walking distance, so you may not need to rent a car. 

If you plan on visiting the North Shore or Ko Olina area, you might want to use a car for transportation. Other than that, it’s best to skip the rental cars if you’re staying in the Waikiki area.

Here are some of the transportation methods I recommend using in the Waikiki area. 

Public Transportation

Waikiki Trolley 

The Waikiki Trolley will take you to over 30 locations, where you can hop on and off at any stop. You can even visit the Diamond Head with the trolley. Buy a trolley pass on the Waikiki Trolley page beforehand. 


TheBus is the public bus service in Hawaii. Using the public bus will help minimize your transportation cost if you’re on a budget. 

Rideshare Service

There are plenty of rideshare cars in Waikiki. You won’t have to worry about not catching a ride. Download the Lyft or Uber app an account before your Hawaii trip if you don’t already have one. 


Planning a Trip to Hawaii- Biki Bicycle

Biki is an affordable bike rental service that’s available in Honolulu. Just purchase a subscription at a Biki station or online from the Biki website and check out a bike. You can return the bike to any Biki station. 

Note: Most activity tours include shuttle services, but check before deciding to rent a car. 

Create Your Hawaii Itinerary

Planning a Trip to Hawaii- snorkeling tour sea turtles

Now you can start planning what you want to do on the island. Talk with your family or friends you plan on taking a vacation with. 

Hawaii is a beautiful tropical state that offers visitors plenty of activities and attractions. Some popular things to do in Hawaii include swimming, surfing, sunbathing, hiking, and sightseeing.

When creating your Hawaiian vacation, culture is one of the most important things to experience. There are many activities and events that offer a glimpse into Hawaiian culture, from music and dance performances to traditional luaus.

Search for activities and attractions on TripAdvisor and GetYourGuide. Take note of where these activities are located and if they offer any transportation services from your hotel. 

There are also many lovely beaches and parks to explore, as well as shops and restaurants.

Don’t pack your entire day with activities! You’ll want to schedule some free time, especially if you’re traveling with your kids. They may get exhausted and feel tired throughout the day. Schedule a relaxing day to take a break to recharge.

When creating your vacation itinerary, it’s also important to be aware of some things that could affect your vacation. For example, the weather can be unpredictable, so it’s a good idea to have a backup plan in case of bad weather.

Keep in mind that it’s impossible to do everything in one trip!

Make Activities/Attraction Reservations (If Needed) 

Planning a Trip to Hawaii- Surfboards

Once you’ve figured out where to go, make reservations for activities. Popular activities such as snorkeling, hiking, and exploring the island can often fill up quickly, so it’s best to have a plan before heading out.

Also, some famous sightseeing spots require you to book tickets, so always check before heading out.

Make Dining Reservations

Planning a Trip to Hawaii- Roy's Lunch

Yes. This one may come as a surprise. If there’s a restaurant you want to eat at, you must absolutely make a reservation beforehand. 

When I visited Hawaii recently, all the restaurants I walked up to were fully booked! Check the restaurant’s Yelp page or OpenTable to see if you can make a reservation beforehand. 

Consider Purchasing a Travel Insurance

Planning a Trip to Hawaii- natural landscape hiking trail in Hawaii

Even if you don’t usually purchase travel insurance, I highly recommend purchasing one. 

Most travel insurances will cover stolen/damaged/lost baggage, medical emergencies, and delay or cancellation of your trip for covered reasons. 

Travel insurance also usually covers natural disasters such as storms and hurricanes. Also, note that there are some active volcanoes in Hawaii! 

Some insurance offers additional options such as “cancel for any reason” (CAFR) that will allow you to receive some reimbursement for your trip costs. Although reimbursement rates will differ for each insurance agency, most CAFR coverage will reimburse 75% of your trip cost.

Purchasing insurance is crucial if you’re planning outdoor activities such as surfing, scuba diving, etc. is a great site to find insurance that best fits your vacation. In just minutes, you can compare quotes and buy travel insurance from top-rated insurers, including AIG, AXA, Travelex, and more.

Insurances will help you give peace of mind knowing that it’ll be okay even if something unexpected happens.

Note: If you’re planning any activities, make sure that they’re included in the insurance. Contact the insurance company to check!

When To Start Planning for Hawaii Trip

Planning a Trip to Hawaii- Nalu

Planning a trip to the Hawaiian islands can be a lot of fun, but starting planning well in advance is essential to get the best deals and ensure you have everything booked.

Generally, you’ll want to start planning at least six months in advance, especially if you’re looking for a specific time of year to go or want to stay in a particular location.

However, there are some things you can do up to a year in advance, so don’t wait too long!

How to Save Money on a Hawaii Vacation

Planning a Trip to Hawaii- Pineapples

Hawaii is a popular travel destination, and for a good reason. The Hawaiian islands offer something for everyone, from stunning beaches to lush rainforests. However, a trip to Hawaii can be expensive.

Some factors contributing to the cost of a Hawaii trip include airfare, hotel costs, and car rental.

Here are several ways to save money on your Hawaii vacation.

Find Package Deals

There are a few reasons why vacation packages are the best way to book your hotel when traveling.

First, vacation packages are usually cheaper than booking your hotel room and flights separately. You can also find some fantastic deals on vacation packages, especially if you book them early.

Another reason to book your hotel with a vacation package is that you can often get extras included in your deal. For example, many packages include breakfast or dinner at the hotel restaurant. This can be a great way to save money on your Hawaii trip and try out some local cuisine at the same time. Other packages may offer in-resort credit that can be used for purchases made in the resort.

Finally, booking your hotel with a vacation package can make your trip less stressful. You don’t have to worry about figuring out where to stay or how to book it – the package deal takes care of everything for you. So if you’re looking for an easy and affordable way to book your next hotel room, consider booking a vacation package.

There are many places to book vacation packages, but some of the best deals can be found online. Some reputable websites that offer package deals include Expedia, Travelocity, and Priceline. If you have a Costco membership, check Costco Travel to see what vacation deals they offer. You can also check with your favorite airline or travel agency to see if they have any package deals available.

Book Offseason

Planning a Trip to Hawaii- Kauai Beach

Vacation prices will vary depending on the time of year you visit, with peak season costing more than the off-season. A way to save is by booking your Hawaii trip during the offseason. Generally, the offseason is from January to March.

Choose Accommodations Wisely

Planning a Trip to Hawaii- Kauai

One of the most expensive factors of a Hawaii vacation besides airline fees would be accommodation fees. Choosing less costly accommodations will significantly decrease the cost of your Hawaii vacation.

If you’re planning to visit Hawaii with a large group, I recommend staying in a hotel together with your friends or family. This way, you can save money by sharing a room!

Cook Your Own Meal or Buy Food From A Grocery Store

Planning a Trip to Hawaii- Costco Poke

Another excellent option for saving money on food is to buy groceries at Costco. Not only is it cheaper than buying food at restaurants, but you’ll also have the option of cooking your own meals. This can be a great way to save money and enjoy some home-cooked meals during your Hawaii trip.

Use a Travel Credit Card

Using a travel credit card can provide many benefits when planning a vacation. Travel credit cards typically offer rewards such as airline miles or points that can be redeemed for hotel stays, car rentals, or other types of travel-related expenses.

By using a travel credit card, you can earn rewards while you’re on your trip, which can help offset the cost of your vacation. They also often come with other perks like free checked bags or airport lounge access.

In addition, many credit cards offer travel insurance, which can provide coverage for canceled trips, lost luggage, and other travel mishaps. Additionally, if something goes wrong while you’re away, having insurance can help to minimize the financial impact.

So if you’re planning a vacation in the near future, consider using a travel credit card to take advantage of its many benefits.

What to Pack for your Hawaii Vacation

Planning a Trip to Hawaii- Waikiki Boat

A Hawaii vacation is a dream come true for many people. The sun, the sand, and the waves are some of the reasons why people love to go to Hawaii. If you are planning to go to Hawaii, make sure that you pack the right things.

Passport or Driver’s License and Insurance Cards

While traveling domestically, it is important to remember to bring your important documents with you. This includes your driver’s license, passport, and insurance cards. If you are in an accident or need to show identification, it’s helpful to have these documents on hand. Additionally, if you are traveling with children, be sure to bring their passports as well. You can ensure a smooth and safe trip by being prepared with your important documents. Check to ensure that all your important documents are valid and not expired.


You will want to pack sunscreen and a hat to protect your skin from the sun. Make sure that the sunscreen is reef-safe. Unfortunately, many sunscreens contain chemicals that can harm coral reefs. Look for one that doesn’t contain octinoxate and oxybenzone.


Another thing that you will need is a good pair of shoes. You will be doing a lot of walking, so make sure you pack something comfortable. If you are going to be hiking, make sure to bring a good pair of sneakers.


You will also want to pack clothes for different occasions. Make sure to pack something casual for hanging out on the beach and something dressier for going out to dinner.

Another thing to consider when packing a trip to Hawaii is the weather. The islands have a tropical climate, which means the weather can vary depending on the time of year you visit. It’s a good idea to check the forecast before you leave, so you can pack accordingly. You may want to pack a light jacket or sweater, as it can get chilly at night.


Finally, make sure to bring your camera! You will want to capture all of the memories of your fantastic trip to Hawaii.

GoPro is the perfect lightweight/small action camera that can capture your Hawaii vacation’s thrills. GoPros are tough and waterproof, so you can take them on any adventure without worrying about them getting damaged. They also have a wide-angle lens, which means you can fit more into your shots, even when you’re swimming, surfing, or snorkeling.

Plus, they’re easy to use, so you can quickly capture your trip’s highlights without fussing with complicated settings!

For International Travelers

There are a few things that you will need to travel to Hawaii.


The first is a valid passport, as Hawaii is a foreign country. Make sure to check your passport expiration date before traveling!

Visa or ESTA

Depending on your nationality, you may also be required to obtain a visa.

A Visa Waiver Program is available for some participating countries. This program will allow you to travel to the U.S. without a visa for stays less than 90 days. The Electronic System for Travel Authorization or ESTA is an automated system that will help determine the eligibility of visitors to travel to the United States under the program.

It’s easy to apply for ESTA online, and most applicants receive a response within minutes.

For more information, check the embassy or consulate of the United States in your country.

WiFi Portable Hotspot

If you’re planning a vacation to Hawaii, one of the most important things to consider is how you’ll stay connected to the internet. While there are some restaurants and cafes that offer free WiFi, it’s not always reliable or accessible. A portable WiFi hotspot is a great solution for staying connected on the go.

Here are some reasons why you should buy a portable WiFi hotspot for your Hawaii vacation:

1. The hotspot will allow you to stay connected to the internet wherever you go, whether you’re in Waikiki or on a remote beach.

2. You can use the hotspot to access email, social media, and other online resources while you’re away from home.

3. The hotspot can be used to download maps, find directions, and book activities on the go.

4. Having a WiFi hotspot will save you money on data roaming charges while you’re in Hawaii.

Solis Lite Hotspot is an excellent Global WiFi Hotspot device that will keep you connected to the web anywhere in the world without a sim card. You can connect up to 10 devices at once, and it has a long battery life of 16 hours! All you need is an account, a hotspot device, and sign up for one of the data plans they offer. This WiFi hotspot is perfect for travelers who want to stay connected while abroad. I know several friends that use this WiFi hotspot in their everyday life!

COVID Restrictions

According to the Hawaii State Department of Health, “there are no COVID-related entry requirements for domestic travelers.” Travelers do not have to complete the Safe Travels application to enter Hawaii. 

International Travelers 

Proof of COVID-19 vaccination is required for non-U.S. citizens to enter the U.S. Visit the CDC website for more information.

Learn Some Hawaiian Words

When planning a trip to Hawaii, it can be fun to learn some of the Hawaiian languages. This will help you to enjoy your trip better and get a taste of the culture. Many online resources can help you learn some basic Hawaiian words. By learning a little bit of the Hawaiian language, you’ll be able to communicate with locals and get a deeper understanding of the culture.

What Next?

Mahalo for reading! I hope this post has inspired you and provided you with helpful Hawaii travel tips to start planning your dream trip to Hawaii. Hawaii vacation planning can take a lot of work. Still, it’s worth it to experience the fantastic beaches and scenery. With a little bit of preparation, you can ensure that your trip is as smooth and enjoyable as possible. Be sure to check out our other travel-related posts below and save this article for future reference.


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