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  • Jack Solomon

Ultimate South Shore Oahu Road Trip Guide

Updated: Jul 9, 2018



Traveling to Hawaii, eh? Lucky you!


Oahu may be a small Island in the middle of the Pacific Ocean, but don’t let that discourage you– you can still have the road trip of a lifetime! But where do you begin?


South Shore Oahu


Despite being a small Island, only 44 miles across at its longest, Oahu is still often divided into four segments: North Shore, South Shore, Windard (East) side, and Leeward (West) side.


As iconic as the North Shore is, the South Shore offers just as much to explore, see, do, and eat!


As a local that grew up here in Hawaii, I’ll give you my best personal recommendations and more in this guide for the ultimate road trip through Oahu’s South Shore and Windward Side.


Best Local Food of South Shore Oahu


Oahu’s South Shore is a great destination for travelers who want to experience local Hawaiian cuisine; whether you want to try something new or eat something familiar, your tummy is sure to thank you!


Before you head out from Waikiki, make sure to stop by the neighborhood of Kapahulu to try some authentic Hawaiian food. I recommend you try kalua pig. The pork is tender and flavorful, and a must-try if you haven’t had it before. It’s served in all kinds of creative ways: in tacos, with rice, or even with cabbage! Kono’s has the best kalua pig on the island in my opinion.


For the seafood fans reading this, you have to try poke (pronounced poke-eh). It’s a Hawaiian staple made with raw, cubed ahi tuna. There are all kinds of flavors, but the most popular are spicy mayo and shoyu (soy sauce). Most people get poke bowls, which is just a scoop of poke (about 1/3 of a pound) over a bed of hot white rice. Most supermarkets like Tamuras, Foodland, or even Whole Foods have high quality poke.


For fans of food trucks, Sandy’s Beach hosts a cohort of food trucks right in the parking lot! You can find everything from Acai Bowls to Shawarma, and even some local Hawaiian dishes. I recommend you give Shaka Bowls a try for fresh acai bowls and poke bowls!


Acai Bowl with Fresh Fruit

If you have a bit of a sweet tooth, Waimanalo town has you covered! Dave’s Ice-cream is an iconic creamery with a ton of unique, Hawaiian flavors including taro, mango, and haupia! For those that want a cold, sweet treat that’s a bit healthier, visit ‘Ai Love Nalo for their vegan soft serve, smoothies, and other delicious vegan delicacies.


Finally, I highly recommend that you try kulolo, a simple, savory Hawaiian desert made from pounded taro and coconut milk. It’s not super sweet, but it’s healthy, delicious, and all natural! Waimanalo Market (right next door to ‘Ai Love Nalo) gets fresh kulolo flown in from Kauai twice a week!


Must See Sights of South Shore Oahu


There’s so much to see on Oahu’s South shore, but there’s no reason to be overwhelmed– I’m here to recommend my personal favorite destinations for you to check out!


On your way towards Oahu’s Windward side you’ll have an extremely scenic drive. While I recommend stopping at multiple scenic lookouts, there’s one in particular you should seriously consider– the Halona Blowhole. From the lookout you can get a great vantage point of Eternity Beach and the blowhole adjacent to it. The blowhole was formed when a lava tube collapsed. On days with rough seas you can watch as ocean water shoots up spraying dozens of feet in the air like a geyser!


Just past the blowhole is Sandy beach. The shore break here can get really gnarly (big, scary) in the summer and it’s thrilling to watch locals bodyboard and bodysurf waves so wide open that you could drive your car through them! I highly recommend against going in the water when there are waves, but the beach is really nice and it’s fun to watch those who are daring enough to surf the dangerous waves. From the beach you can get a nice view of Koko Head crater, and you can even enjoy a bite or two from the local food trucks (see above).


Sandy Beach with view of Koko Head Crater

As you continue to drive, the Eastern tip of the island, Makapu’u point is absolutely gorgeous. Makapu’u beach sits just North of the point and has a great view of the point. Also, the lookout provides a perfect vantage point of Rabbit & Shark Fin Island, two tiny islands off the coast!


Just past Makapu’u is the town of Waimanalo. It’s a country town with rich Hawaiian roots and a strong sense of Aloha. You’ll find uncles and aunties (respectful name for locals older than you) on the side of the road with a tent selling plate lunches, strangers helping strangers pull out of cramped parking lots, and signs for freshly hunted pig! If you want to see what Island life is really about, take some time to stop through. Oh, and don’t forget to throw a shaka or two!


In the town of Kailua lies Lanikai beach. During weekdays the beach can be relatively empty. It’s a gorgeous white sand beach and the perfect location to go swimming, snorkeling, or even kayaking! You’ll need to street park, but there are plenty of side streets available to do so. If you want to spend your day at the beach, I highly recommend Lanikai!

Finally, if you want a good vantage point of the entire windward coastline then stop by the Pali lookout. It sits high in the mountains and overlooks a large portion of southern Oahu. There is a small fee to park, but the experience is well worth it. The wind can get quite strong, so maybe leave your favorite hat in the car!


View of Pali Cliffs and Windward Oahu from Pali Lookout



Best Activities of South Shore Oahu


If sightseeing doesn’t provide enough excitement for you, don’t worry! There’s plenty to do on Oahu’s South Shore from surfing, to hiking, to snorkeling. Whether you’re by yourself or with your family, I have a few suggestions for some unforgettable experiences.


For the hikers reading this, there are two main hikes you should consider.


My favorite hike with a view is the Hanauma Bay Ridge Hike. It’s relatively short, but it’s fairly steep and you’ll certainly get some exercise! The start of the “hike” is paved, but there are plenty of offshoot trails that go “off-road”. It’s tame enough to bring the whole family, and you’ll often see locals walking their dogs! The trail provides a scenic vantage point of the Bay, Koko Head, Hawaii Kai town, and Honolulu off in the distance.

If you arrive outside of Hanauma Bay’s operating hours you’ll need to street-park on Nawiliwili St or Polihale Pl and walk.


Hanauma Bay is also a beautiful beach for snorkeling. After being educated about protecting the fragile reef ecosystem, you can rent masks, snorkels, and fins to explore the marine life– there’s plenty of colorful fish! Remember, Hanauma Bay is closed on Tuesdays.


Another hike you should consider is the Diamond Head Crater hike. You actually start inside of the crater and hike about a mile to the top of the ridge. It’s a relatively easy hike and most of it is paved. At the top you’ll have an amazing vantage point of the coastline below as well as the city of Honolulu. You do have to pay to park, but it’s only $5 per vehicle.


Diamond Head Crater

While on the subject of activities to do on Oahu, I can’t forget to mention the main activity Hawaii is known for– surfing! There are dozens of surf spots along Oahu’s South Shore, but I’m only going to list my top recommendations in this article.


If you’re a beginner, then there really is no better place to learn than Waikiki. The waves are usually pretty small and you can rent surfboards right on the beach at an affordable price. You can even take a surfing lesson if needed.


However, if you’re a little more experienced I highly recommend you check out Diamond Head Beach Park. It’s an iconic surf break and a local favorite. You’ll still need a board so I recommend renting one for the day. But, before you rent you might want to check out the surf report and make sure it’s not too big (or too small) for you! There are multiple parking areas overlooking the surf break, but they can tend to fill up by the end of the day (especially on weekends), so try to get there early on in your day!


When the waves are flat in Hawaii, many locals like to go cliff jumping to get a rush. Some cliffs here get as high as 50 or 60 feet, but that’s a little high for me. One spot that most people can handle jumping off is China Walls. It’s location is a bit strange (in a subdivision), but street parking is usually easy to find. The cliff is a popular fishing spot and even a surf spot when the surf is really big. Depending on the tide, the jump is between 6 and 8 feet. I would only recommend jumping here when the waves are completely flat. As always, be careful when jumping in and climbing back up the rocks. Otherwise, have fun!


Finally, if you want to get up close and personal with a waterfall, then you need to check out the Judd Trail and Jackass Ginger waterfall! The trail itself is beautiful– you follow a stream through the jungle and even a bamboo forrest. The Jackass Ginger swimming hole sits at the bottom of a small waterfall, and it’s right in front of a house (lucky them, huh?). You can cliff jump at the waterfall, although I’d be cautious and see how deep the pool is before jumping in as the water level can vary depending on how much it has rained. If you do decide to cliff jump, there’s also a rope swing hanging from the trees above!

No matter what you decide to do, I’m sure you’ll have a great time! Using these suggestions along with Shaka Guide’s South Shore Oahu Tour, you’ll be all set for the perfect road trip.

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