Two Week Itinerary And Tips for the Hawaiian Islands: Kauai, The Big Island And Oahu

Named as the 50th state of the USA, Hawaii is a chain of islands located in the Pacific Ocean 3000 kilometres from the mainland. With lush green landscapes, hidden waterfalls and beautiful beaches, Hawaii is any travellers dream.

From romantic resorts for honeymooners to family friendly hotels and backpacker hostels here is my guide and suggested itinerary for a two week vacation in Hawaii, covering three of the main islands. It gives the perfect combination or adrenaline, outdoor and water activities, geological wonders and relaxing on the beach.

Days 1-4 Kauai

Appropriately nicknamed ‘The Garden Island’ Kauai offers rugged emerald cliffs, lush waterfalls and much more. It is the northernmost island in Hawaii and most people love it because it has less of a tourist crowd. I actually felt like I was driving through a real life set of Jurassic Park and loved how unique the landscape is.

Getting there and getting around

Domestic Flights on Hawaiian airlines take 35 minutes from Honolulu (Oahu) to Lihue airport and operate a regular intervals each day. You can expect to pay between $80 and $160 USD return.

You will definitely need a car on this island and not to worry, driving is very easy even if you don’t normally drive on the right hand side of the road.

Things to See and Do

• Napali Coast. This is rugged and pristine terrain and it was just magical to see the glistening blue of the waters against the lush jungle greens of the cliffs. The best way to experience it is a snorkelling day trip.
• Hiking. There are endless opportunities for hiking on this island. To start off with try the two mile ‘Sleeping Giant Trail Head’.
• Waimea Canyon (This is Hawaii’s greener and smaller version of ‘The Grand Canyon’ and is breathtaking). Spend a few hours taking a hike and disconnecting. The view from the lookout is fabulous.
• Soak up the ‘cocktail by the pool’ life at a resort that is quieter and less crowded than on Oahu.
• Swim and Snorkel. If you are lucky you could even see turtles in the water beside you. Try your luck at Poipu beach.
• Chase waterfalls. Kauai has some real gems when it comes to waterfalls. Some you can drive to and check out from the viewing point, others you can swim in 🙂
• Kauai Coffee Plantation. If you are a coffee lover you will enjoy taking a walk through the plantation and tasting the variety of coffees, with the option to purchase before you leave.

Where to Stay

• Honu’ea International Hostel $
• The Kauai Inn or Kauai Shores Hotel $$
• Kauai Beach Resort $$ – $$$
• Kauai Marriot Resort $$$

Days 5-8 The Big Island

Otherwise known as Island of Hawaii, The Big Island is known for its volcanoes and amazing stargazing. In my opinion, no trip to Hawaii is complete without a few days over on The Big Island.

Getting there and getting around

Domestic Flights on Hawaiian airlines from Honolulu (Oahu) operate regularly each day to both airports on the island (Kona and Hilo). These usually take between 45 minutes and an hour and you can expect to pay $80-$180 USD return.

Much like Kauai, to explore the best this island has to offer you will definitely need a car.

Things to See and Do

• Hawaii Volcanoes National Park. You can drive through and make scenic stops along the way. If your budget allows I highly recommend taking a helicopter tour so you can see the volcanoes from the sky and get a glimpse of the lava flowing into the ocean.
• Black Sand beaches. This is such a cool experience to be on a beach where the sand comprises of volcanic material. Check out Punalu’u Beach. Make sure you have a good pair of thongs (flip flops for all non-Aussies) because the sand was pretty HOT on our feet!
• Green Sand beach (Papakolea). This is super cool, but not as easy to reach, however, still very doable. You will need to drive and then take a short hike. More information and directions can be found HERE
• White sand beaches. Hawaii is home to some fabulous ones. Check out a few suggestions HERE.
• Mauna Kea (Tallest mountain in the world– if you count the part of it that is under water as well as above). Go up to the Observatory for amazing stargazing !!!! It is honestly like nothing you will ever see with your naked eye back at home. There is a program that is run at the Visitor centre starting at 6pm…but at the time of writing this it is currently closed. Here is the link to their site. Perhaps contact them and see what the options are? Due to the altitude you may not be able to go in Winter (January). If you are travelling with kids I would double check the minimum age a child is permitted to go up to an altitude of 14,000 feet.
• Go hiking. The Big Island has some great landscape and trails to make the most of. Another blogger (The Lovely Escapist) visited earlier this year and wrote a great post on the Waipio Valley Hike which looks stunning and is definitely on my list when I take my next trip back to Hawaii.
• Ka Lae (The Southern most point of the USA). Sometimes the super crazy even jump off here if conditions allow it. But the cliffs are cool and the drive to get there is pretty relaxing and agricultural.

Where to stay

Your two main options are Hilo or Kona (more formally known as Kailua-Kona).  Hilo is cheaper to fly into and has more of a walkable ‘downtown’ area. Kona has the better and more popular beaches. 

• The Big Island Hostel $ (Hilo)
• Kona Seaside Hotel $$
• Lai Nani Oceanfront Estate Bungalow $$$ (20 minute drive north of Hilo).
• Sheraton Kona Resort and Spa $$$

Days 9-14 Oahu

The most visited of the Hawaiian islands, Oahu is famous for being home to the State Capital Honolulu, world class surf breaks and, of course, Pearl Harbour. Oahu offers an excellent range of resorts and shopping opportunities as well as the chance to get ‘back to nature’ once you drive a few miles out of the city.

Getting there and getting around

Honolulu is an international airport with direct flights arriving from a range of cities in Asia, Australia and the US mainland. You can also reach Honolulu from any of the other Hawaiian islands via quick and frequent domestic flights.

You could get away with having no car for a couple of days to save a bit of money if you plan to spend a fair bit of time around Waikiki, but to access the North Shore and have more flexibility, once again a car would be preferable. However, many of the day tours you can book include transport to and from your hotel.

Things to See and Do

• Pearl Harbour. Now, if you go to Hawaii and come back without visiting Pearl Harbour, then I don’t think we can be friends. Well ok, we still can, but I must emphasise how much of a MUST this is.
• Kualoa Ranch. This is by far the number one attraction on the Island for movie buffs and Jurassic Park fans. The landscape that is a part of this ranch was used to film several movies, TV shows and select scenes including Jurassic Park, Pearl Harbour, 50 First Dates, Lost, Magnum P.I. and Hawaii Five-O. I highly recommend the movie sites tour and also the ATV (quad biking). I suggest booking these as seperate back to back activities as this seems to be a little cheaper than the combined packages. You can do this through Viator or directly on the ranch website. There is also a wide range of activities for outdoor enthusiasts such as kayaking and ziplining.
• North Shore surf beaches
• Grab an acai bowl or smoothie from the Sunrise Shack. They also serve awesome organic foods, fresh juices and coffee. The Waikiki one also has ‘lunchable’ items like wraps, salads and sandwiches.
• Attend a Luau. This is such a unique cultural experience. I can recommend ‘Chiefs Luau’.
• Treat yourself by spending a few hours shopping at the Waikele Premium outlets.
• Pineapple Plantation. A cool idea if you have kids and the fresh pineapple juice is sensational.
• Skydive over the north shore if you are feeling super brave or daring.
• Beach activities... Swimming, Stand Up Paddle boarding (SUP) and Surfing lessons.

Where to Stay

• Polynesian Hostel Beach Club $
• Hilton Garden Inn $$
• Outrigger Reef Waikiki Beach Resort/ Moana Surfrider/ Sheraton Waikiki $$$
• Halekulani Hotel or The Royal Hawaiian $$$$

If you would like to add another island to your Hawaiian adventure and are looking for a romantic vibe, then I recommend a couple of days on Maui. If you do make it to Maui, make sure you take a cheeky road trip on the ‘road to Hana’.

Hawaii is one of the most amazing destinations I have been to for beautiful physical landscapes, but it doesn’t come with a cheap price tag, especially for solo backpackers. Despite that, it is definitely worth it!

So when are you booking that ticket? I promise you won’t regret it!