Winter Misery Escapes: Hawaii Edition
A crowdsourced guide by members of our OT community!
Hi friends,
Not sure about you all, but we’re very much in the midst of a false spring in Portland. I get tricked every year, and start to think it’s really real, and then find myself BACK in what feels like winter misery, but worse! Allegedly it’s going to snow this week? Ok, dramatic of me … but this is really where a round two of warm weather escapes starts to feel essential! Plus, spring break week is on the horizon, so know we all have vacay on the brain (right? Not just me?).
I went to Maui in January and had such a nice time, albeit mellow with a five month old baby. Rather than bore you with a recap of my very low key trip, I decided to do you all one better and consult five friends of mine who are basically experts on what to do on the various islands … and I’m excited to share a very extensive (yet non-comprehensive) OT crowd-sourced guide to Hawaii. 🤙🏼
Thank you to Chelsea, Darcy, Kara, Lauren and Leah for taking the time to share your Hawaiian favs with us!
Enjoy!
Rach
Before we get started, sharing guiding principles Chels pulled together for visiting Hawaii. Hawaii is a beautiful place with a rich history and a delicate ecosystem. Always remember: leave it better than you found it, be a contributor, not a taker; and spread ‘Aloha during (but especially after) your trip. 🩷
Maui
As I mentioned above, this vacation was definitely a simultaneously slower pace and more tightly scheduled (I know the parents of babies know what I mean) trip than we’ve taken previously. We had the intention of spending 95% of our time at the resort (you know the vibes … pool, beach, cocktail, nap, repeat), and that was what we did! We did venture out for a meal or two and one excursion (if you’re not whale watching in Hawaii during whale watching season, wyd?!), and it felt like the perfect balance. I was also a little nervous about the flight with Lonny, but we found ourselves in good company - plenty of fellow parents with kids of all ages all just getting through the day on that flight! It was such a special trip! I wasn’t brave enough to take her in the ocean this time, but am excited to visit some of the baby beaches when we go back.
Stay:
We loved the Fairmont Kea Lani. Perfect location, warm and helpful staff and great restaurants on property. I especially loved their take on the Mai Tai, and had a great massage at their spa. We loved taking Lonny in the pool and walking the path along the ocean. All of their rooms are suites, which also made things easier with le bebe.
We’d also considered the Andaz and the Grand Wailea, and have heard great things about both properties!
Four Seasons - according to Lauren, “the Four Season's brunch is delish and I swear you will always see some sort of obscure celebrity (we met Arnold Schwarzenegger & Pamela Anderson/Tommy Lee previously lol).”
Eat:
Da Kitchen for a yummy and casual plate lunch.
Lineage for dinner (a Chelsea rec I can confirm is fantastic! Amazing food and we felt so comfortable there with a baby with big feelings lol).
Plate Lunch Marketplace near the airport was a great find for post-flight starvation.
Monkeypod for their famous mai tai.
And a few more restaurants to bookmark courtesy of Kara and Lauren: Mala Tavern, Star Noodle, Miso Phat, Kihei Cafe, Fond, Sea House, Paia Fish Market, Tin Roof, Tamuras Poke, Tiki Tiki Thai, Mama’s, Spago’s, Nick’s, and The Fish Market.
Activities:
The last two times we’ve traveled to Maui we’ve gone on a whale watching tour through the Pacific Whale Foundation. It’s a magical experience!
The Road to Hana - when you rent a car in Maui, they make you sign a form that specifically waives your right to help from the car company should you decide to drive the Road to Hana and need assistance. Does this make you want to do it?! While it has a reputation for being dangerous in places, it is beautiful and scenic, with many roadside fruit stands and special places to pull off. The Seven Sacred Pools in Haleakala National Park is the destination at the end - touristy, but beautiful! If we were to do it again, I’d definitely consider booking a driver/guided tour to eliminate some of the anxiety.
O’ahu
Chelsea’s favorites! And may I suggest all martini connoisseur and novices alike follow her account, @weratemartinis? A woman of discerning taste!! Her recs are gold, plus she can back it up. Her husband is from Hawaii and she and her family have spent so much time in all over the islands, including getting married there! O’ahu recs courtesy of Chels below, in her own words:
Stay:
Halekulani: The best hotel in Waikiki. Modern, Elegant and quiet. Gracious old Hawaiian style and private location right on the beach makes this hotel an urban oasis. Don’t miss the 6pm hula dancers and Mai Tais at the House Without a Key outdoor restaurant and garden.
Kaimana: The Kaimana has been around forever, but had a refresh a few years ago and has become a new/old hot spot for visitors and locals.
Turtle Bay Ritz (North Shore): Newly acquired by The Ritz, this is the only resort on the North Shore of O‘ahu. We stayed here recently and had a magical experience.
The Four Seasons Ko Olina: A serene stay, as to be expected from The Four Seasons. Our best friend Zach works at the bar, tell him we sent you :)
Eat:
Leonards: An iconic institution and the best malasadas on the island. Eat them warm. Sometimes there’s a line at the location in town so go early.
Liliha Bakery: Get the coco puffs.
HiBlend health bar and cafe: Our go-to for smoothies and acai bowls.
Waiola Shave Ice: Get shave ice often. Try all the flavors.
Kalawpai Market: (4 locations on the island) We love to go for a casual lunch or pick up sandwiches and go to the beach.
Diamond Head Market & Grill for delicious plate lunch- great to take out and go down to the quiet part of Waikiki Beach for a little picnic.
Foodland; Don’t let anyone tell you different. This is the best place to get Poke. We’re partial to spicy ahi, shoyu ahi and kimchi tako.
7 Eleven! On the mainland, no one is suggesting you eat the food from 7 Eleven but in Hawaii … it’s GOOD. Here is where to get your spam musubi.
Drinks:
Skull & Crown Trading Co: Incredible tiki bar in Chinatown
Blue Ribbon Karaoke: Locals only karaoke spot. We went there for our wedding afterparty and it did not disappoint.
Hau Tree: in Kaimana hotel. Felicia the bartender here is world class.
Shop:
Single Double: Incredible vintage shop.
Salvage Public: Local designer and located in the South Shore Market that has a bunch of other great local brands. Worth a visit!
KaKa’ako: Super cute outdoor mall. Lots of local stores, coffee, small bites, etc. HERE. is my favorite store there.
Activities:
Shangri La: One of the most magical places in the world. The Shangri La Museum of Islamic Art, Culture & Design is in the former home of Doris Duke (icon) near Diamond Head. Guided tours are led out of HoMa and can be booked online in advance. Highly recommend
Bishop Museum: This quiet museum houses the largest collection of Hawaiian artifacts. A must-see to understand the Hawaiian culture that made Hawai‘i what it is today.
Beaches:
Ko’Olina: Four lagoons in the area. Open to the public but 1 & 3 share with hotels and resorts. You can’t bring umbrellas but there are some trees for shade. Perfect for babies and small children. (West Side)
Kailua Beach Park/Lanikai Beach: Crystal blue water. Perfect sand. (East Side)
Waimea Bay Beach: An iconic beach. The Eddie Is hosted here. Waves can get BIG and parking is limited but if you can go early, would recommend. (North Shore)
Kaua’i
Darc has spent a lot of time in Hawaii - and we actually went to Honolulu for her bach (truly epic). Grateful for her recap of her first visit to Kaua’i! And it goes without saying that I trust everything she says on any topic to be 100% true and accurate. No further questions, your honor.
Darc says: “We've always been Big Island people - but Kaua'i was gorgeous, chill, easy with kids! We stayed in between Poipu and Koloa on the Southern tip of the island. It is supposedly less rainy than up in Hanalei Bay or Princeville. There's a shared agreement among my family that we vacation for two reasons: eating and beachtime. Beachtime is obviously a little harder and shorter with kids, but we take advantage of our early morning wakeups to adventure and schedule long drives around nap times (like to Hanalei Bay Beach).”
Eat:
Eden Coffee: A sweet coffee truck located next to Kukuiula Market which has delish acai and smoothies at Anakē's Juice Bar inside. Also next to Da Crack Mexican Grinds.
Koloa Fish Market: Perfect for picking up lunch post-beach.
Hamura Saimin: Located in Lihue and incredible!!
Uncle's Shave Ice: My daughter has discovered the world that is shave ice. Specifically rainbow! We also loved the ice cream at Lappert's.
Caba: Discovered this truck on one of our naptime drives in Hanapepe.
Beaches:
Lydgate Beach Park: We love a baby beach and this was the perfect drive - and we got to stop at our beloved ABC Store/Island Gourmet on the way.
Poipu Beach Park: Also great for kids (a playground on-site!), good for snorkeling, and Puka Dog is right there for an easy lunch. And there were sea turtles!
And to close with a parent pro tip: “I'm also all about renting equipment while you're there! We used Nana's Baby Gear and Equipment and they set everything up for us. Made me want to cry lol. We usually also rent the car seats when we pick up the rental car, which sometimes they've seen better days … but one less thing to travel with!”
Hawaii (The Big Island)
Ok, dear readers, this is where the recs really pop OFF. Kara, Lauren and Leah have all vacationed here with their families since the dawn of time (not really but basically), and Lee also got married here. Trust, these are incredibly thoughtful and vetted suggestions.
Leah on The Big Island:
“The Big Island holds a special place in my heart for many reasons, and I often feel it’s overlooked by travelers planning their Hawaiian getaway. To me, the Island of Hawaii is a hidden gem. The contrast of black lava rock against the crystal-clear water is absolutely breathtaking. The island offers an incredible variety of climates, and from the summit of Mauna Kea, you can stargaze like nowhere else. Witnessing the active Kilauea volcano is a once-in-a-lifetime experience! Plus, it’s the only island with both green and black sand beaches. There’s so much history here, too – this island was once the heart of Hawaiian royalty. And for coffee lovers, this is the ultimate destination!”
Stay:
A mutual fav across all three - Mauna Kea Beach Hotel! Everyone loves the hotel’s beauty and history, private and swimmable beach (with spinner dolphins and amazing snorkeling!). Ordering the famous Frederico cocktail at the iconic Hua Tree is a non-negotiable.
Lauren says: “Classic old school Hawaii vibes - a Rockefeller resort that is so special and magical with tons of history. The entire hotel is open air, so it always has a cool breeze and the sound of birds blowing through it. The beach is a calm cove with crystal clear water. Very family friendly but no 'riff raf' - these are well behaved children (lol). Everyone spends time at the beach - one of those few hotels where the pool is pretty unused! At night, massive manta rays feed in the cove which is incredible to witness” She also recommends Mauna Kea’s Copper Bar - perfect for watching hula dancers at sunset, and Manta for those who care more about the 10/10 views than an affordable and/or particularly delicious meal. ;)
And for our fellow hotel merch and points lovers, Kara says: “the cult following is real (spot their signature orange plumeria swag everywhere from Tokyo to Paris on guests who have visited). But don’t worry, you don’t need an insider invite—it’s a Bonvoy property, so you can even stay on points.”
Holualoa Inn: Leah’s favorite! The town of Holualoa’s cute art galleries and local shops are worth a visit, and the Holualoa Inn is perfect for those looking for an artsy, coffee farm vibe. An eight room bed and breakfast with uniquely decorated rooms in local style, situated up mount Hualalai with gorgeous aerial views of the ocean and island. Delish and chef-prepared breakfast that changes daily, plus a coffee cart next door called White Nene Coffee which is worth a trip to in itself – get their coconut iced latte.
Pacific-19: Leah’s pick for a more affordable option located right in Kona! Pacific 19 was recently remodeled and has a simple midcentury modern feel. They offer excursions and expert led activities directly coordinated by the hotel. You can walk to the beach, breweries, restaurants etc from here. They also have a café with Waimea Coffee Co which is worth visiting even if not staying here!
Mauna Lani: Kara’s pick for where laid-back Hawaiian vibes meets modern chic. Fresh off a major remodel, Mauna Lani has officially entered its cool, effortlessly luxe era. Intimate yet expansive, with lush landscapes, stunning ocean views, and a level of understated elegance that makes you never want to leave. Kara says "it’s a dreamy spot for couples, complete with fabulous restaurants, an ultra-serene spa, and some of the best boutique shopping on the island (there's even a Goop store!) And while it’s high-end, it still feels warm, welcoming, and deeply rooted in Hawaiian culture. If you’re looking for romance, relaxation, and a little retail therapy by the beach, Mauna Lani is calling!” Heads up that the beach is not as swimmable, though there are some coves off the hotel with great snorkeling.
Four Seasons Hualalai: Kara’s rec for a celeb hotspot and the most luxurious hotel on the island. No swimmable beach, but flawless service and amazing pools, including the King’s Pond, a swimmable aquarium filled with tropical fish. Many of the rooms also have outdoor showers!
Lauren also recommends Hapuna Beach Resort!
Eat:
Leah’s picks:
Lava Lava Beach Club: If staying up north at the Mauna Kea or any of the resorts in Waikoloa Village, add this restaurant to your list! It’s family friendly and they have live music on the beach at night. For lunch - get the Fresh off the Boat sandwich. For dinner, try the macadamia nut crusted fresh island fish. The spicy lilikoi sauce and papaya coconut rice is to die for.
Walua Social Club: A new restaurant in the heart of Kona town (reservation required!) and we were blown away by the experience here. High end Italian food - their ribs are a must! I was really surprised by the white bean dip with focaccia app, and the Kona Kanpanchi entrée was cooked to perfection. Don’t go here if looking for a sunset view, the focus here is the food and service.
Sushi Sams: This place is UNREAL. It’s run by Chef Sam, who you’ll see behind the counter. I have been to Japan and their sushi is 1000% on that level - probably because all of their ingredients are top tier and flown in from Japan! My favorite is the salmon nigiri - I haven’t been able to find salmon this fresh anywhere. Call during the day to get a reservation!
Aloha Vibes: Right on the water in the heart of Kona, and perfect for lunch and a mid-day cocktail. You can’t beat the views, and they make all their juices freshly squeezed. We had their seared ahi which was top grade quality and the lilikoi-bbq pork sando.
Da Poke Shack: This is a budget, casual dining option. If poke is your thing, you have to stop at Da Shack. It’s a modest to-go place with a few picnic tables outside, but they serve the best poke in town. My favorites are the Shack Special and Pele’s Kiss. They can sell out so go early!
Kara’s favs:
Merriman's Waimea: The original Merriman's location! Drive up the hill into lush Waimea and eat some of the best food of your life. The vibe is warm, welcoming, and effortlessly upscale—not stuffy, just really good. The macadamia nut-crusted fish is legendary, the Kamuela tomatoes taste like actual sunshine, and if you don’t order the kalua pork quesadilla, you’re doing it wrong. Also, get the famous Merriman's Mai Tai, fried green tomato croutons and chocolate purse for dessert!
Canoe House: At the Mauna Lani hotel - sunset optional, but highly recommended. (Lauren also says - the monkey bread is insane!)
The Beach Tree at Four Seasons Haulalai: Beach Tree nails the laid-back but luxe vibe. Fresh pasta, local fish, and wood-fired pizzas served with killer ocean views. Ice cream bonbons for dessert!
Pau Pizza: Best pizza on the island! Grab a box of the Kamuela Tomato & Basil and head down the hill to catch the sunset on the beach.
The Fish and the Hog: This place is casual, unpretentious, and ridiculously good. The kalua pork tacos slap, the brisket is melt-in-your-mouth magic, and the ahi poke? Perfection! Wash it all down with a local beer.
Manuela Malasada: Blink and you might miss it, but Manuela Malasada is 100% worth the roadside stop. Tucked off the highway, this little stand serves up hot, fluffy, perfectly golden malasadas that’ll ruin you for all others.
Umekes: Local and laid-back, Umekes is all about super fresh fish, bold flavors. You can’t go wrong with the poke bowls (trust me, every combo is a winner), but if you’re feeling extra, the furikake fish or garlic chicken will also change your life. Add a side of mac salad and grab a lilikoi lemonade.
Drinks recs, courtesy of Leah:
Ola Brewing Company: Skip Kona Brewing Company and go here! Their beers are local as well as their food menu. We like the lilikoi lime milkshake IPA. They also offer hard juices and seltzer. We ordered their Ali’I fungi pizza and Mahi’ai Salad, both of which were delish. I wish I could replicate the ginger miso vinaigrette on that salad!
Don the Beachcomber: Inside the Royal Kona Resort, the perfect place to drink a Mai Tai and watch the sunset.
Huggo’s on the Rocks: From the team behind Lava Lava Beach Club, another great place for sunset, with your feet in the sand with live music and performances. Go on Friday to see Charles Grace – his acoustics are unreal and the vibe is right!
Shop & Spa:
Kara’s fav is Surf Camp (Waimea): Local brands, epic gear, and the kind of merch you’ll actually want to wear. Whether you surf or just want to look like you do, it’s worth a stop.
Leah loves Petals and Provisions: Located in Holualoa, part flower shop part store. They carry the most unique and local curated items! I get all my souvenirs at this shop, including these unique salt and pepper shakers here. They also carry fresh sourdough from a local bakery that is the best on the island. Worth a visit 1000%.
& she also recommends Pueo Boutique: A locally owned women's and children's boutique in Kona. They carry my favorite children’s brand coco moon. They also carry Aloha bags – which are a must for anyone who likes to travel. I like to shop here for myself or buy baby shower items here!
Malama Pono: Leah loves this small and tranquil spa located in the heart of Kona town. They were very accommodating and customized my massage. Their pricing is reasonable, and their massage therapists are all very experienced.
Activities, courtesy of Kara:
Da Whale Boat Snorkeling (Waimea, in the harbor): Maximum of six passengers. Colorful fish, sea turtles, and occasionally octopuses and we even saw a huge pod of spinner dolphins. Totally unforgettable, great guides, and leaves right from the harbor near the Mauna Kea.
Anelakai Adventures Night Snorkeling with Manta Rays (Kona): The Big Island is known for having one of the largest populations of manta rays in the world! These gentle giants are incredible and even better up close. Embark on their double-hull outrigger canoe tour. After a short paddle from Keauhou Bay, you'll snorkel among manta rays in a small group setting.
Blue Hawaiian Helicopter Tours (Waikoloa Village): Sam and I did this and after so many years of going to The Big Island I learned and saw so much of the island that I never knew existed. We flew over active volcanoes, landed right in front of a private waterfall. The pilots were total pros who make the ride smooth and threw in some epic storytelling.
Private Mauna Kea Summit & Stargazing Tour - Mauna Kea volcano
Watching the sunset from Mauna Kea is unreal, and stargazing from the summit is next level. Have heard amazing things lately about Mauna Kea Summit Adventures.
Kīlauea Iki Trail: 3.2 mile hike in Volcanoes National Park. Gorgeous rainforest trail and you descend into a solidified lava lake.
Day trip to Hawi: Tucked away on the northern tip of the Big Island, Hawi is the kind of place that feels like a hidden gem, even if locals have loved it forever. It’s artsy, laid-back, and the perfect stop after exploring Pololū Valley (which, by the way, you absolutely should). Stroll through the quirky boutiques and local art galleries and eat lunch at Bamboo, or coffee and a lilikoi pastry from Hawi Coffee Company.
Paniolo Adventures (Waimea): Horseback riding tour of your dreams through some incredible landscapes. Located on a massive working cattle ranch in North Kohala, full of paniolo (Hawaiian cowboy!).
& we get a bonus from Darc!: “My two favorite beaches of all-time are Hapuna Beach and Kauna’oa Beach (parking can be tricky but if you get there early, it's worth it!). I dream about them year-round.”
That’s all for our crowdsourced OT guide to Hawaii! Follow our Instagram @opentabsletter to see pics of some of the above recs, and as always, shop all of our issues here.