Oahu, Hawaii Trip Planner

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Oahu Trip Planner

Most visitors have their first experience of Hawaii on Oahu.  You may love the bustling atmosphere and amenities of Waikiki, but if you venture around the island you’ll start to see the tropical scenery, turquoise waters, rich culture and history that attracts many visitors.


How To Get Here

Since 1949, the TransPac sailing race has been held every two years from Los Angeles to Honolulu. So unless you stowaway or hire yourself out to hoist yardarms, your only options traveling to Oahu are by plane or by cruise ship. But since your destination is Oahu, you’re in luck. Oahu means “The Meeting Place” in Hawaiian, and as such, it has the most – and most economical – choices for each.

By Plane

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There’s a substantial choice of airlines servicing Hawaii from the US mainland, along with Air Canada and WestJet from Canada, and all of them fly direct to the Daniel K. Inouye International Airport, which is approximately 6 miles (9.7 kilometers) to downtown Honolulu; 9 miles (14.5 kilometers) to Waikiki, and 20 miles (32.2 kilometers) to Ko Olina.

The US carriers range from large legacy US airlines such as United, Delta, and American, to lower-cost options like Alaska Air and Southwest that service many cities. Travellers can also choose Hawaii’s flagship airline, Hawaiian Airlines, which flies nonstop from major west coast cities, as well as direct from Chicago, Boston and New York.

Little known fact: upon the demise of Pan Am in 1991, Hawaiian Airlines became the oldest domestic airline in the US, founded in 1929.

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By Ship

What could be romantic than a languid sail across the Pacific to what Mark Twain described as the “smooth and delightful route to the Sandwich Islands“. Under normal operating conditions, cruising options include Princess Cruises, Royal Caribbean, Carnival Cruises, Celebrity X Cruises, Holland America Line and Norwegian Cruise Line.

Getting Around

The island of Oahu is only 112 miles (180 kilometers) in circumference, making it the third largest island in landmass of the Hawaiian Island chain. But considering the incredible number of attractions on the island, your on-island transportation can be crucial for the traveler who wants to experience them.  

By Car

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Millions of visitors arrive through Honolulu and stay on Oahu. Every major (and even some minor ones, along with some “mom & pops”) car rental agency services Oahu. 

So you will have a great choice of rental car companies, but be aware that rates and availability vary, especially during the busiest seasons.  Make sure you reserve your car as early as possible, even if you only plan to take a one day rental to explore the island, as a rental car is the absolute best way to get around and experience Oahu. As with most major airports, the rental car agencies are all located in the immediate vicinity, with shuttle service to their facilities. Some companies have agencies have locations in Waikiki too.

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By Bus

Honolulu is considered as one of the best bus systems in the US, with low fares and an extensive coverage of the island, and should not be discounted as a means of getting around Oahu. For example, a single fare of just a few dollars, one can take a route that completely circles the island, and therefore of course, by some of the most famous beaches in the world. But be sure and pack a snack, or be ready to pay another fare if you jump off to visit any of the charming beach towns along the way for a breakfast, brunch or beer.

Just as economical, but much shorter and focused, you can take TheBus to major tourist attractions Hanauma Bay, the Polynesian Cultural Center, and the Pearl Harbor Historical Sites Visitor Center, from where you can tour every monument in Pearl Harbor. 

Little known fact: since its inception, TheBus has been recognized twice by the American Public Transportation Association as “America’s Best Transit System” for 1994–1995 and 2000–2001.

Driving Tips for Oahu

OK, so you have your rental car, and now Oahu is your asphalt oyster, and you have carte blanche to all the delights awaiting you on your terms. But before you put it into Drive, here are a few tips you should keep in mind to help you navigate the island.

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Look (Out)

Even though Oahu is the most developed of all the islands, complete with eight lane sections of freeway, the main sightseeing route around much of the island is a ‘belt road’ that rings the shoreline, and is only two lanes. 

Considering it’s absolutely certain you will be tempted to gaze off to the right or left (at either stunning mountains or dazzling surf), that means you will also be susceptible to slamming into a car that is stopped in front of you. They’ll be stopped for a variety of reasons, but it will be primarily because someone is making a left turn: either they are waiting to make one, or they are politely allowing an oncoming car to make one. So watch out! 

This overt courtesy is known throughout Hawaii as “the aloha spirit,” which brings us to…

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Hear anything like a horn? Nope. That’s because you’ll have to be stopped at a green light for over 30-seconds, or milliseconds away from ramming them before a local will even TAP a horn. That’s not to say you won’t hear one, but when you do, it’s a dead giveaway that it’s a high-blood-pressure visitor who hasn’t decompressed enough to discover their inner “aloha,” and will then soon discover another local term called “stinkeye”. So as the bumper sticker you will eventually see says, “Live Aloha”. Especially when driving.

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Location (Keeping the “L” Thing Going)

Going “circle island” meaning around the North Shore and windward coast? A good tip is to go clockwise when you do, and that means heading north out of Honolulu on H1 to H2, through the Schofield Plain (center of the island), past the North Shore beaches and returning along the windward coast. 

This way, you will a) get to see the sites, but also b) not run into the prodigious traffic that will be leaving the North Shore beaches in the afternoon to return to Honolulu by way of the route you just came up on. If you go counterclockwise, you may find yourself dealing with more traffic. There is no absolute right or wrong way to go around, but these little insider tips may help.

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Waianae Coast

Looking at a map, you might find your eyes trying to trick you into thinking you can drive up the Waianae Coast (leeward or east coast) as a part of a continuous loop of the island. Highway 93 actually finishes as a dead end at the Ka’ena Point State Park. You cannot continue through that way to reach the North Shore. 

Though the scenery on this drive can be attractive, this is not recommended as a sightseeing route for visitors to explore. Best to focus your valuable vacation time on other parts of the island.

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Where to Stay 

No matter what your budget, Oahu can accommodate it. From quaint, mid-century walkups tucked into the off-beach side streets of Waikiki, to the 5-star Four Seasons resorts in Ko Olina, along with a vast choice of vacation rentals, you have literally hundreds of choices, and most will be located in two main areas.

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One of the most famous beaches in the world is also the home of hundreds of accommodation choices tucked within its one square mile of area. This modest size is deceiving, because along with containing expansive resorts like the Hilton Hawaiian Village, brand hotels of every stripe and size, and condotels and vacation rentals at every price point, you can find leafy side streets with quaint walkup apartments, and hidden shops that cater to the nearly 20,000 permanent residents. 

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Of course, servicing this huge array of visitors and residents is an incredible number of recreation options: restaurants, dive shops, sailing and fishing tours, as well as some of best shopping in the world, and for any budget, just like the accommodations choices. 

Throw in the adjacent Honolulu Zoo, Waikiki Aquarium and hike-ready Diamond Head, and it’s indeed possible to have a completely fulfilling vacation experience without even leaving this bustling, beautiful and renowned one square mile.

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Ko Olina

20 miles (32 kilometers) from Daniel K. Inouye International Airport on the more arid west side of the island is the resort area of Ko Olina, which features three major resort hotels and a condominium resort nestled in between four beautiful, man made lagoons. 

This is where you’ll find the Four Seasons, along with Disney’s Aulani (where Mickey, Minnie and Goofy wander the grounds – along of course, with Lilo and Stitch), as well as the Marriott Ko Olina Beach Club and the Beach Villas condominium resort. 

You’ll also find a championship golf course that has hosted many LPGA events, along with a marina, and a mile and a half of seaside pathways winding about the pristine, white sand lagoons and striking volcanic coastline that has attracted Hawaii’s royalty for centuries. With restaurants from two of Hawaii’s most renowned Master Chefs, Roy Yamaguchi and Peter Merriman, and one of Oahu’s premiere luaus, the resort community, like Waikiki, Ko Olina could also be a destination in and of itself. Day visitors are welcome.

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Turtle Bay

Literally on the opposite side of the island from Honolulu and Waikiki, resting on Oahu’s famous North Shore is the Turtle Bay Resort, a self-contained resort hotel that also has an array of vacation rental condominium choices and championship golf course adjacent to the property. The famous beach destinations of Sunset Beach, Waimea Bay and Pipeline surf break are all nearby.

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The windward side of Oahu features some of the most lush hiking and striking vistas on Oahu, along with the venerable Polynesian Cultural Center. It’s a long, but incredibly gorgeous drive to get there, and visitors may want to stay overnight rather than make the long drive back after a day of sightseeing. That’s where the Marriott Courtyard near the town of Laie comes in. The only hotel on the windward side of Oahu. 

Little known fact: before the Ala Wai canal was created in 1928, the square mile area of Waikiki was mostly marshland, where native Hawaiians grew taro… the root of which goes to make poi. 

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When To Visit

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Come on, this is Hawaii. There really isn’t a ‘bad’ time to visit, and some visitors will outright belly laugh when a local mentions “winter in Hawaii.” But here are distinct climate differences through the year, and there are basically just two: a cooler, wetter season (that is considered winter in Hawaii) from December to April, and a warmer, drier season from May to November. 

The winter months feature more tropical storms (including the possibility of hurricanes), and these peak around the month of March. This doesn’t mean there aren’t sunny days in March, there are plenty. It’s just an overall cooler average temperature and the possibility of a storm in that month. On the plus side, you’ll get the chance to see the many pods of humpback whales cavort offshore in their annual winter trek to Hawaii from the northern Pacific. You’ll also be able to see the mammoth waves and death-defying surfers who surf them on the North Shore during those months. 

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Conversely, the warmest and driest months in Hawaii are August through October. This doesn’t mean you won’t have a storm suddenly pop by for a visit, just much less odds of that –and no hurricanes. You’ll also have a higher chance of a day without Hawaii’s famous trade winds, which will mean a very still and humid day that will command you to turn on the AC.

Considering the often unpleasant winter months in the northern hemisphere, you can expect far more crowds (and higher prices) in the winter months, with a similar, schools-out family vacation crowd in June, July and August. So the off-peak, “shoulder seasons” of April to May and September to mid-December are when you’ll find the best values.

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How Much Time Do You Need to Visit Oahu

Just Oahu

There are far more activities and cultural/historical sites on Oahu than any other island, and one could easily spend weeks exploring all there is to see. Indeed, Snowbirds from the US and Canada sometimes spend the entire winter on Oahu. 

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Depending on your list of what you want to experience, and considering the travel time involved, one should try to stay a week on Oahu if they don’t want to feel rushed. However, if your list is robust, you may feel that way even with a week, so it’s a good move to do plenty of preplanning for your trip to figure out what you a) have to see/experience, versus b) what you’d like to see/experience, versus c) what would be nice to see/experience if you have some extra time. Be sure and add some time for relaxation, and d) beach-bumming.

Multiple Islands

A good rule of thumb is to add one week for every additional island you want to visit. 

Little known fact: Oahu means “The Gathering Place” in Hawaiian, and it has been the business and political center of Hawaii for centuries.

Things to See and Do in Oahu

Cool Sights

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North Shore

The beaches and specific location of the North Shore are described throughout this guide, but dedicating at least a half day to explore Oahu’s famous North Shore is not to be missed. Three of the world’s most famous big wave beaches sit here, in what is considered the spiritual home of surfing. Even if the surf is not pumping, these are scenic beaches. But this section of coast offers much more including culturally important places, great eats and the “surfy-meets-hippy” hub town of Haleiwa.

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Halona Blowhole

A little over 11 miles (18 kilometers) southeast from Waikiki on the southern belt road on the island is the Halona Blowhole, a natural wonder where surf spouts up into a geyser through a lava tube. There’s a small parking lot for the lookout, and if you are lucky to get one and the surf is up, you’ll be treated a gorgeous spray of seawater against a brilliant developing sunrise.  

On clear days, the islands of Moloka‘i and Lana‘i can be seen… and which are even more spectacular as the sun rises up over them.

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Makapu’u Point & Lighthouse

One can only describe the views from Makapu‘u Point, the trail leading to it, and even it’s parking lot as incredible. And that’s even without a sunrise. To the north, you can see the eastern, windward coastline; and in the other direction a spectacular vista of Oahu’s southeastern coastline, including Koko Head and Koko Crater. And at the end of the trail leading to Makapu‘u Head, the historic red-roofed Makapu‘u Lighthouse built in 1909, which makes a stunning picture against the deep blue sea below. Especially when the sun rises up over the horizon.

Nu’uanu Pali Lookout

Less than 10 miles (16 kilometers) from Waikiki is one of the most stunning views on Oahu, if not the entire Hawaiian island chain: The Nu’uanu Pali Lookout. Be prepared for a strong breeze from this view, nestled in the pass in the Ko’olau Mountains, that separates the windward coast from the rest of the island. The panorama is guaranteed to render you speechless with awe. And that’s even without a magnificent sunset in the distant horizon. 

Little known fact: Halona, in Hawaiian, means “lookout,” and the halona overlooking the Blowhole also looks over Halona Beach Cove, which is the beach made famous as the location of the love scene in the film, “From Here to Eternity” (extra points if you even know of this iconic film).

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Laie Sea Arch

This one rock peninsular offers two great views. Catch a fun photo looking through the sea arch on its very own island just off shore. One day the arch may collapse, and we will be left with just two small, plain islands. Turn for the view south to see down the length of the windward coast, dominated by the scalloped cliffs and peaks of the Ko’olau mountain range.

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Mokoli’i Island 

This uniquely cone-shaped island reminded viewers of the traditional, rice hat worn by Chinese, peasant farmers as they work the paddys. The traditional Hawaiian name translates to “little lizard”, but that as far more challenging to picture. The view is best enjoyed from Kualoa Regional Park.  

Best Hikes

Diamond Head

Yes, you can go to the top of what is by far Hawaii’s most iconic natural wonder. The climb is short and steep, but there is plenty of assisting structures along the way, and the ultimate reward is worth the exertion: a fabulous, eye-popping vista of Oahu’s south shore. And you’ll be taking in the stunning view from historic and long abandoned military outposts that, until your attention is riveted by the expansive view at the top, will have you wondering how the heck the built them 80 years ago. 


Reservations are required to visit Diamond Head State Monument, including the Diamond Head hike. Visit the hawaii.gov website for reservations and further details.

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Ka’ena Point

Hot, dry, rocky and rugged, but rewarding, describes hiking Ka’ena Point at the extreme north-western point of the island. We recommend starting at the North Shore Trailhead, located on Route 930, west of Haleiwa.   

Hikers experience amazing, craggy lava cascading into pounding blue surf, sandy stretches peppered with nesting shorebirds, and relentless sun. Be prepared for the conditions with a proper hat, footwear, sunblock, and of course, plenty of water.

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A’iea Loop Trail

This mild and peaceful hike is completely graded with no steep inclines to climb, and therefore perfect for casual hikers who want to experience the natural beauty of the Ko’olau Mountains of Oahu. Located in secluded Kea’iwa Park, the trail is a simple, 4.5-mile (7.2-kilometer) path through cool, shady forests of triple canopy jungle of guava, albizia, koa, and pine. Keep an eye out for the wreckage of a bomber from WWII at about the two-thirds mark.

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Ka’iwa Ridge Trail

This short hike located in the hills behind Lanikai, has some strenuous moments – with a rope available to help you up one particular steep slope – but the end of the trail is well worth it. 

After some challenging inclines at the beginning of the hike, the trail breaks through to a fairly even, but uphill ridge with spectacular views on both sides that eventually brings you to a pair of WWII pillboxes where you can relax and catch your breath. Which is only impaired because the view there is so breathtaking.

Cultural Experiences in Oahu

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Pu’u o Mahuka Heiau 

The Pu’u o Mahuka Heiau State Historic Site is located on Pupukea Ridge on Oahu’s North Shore and is the largest heiau (place of worship) on the island, and served a critical role in the religious, social, and political system of Waimea Valley, a major cultural center on the north shore of Oahu. It most likely was a heiau used for human sacrifices, making it an especially sacred place.

Spread over two acres, the ancient site is not only awesome in its size and scope, but being 300 feet above sea level on a high bluff overlooking Waimea Bay, is equally as awesome. 

Little known fact: on the adjacent bluff across Waimea Valley from Pu’u o Mahuka Heiau is a matching heiau, not accessible to the public.

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Bishop Museum

It’s simple: if you want to learn about Hawaii, you visit Bishop Museum

The museum was founded in 1889 by Charles Reed Bishop (founder of what became First Hawaiian Bank) in honor of his late wife, Princess Bernice Pauahi Bishop, the last descendant of the royal Kamehameha family. The Museum is home to an extensive collection of Hawaiian objects and royal family heirlooms, and over the years has expanded to include millions of objects, documents and photographs about Hawaii and other Pacific island cultures. 

To say it is comprehensive is an understatement. It is the largest museum in the state and the premier natural and cultural history institution in the Pacific, recognized throughout the world for its cultural collections, research projects, consulting services and public educational programs. It also has one of the largest natural history specimen collections in the world.

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Iolani Palace

Built in 1882 by King Kalakaua, Iolani Palace was the home of Hawaii’s last reigning monarchs and served as the official royal residence and the center of the Kingdom’s political and social life until the overthrow of the monarchy in 1893.

Registered as a National Historic Landmark and the only official royal residence in the United States, the Palace is has been meticulously restored to its former grandeur, and palace tours transport visitors back to a time when King Kalakaua and his sister and successor, Queen Liliuokalani walked the grand halls. It is a living restoration of a proud Hawaiian national identity and is recognized as the its spiritual and physical cultural focal point.

Little known fact: for several years after the overthrow, Hawaii’s last monarch, Queen Liliuokalani, was held in a house arrest in the palace, and for decades a light representing a candle was kept burning day and night in what was her living quarters in the front upper floor corner.

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Waimea Valley

Waimea Valley, which features a tributary stream flowing into Waimea Bay on Oahu’s North Shore has long been a cradle of Hawaiian culture. Featuring rich agricultural lands, fresh water, abundant offshore marine resources, and good canoe landing sites to reach them, Waimea Valley has always been an ideal place to live. 

Naturally, Hawaiian ali’i (chiefs) and kahuna (priests) searched for areas such as Waimea to establish centers of power, and for 700 years beginning in the 1100s Waimea Valley was the spiritual headquarters for a line of kahuna nui (high priests) earning the valley the name the “Valley of the Priests.”

Today, visitors can learn about the history of Waimea Valley with botanical and history tour walks. There is also food concessions and plenty of parking.

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One of the most iconic cultural experiences in Hawaii is the luau, and there is a wide variety of them in authenticity and scope. Most need to have a little bit of “one size fits all” in them in order to appeal for the wide variety of people who visit the Islands. Two of the best are Germaine’s and Paradise Cove. These luaus not only try to adhere to authenticity, but are also located in wonderful settings perched at the edge of the shimmering blue Pacific …and crucially, on the western shore for fabulous sunsets.

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Polynesian Cultural Center

What can you say? Culture is their middle name. A longtime and renowned attraction on Oahu’s windward coast, PCC (as the locals call it) is about as authentic as you can get, as it is staffed by people from Polynesia who showcase the cultures they literally grew up immersed in. Visitors will learn all about the Tongan, Fijian, Samoan, Tahitian, Hawaiian and Maori (New Zealand) cultures by actually visiting villages specific for each island nation and learn about its history, arts and crafts. Gentle paths and canals and lagoons are interwoven through the 42 acres, so guests can either wander the grounds on foot or visit each village by canoe. The day can culminate with the island’s largest luau, and a spectacular show featuring song, dance, and athletic displays from every culture.

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Byodo-In Temple

This replica of a 1000 year old Japanese temple was built to commemorate 100 years of Japanese immigration to Hawaii. The setting is stunning, backdropped by the sheer, 2000 foot Ko’olau Mountains. Visitors are welcome to visit the Byodo-In Temple and enjoy the peacefulness of the gardens, feed the koi and ring the sacred bon-sho bell to bring happiness and longevity. 

Pearl Harbor

Pearl Harbor is the location where the Japanese executed a sneak aerial attack on the US ships and brought America directly into WWII. The events of that fateful day and the countless lives that were affected are memorialized at the Pearl Harbor National Memorial. For many visitors a trip here is not complete without stepping foot on the USS Arizona Memorial, which is built over the remains of the sunken battleship USS Arizona. Visiting the USS Arizona Memorial is by boat on a US Navy vessel and tickets must be booked in advance.


USS Arizona Memorial boat tour tickets must be booked in advance at recreation.gov.

Best Beaches in Oahu

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Waimea Bay

Waimea Bay is famous for big wave surfing in the winter months, and while this in itself makes it a great beach to watch incredible waves in the winter, it is also a fabulous beach in the summer months when the surf is modest. With calm waters perfect for swimming; beautiful and plentiful white sand; comfort stations, picnic tables and parking, Waimea makes for a great “day at the beach” and well worth the drive to the North Shore. 

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Kailua Beach

Located on Oahu’s windward (eastern) shore, Kailua Beach is the perfect place for family fun. Attached to a 30-acre public park, with plenty of parking, picnic areas and comfort stations, you can spend your day picnicking, kayaking, playing volleyball, diving, swimming, snorkeling and surfing when the surf is up. And because it’s called the “windward side” for a reason, the glistening white sand especially powdery …like confectioner’s sugar.

Venture around the corner to Lanikai for terrific view to the twin island a mile offshore called the Mokes. In Lanikai, be sure to respect all parking and traffic control notices.

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Ko Olina Lagoons

The resort developers created 4 beautiful and protects ocean lagoons, which provide safe swimming and waterplay without the hazards of waves. Using the lagoon is available for the public, but it is important to respect the privacy of the resort grounds and to only park in the public-assigned stalls. 

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Ala Moana Beach Park

Probably best described as “Honolulu’s Beach”, Ala Moana Beach Park is probably the most frequented beach for residents of Honolulu, with a long, wide white sand beach with an easy slope into the calm, lagoon-like waters that face the beach, making it perfect for swimming, snorkeling and stand up paddling. If you have small children, this is by far the safest place they can experience ocean swimming. There are also concessions, tennis courts, picnic areas, parking and comfort stations.

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Because so many things are attached to Waikiki – shopping, dining, hotels – it often gets dismissed or overlooked as a premiere beach. But that’s exactly why all these things developed around Waikiki. Hawaiians started coming to Waikiki hundreds of years ago for precisely the same reason people come today: gentle waves, beautiful sands and overall great conditions for superb swimming, surfing, paddling, and snorkeling.

Awesome Experiences in Oahu

Hanauma Bay

No trip to Oahu is complete without a trip to Hanauma Bay, consistently one of the top three attractions on Oahu. Formed when the seaside face of a volcanic cone broke away, Hanauma (literally meaning “curved bay” in Hawaiian) offers a pristine marine ecosystem that has long been one of the island of Oahu’s jewels by allowing snorkelers to get up close and personal with the vibrant ecosystem, gazing on living coral and feeding the abundant reef fish, which of course includes the Hawaii state fish, the Humuhumunukunukuapua`a.

Although its popularity can add challenges, the City of Honolulu has taken steps to limit the amount of tourist visitors, but its beauty and natural wonders make the trip worth it. Especially after the City started taking extra steps to maintain and improve the nature preserve, which includes informative presentations about reefs, their habitat and the conservation efforts to protect them. 

As part of the conservation efforts, reservations are now required to enter the Hanauma Bay Nature Preserve. 

Little known fact: the Humuhumunukunukuapua`a means “fish with a pig snout” in Hawaiian, (or “Pigfish” for short) in part because the fish makes snorting sounds when beached. 


Reservations are required to visit Hanauma Bay in Hanauma Bay State Park, visit the honolulu.gov website for reservations and further details.

Coral Crater

Buckle up for thrilling adventures at the Coral Crater, where the entire family can enjoy thrilling rides, exciting challenges, formidable obstacles, games, and local food. Featuring ATV rides through dense jungle, zip lines traversing through trees (and allowing children as young as 6 to partake) and a stupendous Adventure Tower, an aerial playground with Hawaii’s largest climbing wall, a free-fall from 50 feet, an airborne obstacle course with 18 different obstacles. If all that isn’t enough to elevate your heart rate, you can try them at night … including zip lining.  

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Kualoa Ranch

Thrilling jungle rides on an ATV? Check. Languid horse rides through tropical pastures? Check. A hike, bike or bus tour through a spectacular, yawning valley that was the backdrop for Jurassic Park and countless other movies  …or even a thrilling zip line plunge over it? Check, check and check. Not contained just to terra firma, there’s even an ocean tour to a secret island in the adjacent bay, where the iconic island of Mokoili’i (aka, Chinaman’s Hat) watches over it all.

Yes, there’s indeed a lot going on at Kualoa Ranch, and has been since it’s official beginning as a ranch and sugar plantation in 1850, making the fact that it has remained intact as one of the most amazing things about it.  History, Hawaiian culture, pop culture, and just plain outright thrills: it’s all there.

Food in Oahu

So “when in Rome,” you get to eat tons of pasta and gain 80 pounds. In Hawaii, with seafood as a staple, you get more healthful choices, but it’s really the decadent ones that will captivate you (along with your left ventricle).

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Shave Ice

They say the simple pleasures are best, and the person who coined this phrase must have had shaved ice in mind. Simply –and literally- ice shavings in a cone with flavored syrup poured in, Shave Ice is a classic example of how it’s the setting that makes the treat, and few settings are more charming than Matsumoto’s old general store in historic Haleiwa Town on the North Shore.

For those who enjoy history, they can visit Waiola Shave Ice, the tiny and quaint, neighborhood shave ice stand where a young Barry Obama used to frequent, and famously returned to as president of the US (and if you’re in the mood for something more sinful, venture a few blocks away and you can have an ice cream at the Baskin-Robbins where he worked while attending high school).

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Sometime between the massive immigrations of the Chinese and Japanese to work the plantations, a small wave of Portuguese arrived in Hawaii, and like all the cultures that have populated paradise; they added indelible pieces of their culture to Hawaii. One is the ukulele, another is the malasada, a mouth-watering confection that is like a doughnut with no hole: small balls of yeast dough and coated with granulated sugar, and sometimes cinnamon. Sounds simple, but the best things are always simple (and sometimes free), and simply the best is found at Leonard’s Bakery. But they aren’t free. 

Little Known Fact: “Uku” means “flea” in Hawaiian, and “lele” means guitar. (Ukulele …get it?) And if you want to impress a local, pronounce it correctly. The first U is NOT pronounced “yoo,” but “ook” – just like the second U, and therefore correctly pronounced as “oo-koo-lay-lee.”

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Pronounced “po-kay,” poke is diced raw fish, blended with a mix of ingredients at the creative whim of the person making it. It has been a healthy staple in Hawaii since ancient times, and is as much as a culinary art form as sashimi, but the unquestionable key to what makes the best poke is the freshness of the fish. 

That gave tiny Tamashiro’s Market on North King Street, featuring the freshest fish in Hawaii straight from the boats each morning, a leg up since it opened its doors in 1947. 

While Tamashiro’s reigned supreme for decades as the best (and it is still superb), excellent, fresh poke can now be found at Tamura’s Market, as well as the local supermarket chain, Foodland, founded in 1948 as Hawaii’s first modern supermarket). 

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Fish in General

For those wanting to check the source, they can visit the Honolulu Fish Auction. The center of the Commercial Fishing Village on Pier 38, it’s the only fish auction between Tokyo and Maine. In fact, it’s the only fresh tuna auction of its kind in the United States and it is based on the famous Tokyo auction, where large fish are sold individually rather than by the boatload to a wholesaler. 

Here you can watch Hawaii’s deep sea fishing boats tie up and unload their catch into huge bins filled with ice, and then whisked into a modern market where Hawaii’s top chefs line up to inspect and bid on all kinds of fresh catch that will be gracing delectable meals later that very day. The bidding sometimes gets fervent on particularly prized fish, but take note the bell rings at 5:30, and the auction doesn’t last long.  

Little Known Fact: Hawaii consumes three times as much raw fish than the national average, and up to 100,000 pounds of fish is auctioned at the Honolulu Fish Auction every day. Oahu with GyPSy Guide Driving Tour App

Loco Moco

Modern Hawaii history is completely steeped in plantation culture, where great waves of labor were imported to work the sugar cane and pineapple fields. This was extremely hard work, and subsequently (and now for many, consequently) the Hawaii diet consisted of extremely high-carb, high fat dishes. 

The poster child for this cuisine would have to be the local staple, Loco Moco, (AKA, Fibrillation Deluxe). The ingredients speak for themselves: a mound of white rice, topped with a slab of hamburger, with a fried egg laid on top of that, and crowned with a slathering of brown gravy. Driving not recommended after ingesting, as post-dining consciousness is not a guarantee for those unaccustomed to such flagrant middle finger to the AMA. But like all indulgences, if you’re going break some rules, do it with the best, and this would have to be the Highway Inn, in Waipahu and Kaka’ako. Fueling Hawaii’s hard workers since 1947. 


The influx of so many different cultures in Hawaii has created a wonderful array of variations of common dishes from each country. One of the more delightful is the manapua, a big, fluffy steamed bun stuffed with everything from sweet char siu pork, to kalua pork and sweet potato. 

Manapua is Hawaii’s version of the Chinese bao, and the absolute best is found at the Royal Kitchen, at the edge of the Chinese Cultural Plaza on River Street. 

Little known fact: Kalua Pork (or Kalua Pig) is from a whole pig long-cooked in a Hawaiian underground imu (oven), commonly seen –and served- at luaus. 

Coco Puffs

Residents of Oahu have been cuckoo for Coco Puffs for 70 years, and this isn’t the cereal. The Coco Puff that Honolulu has been wild about is a small puffed pastry filled with creamy chocolate pudding and topped with a thick, vanilla and coconut frosting. Even though there was never a wave of French immigrants to Hawaii, it is Hawaii’s version of an éclair. 

Or at least Liliha Bakery’s version of it, as these scrumptious treats are unique to this venerable institution that has been baking fresh cakes and pastries in Honolulu since 1950. 

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For those who feel they can handle a bowl of ramen without suffering a sudden PTSD attack recalling the Styrofoam gastro-salt-plug that was part of some misbegotten night (or day) in their college years, they need to venture to Lucky Belly in Chinatown. 

This is the way ramen is supposed to be: rich, succulent and superbly flavorful, with a mix of flavors that defy description; just silence and enjoyment. 

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Best Places to Enjoy the Sunset

Obviously, anything on the west side is crucial, and Waikiki has a lot of beachfront real estate facing west, along with some wonderful restaurants and bars. You simply can’t go wrong watching the sunset from Waikiki. 

However, there are more intimate, and spectacular spots to see the moving majesty of the sun calling it a day when dipping into the blue Pacific horizon.

Equally spectacular as a Hawaiian sunset is a Hawaiian sunrise, and this is where Waikiki is at a tremendous disadvantage. But there are several great spots to watch the glory of a new day that are not that hard to get to.

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The North Shore

The North Shore is renowned for three things: 1) massive winter surf, 2) the death defying (some say crazy) surfers it attracts, and 3) the tremendous amount of tourists who come to see both. 

Keeping in mind that it is a two-lane blacktop that services the entire north and windward coasts, here are some tips for seeing this incredible, and frankly mesmerizing spectacle. 

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Best Places to Watch Surfers: Sunset, Waimea and Ehukai

There is enormous surf all along the North Shore, but these three beaches are the best from which to view the amazing athletes who surf them. In part because the undersea terrain fronting each beach (or in the case of Waimea, the adjacent point) create almost perfect waves that attract these intrepid daredevils. 

They have also been selected because they all offer parking and comfort stations for those who come to be amazed. These amenities may be modest in some cases (Sunset and Ehukai) but it’s better than nothing –and much safer than parking off the highway in some weeds and making a dash-of-death across the highway. 

Little known fact: the surf breaks in Hawaii often do not match the beaches they are next to. For example, while the surf breaks Sunset and Waimea are named after their adjacent beaches, the break fronting Ehukai is the world-famous Banzai Pipeline. 

Second little known fact: ‘Pupule’ means “crazy” in Hawaiian. 

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Best Places to Watch Surf: Mokuleia

The North Shore is bifurcated by the little town of Haleiwa, with the famous surfing beaches east of town, and this long stretch of beach on the western side.  This entire coast often does NOT have optimal conditions for surfers, but that means it’s super-optimal for minimal traffic, ample parking, and great, uninterrupted views of mesmerizing surf. Beware, though, it is often windy, and also not good for swimming. Which brings us to…

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Best Places to Swim

You can swim most places on the North Shore in the summer months, because the surf is often akin to a bathtub. But in the winter months your best bets are Haleiwa Harbor and the adjacent beach park, and Waimea Bay – but that can sometimes be challenging for novice or less-than-in-shape swimmers. 

Pro Tip: If you see a sign warning you about the surf, it’s wise to take serious note of it. Watching lifeguards pulling someone out of the water past a sign warning them not to go in the water is a regular occurrence.

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Hungry? Head to Kahuku

Grab some fresh shrimp in the shrimp stands and food trucks around Kahuku. The local favorite is Giovanni’s, located across from the Kahuku Medical Center (just a coincidence, but you may have an urge to dash there if you order the spicy plate). 

There are dozens of charming local cafes and restaurants throughout historic and thoroughly enchanting Haleiwa Town. A highlight is Haleiwa Joe’s, which features a delightful lanai with a superb view of Haleiwa Harbor and Marina. 

Little known fact: Kahuku means ”the point” in Hawaiian, and the town is so named because it is near the northwestern point of land on the diamond-shaped island.

Oahu Packing List

Clothing: If you don’t like shorts, you’re going to the wrong destination. Pack at least two pairs. One casual, one “dress.” Seriously, it all of course depends on your plans. Everything Oahu has to offer runs the gamut from budget to luxury, so if your planning on a week of burgers at the beach concessionaire, it’s best to have backup shorts for potential ketchup stains. 

But if you’ll be sitting down for some white linen tablecloth fine dining, casual attire is still OK, but make sure you have something appropriate. And for fine dining in Hawaii, that pretty much only means a collared shirt or nice blouse, and if you’re wearing sandals, they better be pretty damn good ones. Plus, if you’ve ever had the notion about starting a collection of “aloha wear,” this is the place to do it.

Little known fact: Hawaiian shirts are highly collectible, and some of the more rare ones from the 1920s and 30s can fetch thousands of dollars (and you can see some of these – and even buy them – at Bailey’s Antiques and Aloha Shirts).

Footwear: In Hawaii, they are called “rubbah’ slippahs” … elsewhere, “flip-flops” or “zoris.” Whatever you call them, “pack ‘em if you got ‘em.” If not, look to buy some when you arrive. You’ll have about a zillion choices. If you are planning some hikes, well, you know what to do. Just be assured that your feet will get wet.

Sun Protection: You’ll have TWO zillion choices on this one, but if you are serious about protecting yourself, use a minimum of 30 SPF.

When buying sunscreen, be sure to double check the ingredients to make sure that it doesn’t contain chemicals such as oxybenzone and octinoxate. Hawaii has introduced a ban on these sunscreens to help protect against coral bleaching and marine life, but some companies will still use labels such as “Reef Safe” or “Reef Friendly”. Unfortunately these labels aren’t reliable as there is no agreed upon definition and you may even want to consider buying a swim shirt or rash guard, which are more effective.

Pro Tip: Look for sunscreen varieties that hold up in water.

Wet Bag: Hawaii banned plastic bags a while back, so it’s handy to have something to throw your wet beach gear, muddy trail shoes, or if you’re like us – to pick up any trash that you might find along your journeys.

Top Tips for Visiting Oahu

  • Embrace Aloha: It's why you're coming right? So wind down, be patient, be kind, see and respect others and the land and you'll take home much more than a suntan.
  • Respect the Ocean: Even for strong swimmers the surf in Hawaii is stronger, with waves that break right on the shorebreak and powerful tides. Always keep one eye on the ocean and give the lifeguards a break and follow any guidance.
  • Rain: It’s perfectly normal for it to rain somewhere and at any time in Hawaii every single day, but it can arrive and depart all within 20 minutes. However, you might run into a storm that lasts all day. So if you have a little extra room, try to bring along a lightweight rain jacket. Which brings us to…
  • Rental Car: Never leave the windows or top down in your rental car, no matter how glorious the weather. It can be absolutely cloudless for hours on end, then suddenly cloud up and rain within minutes.
  • Irregular Cell Service: Some carriers have better coverage than others on Oahu. For your first “circle island” trip, proceed knowing that you might enter areas with little or no coverage.
  • Take Cash: If you are touring around the island, Hanauma Bay Parking, some shrimp truck vendors and fresh fruit stands don’t take credit cards.
  • Bring Hand Towels & Mints: Yup those shrimp trucks have garlic. A lot of garlic.
  • Bring Binoculars: Great for close up views of wildlife, cliffs and surfers at North Short beaches.