Growing up in Honolulu, there was little I found more exciting than the glamour and energy of Waikiki. I was blessed to grow up right in the thick of it, and there was no shortage of fun to be had! One of the things that sets Oahu apart from other island destinations is the glittering playground that is Waikiki, and a few minutes away by car, you can feel like you’re in another world.

One of my favorite things to do on Oahu has always been to hop in a car and drive around the island. I have many fond memories of this, and I can track my teenage years and beyond by these island excursions. They start out in my early teen years with my dad, with him pointing out his favorite beaches (and sometimes turning around and driving by them several times), while my younger brother and I complained in the backseat, of course. These family trips eventually gave way to me and my best friend spending a Saturday cruising the island while we talked about music, school and picked out places for our future weddings (spoiler alert: we both got married in Hawaii!). As time went by, first dates were spent at various scenic lookouts, friends new to Hawaii were introduced to the magic of the “circle island drive”, and finally, early in my 30’s and no longer living in Hawaii, I was back in the car with my dad – this time while he and I both showed my soon-to-be-husband our favorite beaches.

There is something magical about this drive – by the time you wind your way back “townside”, and catch that first glimpse Diamond Head glowing in the afternoon sun, it’s hard to explain it, but it is as if your soul has been recharged!

While the Island Exploration Tour has always been one of the most popular activity choices of our Oahu-based All Inclusive Packages, renting the Jeep or Convertible for the day and driving the island is one of my favorite recommendations for our clients. Both the tour and rental car each have many benefits, but today I am focusing on driving the island on your own. This may be the best option if you want the freedom to personalize where and when you make stops, control the length of your day, plan on stopping at certain places for a swim, hike or meal, or prefer the intimacy of just you and your travel companion/s. Below, I am going to outline a sample itinerary for you – this is the route I prefer, and the stops I like best, but by no means is this an exhaustive list – the possibilities are endless! So, buckle up, and let’s take a drive in one of the prettiest places you’ll ever see….

Departing from Waikiki’s sunny south shore, we head east, towards Oahu’s lush, green-drenched Windward side, me and my dad’s favorite part of the island. From there we curve our way up to Oahu’s famed North Shore, a mecca for surfing enthusiasts, and my husband’s favorite side of Oahu. We then drive through pineapple fields, with a stop at Dole Pineapple Plantation, if you like. Afterwards, we will begin to drive south, back towards Waikiki. Listed below are places and locations you will pass on this drive, and an asterisk notates the ones I recommend are worth a stop. These locations are listed in the order you will come to them, if you head east towards Diamond Head as you leave Waikiki. You will receive a detailed road map when you rent your car. I suggest you head out immediately after finishing breakfast to give yourself plenty of time to enjoy the day. It takes about four to five hours, give or take, to complete your loop, including stops. Be sure to leave plenty of time to account for possible traffic (in the winter months when the North Shore swells are in, the 2-lane road near Sunset Beach can come to a standstill due to surfers and wave-watchers, and depending on the time of day, the freeway routes home can be congested) and to stop everywhere you want, with enough time to turn in your rental car and make it to your dinner that evening.

Just a quick note. The residents of Hawaii live every day with the spirit of aloha, and they take tremendous pride in sharing their beloved islands with the thousands of visitors who come annually. Please reciprocate this aloha by being respectful of their islands, and never park or walk through private property. Some locations are in residential areas, and have extremely limited street parking, so if parking isn’t available, you may have to skip some of these stops. Please don’t park in private driveways or yards, or cause excessive noise especially during early morning or late evening hours. Also, please remove any trash you bring in. Mahalo!!

• KAPI’OLANI PARK

• DIAMOND HEAD LIGHTHOUSE

• DIAMOND HEAD LOOKOUT*

• KAHALA AVENUE ESTATES

• WAI’ALAE BEACH PARK*

• HAWAII KAI LOOKOUT

• HANAUMA BAY LOOKOUT* (If you are going here on another day, skip this stop)

• HALONA BLOW HOLE LOOKOUT* (Eternity Beach is to the right of the parking lot)

• SANDY BEACH

• MAKAPU’U LOOKOUT*

• MAKAPU’U BEACH* (worth the walk if you plan to stay awhile, otherwise the lookout will suffice)

• RABBIT ISLAND

• WAIMANALO BEACH PARK* (my dad’s favorite!)

• SHERWOOD BEACH* (turn right on Aloiloi St. Street parking only)

• WAIMANALO TOWN* (Dave’s Hawaiian Ice Cream is located in a strip mall right along the road. Worth a stop if you’re hungry. Try the green tea flavor!)

• KANEOHE TOWN

• HE’EIA STATE PARK*

• HE’EIA KEA BOAT HARBOR

• HYGIENIC STORE* (nothing to see here, just a convenience and general store, but if you need to stop, do it here and not the “big name” chain store across the street. #supportlocal. Stands in parking lot usually selling huli huli chicken and pickled mango.

• BYODO-IN TEMPLE* (you will need to back track a little, but worth it! $5 adult and $2 child admission. Afterwards, head northeast, back to Kamehameha Hwy)

• SUNSHINE ARTS GALLERY* (Charming little gallery showcasing local artists. Shipping available)

• SUNRISE SHACK* (Yellow shack along the road selling food, coffee and souvenirs)

• TROPICAL FARMS – MACADAMIA NUT OUTLET* (THE place to get mac nuts and coffee! They offer seven different mac nut flavors, as well as a wide selection of Kona coffees and island goodies, complimentary samples offered. A must see!)

• KUALOA RANCH

• KUALOA REGIONAL PARK* (Best place to view Mokoli’I, also referred to as Chinaman’s Hat)

• AHUPUA’A ‘O KAHANA STATE PARK* (Beach park located by Kahana Bay, my personal favorite. The Beach Swing is located nearby)

• PUNALU’U BEACH

• HAU’ULA BEACH PARK

• POLYNESIAN CULTURAL CENTER

• LA’IE POINT STATE WAYSIDE LOOKOUT* (Trust me on this one)

• KAHUKU TOWN* (On the right, near the Kahuku Sugar Mill, you will see a cluster of Shrimp Trucks. They are all pretty similar. Try the garlic shrimp plate lunch, it’s an island favorite!)

• TURTLE BAY

• SUNSET BEACH*

• SHARK’S COVE

• PU’U O MAHUKA HEIAU STATE HISTORIC SITE* (Largest heiau (religious site) on Oahu. Impressive views of Waimea)

• WAIMEA BAY (Dreamy beach popular with locals and visitors. If you plan on staying awhile, it is worth a stop. Also, home of the famous Waimea Rock)

• PAPA’ILOA BEACH*

• HALE’IWA TOWN* (Quintessential North Shore surfing town. Eclectic shops, restaurants and the famous Matsumoto Shave Ice. A must stop!)

• WAIALUA (Former sugar mill town. Worth a drive-thru, at least, but you can also take a tour at the historic Waialua Sugar Mill.)

• MOKULE’IA (Site of several filming locations for ‘Lost’. Scenic drive to Ka’ena Point, where road ends. Must back track towards Kamehaha Hwy at this point)

• DOLE PLANTATION* (Explore pineapple varieties, try the pineapple maze, or ride the pineapple train. Extensive gift shop selling fresh pineapples (shipping available), souvenirs and famous Dole Whip.)

• WAHIAWA TOWN (Once a sleepy North Shore town, has experienced a revitalization in recent years.)

• DRIVE TOWARDS HONOLULU (From here, the fastest way back to Waikiki will be to take the H2 Freeway, which will then connect to the H1 Freeway. You will pass through the towns of Pearl City and Aiea. Be on the lookout for a glimpse of Aloha Stadium along the freeway in Aiea!)

• PALI LOOKOUT* (This is definitely out of the way as you head home, however worth a visit. From the H1, take the Pali Exit and head mauka (mountainside). This will be left, if you are driving towards Waikiki from Aiea. After you leave the lookout, be sure to take the exit heading back to Honolulu. From here you can get back on the H1 Freeway heading east, or you can drive through downtown Honolulu, home of Chinatown and the State Capitol, to name a few. Please be aware that most attractions and businesses downtown close between 4:00 – 5:00pm., Monday – Friday.)

• RETURN RENTAL CAR IN WAIKIKI, AND ENJOY YOUR EVENING!