Ready for a tropical adventure with a little bit of island hopping between Oahu and the Big Island of Hawaii?
Last updated: February 21, 2025
Time for Hawaii Island Hopping
When the ocean took a summer break from the large winter swells, the temperatures of the water off the shore rose, and Hawaiian green sea turtles swarmed local beaches to lay eggs in the warm sand, we went on a 8-day trip to explore cultural and natural wonders of Oahu and the Big Island of Hawaii.
Oahu – Big Island of Hawaii Trip: Planning and Things to Know before Traveling
The choice of the islands was somewhat obvious. We had visited Kauai a few years ago. A year prior to this Oahu – Big Island trip, I had had an opportunity to circumnavigate the island of Maui with my brother’s family. That left us with two of the four biggest Hawaiian Islands we’d never stepped our feet on.
Oahu and the Big Island of Hawaii are the third and the largest islands of the Hawaiian Archipelago, respectively. Jam-packed with lash tropical vegetation, picturesque beaches, and relaxing coastal towns, the islands couldn’t be more similar and different.
Home to the capital of Hawaii, Honolulu, Oahu transmits a big city vibe. The South Shore of the island is notorious for oceanfront high-risers, sandy beaches of Waikiki, and traffic jams on the way in and out of the Honolulu area. The North Shore of Oahu is the complete opposite, submerged in tranquility and natural opulence.
The Big Island of Hawaii is calmer. With miles of empty roads, hundreds of coffee and macadamia nut farms, deserted beaches early in the morning, and ancient Hawaiian sites galore, the place enhances your Oahu – Big Island trip with dramatic sights and plenty of local economy and history lessons.
Oahu or the Big Island: Which Island Is Better?
It’s hard to say which island is better? Oahu with its large-city ambiance or the more serene Big Island where life goes unhurriedly? The two islands show different sides of Hawaii, similar, yet not exactly the same.
The truth is, after spending five days on Oahu and three days on the Big Island, I still can’t say with a 100% certainty that I like one island better than the other. Each has nooks and crannies that are dear to my heart and a few areas I won’t be upset to skip next time we visit Hawaii.
It all boils down to your individual preferences and expectations. If you long for a tropical, big-city-life experience, head straight to Oahu and don’t even think twice. For volcanoes, hiking, and rural lifestyle, book a flight to the Big Island.
8-DAY OAHU – BIG ISLAND OF HAWAII TRIP
FLYING INTO HONOLULU, OAHU
We landed in Honolulu late at night before our first official day of the Oahu – Big Island trip started. Having booked an Airbnb with a rare free parking on the premises in the Waikiki area helped avoid some logistic issues (read parking, which is expensive in Honolulu!) and save some money.
DAY 1: HONOLULU AND WAIKIKI, OAHU
A three-hour time difference between Hawaii and California played out in our favor. According to the Hawaiian time, we were up way before the clock struck 7 and ready to start our adventures on Oahu despite last night’s late arrival.
Stop 1: Pearl Harbor National Memorial
When on Oahu, you must visit Pearl Harbor National Memorial. Yes, it’s touristy, busy, and, frankly, a cliche landmark to see. On the other hand, the place is one of the most important pages in the history of the U.S.
Pearl Harbor had been a naval base and home to the U.S. Pacific Fleet for nearly 40 years. On December 7, 1941, its fate changed forever when Japanese fighter aircraft attacked Oahu, dropping their destructive bombs on the harbor and the surrounding area. More than 1,000 soldiers and civilians were killed. This brutal attack forced the U.S. to officially enter WWII.
Since the place is located roughly 8 miles northwest of downtown Honolulu, we anticipated it to get busy quickly and early. It surely did. Yet starting our first day on Oahu with a visit to this popular destination still gave us enough space for privacy and exploration at our own pace. By the time we were leaving about one hour later, the line at the entrance to the memorial doubled in size.
Stop 2: Byodo-In Temple
The next on our Oahu – Big Island itinerary was a place I’d wanted to visit before I even knew where and which continent, let alone the Hawaiian Island, it was. The Byodo-In Temple is considered one of Oahu’s hidden gems. A replica of the Japanese temple in Uji, the religious center was built in 1963 to commemorate the 100th anniversary of the first Japanese immigrants to Hawaii.
After a welcoming immersion into Japanese culture, we got a brief glimpse of the Ho’omaluhia Botanical Garden, Oahu’s largest garden. The trip was short, but impactful enough to make us come back on our last day on the island before flying to the Big Island.
Stop 3: Waikiki
The rest of the day, we spent in the famous Waikiki area, a place so vibrant and lively that you may need more than a day to explore. A favorite beach destination, this corner of Oahu is an urban paradise in a classic Hawaiian way.
From the ocean side, it’s defined by turquoise blue water with gentle waves and sandy stretches of land. Across the road, a row of trendy restaurants and gift shops line Oahu’s South Shore.
After a brief rest from sightseeing, we made our way to Kuhio Beach in Waikiki, just in time for a free hula show near the Duke Kahanamoku Statue. The 9-foot bronze sculpture of a man standing near a surfboard with his arms open honors a famous Hawaiian surfer and Olympic gold medalist who grew up riding the waves right here, in Oahu’s favorite beach destination – Waikiki.
DAY 2: HIKES, LOOKOUTS, AND HIDDEN GEMS
Stop 1-2: Tantalus Drive Lookouts and Nuuanu Pali Lookout
Start your second day on Oahu with admiring soft sunlight spreading above the Honolulu area. We’ve been to several iconic overlooks both on Oahu and the Big Island of Hawaii during this trip. But Pu’u Ualaka’a State Park and later the Nu’uanu Pali Lookout stood out with the expanse of the coast they covered and breathtaking vistas they present every single time.
Stop 3-4: The South Shore
The coastline south of Honolulu itself can take several days to explore. Naturally, since we had only 8 day for the entire trip to both Oahu and the Big Island of Hawaii, we had to narrow down our interests or at least be mindful of the time we spent in one place.
A profusion of spectacular places are nestled along the South Coast of Oahu, in different proximity to the capital of Hawaii. Diamond Head State Monument is usually the place that tops almost every Oahu itinerary. Located about 3 miles east of Waikiki, the vocalic cone boasts a short, but steep trail that ends at the summit with outstanding views of Honolulu and the southern section of Oahu.
You can get similar views, but far less “traffic” from the Koko Head Stairs. The 1.6-mile, round-trip trail ascends a steep staircase that can take a toll even on an experienced hiker. But once you reach the top of the crater and look back to where you’ve come from, you know you’ll do this hike again and again.
Stop 5-6: Hanauma Bay and Halona Blowhole
A crescent white-sand beach with aquamarine water, Hanauma Bay offers some of the best opportunities for snorkeling on the entire island of Oahu. Its close proximity to Honolulu is another bonus point. On the other hand, such easy and quick accessibility is one of the main downsides, as way too many people snorkel here every day.
From Hanauma Bay drive further east. Approximately 2 miles down the Kalanianaole Highway (HI-72) is located another landmark you want to add to your Oahu – Big Island itinerary. The Halona Blowhole (halona literally translates “lookout” from Hawaiian) overlooks a rough rocky shore with an underwater cave. Once the water gets trapped inside the cavern, it gets pushed up, resulting in a geyser-like outburst.
Blowholes are scattered across the shoreline of Oahu and other Hawaiian Islands, including the Big Island, Kauai, and Maui. Awe-inspiring and visually pleasing from a distance, these natural phenomena are some of the most dangerous places in Hawaii.
TIP: Thus, you must never get too close or, worse, try to look inside a blowhole to avoid being sucked in. The stories of the survivors, if there are any, are not widely discussed. But tragedies serve as warnings for locals and visitors alike.
Stop 7-8: The Start of Our Hidden Gems (Oahu and the Big Island) Search
If you look for more serene experiences, head to the Koko Crater Botanical Garden or Kawainui Marsh Wildlife Sanctuary. Unlike its face side (the Koko Head Stairs), the botanical garden sees far fewer visitors hiking and admiring lush tropical flora that has adapted to the dry climate of the crater.
Kawainui Marsh sits farther away from the radar of the majority of Oahu and Big Island visitors. Tucked away behind a residential area, the place is a bird-lover paradise. You can spot red-crested cardinals, endangered moorhens, stilts, and black-crowned night herons along a 3-mile trail favored by locals.
DAY 3: OAHU’S WATERFALLS
When on Oahu or the Big Island of Hawaii, you must find time for waterfall viewing, hiking, or swimming. You choose your cup of tea.
We started our waterfall excursion on Oahu with hiking to its most famous waterfall, Manoa Falls. Once a movie set for a Jurassic Park episode, the area exudes a prehistoric atmosphere with a dense jungle embracing the trail tightly on both sides and slippery rocks sliding under your feet.
Next to the entrance into this Jurassic Park realm, you will find the overlooked Harold L. Lyon Arboretum. The secluded botanical garden is home to a seasonal ‘Aihualama Falls. In the mid-summer, however, this Oahu’s waterfall was hard to detect. Only a wet imprint on a sheer rocky wall was what was left to remind of the gurgling site that would re-emerge a few months later.
Before we found the ‘Aihualama Falls Trail, an entirely different jungle path with an almost identical name, The ‘Aihualama Trail, took us to the Pauoa Flats Lookout. We had this precious gem of Oahu all to ourselves for a while before sharing it with a group of three other hikers. The men left soon after they had arrived, leaving us to soak up the unspoiled beauty of Oahu in solitude once again.
We had the most unexpected Oahu waterfall hunt just a day before leaving for the Big Island. Not even a hike, but a nice morning walk shaded by a dense canopy of tropical trees, Kapena Falls looked like another Jurassic Park adventure. Solitary and completely deserted, if you dare to chase it early in the morning.
Tip to Make the Most of the Oahu – Big Island Trip
Even if you are not a morning person, force yourself to walk up early during these 8 days you spend on Oahu and the Big Island of Hawaii. There is a particular magic to the islands that can be seen and felt during or soon after the sun rises.
DAY 4: THE NORTH SHORE OF OAHU
The next two days, we spent on the North and East Shores of Oahu before returning back to Honolulu and flying to the Big Island the morning after.
Quieter, with a rural feel about it, the North Shore loses all the noisiness of the South Shore. More hidden gems and local experiences present themselves once you leave the crowded beaches of Waikiki.
The North Shore, however, has its own show stoppers. One of them is the Dole Plantation. The first internationally-known pineapple plantation, the property expanded its territory both physically and as a world’s biggest supplier of canned pineapple.
Today, it’s also one of the leading entertainers on Oahu. You can still find pineapples and an array of other exotic fruits growing in the fields of the plantation. But also get ready for the world’s largest maze, a train ride into those iconic fields, and an expansive garden with fruits and trees from Hawaii and other tropical regions.
After a few-hour visit to the Dole Plantation, we focused on finding Hawaiian green sea turtles that, as we hoped, would soak up the warm afternoon sun on the secluded beaches of the North Shore of Oahu. They say turtles abound at Laniakea Beach, and so are visitors. So we skipped it. Instead we collected rocks and memories at more secluded beaches, such as Haleiwa Ali’i and Three Tables.
If traditions of Hawaiian culture cast a spell on you, visit the small town of Laie, home to the Polynesian Cultural Center and the Laie Hawaii Temple.
And don’t rush to leave the North Shore of Oahu until you visit its charming Waimea Valley, hike to Waimea Falls, or snorkel at Sharks Cove.
DAY 5: THE END OF OAHU CHAPTER: GETTING READY FOR THE BIG ISLAND OF HAWAII
Use the last day to visit places you’ve missed or revisit your favorite spots on Oahu. A plethora of scenic beaches that are far less crowded than those on the South Coast dot the western shoreline of the island. Check them out and go for a swim or a rough “massage” as the swell can be high and toss you around like a puppet.
After surviving the turquoise, but not the gentlest ocean waves (it also depends on the time of the year you visit Oahu and the Big Island of Hawaii), spread your blanket on a white sand, grab a fresh coconut from a nearby coconut stand, and spend the rest of the day enjoying the sun, ocean, tropical fruits, and maybe even a book.
Some of the beaches you may want to use as guiding points include Waimanalo, Kailua, and Lanikai beaches.
Alternatively, you can finish your 5-day trip to Oahu before embarking on an exciting 3-day journey to the Big Island back on the South Shore. We had barely scratched the surface of the Ho’omaluhia Botanical Garden during our first day here. So it was a good opportunity to revisit the plant sanctuary and pay a visit to its remote neighbor, the Lyon Arboretum.
TIP: The latter is free, but requires a prior reservation.
The last day on Oahu can also be a great opportunity to see more of the island from above. Several short, but steep pillbox trails are scattered across the shoreline and offer spectacular views of the capital island of Hawaii.
Finish the day in Honolulu, preferably somewhere closer to the Daniel K. Inouye International Airport so you can have an easy and relaxing start of your adventures on the Big Island the following morning.
DAY 6: KONA, THE BIG ISLAND OF HAWAII
We spent the next three days imitating the guide-led Grand Circle of the Big Island of Hawaii, but adding several off-the-beaten-path destinations to see the island from a local’s point of view.
The first was the Kona Coast. Since we flew into Kailua-Kona, it was a given to start our three-day Big Island trip with exploring the coastal area. Two-thirds of the West side of the Island of Hawaii is considered the Kona District.
Historic Landmarks
The region includes such historic places as Kaloko-Honokohau National Historical Park, Kamakahonu National Historic Landmark, Kealakekua Bay State Historic Park, and Pu’uhonua o Honaunau National Historical Park.
The latter left us suspended between a complete awe and a slight tremble that we almost missed this postcard-perfect location that could easily be the highlight of any Oahu – Big Island trip.
Kona Coffee and Bee Farms
The chances are the word Kona rings a bell even if you can’t place it. The Kona District is one of the largest exporters of the premium Hawaiian coffee. Hundreds of farms, including macadamia farms dot the western side of the Big Island. We had to see one of these agricultural sanctuaries in person.
Our morning excursion to Greenwell Farms was accidental and inspiring. Galvanized by what we heard and saw, we even made an attempt to check out a neighboring bee farm.
But the last tour of the day had started shortly before we arrived. So we ended up sampling different flavors of local honey at a gift store. The flavors were so profound and so different that you could hardly believe that these honeys were collected on the same island, let alone the same coastline.
The Southernmost Point of the U.S.
We called it a day at Colony I at Sea Mountain Resort in Pahala. But not before we enjoyed the golden hour and watched locals fish at Ka Lae, the southernmost point of the U.S.
The resort we called home for the first night during our second leg of the Oahu – Big Island trip sits within a five-minute walk of Punaluu Black Sand Beach.
DAY 7: HAWAII VOLCANOES NATIONAL PARK AND THE CAPITAL OF THE BIG ISLAND
You need more than one day to trek along barren caldera trails, sprint through tropical rainforests, and descend into ancient lava tubes in Hawaii Volcanoes National Park. Sadly, we didn’t have this much time. So, we had to be quick and selective as we had a lot more to see and explore before this Oahu – Big Island trip would come to an end.
The national park occupies the southeastern section of the Hawaii Island and encompasses the peaks of two world’s most active volcanoes: Kīlauea and Mauna Loa. This is the place where you want to go to see streams of molten lava. Be aware, though, the phenomenon is not always present.
The second half of the day and the morning of the following day we devoted to Hilo and its surroundings. The capital of the Big Island of Hawaii, the area boasts a profusion of urban gems and natural wonder, nestled both inside and on the outskirts of Hilo.
DAY 8: THE END OF THE GRAND CIRCLE OF THE BIG ISLAND AND FLIGHT BACK TO OAHU
It was the last day of our more than a week-long trip to Oahu and the Big Island of Hawaii. But it felt like we’d been to the islands for months, exploring their famous and hidden sites through and through, and still leaving a ton more to see the next time. The plan was to drive through the last section of our self-guided Grand Circle of Hawaii Island.
After stocking up on fresh coconuts and Aloha shirts for Dylan at the Hilo Farmers Market, we headed to Akaka Falls State Park. Submerged in lush tropical greenery, the area is famous for the 442-foot-tall Akaka Falls.
A couple hours later, it was time for Waipio Valley Lookout (access to the valley itself was temporarily closed for non-locals) and Pu’ukohola Heiau National Historic Site. The latter preserves ruins of the last major ancient Hawaiian temple.
We arrived in Kailua-Kona, one of the two largest cities on the Big Island, a few hours before our evening flight back to Oahu. Just enough time to see more of the downtown area or even take a swim near Kailua Pier.
The flight to Oahu took approximately one hour. We stayed at the Airport Honolulu Hotel and took an early flight back to LA the next morning.
