Ultimate 2 Weeks in Hawaii Itinerary: Visit Multiple Islands

Are you on a mission to visit multiple Hawaiian islands in one go? I’ve visited all 4 main islands in Hawaii — Oahu, Kauai, Maui, and the Big Island — and all are worth seeing. They’re different, special in their own ways, so why choose just one Hawaiian island to visit? Visit them all!

With only 2 weeks in Hawaii, you’ll find that visiting multiple islands will mean more travel days and a faster pace — you’re gonna be doing a LOT. However, it is possible and oh so fun.

What’s the Difference Between Each Hawaiian Island?

Big Island

The Island of Hawaii is nicknamed the Big Island as it’s the largest Hawaiian island. It is a great island to visit if you like adventure, want to see some of the most active volcanoes in the world, and want to experience a tropical environment.

The Big Island has black sand beaches, waterfalls, hundreds of Kona coffee farms, incredible snorkeling, and so, so many adventurous activities.

The Big Island gets about 2 million visitors a year.

Maui

Maui is a great island to visit if you want to relax and be around less crowds, see sea turtles (from a safe distance), hang out on gorgeous beaches, hike, and have the options of driving to the summit of a volcano and driving through a rain forest down the highway to Hana.

Maui has such a mix of things to do, it’s really a choose-your-own-adventure kinda place. It has a very chill, laid-back vibe and is just very peaceful.

Maui gets about 3 million visitors a year.

Oahu

Oahu is the island to go to if you like city nightlife, don’t mind a lot of crowds, and want to shop till you drop in Hawaii.

Oahu is the most visited island (almost half of all visitors to Hawaii come to this island), though it’s not the biggest.

There are a LOT of people here, visitors and residents alike; and you’ll also find some of the biggest attractions here — like Kualoa Ranch, Disney’s Aulani Resort, Pearl Harbor, and the Polynesian Cultural Center.

Because of zoning laws, most hotels are in Honolulu near Waikiki Beach, which has a similar vibe to Las Vegas’ strip, not very relaxing, but potentially a lot of fun if this is your thing.

Oahu gets about 6 million visitors a year.

Kauai

Kauai is the island to visit if you like hiking, want to see the Na Pali Coast, love being surrounded by greenery, and would like to visit a place where there are more wild roosters than people (6 to 1).

Kauai is nicknamed the Garden Island as it is very lush and green and, yes, the roosters really do run amok throughout the streets.

Kauai has a lot to do and yet it’s the least visited island (only about 12.5 percent of Hawaiian tourists come to Kauai).

Kauai gets about 1.75 million visitors a year.

How to Spend 2 Weeks in Hawaii

This 2 weeks in Hawaii itinerary is 16 days long, instead of 14 days, as it it includes the prior weekend. So if you leave on a Saturday, you will return on a Sunday two weeks later (10 working days and 6 weekend days).

You’ll see in this itinerary, I’m a bit partial to the Big Island and Kauai, allotting more days on those islands. If you have more vacation days, you can add more to your time on Maui or Oahu. But if two weeks is the absolute max you have, feel free to adjust the itinerary, spending more days on the islands that interest you and less time elsewhere.

How to Travel Between Islands

The best, fastest, and only way to travel between islands is by plane. I wondered if a boat ride would be cheaper or faster, but alas, it is not even available. There is no ferry service between the islands — so the only way to travel by boat is if you’re on a cruise.

Flights between islands are pretty cheap however, less than $100 usually, and take between 30 to 45 minutes, depending on the islands you’re flying to and from.

Check Hawaiian Airlines and Southwest Airlines first for inter-island flights as these are the major airlines servicing Hawaii.

ISLAND 1: OAHU (3 DAYS)

With only three days in Oahu, you’ll need to focus each day on a certain section of the island, doing the most you can with the time you have. I stayed in Honolulu my entire time in Oahu and was able to visit the North Shore and eastern and western parts of the island. You’ll need a rental car, of course, but it’s definitely possible.

Arrival at Daniel K. Inouye International Airport (HNL)

The international airport in Honolulu is the one where most flights land, so it makes sense to start here in Oahu. Welcome to Hawaii!

Oahu can be a bit overwhelming with how crowded it is. I am honestly glad my first experience in Hawaii was on the Big Island, so you can also adjust the itinerary to visit Oahu last, if you are worried about the crowds and chaos of Honolulu. I have a lot of suggestions below of things to do outside of Honolulu, though, while in Oahu. Oahu is definitely a beautiful island and shouldn’t be missed.

You’ll be flying into Daniel K. Inouye International Airport (HNL), which is the largest international airport in Hawaii. A variety of airlines service this airport.

Grab Your Rental Car

A car is definitely needed if you plan to explore outside Waikiki Beach, which I definitely recommend doing so.

There is public transportation on the island, but my research showed using the bus would take up a lot of extra time getting from place to place, which isn’t ideal when you’re trying to fit in as much as you can in three days.

There are 10 rental car companies at the Daniel K. Inouye International Airport (HNL), including Alamo, Avis, Budget, Dollar, Enterprise, Hertz, National, Payless, Thrifty, and Sixt.

Whichever company you go with, book early to secure your car ahead of time. Cars are limited on the island and tend to book up early.

To make it easier, you can search through all of the car rental companies in the widget below, comparing them to find the best price.

Where to Stay in Honolulu

Oahu is one of the smallest islands and is suffering from overcrowding and overtourism, probably more than any other Hawaiian island. That being said, zoning laws are a lot stricter here. Most hotels are restricted to Honolulu with very few elsewhere on the island.

I’d suggest making Honolulu your home base to explore the island.

Be mindful of hotel fees. You can’t really get away from the parking and resort fees at almost any hotel in Honolulu. You just have to suck it up and pay it.

Budget Hotels in Oahu:

• Holiday Surf Hotel
• Vive Hotel Waikiki
• The Beach Waikiki Hostel

Mid-range Hotels in Oahu:

• Queen Kapiolani Hotel
• Outrigger Waikiki Hotel
• Moana Surfrider
• Park Shore Waikiki (where we stayed)

Luxury Hotels in Oahu:

• Disney’s Aulani Resort
• The Kahala Hotel and Resort
• Turtle Bay Resort (North Shore)
• The Royal Hawaiian

I recommend Park Shore Waikiki; we stayed here on the ninth floor and enjoyed incredible views of the ocean and Diamond Head. The room was a bit small, though, and the hotel charged a daily parking fee (currently $48/night) in addition to its daily resort fee.

What to Do for 3 Days in Oahu

With only 3 days in Oahu, what should you prioritize?

My favorite and most recommended activity in Oahu is the jeep or ATV tours at Kuloa Ranch. Make a day of it and visit Byodo-In Temple and Tropical Farms Macadamia Nut Farm on the way. Afterward, stop at Kualoa Regional Park Beach, which looks out to Chinaman’s Hat Island. It’s a more peaceful beach with less crowds and great views.

I’d also suggest fitting in a tour of Iolani Palace to learn the history of Hawaii and its former reigning monarchs.

Lastly, I’d definitely recommend getting out of Honolulu to explore the more natural parts of the island. So hit up Waikiki Beach only if you have some down time and nothing else to do.

For more ideas and details of what to do in Oahu, see my 5 day Oahu itinerary.

ISLAND 2: BIG ISLAND (5 DAYS)

The Big Island is probably most famous for its five volcanoes — Kīlauea, Mauna Loa, Mauna Kea, Hualālai, and Kohala. Four of these volcanoes are active, and two are extremely active, erupting every few years or even every few months.

The Big Island has a diverse range of landscapes. You’ll find tropical rain forests, lava fields, black sand beaches, and even deserts.

There is a lot to do and see in the Big Island, so five days will just scratch the surface.

Arrival at Hilo International Airport (ITO) or Kona International Airport (KOA)

The Big Island has two main areas, Kona and Hilo, one on each side of the island. Both have their own commercial airport, Hilo International Airport and Kona International Airport.

It takes about an hour and a half to two hours to drive from one side of the island to the other.

You may be wondering which airport you should use and whether you should stay in Hilo or Kona?

The answer is you should fly into either airport and stay in both areas.

This itinerary splits your time between both Hilo and Kona as it’s much more convenient than trying to stay in one place and drive out to the other side of the island only to come back, again and again.

Grab Your Rental Car

A car is definitely needed to explore the Big Island because, as the name suggest, it’s a pretty big island, and I wouldn’t recommend relying on public transportation if you’re trying to see a lot in a short time.

What’s nice is that you don’t have to take a shuttle to reach the car rental center at Hilo Airport, you simply just walk across a small street, and there you are.

Be sure to book your rental car as soon as possible as cars are limited on the island and tend to book up.

To make it easier, you can search through all of the car rental companies at Discovercars.com for Hilo Airport or Kona Airport, comparing them to find the best price.

Where to Stay on the Big Island

I’d suggest staying three nights in Hilo and two nights in Kona.

Recommended Hotels in Hilo, Hawaii:

• Hilo Hawaiian Hotel
• Hilo Bay Oceanfront Bed and Breakfast (where we stayed)
• SCP Hilo Hotel
• Grand Naniloa Hotel Hilo: Doubletree by Hilton

Recommended Hotels in Kona, Hawaii:

• Royal Kona Resort
• Outrigger Kona Resort
• Four Seasons Resort Hualalai
• Aston Kona by the Sea
• Courtyard by Marriott King Kamehameha’s Kona Beach Hotel
• Holiday Inn Express & Suites Kailua-Kona

What to Do for 3 Days in Hilo, Big Island

Hilo is the largest city on the Big Island, but it feels more like a small beach town. Hilo, which means “to twist” due to all the twisting rivers in the region, gets a lot of rain each year so expect a wet, humid climate.

What should you prioritize while staying in Hilo?

The most popular thing to do in Hilo is to take a day trip to Hawaii Volcanoes National Park. I agree with this. You really can’t miss visiting the most active volcanoes in the world.

I also highly recommend visiting Akaka Falls State Park and getting an acai bowl from Makani’s Magic Pineapple Shack.

What to Do for 2 Days in Kona, Big Island

Kona is perhaps most famous for its coffee. The Kona coffee belt is home to about 800 coffee farms, many of them small, family farms. The fertile, volcanic soil help Kona produce some of the finest coffee in the world.

In Kona, you’ll find some incredible snorkel spots, beautiful beaches, and some incredible views of the ocean.

While staying in Kona, what should you prioritize?

First of all, you must visit one of the famous Kona coffee farms. That’s a given. I’d also suggest visiting the Punalu’u Black Sand Beach on the way from Hilo to Kona. You also can’t miss the Puʻuhonua o Hōnaunau National Historical Park and snorkeling at Two Step.

For more ideas and details of what to do on the Big Island, see my 7 day Big Island itinerary and my 18 best things to do on the Big Island post.

ISLAND 3: MAUI (3 DAYS)

Maui is an incredible Hawaiian island that both sea turtles and people love. Maui is the both the second largest Hawaii island and the second most visited Hawaii island. It’s nicknamed the Valley Island. On Maui, you can easily get away from the crowds of Oahu while still experiencing the beauty and adventure that Maui has to offer.

Arrival at Kahului Airport (OGG)

You’ll arrive in Maui at Kahului Airport (OGG). The flight shouldn’t be long, so after you check into your lodgings you should have plenty of time to explore.

Grab Your Rental Car

A car is definitely needed if you plan to explore Maui and do a road trip to Hana or Haleakala as it just makes life easier.

Be sure to book early to secure your car ahead of time. Cars are limited on the island and tend to book up well in advance.

To make it easier, you can search through all of the car rental companies at Discovercars.com, comparing them to find the best price.

Where to Stay in Maui

I’d recommend finding a hotel or condo in Kihei, Maui, as it’s a very central location, in the middle of the island, close to everything. It was very easy to do day trips to Hana and Haleakala while also being close to the beaches and the towns.

Where we stayed: We stayed in a condo on Sugar Beach (in Sugar Beach Resort) near Kihei Town and loved it. We were walking distance from an ABC Store and a farmers market as well as steps from the beach (plus there’s a pool).

Most of the condos in Sugar Beach Resort are short-term rentals. Some are ocean front, some are on the ground floor, most have one bedroom, some have two. Look through all the options and take your pick!

Recommended Hotels in Kihei, Maui:

• Maui Coast Hotel
• Wailea Beach Resort: Marriott, Maui
• Mana Kai Maui
• Four Seasons Resort Maui at Wailea

What to Do for 3 Days in Maui

With only three days in Maui, I’d recommend spending at least one day on a road trip to either the summit of Haleakala or the town of Hana (or spend two days doing both).

Driving to the top of Haleakala, an extinct volcano, is a must do in Maui.

And the Road to Hana is famous for its scenic drive through a beautiful rain forest and past numerous waterfalls. On the drive you’ll make over 600 turns and cross over 45 bridges until you reach the charming town of Hana. It’s definitely a once-in-a-lifetime experience.

Lastly, I highly recommend that you search for sea turtles in Maui as sea turtles seem to love Maui, and we had the best luck finding them on this island.

(As exciting as it is to see a sea turtle in the wild, please remember that sea turtles are an endangered species and protected under Hawaiian state and federal laws. If you spot a sea turtle, keep a safe distance away and do not disturb them.)

For more ideas and details of what to do in Maui, see my 3 day Maui itinerary and my posts about things to do in Haleakala National Park and the best stops on the Road to Hana.

ISLAND 4: KAUAI (5 DAYS)

Kauai is the least visited Hawaiian island of the main four, and you’ll find things are slower and chiller here.

Surprisingly, 90% of Kauai’s land is undeveloped. The mountains in Kauai surround the rain forests, creating a lush, wild landscape that is a bit unreachable. Most of the developed parts of Kauai are on the coast lines.

Kauai has so much untouched nature to explore — from its mountains to its rain forests to its beaches.

There is truly so much to do in Kauai, I’m not sure why it doesn’t have more tourists.

Arrival at Lihue Airport (LIH)

You’ll fly to Kauai at Lihue Airport, where outside you’ll see not just shuttles waiting to take you to the rental car center but also roosters and chickens clucking about. Welcome to Kauai!

Grab Your Rental Car

A car is definitely needed if you plan to explore as much of Kauai as possible. Plus it just makes life easier.

There is public transportation on the island, but my research showed using the bus would take up a lot of extra time getting from place to place, which isn’t ideal when you’re trying to fit in as much as you can in a few days.

However, I would recommend using the Go Ha’ena Shuttle on the day you plan to explore the North Shore (especially Ha’ena State Park or Limahuli Gardens) as this really helps reduce traffic and overtourism in the small area. You’ll need to make reservations for the day you plan to visit, but the shuttle comes by every 20 minutes from 6:20 a.m. to 6:40 p.m.

For rental cars, be sure to book early to secure your car ahead of time. Cars are limited on the island and tend to book up well in advance.

To make it easier, you can search through all of the car rental companies at Discovercars.com, comparing them to find the best price.

Where to Stay in Kauai

There are 4 main regions of the island of Kauai:

• South Shore
• North Shore
• East side (Royal Coconut Coast)
• West side (Na Pali Coast)

You can’t drive all the way around the island as the mountains on the Na Pali Coast prevent this. A road covers about 3/4 of the island’s diameter — from Haena State Park on the North Shore to Polihale State Park in the west side.

It takes about 2 and a half hours to drive the complete distance from one end of Kauai to the other.

It’s most advantageous to stay in the east side region (Royal Coconut Coast) as it’s roughly at the center of the island’s main road, where it’s easy to reach either the South Shore or the North Shore.

No matter where you stay on Kauai, you’ll find it’s easy to drive to each part of the island as it’s not that big.

Where I’ve stayed: I’ve visited Kauai three times now and I’ve stayed at the amazing resort called The Royal Sonesta Kauai in Lihue, near the airport, as well as at the Hilton Garden Inn Kauai Wailua Bay.

Recommended Hotels in Kauai:

• The Royal Sonesta Kauai (Lihue)
• Sheraton Kauai Coconut Beach Resort (East side / Royal Coconut Coast)
• Hilton Garden Inn Kauai Wailua Bay (East side / Royal Coconut Coast)
• Outrigger Kauai Beach Resort and Spa (East side / Royal Coconut Coast)
• Kauai Shores Hotel (East side / Royal Coconut Coast)
• Grand Hyatt Kauai Resort (South Shore)

What to Do for 5 Days in Kauai

The east side’s Coconut Coast is a beautiful region that’s sure to leave you in awe, which is why I’d recommend visiting it first on your Kauai itinerary.

With only five days in Kauai, what should you prioritize?

My favorite activity in Kauai is snorkeling at Lydgate Beach Park. What makes this spot so perfect for snorkeling is that there’s a lava rock wall enclosure in the water, keeping the waves out. You’re able to snorkel easily without getting tossed around in the ocean. Not only that, but this beach also features clear blue water and tons of tropical fish! It is incredible.

I’d also recommend strolling through the large tropical garden at Smith’s Family Tropical Paradise, where you can discover a Polynesian village, bamboo, roosters, peacocks, a lake, and many, many flowers and plants.

The Smith family also runs a boat tour down Wailua River to the Fern Grotto, another must do.

You also must dedicate at least one day to visiting the North Shore, specifically Hanalei. I loved Hanalei so much, I still think of that dreamy, beautiful place.

The best meal we had in Kauai was at Tidepools. The ambience there is incredible — much of the seating is open-air and surrounded by koi ponds. So add that to your list as well!

I could go on and on about things to do in Kauai, so I’ll just list the rest below.

For more ideas and details of what to do in Kauai, see my 7 day Kauai itinerary post and my 22 cheap and free things to do in Kauai post.

What to Know Before Traveling to Hawaii

There are four main islands where people live and visit in Hawaii — the Big Island, Maui, Oahu, and Kauai. I’ve heard the wonders of Hawaii all my life but never understood it until I visited for myself.

Every island is unique and beautiful in its own right. No matter which one you visit, you will leave inspired and in awe. Here are some things to know before you go in order to be a respectful traveler.

Is Hawaii Suffering from Overtourism?

Yes, quite simply. There’s been numerous articles recently about how Hawaii is suffering from overtourism due to a post-pandemic travel boom, affecting its residents.

Some ways to help are to postpone your travel plans to Hawaii, visit one of the less-visited islands (such as the Big Island or Kauai), and/or visit during the low season (avoiding the summer and any school breaks).

You can also help by supporting local Hawaiian businesses (not corporations) and taking part in cultural classes or activities while in Hawaii.

How Do I Respect Hawaii as a Visitor?

Hawaii is a beautiful place — and the Hawaiian government and citizens do an amazing job at preserving the beauty. Did you know billboards are banned in the state of Hawaii in order to maintain natural beauty? As a visitor, please help contribute to these preservation efforts.

• Before traveling to any Hawaiian island, become familiar with how to be a respectful and responsible traveler to the islands and pledge to travel pono.
• Learn about the Hawaiian history and culture.
• Protect the oceans by not littering, reducing plastic use, and wearing reef-safe sunscreen (Hawaii is the first U.S. state to ban coral-harming chemicals in sunscreen).
• If hiking, don’t go off the trail and follow all signs and rules in place.
• And most importantly, be kind! Have your best attitude when interacting with other people on the island, both locals and travelers alike. It’s actually a law in Hawaii — the law of aloha “is the coordination of mind and heart” and each person must “think and emote good feelings to others.” So while in Hawaii, do as the locals do, and live aloha.

What’s the Weather Like in Hawaii?

Pack your summer clothes as Hawaii’s temperatures are around 80 degrees year-round. The only exceptions are in the higher elevation areas of Volcano, HI on the Big Island and Haleakala in Maui where it does get chilly. Otherwise, there isn’t a need for a jacket. Rain comes in and out but usually doesn’t last long. Still, try to check your weather app before arrival for more specific information.

Will I Need to Rent a Car?

Yes, definitely. There are buses in Hawaii but public transportation overall isn’t very efficient, especially if you’re trying to go as many places as possible in a limited amount of time.

Book a rental car as far in advance as possible as each of the islands are fairly small and many rental car companies had to consolidate during the pandemic.

How Is Driving in Hawaii?

Very easy! Roads are paved and in good condition. There’s usually not much traffic (except in the busy Honolulu). I had no probably navigating with general navigation apps like Google Maps or Apple Maps (except in more remote areas like the Road to Hana).

And fellow drivers are pretty courteous.

Many times, someone pulled out a Shaka hand sign for letting them pass or cut in front.

(The Shaka hand sign is where someone displays a fist with only their thumb and pinky finger extended. It means “thank you” or “good vibes.” It’s similar to the “hang loose” hand sign, if you’re more familiar with that one.)

What to pack for Hawaii?

Here are some of my favorite things I brought with me to Hawaii:

• Reef-safe sunscreen
• Snorkel set
• Waterproof phone pouch (to take photos underwater)
• EPA-registered insect repellent. There are mosquitoes in Hawaii, and while it’s rare for one of them to be carrying a virus, it’s best to spray yourself with insect repellent regularly to prevent those pesky bites. Be sure to use an EPA-registered insect repellent that has one of 5 active ingredients recommended by the CDC. The EPA has a search tool to help you locate a registered, effective insect repellent. My recommendation for a natural option is to use the EPA-registered Cutter Lemon Eucalyptus Insect Repellent Spray, which uses oil of lemon eucalyptus as its active ingredient.

Favorite travel essentials

• I really recommend these compression packing cubes. They’re very thick and durable and allow you to pack more than you expect.
• I also love this travel backpack that opens like a suitcase, fits almost as much as a carry-on, and has tons of pockets as well as a strap to attach to your luggage handle. It makes traveling so much easier and more organized. It also fits nicely under the airplane seats.
• I bring this AirFly receiver for AirPods with me on long-haul flights, so I can connect to the plane’s video screen with my own AirPods.
• I no longer hop on a flight without wearing my Sockwell compression socks because they really do help relieve/prevent leg cramps from sitting so long in one place. I have the lotus pattern, but there are other patterns to choose from, such as this cat pattern or this flower pattern. See all sock patterns in the Sockwell storefront.
• For Americans, I recommend getting the Capital One Venture X credit card to relax and eat free food in select airport lounges. I’ve had my Capital One Venture X credit card for a few years now, and accessing airport lounges is my absolute favorite perk of the card. Every lounge is different, but most have a buffet available where you can eat and drink to your heart’s content. The annual fee of this card is high, but it evens out with the $300 annual travel credit and 10,000 anniversary miles you get (on top of lounge access and free TSA PreCheck or Global Entry)!

Other Posts to Help You Plan Your Trip to Hawaii

If you need ideas on what else you can do on each island, check out my one-island itineraries for Maui, Oahu, the Big Island, and Kauai.

22 Cheap and Free Things to Do in Kauai

18 Best Things to Do on Big Island of Hawaii

How to Follow the Blackpink Hawaii Summer Diary Itinerary

Best Stops on Maui’s Road to Hana (with Map)

12 Things to Do in Haleakalā National Park

Day Trip to Hawaii Volcanoes National Park Itinerary

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