The Best Hawaiian Islands to Visit on a 10 Day to Two Week Hawaii Itinerary

Hawaii is a bucket list state for many people. While it may not be one of my top favorite places to visit, spending time in Hawaii is always relaxing. Plan to use this one to two week Hawaii itinerary to plan a fun-filled and relaxing vacation to the islands. 

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History of Hawaii

Hawaii was once an independent nation prior to becoming part of the United States. The earliest setters are believed to be around the year 1000 from Polynesia. The population continued to grow with chiefs in charge of various kingdoms. 

In 1778, James Cook was the first explorer to come to the islands. Throughout the next several hundred years, more explorers came to the islands. During that time, the chiefs of Hawaii continued to fight each other for power. 

On January 17, 1893, the current Queen was overthrown and it became a provisional government ruled by the United States. Throughout the years, more people from various areas migrated to Hawaii. Finally, on August 21, 1959, Hawaii officially became the 50th state of the United States. 

Best Time to Visit Hawaii

Although Hawaii is known for having pleasant weather year-round, I do not recommend spending two weeks in Hawaii in the summertime. This is when the islands are the most crowded and prices are very expensive. You can find better deals if you visit in the fall or spring. Wintertime can be a good time to visit as well but keep in mind the swells are a lot bigger during that time.  

How to Get to Hawaii

Everything about Hawaii can be expensive, but recently, there have been some amazing airfare deals to Hawaii, especially from California and the western United States. Most flights will have a layover along the west coast.

Each of the islands has one main airport, with the exception of the Big Island, which has two. For this two week Hawaii itinerary, you will fly into the Daniel K. Inouye International Airport on Oahu and island hop from there. Interisland flights tend to be pretty affordable. 

GoCity Pass

GoCity offers a ton of different sightseeing passes for cities around the world. These passes allow you to visit the best of each city for one low price, rather than paying individually for each attraction. I have used it in several cities around the world and would recommend getting a GoCity pass! Check out the options for the Ohau GoCity pass here. This is a great way to save money on Oahu!

About This Itinerary

If you only have 10 days to spend in Hawaii, opt to visit Oahu and the Big Island and skip the Maui portion of this itinerary. For a one week Hawaii itinerary, I recommend Oahu and Maui, especially if you can get to Maui using points. If you want a two week Hawaii itinerary, opt to follow the following plan. You can also go to Kauai instead of Maui. 

Day 1: Home to Oahu, Hawaii

Hotel Option: Hale Koa (for Military), Hilton Hawaiian Village, or Holiday Inn Express Waikiki

Today, start your two week Hawaii itinerary by flying into Oahu, the first of the three islands you will visit. Oahu is the most populated and busiest of the Hawaiian islands. However, that does not mean you will not find amazing things to do. 

Your first stop after the airport should be to grab lunch at Zippy’s. This is a Hawaiian fast food place and everything here is delicious. My favorite is the loco moco with the macaroni salad. 

Take it easy today and spend time exploring Honolulu and Waikiki Beach. You can opt to spend some time relaxing on the beach or go on a hike. Diamond Head and Manoa Falls are two of the more popular hikes on the island. If you want a lesser known hike, opt to hike to the Makapupu Tide Pools. 

Tonight, grab dinner at Duke’s a Waikiki staple that offers great views of the sunset. If you want something less crowded and commercial, opt to eat at Momosan Waikiki, which has some of the best ramen on the island. After dinner, head to Waikiki Brewing Company for an after dinner drink or grab a drink at one of the many local bars. 

Day 2: Oahu, Hawaii

Start your second day of this two week Hawaii itinerary with a trip to North Shore. Before hitting the road, grab some yummy Taro donuts from Holey Grail Donuts. Then head to the Dole Plantation. 

The Dole Plantation is known as Hawaii’s Pineapple Experience. It started as a fruit stand and has since grown into a huge farm. At the Dole Plantation, I recommend getting the combo ticket so you can ride the train, visit the gardens, and go through the Pineapple maze. Once you are done experiencing the property, grab a dole whip from the shop before continuing onto North Shore. 

Next, grab lunch at one of the many food trucks located along Highway 83. The shrimp truck is really popular but there are many other options for non-seafood eaters. 

After lunch, head to the gorgeous North Shore beaches. If you are into snorkeling, you will want to stop at Shark’s Cove. There is not much of a beach, but there are several pools perfect for snorkeling for this two week Hawaii itinerary. 

If you are more interested in relaxing on a beach, head to Turtle Bay. This beach is located next to the Turtle Bay Resort. It is nice because there is a ton of parking, and there are bathrooms and a restaurant nearby. Another popular beach is Laniakea Beach because you might be able to catch a glimpse of the sea turtles.

Before heading back to the hotel, make sure to stop at Motsumotos and Aiokis for some of the best shave ice on Oahu. For tonight’s dinner, eat at my personal favorite restaurant on Oahu: Mud Hen Water. This is a small plate restaurant that serves a lot of Hawaiian dishes with a twist and uses local ingredients. 

Day 3: Oahu, Hawaii

Start day three with breakfast at Yogurstory, famous for its Taro pancakes. This place can get pretty popular, so make sure to add your name to the waiting list on Yelp before heading to the restaurant. 

Today, you will spend most of the day enjoying Hanauma Bay. This area was formed by a volcano 32,000 years ago. Now, the area is perfect for snorkeling with views of coral, basalt, and tons of fish. There is an on-site place for snacks or you can bring your own food. They also have the equipment you can rent if you do not bring your own. 

After spending however much time you would like at Hanauma Bay, head back to Waikiki to wander around the area or spend more time relaxing at the beaches. 

If you want a fancier place to eat for dinner, head to Roy’s, which is known for its Hawaiian infusion food. You will not be sorry if you dine here as part of your two week Hawaii itinerary. 

Day 4: Oahu, Hawaii

As part of a two week Hawaii itinerary, you MUST get malasadas at some point.  A Malasada is Portuguese fried dough. The traditional ones are served with sugar but are often filled with fruity creams or chocolates. This morning, grab some from Leonard’s Bakery. 

Next, head out to Kualoa Ranch, a 400-acre preserve on the eastern end of Oahu that contains three valleys. It is a popular filming location and offers a variety of tours that take you around the preserve. You can opt to do a multitude of activities, but I recommend the Raptor Tour. This tour takes you all around the preserve in multi-person ATVs that your group gets to drive.

After you finish your adventures at Kualoa Ranch, head to the Ho’omaluhia Botanical Gardens. This is a free alternative to Kualoa Ranch which offers picturesque spots and 400-acres of gorgeous scenery. 

Finally, stop at the Halona Blowhole, a rock formation that contains a large blowhole. It has a really cool lookout. You can even relax at the beach right next door or head to some of the beaches on the eastern side of the island like Kualoa Rock Beach or Lanikai Beach. 

Tonight, grab dinner at Quiora, a high-end Italian restaurant that offers an awesome view of the area. Make sure to make a reservation, especially if you want to go at sunset. It is the perfect way to end the Oahu portion of your two week Hawaii itinerary.

Day 5: Oahu, Hawaii to Maui, Hawaii

For your last day on Oahu, first, grab breakfast at Basalt Waikiki Restaurant. They have the most delicious charcoal pancakes and other fun eats. Make sure to make a reservation online. 

Today, spend the day exploring the Pearl Harbor Sites. If you are not interested in exploring all of them, you can always just do the memorial and then head back to the beach or to the Ko Olina beaches. 

The USS Arizona Memorial is the must-visit of the Pearl Harbor Sites. You will want to reserve tickets ahead of time online. Boats leave every 30 minutes and once at the memorial, you get 10 minutes to view the site. 

The other Pearl Harbor Sites include the USS Bowfin Submarine Museum and Park, the USS Oklahoma Memorial, the Battleship Missouri Memorial, and the Pacific Aviation Museum. You can easily spend the entire day at these sites. If you choose to see them all, make sure to get the  Passport to Pearl Harbor ticket that covers admission to all of them. 

After spending time at Pearl Harbor, grab dinner at Himalayan Kitchen, a delicious Indian food restaurant. The dishes are pretty big so plan on sharing them with the table. You could also go eat at Hana Koa Brewing Co if you want something more laid back with good cocktails. 

It is up to you if you want to fly to Maui tonight or wait until the next morning. I recommend trying to catch a flight tonight so you have a full day in Maui tomorrow as part of your two week Hawaii itinerary.

Day 6: Maui, Hawaii

Hotel Option: AC Hotel by Marriott or Westin Kaanapali

Start your first day off in Maui with take some time to check into your resort and get acquainted with Maui. There are a ton of awesome beaches all around the island. If you prefer, you can opt to drive the Road to Hana today instead. 

If you choose to have a chill day, make sure to grab a shave ice from Ululani’s. In my opinion, it is the best shave ice on all of the Hawaiian islands. 

When you get hungry, grab lunch at Pita Paradise or Da Kitchen. Both have delicious meal options and make for easy lunches you can take with you to eat on the beach. 

This afternoon, stop at Esters Fair Project for some tropical cocktails and get out of the sun for a bit. Tonight, eat dinner at 5 Palms for great sunset views. They also have yummy food and cocktails. Get to bed early to be ready for tomorrow’s adventure to Haleakala. 

Day 7: Maui, Hawaii

Today, head to Haleakala National Park to watch the sunrise. It is something you must do on your two week Hawaii itinerary and worth getting up early. You will need to book a reservation ahead of time online. I recommend getting there by 5am to stake out a spot. 

Next, hike the Keonehe‘ehe‘e (Sliding Sands) Trail. This trail takes hikers down into the crater of the volcano and offers amazing views of the area. Plan on hiking about 2 miles of it before turning around. 

After you are done hiking, stop at the Leleiwi Overlook for even more views of Haleakala National Park. Then, head to Hosmer Grove to do one last short hike through a non-native forest. This forest is full of different trees that were brought from other places to see what could grow on the islands. 

Once you are hungry, head to Restaurant Marlow for some delicious pizza and salad options. If you want a drink when you are done, head next door to Mahalo Aleworks for some delicious beers. 

If you have any extra time, you can always opt to relax on the beach or at your resort for the rest of the evening. 

Day 8: Maui, Hawaii to Big Island, Hawaii

For the start of your second week of this two week Hawaii itinerary, head out on a snorkel tour to Molokini Crater. I highly recommend the Pacific Whale Foundation. They are a non-profit organization that helps protect and research whales. They offer several types of tours as well if snorkeling is not your thing.  If you want cheaper options that do not include as many things, Viator and Get Your Guide have some other options.

We booked the Molokini and Turtle Arches Snorkel Tour. It included all equipment, breakfast, lunch, and a large staff. The staff is very knowledgeable and also acts as lifeguards. The first stop of the tour is at the Molokini Crater which has some of the best snorkeling on the island. After about an hour, you will head to a second location to try and spot some sea turtles. 

Once you finish with the snorkel tour, head up along the western coast of Maui for a drive.  Whalers Village is a fun place to stop with many shops and restaurants. If you are hungry or want a drink make sure to stop at MonkeyPod Kitchen. They have some of the best Mai Thais on the island. 

At the McGregor Point Lighthouse, you can catch fabulous views of the islands of Lanai and Kaho’olawe. After spending some time along the western coast of Maui and then head back to your resort and get ready for your next day in paradise. 

It is up to you if you want to fly to the Big Island tonight or wait until the next morning. 

Day 9: Big Island, Hawaii

Hotel Option: Hilton Waikaloa Village, Holiday Inn Express Kailua-Kona, or Airbnb in Hilo

Spend the last part of your two week Hawaii itinerary exploring the Big Island of Hawaii. On the first day, opt to spend it exploring the Kona area. Grab breakfast at the Coffee Shack which offers impressive views of the western side of the island. They have delicious coffee drinks and bakery items as well as lots of food choices. 

Next, head to Pu’uhonua O Honaunau National Historical Park, a park that preserves the landing sites where Hawaiians who broke ancient laws would flee to. There is a self-guided trail to follow past various important sites around the park. It will take you about an hour to walk through the park. 

Afterward, head to Two-Step, a natural preserve located on the western part of the Big Island. It is a great place for snorkeling and scuba diving that offers impressive coral reefs. If you are lucky you might even catch a dolphin swimming around. Two-Step should be on any snorkel-lovers two week Hawaii itinerary. 

There are other small beaches you can head to in the Kona area or you can spend some time walking around town. Make sure to stop for shave ice at Scandanavian Shave Ice, the best shave ice on the island. 

This evening, grab dinner at Foster’s Kitchen, the perfect place to watch the sunset. Both the food and cocktails are delicious. If you want an after-dinner drink, head to Don’s Mai Tai Bar and Restaurant where they have a ton of different Mai Tais for you to try!

Day 10: Big Island, Hawaii

For the second day on the Big Island for this two week Hawaii itinerary, head to Hawaii Volcanoes National Park. This park contains two active volcanoes and an impressive volcanic landscape. Make sure to check-in at the Visitor’s Center first as some parts of the park may be closed due to volcanic activity. 

First, stop at the Thurston Lava Tube. This 1.5-mile hike takes you to a 500-year-old lava tube. Once you complete this hike, you can add on the Kilauea Iki Hike. This hike is a bit more strenuous but totally worth it to hike across the crater of an inactive volcano. 

Spend the afternoon driving the Chain of Craters Road. This 18.8-mile road takes you out to the coast with awesome views overlooking the ocean. There are multiple stops you can make along the way. Lava once flowed where the road now stands, thus creating a very distinct landscape. I highly recommend taking it all the way out to the Holei Sea Arch. 

Day 11: Big Island, Hawaii

For your third day on the Big Island, opt to spend it visiting the southern part of the island. First, stop at the Punalu’u Bake Shop, the Southernmost Bakery in the United States. Everything is baked fresh daily, so you want to make sure to get there early before the best flavors run out.  I recommend grabbing several Malasada which is kind of like a donut with cinnamon sugar. 

Next, head to South Point, the actual spot of the Southernmost part of the United States. You may have thought it was in Key West, but that is the Southernmost part of the Continental United States. At South Point, you have the option to jump into the water, but make sure to check the currents first. 

After visiting South Point, head to Papakolea Green Sand Beach, known for having unique green sand. You can opt to hike out there, but I recommend hiring a local driver as it is a 3-mile hike each way. Papakolea Green Sand Beach is very remote, so there are no restrooms or other facilities out there. Make sure to wear a lot of sunscreen, and your swimsuit, and bring food with you. 

End the day with a visit to Punalu’u Beach, a gorgeous black sand beach on the southern part of the island. You may even see sea turtles there. It is the perfect way to end the this day of this two week Hawaii itinerary.

Day 12: Big Island, Hawaii

Today, head up to Mauna Kea, one of the volcanoes on the island. You will have some awesome views of the island and the possibility of snow if you visit during the winter months. Mauna Kea is over one million year old and sits at 13803 feet above sea level.

On the way up to Mauna Kea, complete the Pu’u Huluhulu Hike to help acclimate to the altitude. It is a short hike up a hill where you are, you are rewarded with a view of the surrounding volcanic area. 

After completing the short hike head up to the visitor’s center at 9200 feet and stop to acclimate further. Once you reach the top, you will be able to take in the views of the area and this is where the snow will be if it is wintertime. 

This afternoon of your two week Hawaii itinerary, spend time relaxing at the beach or your resort.

Day 13: Big Island, Hawaii

For your final day of this two week Hawaii itinerary, head to Pololu Valley. This is the northernmost of the Valleys along the Kohola Mountain and it offers spectacular views. You can opt to visit the lookout, but it is well worth the 0.6-mile hike into the valley. The trail is a bit rocky, but not too strenuous. 

Once at the bottom, there is a cool forest with hiking trails and a black sand beach. The area has a ton of rope swings that are fun to play on and make for some great pictures. 

After visiting Pololu Valley, head along Highway 250 from Kapauu to Waimea for scenic views through the area. Along the way, stop at Village Burger Kamuela for lunch. They have really fun burger options and sauces for their fries. 

If you want to try out more malasadas, you can stop at the Manuela Malasada Co.

Day 14: Big Island to Home

Today, depart Hawaii for home. If you have a later flight out tonight, you can opt to explore other areas of the Big Island such as Hilo or Waipio Valley. 

Waipio Valley was once home to the Hawaiian Kings and was densely populated. Now, it is a secluded valley with gorgeous beaches and taro farms. It is a very strenuous 0.6-mile hike to get down into the valley, so I recommend hiring a driver. 

If you opt to spend time in Hilo, you can visit the Kaumana Caves, a tropical park that descends into a massive 1881 lava tube cave. Next, head to Wailuku River State Park, where you can see Rainbow Falls. If you want to see sea turtles, head to Richardson Ocean Park or Carlsmith Beach Park. 

Other things to do in the Hilo area include the Hawaii Tropical Bioreserve and Garden, and the Mauna Loa Macadamia Nut Visitor’s Center. It also has some really awesome places to eat. Hilo is a fun stop on a two week Hawaii itinerary.

Shaka Guide

Shaka Guide is a GPS self-guided audio tour that you can download to your phone. Currently, they have one for each of the Hawaiian islands. They provide great background information about the area. The best part is you do not need the internet to use them. Click below for the Shaka Guide for each island. 

Final Thoughts on Two Week Hawaii Itinerary

If you have more time, add on a few days in Kauai or more time on any of the islands. There are a ton of Hawaii road trips you can take on all of the islands. Hawaii is also an easy pit stop when heading to Japan or New Zealand. 

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