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A 10 Day Hawaii Itinerary

9 Day hawaii itinerary

Over the past 18 months, we have had the pleasure of visiting America’s beautiful chain of islands in the Pacific twice. On the first trip we spent 5 days on Hawaii and 3 days on Oahu, and on the second trip, we spent 5 days on Maui and 4 days on Kauai. It would be really hard to see all four of these beautiful islands on one 10 day trip, so this post will cover a 10 day Hawaii itinerary for the Big Island (Hawaii) and Oahu, just like our first trip.

Getting a Cheap Flight to Hawaii

9 Day hawaii itinerary

One of the reasons we were able to visit Hawaii twice in the past 18 months is due to increased competition to the islands between all of the US’s major airlines. We have seen flight deals as low as $220 round trip from the west coast to Hawaii and fares as low as $400 from major east coast markets to Hawaii. With Southwest Airlines launching flights to Hawaii, I’d expect fares to continue to stay lower for the foreseeable future, so start practicing your hula and get ready to visit paradise! While all of the major airlines fly to the Big Island, Maui, Oahu, and Kauai, I’ve noticed the cheapest flights to Hawaii have been into Honolulu. You can search for flights to Honolulu here or to the big island here.

We jumped on a deal from San Jose since we planned on visiting Mallory’s sister and checking out Monterey and Big Sur after our trip to Hawaii.

Our 5-Day Big Island Itinerary

For the first 5 days of our Hawaii adventure, we stayed on the big island. Personally, we think the big island is the best island to visit in Hawaii. There were fewer crowds, there is a ton of stuff to do, and there is nowhere else in the world that has more of the world’s biospheres in one place. The big island is also the only island with recent volcanic activity, so if you want to see a live volcano up close and personal make sure the big island is on your Hawaii itinerary.

Best activities for your Hawaii Itinerary

Scuba Dive with Manta Rays

9 day hawaii intinerary manta ray

Without a doubt, the coolest experience we had during either of our trips to Hawaii was a night dive with manta rays. Every night these gentle giants come into Keahou Bay just off the coast of the Sheraton Kona Resort. The water is warm and shallow, so you’ll have nearly an hour of bottom time to take in the beauty of these magical creatures that come to the bay to eat plankton. If you are scuba certified you must add this to your Hawaii itinerary, but even if you aren’t, there are several options to snorkel with the manta rays in Kona.

Climb an Active Volcano

9 day hawaii intinerary
Colorful panoramic view of volcanic cones from the peak of the Haleakala Crater

Unfortunately, while we were on the big island Kilauea was very active causing the closure of Volcanoes National Park making it impossible for me to climb an active volcano. The big island does have two other large volcanoes, Mauna Loa, and Mauna Kea, which is the highest point in the Hawaiian Islands, but unfortunately, we didn’t have time to make it all the way to the top. In the winter months, it’s not uncommon for there to be snow at the tops of Mauna Loa and Mauna Kea making Hawaii one of the only places you could ski in the morning and surf in the afternoon!

Get an Aerial View of the Island

Hawaii is famous for its helicopter tourism. Dozens of companies will take up around the island and find a remote waterfall to land by and snap some shots. After our helicopter trip got canceled in South Africa, I have been itching to get in the air somewhere else. You can check prices for a Big Island helicopter tour here.


9 day Hawaii Itinerary
Observatories on top of Mauna Kea mountain peak. Astronomical research facilities and large telescope observatories located at the summit of Mauna Kea on the Big Island of Hawaii, United States

Because of the height of Mauna Kea, it is a great place to catch a glimpse of a dark night sky! It is of course home to a number of independent astronomical observatories because of the view. You can drive up to do some stargazing by yourself, or check out this highly recommended tour that takes you to a Kona Coffee farm for a Hawaiian BBQ dinner before heading up the mountain to catch a glimpse of the stars and dark night sky.

Relaxing Poolside/Beachside

There are so many exciting activities available on the big island, but make sure you take at least a day to just relax by the pool and/or beach in the warm Hawaiian sun. The western coast of the Big Island is where you will find most of the luxury resorts it is also the driest portion of the island where you can count on sun most days.

Where to Stay on the Big Island

While you will find some smaller hotels and resorts on the east coast of the Big Island near Hilo, or in the north near Waimea the majority of hotels and resorts are on the Kona Coast. Below are some of the highest-rated hotels to complete to your big island itinerary.

The Four Seasons Hualalai

Mallory on the balcony of our room at the Four Seasons Hualalai

Ranked by U.S. News as the top resort in the USA in 2019, the Four Seasons Hualalai is about 30 minutes north of the Kailua-Kona Airport. We have stay a lot of amazing places in all of our travels around the world, but there is something really special about Hualalai. You can read my full review of this beautiful resort here. Book your stay in paradise now!

Sheraton Kona Resort

Just to the south of Kona International Airport tucked away in a little bay is the Sheraton Kona Resort. Directly offshore from the resort is where hundreds of snorkelers and scuba divers gather each night for a chance to swim with the manta rays. Now part of Marriott’s Bonvoy program you can check prices or even use your Marriott points to score a night at this lovely 4-star resort.

Hilton Waikoloa Village

Another option on the sunny Kona coast is the Hilton Waikoloa Village. With more than 60 acres directly on the Pacific Ocean you won’t find many properties that have better views on the island. The Hilton has 14 bars and restaurants and 3 pools, so five days might not be enough time to enjoy this beautiful resort. You can check prices for the Hilton Waikoloa Village or book using Hilton HHonors points.

Waikoloa Beach Marriott Resort

The final resort that I’ll recommend for your big island Hawaii itinerary is the Waikoloa Beach Marriott Resort. Located directly adjacent to the Hilton, the Marriott also features three pools, direct access to white-sand beaches, and two championship golf courses. Check prices for the Waikoloa Beach Marriott or book with your Marriott points here.

Our 3 Day Oahu Itinerary

The South Coast of Oahu

After an amazing few days on the Big Island, you can take an easy 30-minute flight from Kona to Honolulu. When you arrive at Daniel K Inouye International Airport in Honolulu you are just minutes from the popular area of Waikiki Beach where you will find most of the popular resorts on the island. Honolulu is a legitimate big city in the middle of the Pacific Ocean, so don’t be surprised when you run into traffic jams during rush hour.

Where to Stay on Oahu

Figuring out where to stay on Oahu is probably the most important part of finalizing your Oahu Itinerary. For the most part, you can divide the island into three sections. Waikiki Beach where you’ll find major resorts and lots of shopping, Ko Olina on the Southwest side of the Island where you find some luxury resorts including Disney’s Aulani Resort, and the North Shore, paradise for surfers and home to the world-famous Pipeline Masters surf competition where the best surfers in the world compete to take home the title of world champion. Below you’ll find a couple of suggestions of where to stay on Oahu for each area.

Where to Stay on Waikiki Beach

We stayed at a lovely resort called The Moana Surfrider Resort in the heart of Waikiki Beach. The Moana Surfrider is a historic hotel part of Marriott’s Westin Resorts portfolio, so you’ll be able to book this resort using Marriott Bonvoy points. Centrally located in Waikiki you are steps from some of the best restaurants and shopping in Hawaii. Book your stay at the Moana Surfrider Resort now!

Another option is the Royal Hawaiian Resort. This instantly recognizable pink resort is right next door to the Moana Surfrider in the heart of Waikiki Beach. It features award-winning restaurants and is home to Waikiki’s only ocean front luau. Check availability and prices for the Royal Hawaiian Resort.

Where to Stay on the North Shore of Oahu

If you want to escape the congestion and craziness of Waikiki, head north to the North Shore of Oahu for a much more relaxed vibe. The highest-rated north shore resort is Turtle Bay Resort. With 7 bars and restaurants, two championship golf courses, and endless activities, you won’t want to leave Turtle Bay Resort. Check prices and book here.

Other Oahu Resorts to Consider

Image Credit Horan, Christian/ Four Seasons

The last area I mentioned above is Ko Olina on the southwest portion of Oahu. Ko Olina is home to two incredible looking resorts, Disney’s Aulani property and the Four Seasons Resort Oahu at Ko Olina. Disney’s Aulani Resort is perfect for families with young children traveling to Hawaii. Aulani brings the magic of Disney to the Hawaiian Islands with character experiences, shows and entertainment, and a complimentary kids club. Check prices and availability for Disney’s Aulani Resort.

If your looking for the most luxurious place to stay on Oahu, look no further than The Four Seasons Resort Oahu at Ko Olina. U.S. News ranked the Four Seasons Oahu as the 43rd best resort in the US. This gorgeous resort on Oahu’s southwest coast is the perfect place to unwind and relax. Check availability prices for your Oahu Itinerary here.

Things to do in Oahu to add to your Oahu Itinerary

Hike up to the Haiku Stairs or Stairway to Heaven Oahu

At the top of the stairs is one hell of a viewpoint, but taking the entire haiku ladder is currently illegal as parts of the pathway have fallen into disrepair. Luckily, according to our friends at Elite Jetsetter, there is a legal way to get to the top of the stairs that can be weather dependent, so pray for good weather!

Take a Surfing Lesson at Waikiki Beach

Being in the birthplace of surfing, no Hawaii itinerary would be complete without trying to catch a wave or two. What better way to spend an afternoon than learning how to surf! Even if you’ve never tried surfing, Waikiki Beach is known as one of the best places in the world to learn how to surf thanks to the long rolling waves in its protected bay. Book your private surf lesson here.

Find a Waterfall

picturesque bali locations
Tibumana Waterfall in Bali usually doesn’t flow quite this strong and you can get behind it, but because of all the rain there were some mudslides so no one was allowed behind it

I just spent the last fifteen minutes reading (looking at pictures) a couple of blog posts about Oahu’s waterfalls, now I’m convinced that we need to make it to one while we are there because they all look beautiful!

Visit the Pearl Harbor Memorial

While I encourage you to try all of the fun activities on both your Hawaii itinerary and Oahu itinerary, no trip to Honolulu is complete without visiting a more somber site in Oahu’s history, the Pearl Harbor Memorial. We spent an afternoon at the Pearl Harbor and USS Arizona Memorial and it definitely left us a bit sad, but appreciative for those who lost their lives serving our country during World War II.

The End of Our 10 Day Hawaii Itinerary

Including travel, we were in Hawaii for about 10 days. It’s easy to fall in love with this little chain of islands in the middle of the Pacific Ocean. Like I said above we returned to Hawaii less 8 months after our first trip to check out Maui and Kauai. If the prices for flights to Hawaii continue to stay low you can guarantee that we will be back in the land of Hula sooner rather than later. Have you visited the Big Island or Oahu? I’d love to hear about your experience in the comments below!

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From the Big Island to Oahu- This is a perfect 9 day Hawaii Itinerary for the dream trip you've always wanted to take. Full of Activities, what to see, and cultural experiences this Hawaii Itinerary checks all the boxes.


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