Roam 2 Ways / Oahu, Hawaii
GO: April - early June, September - November
Oahu has great weather year round; in fact, many people believe it has the best weather of all the islands, with average temps ranging from the low to upper 80’s, year-round. Hawaii really has only two seasons, both of them are warm and tropical. The summer (Apr-Oct) is the dry season, and the winter (Nov-Mar) is the rainy season. Despite the rain, the high tourist season falls during the winter months. Although, when it does rain it tends to be in quick gusts and concentrated on the east side of the island. While it may be rainier in the winter, it’s the ideal time for surfing and whale watching.
There are many direct flights to Oahu’s Honolulu International Airport (HNL), which is the main airport servicing Hawaii. From Minneapolis (MSP) and other major Delta hubs, you can fly direct to HNL. If you leave early in the morning you will arrive on the island of Oahu in time for dinner, making the time change a fairly easy adjustment. The direct return flight is a red-eye so don't plan anything (besides sleeping) on the day you get home. Consider flying overnight on Sunday, instead of Saturday as it can often save you quite a bit of money. You’ll want to rent a car to explore the island during your trip, and the Honolulu airport has the most affordable rates.
Oahu is the third largest Hawaiian island and one of the most popular vacation destinations in the world. The island is carved into five dynamic regions, all very diverse. Honolulu and Waikiki are the most popular and tourist-dense, but travel a little further and you will find that each region has its own unique appeal. From the laid-back surf towns like Haleiwa on the North Shore, to The Windward Coast where you will find vast landscapes and the picturesque Lanikai Beach. Don’t forget Central Oahu where you can pay your respects at Pearl Harbor and tour the well known Dole Plantation. With lush scenery and serene beaches everywhere, the island boasts an abundance of natural beauty, including the Leeward Coast which lies at the foot of the Waianae mountain range and boasts the luxurious resort area, Ko Olina.
Jackie Just, Work and Play Trip
Jackie lives in Minneapolis with her husband of 17 years and their two boys. Much of her time is spent shuffling her two athletes to games and practices, so when they find an opening between sports seasons they seize the opportunity to travel. Needing some sun and a little escape, she did just that, and joined her husband on a work trip to Oahu. While he was stuck in a conference room, she learned to make Lei’s, relaxed poolside, took walks through the lush botanical gardens and set off solo to explore the island. At night they met up to taste Hawaii’s spectacular food scene and seek out the best Mai Tai to watch the sunset with.
Hawaii has the highest per capita consumption of Minnesota made SPAM in the US. It’s so popular that it is sometimes referred to as "The Hawaiian Steak". There is even an annual Spam-themed festival on Oahu that takes place every spring, known as the "Waikiki Spam Jam.” Local chefs and restaurants compete to create new Spam-themed dishes, which are then sold in a massive street fair on Kalakaua Avenue in Waikiki. If you are there in April you can’t miss it, so just join in the fun. The Spam musubi is worth a try, consisting of a slice of grilled Spam on top of a block of rice, wrapped together with nori, it's like Spam sushi!
Sheraton Waikiki / reservations
The highlights of this property begin with the sweeping views of Waikiki beach from our balcony, as well as the on-site cafe that allowed me to enjoy those views every morning with Hawaiian sourced Kona coffee and a chocolate croissant. The thoughtful and comfortable nooks around the property make this large hotel feel much more intimate. Additionally, the vast infinity pool with complementary floaties allows you to sit, relax and glide around with an umbrella drink. Beach chairs are available to rent, so we just threw down our towels in the sand. Alternatively, there is plenty of complimentary seating by the pools and on the lush hotel grounds.
If you want to stay on Waikiki another hotel option is the The Royal Hawaiian next to the Sheraton. This historic pink hotel is lovely and seemed to offer more beach space. A third option to consider is the coveted Moana Surfrider with it’s private beach and freshwater pool.
Rtip: If you are looking for a smaller property in Honolulu with more of a boutique feel, take a look at ‘Alohilani Resort (60 steps from the beach) or the Surfjack, (just a short stroll from Waikiki). If you want to escape the hustle and bustle of the city, consider staying on the more laid back North Shore. People rave about the Turtle Bay Resort but they also have many great home rental options in that area.
Personally and professionally I find myself surrounded by flowers and plants, so it was only natural to explore the flora and fauna of this lush paradise. I particularly enjoyed an afternoon at the Wahiawa Botanical Gardens learning the craft of Lei making with talented local artisans. If this interests you, check out the Friends of Honolulu Botanical Garden’s events page for locations and seasonal offerings.
Savor the Sunrise & Sunset
With a 5 hour time difference and a little jet lag, it’s easy to catch the sunrise over the mountain and see the early surfers catching some waves from your hotel window. Spend the day at Waikiki beach and make sure you stay for the sunset. If you find yourself on the west side of the island during your travels, do yourself a favor and find a beach to watch the sun say goodnight. If you are on the North Shore, the aptly named Sunset Beach faces slightly west and is a great place to stop.
Halfway between Japan and the mainland United States, Pearl Harbor and its monuments are a welcoming place where visitors and survivors can reflect on the events which led to the World War II. While certainly one could make a full day of this historic location, we chose an edited version specific to the USS Arizona Memorial. Accessible only by a short boat ride, the memorial straddles the sunken hull of the battleship. Because Admission to the Arizona Memorial is free, it is usually fully booked by mid-morning. We chose to arrive at 6:30am before the visitor center opened as we were easily up that early due to the time zone. The experience lasted an hour and 15 minutes and included a 23-minute documentary on the history of Pearl Harbor. If you want to skip the lines, book your ticket on-line and in advance.
Take a Drive
Rent a car for the day, download the Shaka Oahu app and pick and choose the places you want to visit along the way. The app’s audio guides are locals who tell you stories about Hawaiian history and culture while giving easy driving directions from location to location. I recommend the circle island option and plan for 4 – 8 hours depending on how many stops you have time to make. Some of my favorite stops were the Byodo-In Temple, and Kualoa Ranch, where Jurassic Park, 50 First Dates, and the original Karate Kid II were filmed and Kahana Bay Beach, where we got lucky and had the entire stretch of sand to ourselves.
Laniakea Beach (Turtle Beach), North Shore
On your way to exploring Haleiwa Town make a stop at Laniakea Beach and take in the beautiful ocean views. If you’re lucky, you may catch a glimpse of a few Green Sea Turtles sunbathing in the sand. Keep in mind this area can get congested between 11-2. Instead, many people avoid the crowds and make the trip for a very memorable sunrise or sunset.
Kahuku Farms Café, North Shore
Kahuku Farms Café is true farm to table. The large majority of ingredients on the menu are from their own farm. Those that are not, are sourced by a neighboring farm in the area with similar “beyond organic” farming practices. My favorite was the Grilled Banana Bread and Papaya Power smoothie which is complimentary if you also take their 30-min smoothie tour, which we highly recommend as it gets you up close and personal with many of the local fruit grown on Oahu. Make sure to stop by their store for culinary and bath and body souvenirs.
Food Trucks, North Shore
The shrimp trucks on the North Shore are a can’t miss! Giovannis garlic shrimp gets all the press and their buttery shrimp is good, but I say skip the long line (and all of the trucks) and head straight to Kalbi on Fire’s yellow graffiti food bus. Order the Korean chicken & beef combo platter — it’s so good I still think about it. Another great option in this cluster of food trucks is Kalenas Hut, you’ll likely smell the teriyaki chicken from the parking lot and you’ll probably see the owner himself with a huge, contagious smile grilling up your meal. The chicken/rice/cabbage is the way to go at this unassuming food stand.
“We drove 40 minutes twice on our trip for the crave-able chicken at Kalbi on Fire.”
Leonard’s Bakery, Honolulu
For over 65 years, Leonard’s Bakery has been serving sugary, delicious malasadas - a traditional Portuguese doughnut without a hole. Order with a filling if you’d like, but be sure and order one made fresh and hot! They pair perfectly with a cup of coffee and are only a little over a $1.
Roy’s Waikiki, Honolulu
You’ll find great service, great cocktails and great sushi at Roy’s in Honolulu. Eat inside if you want to be fancy or find a spot at the outdoor bar and keep it casual. Oh, and ask your server to guide your experience. Our server recommended the Crispy Zucchini (Seared Bao Bun, Pickled Cucumber Relish, Soy Reduction). We would have never ordered this on our own but was a favorite for sure!
Take a good hat. Currently, my favorite style is the Tula Somerset with hand woven palm and grosgrain ribbon. It’s also UPF 50+ and nice and sturdy to travel with. Please protect the environment by bringing along reef safe sunscreen. It has recently been discovered that certain chemicals from sunscreen are harming the coral reefs and it’s an obvious concern among locals. Read more about the bill that was passed to protect Hawaiian ecosystems here. Finally, wine is expensive on the island. If you can, pack a couple bottles in these great Jet Bags.
Jennie Sewell, Bi-Annual Family Beach Trip
Jennie is a Minnesota native, but calls a bubbly drink a "soda" because she grew up in Florida. She is a designer and daydreamer at heart. By day runs her photography business, tries to keep her two kids and husband from eating Doritos at every meal, and by evening (preferably with headphones and a glass of wine) pretends that she is a painter. She believes the best part of living in the Minnesota is enjoying the beautiful spring - fall months near a lake, and traveling as much as possible during the long winter months. Her Bi-annual family trip to Oahu includes 17 people- two grandparents and three families with kids ranging from 6 to 16 years old. They rent two vans and a convertible, and "fight" over who gets to ride in the cool car.
Marriott’s Ko Olina Beach Club / Reservations
We stayed in a time-share unit at the Marriott in Ko Olina on the west side of the island. Here you will find a two-mile stretch of beachfront properties that are lined with a series of large lagoons. They were carved out years ago to create a natural fresh water flow and lava rocks were placed to break the waves, resulting in an idyllic ocean swimming, snorkeling and beach space. Within this stretch of property there are beautifully manicured lawns, palm trees and a paved sidewalk connecting the Aulani Disney Resort, The Four Seasons Resort and also a few independent condos and villas that are available for rent. The well groomed path is lit at night (with bathrooms and garbage cans along the way) creating a very safe and kid-friendly atmosphere. One of my favorite features here is the pool. It is especially fun for kids with it's multiple pools flowing into each other, water falls, tunnels and even a slide. We love swimming at night with lava rocks and tropical plants looking extra awesome when they are lit up in the evening.
“Only 30 miles from Waikiki, Ko Olina seems worlds away from the hustle and bustle of the city.”
Surf Lessons, Waikiki
One of our favorite activities was to take surf lessons with Surf HNL on Waikiki Beach. Kids of all ages can ride tandem with an instructor if needed. There are also lessons offered in other places around the island, make sure to ask what the student to teacher ratio is, and if they offer a photo package that includes photos and/or video of your group during your heroic attempts and epic wipe-outs.
Watch the surfers at Pipeline Beach, North Shore
Be sure to head up to the North Shore to watch the surfers. You can check the local info to see which day will have the best surf-able waves. Pipeline Beach (Banzai Pipeline) is a beautiful and mesmerizing patch of ocean with aggressive riptides and potentially huge swells. It's not a place for kids to play in the water, but the expansive beach is a great place to hang out and watch the surfers brave the giant waves. Near Pipeline Beach, stop in the small town of Haleiwa known for it’s food trucks and great shops, like Guava Shop. Here you’ll also find Motsumoto famous for its shave ice (there's no d!). My kids especially like it with ice cream in the center, but you can customize all sorts of options with dozens of flavors ranging from Lilikoi and Ume to Pickled Mango and White Cake.
Waimea Valley and Falls, North Shore
We enjoyed visiting Waimea Valley and Falls (don't follow GPS to the "Falls", be sure to go to the "Valley"). The one mile stroll through the botanical gardens was very easy, perfect for young kids or if you are looking for a leisure walking hike. Wear your bathing suit and bring a towel because at the end you can jump into the falls. It is chilly and getting in and out takes some dexterity, but everyone had a great time. Bring a few bucks to tip the lifeguard for the use of their complimentary life jackets.
Rtip: Make a stop at Waimea Bay before your hike to the falls, the earlier the better as the parking lot fills up fast and there is limited street parking. This beach is a favorite of Oahu locals, not only because of the calm waters, but for the rush of launching off the huge rock into the ocean below. Don’t forget to stop for a ceviche poke bowl at the nearby Aji Limo Truck when you’re in the area.
If you are an adventurous eater or chef, make a trip to Waipahu Festival Marketplace, an inexpensive Japanese open market for all kinds of seafood, meat and veggies. Grab lunch while you wait for your fish to be butchered (they will also clean it and put in on ice for you). Bring cash and know that there are multiple vendors, so each will need to be paid separately.
For me, I’ll never miss a sunset. Grab a cocktail and sit back and enjoy every drop of that golden light.
North Shore Tacos
I am a sucker for a good food truck, and the North shore does it right. 'North Shore Tacos,' near Pipeline beach even accommodated my son's shellfish allergy. With so many delicious options, I wish we were there longer to try the various food options like Jackie’s aforementioned favorites.
My Cafe, Kapolei
Near Ko Olina and our hotel is 'My Cafe' an intimate casual breakfast or lunch spot serving fresh local ingredients. They are known for their killer pancake flight but I had a smoked salmon everything bagel that was pretty spectacular.
Rtip: Another legendary place for breakfast is at Bills Honolulu where you can enjoy ricotta hotcakes with banana and honeycomb butter.
Mina's Fish House, Kapolei
From our resort we could walk to the Four Season's resort to dine at "Mina's Fish House" (open to the public). It is a beautiful atmosphere, nestled very close to the ocean and every table in the outdoor seating space is lovely especially at sunset. We shared a beautiful full fish (served de-boned) family style.
Dole Plantation, Wahiawa
You may want to visit the Dole Pineapple Plantation for the freshest pineapple right from the source. Their pineapple ice-cream ( or Dole Whip) is a fan favorite with our group.
Island Vintage Coffee, various locations
This popular coffee brewer has a chain of locations around Oahu and Maui and we were lucky to have one close to our resort. This is a classic go-to for a delicious Hawaiian cup of Joe. They also have terrific açaí bowls if your hungry.
Rtip: If you are downtown Honolulu and you need a healthy bite or a pick me up, check out ARVO cafe inside of botanical garden, Paiko with it’s flower bar, pop up workshops and great home decor!
Lava Tube, Waikiki
For a fun, kitschy tiki bar with a great Mai Tai’s you must stop here. This little, tucked away bar has terrific service, and the Mai Tai specials are only $5.
Kona Brewing Company, Honolulu
If you like Kona Brewing Company then you should stop for an ice cold Big Wave Golden Ale at their restaurant on the docks of the Koko Marina. If beer is your thing you may want to add the Waikiki Brewing Company to your list, people rave about their handcrafted house beer.
I always over pack, but so far I have never ended up needing jeans or a jacket. The vibe is laid back and I mostly end up wearing swimsuits, sandals, light sundresses and shorts. I listen to audiobooks like it’s my job, so I make sure to download a few before I go on vacation. I love Crewcuts for kids swimwear and I always make an appointment at Nani Nalu in Minneapolis to get fitted for the best swimsuit for my trip.
Click our link here to see everywhere we recommend you visit in Oahu.
Tell us which sister’s itinerary you prefer in the comments below.