How to Visit Multiple Hawaiian Islands in 2 Weeks (itinerary included) - The Hawaii Vacation Guide (2024)

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When planning a trip to Hawaii, the first big decision is what Hawaiian Island should I visit? The challenging decision may result in choosing multiple Hawaiian Islands. This is how you can visit four Hawaiian islands in two weeks, or less.

Visiting all four Hawaiian Islands makes for a hectic trip of flights, hotel transfers, and non-stop activities. We usually discourage travelers from such an itinerary, especially those with kids. We adamantly advise against such a trip in our 5 Mistakes When Island Hopping video.

Our advice did not stop newsletter readers Dave and Mary. Flirting with disaster, they embarked on a 13-day, four-island tour. These audacious travelers came out the other side still married and with some lessons to share. You can find more of Dave’s Hawaii and Europe photos on Instagram @davemcquaid.

Thanks to Dave for being our first guest writer at The Hawaii Vacation Guide. Dave is sharing his itinerary for visiting all the major Hawaiian islands and his lessons learned.

Dave & Mary McQuaid are adventurous travelers and have been to all 50 U.S. states and 17 countries in their 34 years together.

Editor’s Note: Consider taking our Which Hawaiian Island to Visit Quiz or reading Which Hawaiian Island to Visit? before reading this article.Plus check out The Best Hawaiian Island to Visit to narrow down your choices if visiting all 4 is (understandably) too daunting!

SAVE $37! If you plan to visit all four islands or need help choosing which three to visit, use the coupon code VOYAGE to get a FREE Wayfinder Itinerary when you buy 3 itineraries.

Can You Visit the Four Major Hawaiian Islands in One Trip?

Yes, if you plan carefully, and are prepared for a few compromises.

If you’re like most folks who plan a Hawaii trip, you’ve got to balance your visit with available vacation days, family schedules, and other commitments. But you also want to make the most of the cost and time required to fly to Hawaii. So, you want to see as much as possible on your trip. For some, this might be a once-in-a-lifetime Hawaii vacation. While a four-week Hawaii visit might be ideal (and many international travelers do this), it’s just not possible for many.

The good news is it is possible to visit all four major Hawaiian islands in two weeks if you follow this advice:

• plan well
• stay flexible
• realize you won’t see everything on every island.

Here’s how we did it, as well as the fifteen lessons we learned.

Learn more about each Hawaiian island here:

• Maui Travel Guide
• Oahu Travel Guide
• Big Island Travel Guide
• Kauai Travel Guide

Four Hawaiian Island Itinerary

Here is our full 13-day itinerary for visiting the four major Hawaiian islands. It was a whirlwind trip but fun.

By sharing our itinerary and the trip planning resources below, we hope we can help you plan a similar adventure to Hawaii.

See Jordan and Erica’s Island Hopping Guide to better understand how to travel between the Hawaiian Islands.

Day 1. OAHU KO OLINA RESORTS

We flew from Los Angeles on the first Southwest flight of the day to Oahu. We picked up our Turo (more on that in the lessons learned below) and drove straight to Aulani Resort by Disney in the Ko Olina resort area, arriving shortly after noon.

We had rented Disney Vacation Club points for 2 nights, making what would have been a pricey stay more affordable. An afternoon in the pool, exploring the beautiful resort, and riding the lazy river was the perfect relaxing start to our trip.

We closed out the evening with a sunset dinner at the resort’s ‘Ama’Ama restaurant. The meal was one of two fine dining experiences we had planned, and while expensive, the food and service were amazing. You can also close your evening off with a Ko Olina Sunset Sail or Stargazing in Ko Olina Experience.

Day 2: OAHU DISNEY RESORT

I left very early for a sunrise hike on the windward side of the island (unfortunately, thwarted by incessant rain and low clouds). At the same time, Mary enjoyed Aulani’s many pools.

Shortly before 11, we enjoyed a hearty Disney character breakfast (yes, we’re kids at heart) at the Makahiki restaurant.

The showers from the island’s east side were now directly overhead, so we stayed indoors and did some shopping. Although frustrated we couldn’t be a little more active, this forced downtime was probably beneficial with several full days ahead of us.

Editor’s Note: If it rains on your vacation, here is What to Do in Hawaii When it Rains.

The clouds cleared before dinner, so we strolled along the Ko Olina boardwalk to some of the other resorts and watched the sunset from the edge of one of the lagoons before a pizza dinner (with pineapple – because Hawaii, of course!).

Day 3: OAHU WINDWARD COAST

We checked out of the Aulani and headed across the island to the fabulous Kualoa Ranch for a morning e-bike adventure in the Jurassic Valley, famous for Jurassic World, Lost, and dozens of other Hollywood productions.

The ranch has a wide range of tours, including bus, horseback, and UTV, which all take you into the valley between lush, majestic peaks. It’s quite an experience, even if you’re not a movie buff. Explore the best Kualoa Ranch tours here.

After lunch, we headed north up the coast to the Polynesian Cultural Center for the rest of the day. We enjoyed interactive experiences from several different Polynesian islands (including a ukelele lesson, hunting practice, taro farming, and a wedding), before enjoying a festive luau and a night-time Broadway-style show, complete with fire walkers and tribal battles.

There are a lot of things to do at the Polynesian Cultural Center so book the right ticket for your visit: Alii Luau vs Gateway Buffet: How to Decide.

We found it to be a highly educational experience, even though we felt it was a bit of a theme park vibe. We crossed the island to our new digs for the next 2 nights, an Airbnb condo a block away from Waikiki Beach.

Related article: Is Airbnb legal in Hawaii? Yes, but it’s complicated

Day 4: OAHU WAIKIKI DAY

We had 6:00 AM reservations to hike the Diamond Head volcano crater (advanced reservations are required), so we set out early and conquered the trail before it got hot.

The trek up is relatively easy – lots of stairs and some uneven footing, but mostly paved. Strollers can’t go up the rocky trail.

The views from the top overlooking the ocean and Honolulu are impressive.

But even by 7 am, it was getting crowded at the top. We returned to Honolulu and visited Waikiki Beach for the rest of the morning. While not the most attractive beach on Oahu, Waikiki is iconic – and being a Saturday morning, it was packed. The afternoon was laundry time and shopping along Kalakaua Avenue.

Related articles:

• 10 Best Beaches on Oahu
• Which Part of Oahu Should You Stay?
• 40 Things to Do on Oahu

Day 5: KAUAI HELICOPTER TOUR

We took the first non-stop Southwest flight from Honolulu to Lihue Airport on Kauai. From leaving our Airbnb at 7:20 AM in Honolulu to retrieving our luggage on Kauai at 10:50 AM, the entire trip took only 3.5 hours, giving us a good chunk of the day left.

We had booked a doors-off helicopter tour with Jack Harter Helicopters at 12:45, which was an amazing experience.

Editors Note: For flying the Napali Coast by helicopter or airplane, check out this doors-off helicopter tour.

Pro tip: Wear layers – we had on long pants and jackets and were still quite chilled!

Their 65-minute flight took us across the island, along the NāPali coast, and into a number of valleys and cliff cathedrals along the way. The trip was breathtaking, even with a bit of rain mixed in.

We then retrieved our Turo and drove to our Airbnb near Poipu Beach, one of the best beaches in Hawaii.

Related articles:

• Hawaii Discount Car Rental Options
• Where to Stay on Kauai

At this point, we learned that the charter boat company we had booked for the next evening’s sunset cruise along the NāPali coast was canceling the sailing due to anticipated rough seas. We knew this was a somewhat common experience in the winter, but thought we’d be clear in May.

After a couple of frantic phone calls, we were able to book the last two seats on a morning trip two days later, the day we would be flying to Maui. We enjoyed the sunset, and a few sea turtles at Poipu Beach before a late dinner.

Day 6: KAUAI SOUTH SHORE DAY

With the canceled sunset cruise having consumed the majority of our day (the cruise was to have left from the harbor around 2 PM, and it was about an hour away), we got what proved to be a welcome respite.

We spent the morning by the pool and heading into Old Koloa Town for lunch (Kauai food trucks are the best) and shopping at the local stores.

We had an early dinner and stopped for sunset at the Kukuiʻula Harbor Beach. Then we headed back to our lodging to repack our suitcase (by now starting to bulge with souvenirs) for an early departure.

Day 7: KAUAI NAPALI COAST AND MAUI TRANSFER

We checked out of our Airbnb very early and started the trip to the small boat harbor near Kekaha for our rescheduled NāPali boat tour with Makana Charters.

Editor’s Note: Watch a video on a Napali Coast Sail and Snorkel tour here to understand sailing the coast.

There are a number of companies that provide charter tours, but we chose this one because their harbor is closer to the tallest portion of the NāPali coast.

The seas were still quite rough, but manageable while in transit. It was only when the boat anchored for snorkeling and swimming that the pitching and rolling got to be a bit much for some passengers. The crew and captain were outstanding guides and made the cruise, and the amazing scenery, a highlight of our trip.

Editor’s Note: If you’re low on time, check out this popular Kauai Mountain Tubing tour.

Once we docked and got our land legs back, it was a mad dash back across the island in afternoon school traffic along two-lane roads to make our flight to Maui. After a few stressful moments, we arrived in time at the gate, only to find our Southwest flight was delayed because there was no flight crew.

Fortunately, this was the only flight-related hiccup on our trip, and we still made it to Maui in time to check into the wonderful Ka’anapali Beach Hotel (one of the best beach hotels on Maui), an affordable but beautiful option.

Explore the Maui Where to Stay directory for hotel and vacation rental options.

Day 8: MAUI ROAD TO HANA

We took the recommendation of this site and booked a Road to Hana tour through Valley Isle Excursions (save 10% with code HVG10 by booking here). We figured we shouldn’t test the route’s alternate name: Road to Divorce.

You can find a Complete Road to Hana Guide here.

After a 6:45 AM pickup at our hotel and a light breakfast, we started out on the winding route which took us past waterfalls, lush forests, multicolored foliage, jagged coastlines, black sand beaches, and witty commentary from our guide.

With stops for banana bread, lunch, and ice cream/shave ice, there was no shortage of food along the way! We returned to our hotel shortly before sunset.

Day 9: MAUI HALEAKALA SUNRISE AND LAHAINA TOWN

At 2:30 AM (yes, AM!) we boarded another bus, this time headed to the top of Haleakalā for sunrise. Valley Isle Excursions came through again and you can get 10% off here with promo code HVG10. The tour guide Alika (the same guide that Jordan and Erica had, in a random coincidence!) kept us warm, entertained, and informed as we made the drive, while still allowing for plenty of early morning napping.

Sunrise was beautiful and awe-inspiring, and we enjoyed the robust breakfast at the Mill House.

We spent the afternoon napping at the pool and beach and strolling along the Ka’anapali Boardwalk. The rain started to roll in, so we headed to Historic Lahaina for dinner, to see the enormous banyan tree, and generally act like tourists. There are a lot of things to do in Lahaina.

Day 10: MAUI UPCOUNTRY TOURS

We booked two farm tours today: the Maui Gold Pineapple Tour and the Maui Chocolate Tour. Maui has a lot of amazing farm tours.

The overnight rains had taken their toll, and while driving to the pineapple plantation we got a call saying the the fields were too muddy to operate the tour. They offered to reschedule, but since we were leaving the next day, we couldn’t.

So, we pulled out our trusty Maui Wayfinder Itinerary and called an audible.

Since we were in Upcountry Maui, we stopped at the Komodo Bakery in Makawao for malasadas and found a little art and stationery store across the street.

We then stopped by the Maui Gold company store and picked up a couple of pineapples, packaged as a carry-on.

We then headed back to Lahaina for the Maui Chocolate Tour (which, thankfully was still operating due to less rain on the west side of the island).

We got to see cacao being farmed, and a guide led us through a tasting of a variety of chocolates made right there on the island.

We did another load of laundry, spent some time at the pool and beach, and visited the Honoapiilani Food Truck Park for dinner.

Related Articles:

• 33 Things to Do on Maui
• How to Plan a Trip to Maui
• How to Have an Authentic Hawaii Experience

Day 11: BIG ISLAND TRANSFER DAY

We left the Ka’anapali Beach Hotel after a beautiful traditional kukui nut lei ceremony and headed to the airport for our flight to Kona.

About 3.5 hours after leaving our hotel, our Southwest flight had landed in the open-air Kona airport right around noon.

We had originally planned to head up to Mauna Kea for a late-night stargazing tour, but we had canceled a couple of days prior when we began to feel “toured out” and the weather forecast on the mountain looked suspect.

So instead, we made our way to our Airbnb in Kailua-Kona and spent a little time at the pool. We explored the touristy shops along the coast and watched an outrigger canoe competition before stopping for dinner overlooking the ocean.

Explore the free Big Island Travel Guide to learn more about the island.

Day 12: BIG ISLAND CIRCLE ISLAND TOUR

The Big Island is BIG, as we learned on our Grand Circle Tour today. A luxury coach picked us up near our condo at 7:30 AM, and for 11 hours we circled the island.

The morning included breakfast at a Kona coffee farm, snacks at Punalu’u Bake Shop, sightseeing at the Punalu’u Black Sand Beach, lunch, and a tasting at the Volcano Winery.

The afternoon included multiple stops in Volcanoes National Park, including overlooking the Kīlauea crater and a walk through the Thurston Lava Tube, and a trip through Hilo and stops at two waterfalls.

Overall, it was a wonderful way to survey the whole island in (relative) luxury, with drinks, snacks, hot and cold scented towels, jackets, umbrellas and plenty of narration along the way.

Dinner, a little souvenir shopping, and repacking suitcases (again!) closed out the night.

Day 13: BIG ISLAND TO HOME

Before our afternoon flight to LA, we drove down the coast to the Pu’uhonua O Honaunau National Historical Park, where we saw a reconstruction of the Place of Refuge.

The park helped illuminate some of what we’d learned about traditional Hawaiian culture in our two weeks on the islands. After a lunch stop for Loco Moco, we headed to the airport to clear Agricultural Inspection and head back to the mainland.

Visiting All the Hawaiian Islands: Things We Learned

Would we do it again? Absolutely! We usually aren’t a go-to-one-place-and-sit-for-vacation kind of family, so a 2-week vacation at a single resort on a single Hawaiian island wasn’t in the cards for us.

We like to do as much as we can and get an overview of the places we visit. So we thoroughly enjoyed all that we could cram into our 13-day trip. But we learned a few things along the way:

1. If you’re going to schedule a whirlwind tour of the islands, be sure to plan a good mix of relaxing and action time. We were actually grateful for a couple of the cancellations that we encountered, as that gave us some much-needed downtime.
2. Be flexible. Although it’s paradise, inclement weather still happens, which can mean choppy seas, challenging air currents, and muddy fields. And while we only had one minor airline hiccup in our 7 flights, we recognize that we were fortunate.
3. If you have a tour or attraction you want to experience, book it early in your stay on that island. That way, if the operator needs to reschedule, you’ll have a better chance of re-booking on a subsequent day in your stay on the island. See for the best local tour operators.
4. Turo rental cars are a great idea in theory, but they had some real challenges in Hawaii. If a car you’ve reserved gets in an accident before you arrive, you may be left without a rental, or at least one that doesn’t match the features or condition of the one you reserved. In addition, most of the Hawaii airports have put significant restrictions on where Turos may be left or picked up, which complicates getting your car. We reserved our Turos months in advance, and the cost savings over rental agencies were significant (about 25-30%). However, we did some spot-checking once we were on the islands and found rental agency rates had dropped significantly, all but erasing the Turo advantage.
5. Although these are laid-back islands, they are also where people live, work, and go to school. Many of the main arteries on some of the islands are still two-lane roads, which can mean traffic jams. While it’s not LA or New York or London or Tokyo, you might still be stuck behind a LONG line of cars going in the same direction as you. So plan ahead and check Google or Apple Maps timing a few days in advance.
6. It is possible to fit in other experiences on an island-hopping travel day if you choose your flights carefully. If you fly Southwest, choose a non-stop flight from island to island. Avoid going through Honolulu, as the layover there will add hours to your trip and effectively waste the day. We found that by reserving early, we could usually get a direct island-to-island flight for $49 or $59. For the Maui to Big Island flight, we chose to fly Hawaiian, as Southwest didn’t have a timely direct flight. See the Island Hopping Guide for more tips.
7. If you fly Southwest (as we did for most of our inter-island flights), know that the planes aren’t usually full. That means that it’s not necessary to pay extra for an early boarding group. This was our experience and we traveled in June, a busy time on the islands.
8. The ubiquitous ABC Stores can be your friend. They stock foodstuffs, cosmetics, various supplies, and souvenirs, and each store is consistently stocked and clean.
9. If you choose to visit the Polynesian Cultural Center on Oahu, the popular ticket to book is the Island Villages experience plus the Ali’i Luau and HA: Breath of Life show. Get there as SOON as the gates open. We ended up missing a couple of attractions since we arrived about an hour after opening. Need help to decide on tickets? See this Ali’i Luau vs Gateway Buffett review.
10. Check sunrise/sunset times relative to where you live. We found the sunrise much earlier than we were used to (and the skies were bright FAR before sunrise), and the sunset was a good bit earlier as well.
11. Clear off memory space on your phone before you travel. You WILL take hundreds, possibly thousands, of photos and videos, and you don’t want to run out of space (like I did in a helicopter above the Na Pali Coast!).
12. If you visit Oahu, make time – at least a day – to visit Pearl Harbor. We visited Oahu briefly a few years ago and saw it then, so we didn’t include it on our itinerary this time. But everyone should see it at least once.
13. As Erica and Jordan stress, plan your trip well in advance – they’ve got a full set of guidelines here. But also, be aware that the sooner you book something, the more likely it is to change. We had one experience change names, another change itinerary, and another change their operating schedule.
14. When flying inter-island, you usually don’t need to endure the airport agricultural inspection. However, when flying to the mainland, you almost certainly WILL have to have your luggage inspected, which takes time. We noticed, especially in Maui, this was by far the longest airport line.
15. Consider paying for TSA Pre-Check. At less than $80, we found it money well spent since we had seven different flights getting to, and around, Hawaii. In some airports, the regular TSA line wasn’t that long, but in others, it was a big time-saver. And not having to take off your belt/coat/shoes, or remove your liquids or laptops, is a huge stress saver when you’re going in and out of that many airports!

Have fun! It’s a vacation, not a competition. Miss something? All the more reason to come back!

Check out Erica and Jordan’s Wayfinder Itineraries to help you plan your trip to Hawaii. The Maui Wayfinder Itinerary was a life-saver on this trip.