How To Plan A Hawaii Trip |The Ultimate Guide By A Local

Planning a vacation is hectic and time-consuming. Hawaii is a popular vacation destination and with good reason. The tropical climate, stunning landscapes, and abundance of activities make it a great place to visit. 

If you’re planning a trip to Hawaii, there are a few things you need to know to make the most of your time there. 

In this blog post, we’ll give you some tips on how to plan your perfect Hawaii trip. 


How To Plan A Hawaii Trip

Book And Plan In Advance

You’ve probably already heard that booking your airline tickets and hotel reservations is essential as far in advance as possible for the best deals, but what about booking activities or tours?.

Booking in advance saves you money because there are often significant discounts.

Planning, you have a wide selection of hotels and flights to choose from when you book in advance because most people don’t plan that far ahead. 

Lastly, it’s very common in Hawaii shows; activities are booked out for weeks and even months out. Always check what activities you would like to do, so you book them before it all sells out.

Which Hawaii island should I visit?

There are five major islands in Hawaii: Oahu, Kauai, Maui, The Big Island, and Molokai.

These islands have a lot in common with each other.

For example, they all have beautiful beaches, luxurious resorts, and incredible views of nature that look like something from a postcard.

 But it’s the little things about each island that make them different from each other – some are better than others for first-timers.


 Big Island is the most affordable island compared to the other four major islands.   

 You can do many activities at Big Island that you won’t find on the other islands. 

For example, go into an active volcano Mauna Loa, swim with dolphins in Hilo, climb a mountain to see a fantastic view of the island Hawaii Tropical Botanical Garden, or take surfing lessons in Kona [depending on the season and your skill level].

Best Known for: Mauna Loa Volcano

Unique to this island: 

  • Snorkeling with Manta Ray at night
  • Seeing active volcano


Oahu, Hawaii is perfect if you’re more of a city-dweller, Oahu would be the best choice, as it has the most metropolitan area in Hawaii.

Oahu offers a little something for everyone here, from outdoor activities and water sports to Oahu’s great nightlife activities. 

No matter if you’re looking for the perfect Oahu Hawaii vacation or where to stay in Oahu, Oahu will not disappoint!

Oahu is best known for :

Waikiki Beach, North Shore surfing competitions

Unique things to do in Oahu:

  • Drive up to the top of Diamond Head for breathtaking views of Waikiki Beach 
  • Swim with shark CAGE FREE
  • Kayak to Kaneohe sandbar
  • Explore Oahu like a Local 


Maui is also famous among honeymooners, who enjoy its warm water and striking beaches.

Maui is made up of three main areas: Kihei/Wailea/Makena, Lahaina/Kapalua, and Hana.

Outdoorsy people will enjoy Maui’s Kihei/Wailea/Makena, which offers some of the best waves in the world.

Culture lovers can take advantage of Maui’s beautiful beaches and fantastic landscape.

Maui is perfect for families, and many resorts are catered for families.

Maui is also an excellent destination for honeymooners as Maui offers plenty of romantic activities that Maui has to offer, from Maui’s fabulous luaus to Maui’s Flame Tree Barbeque and Maui’s world-famous sunset. 

Maui is known for Luxury Resorts

Unique things to do in Maui:

  • Go humpback whales sighting
  • Drive Road to Hana
  • Haleakala National Park


Kauai Hawaii is known as “The Garden Island” because of its beautiful natural landscape.

The Isle of Kauai has been called “The Garden Island” due to its lush landscape, perfect for hiking and exploring. It is also the oldest and northernmost of all islands in the Hawaiian Archipelago. 

Water activities are abundant, with more than 140 world-class beaches on seven different beach bodies. 

 The west side has Waimea Canyon, which they say is one of nine epic wonders of the USA!

 A perfect holiday spot for families or couples to spend quality time together.

As one of the least populated islands in the Hawaiian Archipelago, it is more peaceful and less crowded than most other islands, and this also provides fewer safety issues for visitors to worry about.

With so many sights to see in this beautiful island paradise, it would be best to plan an entire week even to begin trying to experience all Kauai Hawaii has to offer.

Kauai is perfect for adventure seekers who can enjoy exploring lush mountainous terrain throughout their journey.

Kauai is Best Known for Na Pali Coast

Unique to this island:

  • Hike to Red Dirt Falls in Waimea Canyon.

Molokai is an island that showcases what traditional Hawai’i was like before mass tourism altered everything about Hawaiian culture and life. 

Molokai island is home to several world-famous spots such as Halawa Valley and Kalaupapa National Historical Park, which many travel enthusiasts have described as ‘bucket list’ places that everyone should see before they die! 

Last but not least, because of its serene environment and unique history, Molokai has been named one of the most beautiful islands in Hawaii.

Molokai is Best Known for Molokai’s Sea Cliffs

Unique to this island: 

  •  Explore Soaring Sea Cliffs
  • Try “hot bread.”

When is the best time to visit Hawaii?

how to plan a Hawaii trip expert advice from a local
Photo by Jeremy Bishop from Pexels

Certainly, you want to vacation in Hawaii but must decide when is the best time to visit.

When planning your trip, you should check for available activities exclusive to Spring or Winter.

Each Hawaii island has its micro-climate depending on where you stay. 

The trade winds influence the island’s weather.

The North and East coasts get the most rain compared to the South and West coasts. 

Everything costs are higher during the high season(December-March) low season (April-November). 

The average daytime summer temperature at sea level is 85° F (29.4° C), while the average daytime winter temperature is 78° (25.6° C). Temperatures at night are 10° F lower than in the daytime.

January and September are the cheapest months, and June and December are the most expensive. 

I recommend visiting Hawaii in late April, May, June, September, and October for the best weather, prices and fewer crowds. 

We used the table below as an example trip for two from NYC for seven days and six nights; this is the average cost when staying at a hotel during the summer using Skyscanner.com, my favorite for flight deals.

IslandsBig IslandOahuMauiMolokaiKauai
Accommodation (3 stars)$1073$1149$1853$1028$1353

Read more about the cost breakdown for a trip to Hawaii.

How many days should I visit Hawaii?

flight to hawaii
Photo by Shoval Zonnis from Pexels

If you’re thinking about taking a trip to Hawaii, it’s natural to want to make sure you see all the best sights and take in as much of the culture as possible.

However, it can be overwhelming if you’ve never been before and aren’t sure how long you should plan on staying. 

I know it’s a long flight to get to Hawaii, and I recommend only visiting one island and enjoying the fullest. 

Seven days is reasonable to enjoy any island while relaxing and experiencing Hawaiian culture.

Spending an 8-12 hour flight to get to Hawaii dealing with jet lag and enjoying everything Hawaii has to offer gives you more than enough time.

Where to stay in Hawaii?


active volcano in hawaii
Photo by Jack Ebnet on Unsplash

 The Big Island is the largest compared to the other Hawaiian islands combined, and it’s the youngest of all the archipelagoes. 

It’s important to consider what you would like to see during your visit to the big island.

The good thing about Big island is that there is something for every budget.

From upscale luxury to budget-friendly accommodations.

East of the island(Hilo) is the volcano area.

Westside(Kona) restaurants ,shopping,hotels for all budgets,beaches.

North Shore is great for water sports enthusiasts 

South is perfect for watching amazing sunsets and sunrises but lacks significant accommodations.

Accommodation Recommendations on BIG ISLAND

The best place to stay for families is to head to Waikoloa village for family-friendly accommodations. 

The best place to stay for luxury lovers your best bet is to head to Kohala. Kohala has top beachfront resorts and some of the best beaches found anywhere. 

The best place for backpackers/budget-friendly is Kona. Kona has beachfront accommodations near the beach and has B&B options, and Kona has excellent restaurants, shopping, and beaches. 

Boutique Hotels on the Big Island

Holualoa Inn


Waikiki pond
Photo by Amanda Phung on Unsplash

Oahu comprises three main areas: Honolulu, North Shore, and The Windward Side.

Outdoorsy people will enjoy Oahu’s North Shore, which offers some of the best waves in the world, while culture lovers can take advantage of Oahu’s beautiful beaches and scenic landscapes or Oahu’s famous luaus.

Oahu is perfect for families with children.

Oahu is also an excellent destination for honeymooners as Oahu offers plenty of romantic activities that Oahu has to offer, from Oahu’s fabulous luaus to Oahu’s famous secluded beaches and Oahu’s world-famous sunset

Accommodation Recommendations on OAHU

The best place to stay for first-timers is the Waikiki area.

Waikiki is a hotel super close To the famous Waikiki beach where you can spend more of your time.

Waikiki has beaches, shopping, restaurants, and excellent water activities, all walking distance.

Waikiki is great for families and for budget-friendly travelers

If you are a fan of Boutique Hotels, definitely check out Kaimana Beach Hotel

$$$ Halekulani

$$ The Laylow, Autograph Collection 

$ Aqua Oasis

The best place for budget-friendly hotels in Waikiki

Hokulani Waikiki by Hilton Grand Vacations Club

VIVE Hotel Waikiki

Castle Bamboo Waikiki Hotel

The best place to stay for luxury lovers is to head to Koolina.

Koolina is a tiny village of luxury resorts with man-made lagoons to swim with no strong current water and lay out to tan. Koolina is a 30 min drive from Honolulu.

Four seasons hotel Koolina

Trump (Waikiki)


Turtle beach resort (north shore)


molokini in Maui hawaii

Maui has something for everyone- from busy cities to tranquil beaches.

If you’re planning a trip to Maui, deciding where to stay can be tricky. There are many different areas to choose from, and each has its own unique personality.

Maui has five popular areas to stay Kaanapali,Lahaina,Hana,Kihei.

Accommodation Recommendations on MAUI

The best place for first-timers to Maui is to stay on the island’s Westside. The island’s west is the most popular due to its lively streets and beaches. You can also find hotels on the beaches from high-end hotels to budget-friendly hotels. These areas are also great for families because they are safe areas.

$$$ Montage Kapalua Bay

$$ Aston Maui Kaanapali Villas

$ Best Western Pioneer Inn

The best place to stay for luxury lovers is Wailea and Ka’anapali area. Wailea is located in the south of the island, and Maui is famous for there luxury resorts. Wales has many luxury activities and even luxury cars to rent during your stay.

Grand Wailea Resort Hotel & Spa

Andaz Maui at Wailea Resort 

Four Seasons Resort Maui 

The best place for backpackers/budget-friendly, Kihei, Paia. Kihei has many restaurants, beaches, and residential neighborhoods. Kihei is located in a central location, making it easy to travel and explore the rest of Maui. Paia has a more laid-back small town for surfers along Maui’s north shore.

Kohea Kai Maui, Ascend Hotel Collection


If you’re looking for an unforgettable travel experience, look no further than Kauai.

This enchanting island has something for everyone, from dramatic cliffs and rainforests to world-famous beaches and luxurious resorts.

Kauai is home to some of the most beautiful scenery in the world.

The island’s soaring cliffs, pristine beaches, and dense rainforest provide plenty of natural beauty to explore.

You can go hiking, biking, or kayaking through the many lush forests and valleys, or take a scenic drive along the coast to see all the best views.

Kauai offers a wide array of activities and attractions

Accommodation Recommendations on KAUAI

The best place for first-timers to stay is Kauai’s south side. The south side has everything from popular attractions and outdoor activities.

Keep in mind that there aren’t that many hotels on the island, so I recommend booking in advance to have more hotel selection.

$$$ Sheraton Kauai Resort Villas 

$$ Kauai Shores Hotel

$ Marriott’s Waiohai Beach Club 

The best place to stay for luxury loversWailea is located in the island’s south. Maui is famous for there luxury resorts. Wales has many luxury activities and even luxury cars to rent during your stay.

Royal Sonesta Kaua’i Resort Lihue 

Koloa Landing Resort at Po’ipu, Autograph Collection

Kauai Beach Resort & Spa 

The best place for backpackers/budget-friendly is Kapa’a is a great location. It’s an affordable area with many close beaches and trails to explore.

The ISO 

Aloha Beaches


There are no major resorts or luxury hotels on Molokai, which makes people love Molokai even more. There are a few hotels and vacation rentals in the center town of Kaunakakai and Maunaloa.

Hotel Molokai

How do I get around Hawaii?

car rentals
Photo by Elviss Railijs Bitāns from Pexels


If you’re planning a trip to the big island of Hawaii, renting a car is the best way to get around. There are plenty of things to see and do on this vast island, and a car will give you the freedom to explore at your own pace.

Plus, thanks to Hawaii’s great weather, you can enjoy driving around even during the hottest parts of the day.

So if you’re looking for an easy way to get around big island Hawaii, renting a car is definitely the way to go!

Ridesharing is also available on the island.

Taxis are mostly seen at the airport and are expensive.

The bus is a great way to explore near your hotel, keeping in mind that it only operates during the weekdays and its cash is only $2


Renting a Car

There are many options for transportation when visiting Oahu, Hawaii. However, renting a car is the best option for first-time visitors.

Here’s why: renting a car gives you the freedom to explore all that Oahu has to offer at your own pace; there is no need to rely on someone else’s schedule or tour; rental cars are affordable, and there are many different types of vehicles to choose from, so you can find one that fits your needs and budget; and finally, driving in Hawaii is easy – the roads are well-marked, and the locals are friendly and helpful.

So if you’re looking for an island vacation that allows you to explore at your own pace, rent a car, and enjoy all that Oahu.

The Bus

Oahu has a bus network that can get you anywhere on the island.

Taking the bus is the most affordable ($2.75)way to get around Oahu. That being said, it’s not the best because it’s the slowest way to get around, and arrival times can be unpredictable.

Ridesharing apps,Uber and Lyft are available options and great to use in the Honolulu area.

The more remote areas will have more extended time. Keep in mind the prices will be HIGH.

A short trip from Waikiki to Ala Moana Center 2.3 miles cost me $18.20 at night. The prices tend to be higher.


Like anywhere in the world, there are taxis available but at high prices.


Renting a moped is a great way to tour Waikiki and the island because it’s small and easier to park. It’s better to rent for more days than just renting it for one day.

Best for experienced drivers with a motorcycle license.


Maui is tough to explore without a car.

The bus system has shops around the major towns, and if you wanted to explore the road to Hana or Haleakala National park, you wouldn’t be, unfortunately.

Staying in the small towns or resort areas, you can take the bus or even ride a bike.

The main bus connects between major towns for a one-way fare of $2 and a day pass for $5.

Taxis and Ridesharing operate in major towns and touristy areas like the bus.


The best way to get around Kauai is going to be by car.

Kauai has a bus system but is not great for tourists. The bus doesn’t stop near-total areas or the airport or bring a suitcase on the bus. Taxis on the island are not popular either.

Many hotels do provide a shuttle to and from the airport. There are ride-sharing apps available but not many cars, and you will have a higher waiting time than you are used to.


Molokai being more remote, there is no public transportation. Your two options are renting a car or by taxi.

➡️ Click HERE For The Best Rental Car Rates In Hawaii⬅️

What are activities to do while visiting Hawaii?

 beaches in Hawaii

Things to do in Big island 

  • Swim with Manta Rays
  • Helicopter tour over an Active Volcano
  • See ‘Akaka Falls
  • Zipline over a waterfall
  • Go whale watching in Winter.

Things to do in Oahu

🌺 Toa Luau At Waimea Valley

🤿 Go Snorkeling with Sharks Hawaii with One Ocean Diving

🚁 Full Circle Helicopter Tour Of Oahu

🦖 Drive Your Own 4WD UTV Through Kualoa Ranch

Need things to do at night check this post out.

Things to do in Maui

  • Go whale watching in Winter
  • Do a rainforest waterfall hike
  • Hike the crater at Haleakala National Park
  • Drive (or fly over!) the Road to Hana

Things to do in Molokai

  •  Explore Soaring Sea Cliffs
  • Try “hot bread.”

Things to do in Kauai

  • Hike to Red Dirt Falls in Waimea Canyon.

Here are the best-hidden gems on the Hawaiian islands to check out.

When is the best time to visit Hawaii?

More Planning Trip to Hawaii FAQ

How much, on average, does a Hawaii trip cost?

Hawaii is expensive, and on average, you are looking to be spending the most money on accommodation. 

Prices vary by island, and the season price ranges from $2570 to $5279.

How far in advance should you book advance?

I recommend at least 3-6 months in advance at least. 

If you can book sooner, you will have more selection available. 

More than 10 million people in 2019 visited Hawaii.

What is the cheapest time of year to visit Hawaii?

The cost may vary, During the high season(December-March) low season (April-November). 

January and September are the cheapest months, and June and December are the most expensive. 

What do I need to pack Hawaii?

  • Sunscreen: You’ll need sunscreen for Hawaii. Chemical sunscreens are ILLEGAL in Hawaii. Use reef-safe sunscreen if you plan to go into the ocean. Ordinary chemical sunscreen kills the corals. 
  • Sundress: are perfect for hawaii you look more dressed up and not over dressed.
  • GOPRO: must capture all your underwater moments. Hawaii has some of the clearest water and amazing marine life in the world.
  • Reef Shoes-Most beaches have rock or reef on the bottom. It is great to have to have an enjoyable swim with a piece of mind knowing that you won’t be getting cut.
  • Travel Insurance: Now with covid is great to have to know that you are covered while travel.

Don’t want to forget anything, check this Hawaii packing list article.

How to Plan a Hawaii Trip Summary

So hopefully, this gives you a better idea of what you need to do when planning your dream trip to Hawaii.

 I know I’ve covered a lot in this post, so if you have any questions, feel free to ask in the comments below, and I’ll get back to you as soon as possible. 


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