Oahu & Kauai, Hawaii

Katie Oliver
Nov 13, 2019
8 min read

Updated: Feb 5

October 2019

Aloha!! We are so lucky to have gone to Hawaii for our 1 year wedding anniversary. It was BEAUTIFUL! We chose to split our time between the islands of Oahu and Kauai. Oahu is home to Honolulu, the capitol of Hawaii, as well as other famous sites including Waikiki, Pearl Harbor, and Bonzai Pipeline. Kauai, also known as the garden isle, is one of the oldest islands in Hawaii and is sprawling with lush greenery. It is also known for some great hiking in Waimea canyon (the grand canyon of the Pacific) and along the Napali Coast.

Tom and I filled our trip with snorkeling, hiking, scuba diving, and lots of good poke & sushi! We will give you all of our recommendations for the best food, beaches for turtle encounters, hikes, etc that we came across and the best times to do things while you're there.

Check out our other pages for our FULL itinerary & highlight video!

Oahu, HI

The Best Eats

Haleiwa Joes: Our favorite meal all trip! Recommended to us by a local

Maguro Spot: Best poke I've ever had

Kokonuts Shave Ice: Best shave ice all trip

Tiki's Grill & Bar: great happy hour beachfront at Waikiki

Beachhouse at the Moana: our fancy celebratory anniversary dinner

Must Do, Must See

Waikiki: beach, shopping area, rental bikes (Biki)

Pearl Harbor: We got there when it opened to get tickets for the USS Arizona Memorial before they sold out. You can also reserve tickets in advance. We bought tickets for tours of USS Arizona Memorial & USS Missouri and also utilized the free museums. For us, the $75 passport that included Aviation Museum and the USS Bowfin Submarine were not necessary. We were busy there from about 7:30am to just past noon.
Dole Pineapple Plantation: World's largest maze, train tour of pineapple fields, demonstration on picking and cutting a pineapple
Surf Lessons: Hans Hedemann Surf School - reasonably priced 1 hour group lesson on Waikiki. Even went back later in our trip to rent a board!
Scuba Dive: Sea Tiger wreck dive and reef dive with sea turtles with Living Ocean Scuba

Favorite Hikes

Ka'au Crater Rim (7.3 miles, heavily trafficked, hard difficulty): this was our favorite hike! Very challenging! Three water falls, rock climbing, scaling the rim of the crater with steep edges. Perfect for thrill-seekers!
Diamond Head (1.8 miles, heavily trafficked, easy difficulty): this beautifully monstrous landmark paints the background of Waikiki. The first US military base on Hawaii, Diamond head is full of history, and finishes with beautiful views of Honolulu. This adventure is accommodating to a wide variety of people - we saw kids around the age of 6 all the way up to grandparents around the age of 75. If you're not an avid hiker, this may be a good option to get your steps in and enjoy the great outdoors. We chose to go around 3pm - this allowed for less crowd (its very busy early in the morning as people try to catch sunrise) but did result in increased heat.
Stairway to Heaven (3 miles, 4,000 steps, heavily trafficked, hard difficulty): illegal, subject to $1,000 fine - if you get caught. See below for tips & tricks on this once-in-a-lifetime experience

Lanikai Pillboxes (1.8 miles, heavily trafficked, moderate difficulty): the first 5 minutes of the hike are the most brutal! Stick with it, the views are soooo worth it! We packed a lunch to enjoy at the second set of pillboxes. Refresh afterwards at Lanikai Beach!
Koko Head (1.8 miles, 1,050 steps, heavily trafficked, hard difficulty): this is an old railroad track that climbs the side of Koko Crater that has now become a torture device for tourists and locals alike! As you climb, step-by-step, your thighs and lungs burn in synchrony! It was a very daunting but rewarding experience. It will take you 30 minutes to 1 hour+ to get to the top depending on your fitness level. Bring water and don't be afraid to step to the side and catch your breath - everyone does it!

Olomana Ridge (4.4 miles, heavily trafficked, hard difficulty): we parked off Maunawili Rd just before it meets with Auloa Rd. Nearly the first half of the hike is walking to the trail head from your vehicle. You have to follow the road towards the private golf club - you will walk right past a guard station but they don't stop you if you are on foot. The trail head will be on your left and is marked by signs. The trail itself is step and you quickly meet a steep ridge line - proceed with caution. Most people go to the first peak where the view is the best, and then turn back. We ventured on to the second peak which was slightly more challenging, but did not advance to the third peak. The third and final peak is the most dangerous and has taken numerous lives. Please be careful! The view from the first peak are beautiful and totally worth the climb!

Best Beaches

Queen's Beach: beginners surfing
Haunuma Bay: best snorkeling overall, wildlife preserve, sea turtles
Sunset Beach: huge waves (Bonzai Pipeline) in the "winter" season
Lanikai Beach
Sharks Cove: large tide pool to swim & snorkel

**Most of our days consisted of an early hike in the morning and an afternoon snorkel & nap on the beach! The time change from Houston had us up early anyways and this enabled us to get an early start and have a lot of the hikes & waterfalls to ourselves.

Tips & Tricks

Transportation: rental car is recommended - we saw others that used buses which get you most places, Uber is also available as an option.
Hiking: we used the app "All Trails" for all of our hiking information, details, and maps. Sign up for a free account! Also, all of our trails were VERY muddy - hiking shoes would be great for traction however you will ruin them with the red clay mud. We hiked in croc tennis shoes that were ok to get wet and the mud would wash right off. Please also take lots of water and snacks with you! For some hikes, both Tom and I had our own camel backs for water.

Stairway to Heaven: illegal - security is always at the base of the stairs but can be avoided. The neighborhood at the trail-head is occasionally patrolled by police. This map shows you three possible routes to get to the trail-head. We were told by a local living in the neighborhood that the best time to do the hike is shortly after 9am through option 1 - the main gate. The gate is open for the private school and the morning school traffic is done. We went through the gate at option 1 and hugged the left side of the road until we saw the first sign of a trail. The trail opening is on the left, directly across from a little shack. We then followed the path to where it merged with the green path and then on to the bamboo forest. This path can be tricky as it is lightly traveled, but there are pink tags (trail markers) every so often. Early on, you will come across a fence that is pressed down by the help of some big fallen trees - cross the fence line there and continue to follow the pink tags. The police are mostly trying to prevent people from attempting this hike in the dark. It is dangerous and you do have to navigate through a bamboo forest on a lightly traveled trail to get by the security guard, but it is 100% doable and totally worth it!
Sunscreen: Hawaii has passed laws requiring reef-safe sunscreen! We bought ours from Costco in Honolulu
Accommodations: We stayed at mostly Airbnbs on Oahu. Spent a few nights in Waikiki, drove up to the north shore & stayed one night there, then back to Waikiki! We preferred Airbnbs here as the hotels can get really expensive in this area, however you may be able to find a deal. We stayed a few blocks off the beach and chose to walk around Waikiki most days due to limited & expensive parking. The hotels typically ran $200+/night and most of our Airbnbs were $80-$150/night.