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How to Escape Winter (Hawaii Edition)

Location: Hawaii

It’s been a little over a year since I last visited Hawaii. It was my first time visiting the islands, but I absolutely fell in love with the natural beauty & unique characteristics of Kauai and Maui. Almost a year later, Kirsten and I returned to “Let Hawaii Happen”, this time to escape winter in NYC to visit Oahu, Maui and Lanai.

As I first discovered last year, the best part of traveling to Hawaii are the unplanned moments during an otherwise planned vacation. Of course anyone who travels to any destination will have their points of interest or specific things on their itinerary that they want to experience. What I loved about traveling to Hawaii were those spontaneous moments in between. We partnered with Hawaii Tourism United States to craft an itinerary that would allow us to experience Hawaii beyond the familiar clichés, and to discover an authentic Hawaiian experience. Although our trip was complimentary, all opinions are my own.


We spent five nights in Oahu, with the first two in the North Shore at the Turtle Bay Resort and the remainder at The Surfjack Hotel & Swim Club in Honolulu. Anyone visiting Oahu who wants a more low-key vacation I highly recommend staying at the North Shore. Visiting during the winter months is a perfect time to witness epic waves, as it’s a surf mecca that attracts the best surfers in the world. Anytime between November and February are the best times to watch big wave surfing. If you want a more peaceful atmosphere for casual surfing or swimming I recommend visiting from May to September.

For those travelers who like a much more urban environment, Honolulu on the south end of the island is perfect for you. The strip along Waikīkī provides awesome shopping and your choice of five beaches in the district to choose from. We really enjoyed our time staying at The Surfjack, with its modern take on traditional island décor, a designer boutique, a fabulous restaurant and an ideal location it’s a great option.


Explore Waimea Valley
Visit the Byodo-In Temple
Go on a mural tour in the Kākā‘āko Arts District
Brunch at Arvo Café
Shop in Downtown Honolulu’s Local Boutiques
Dine at Mahina & Suns (located at The Surfjack Hotel & Swim Club)
Grab breakfast at the Diamond Head Farmers Market (be sure to get there early!)
Visit the Queen Emma Summer Palace
Hike the Manoa Falls Trail


We continued our adventure by taking a short flight – just a hop, skip and a jump from Honolulu to Maui. We felt spoiled as we spent five nights at the Four Seasons Resort in Wailea which has a great property with loads of cabanas to either lounge by the pool or the beach and provides a nice spot for snorkeling.   

One of the pleasant surprises during our time on Maui was our visit to the Haiku Mill for a historical botanical tour. It felt like taking a trip back in time touring the ruins from the Mill’s prosperous days in the mid-1800’s as Maui’s leading producer of sugar. The property was absolutely stunning – perfectly curated with dozens of incredible antiques, collected from flea markets in France. Needless to say, it left Kirsten (a self described Francophile) in absolute awe and we both couldn’t stop taking photos. If you’re ever in Maui, a stop here is a must – but be sure to make a reservation for a tour.

We also found ourselves waking up at 2am to get out the door by 2:30am local time in order to make the 1.5 hour drive from the hotel to the summit of Haleakalā National park. We were advised that parking at the 10,000 foot summit typically gets full around 4:30am, so we wanted to make sure we got a front-row seat for sunrise. If you don’t mind the lack of sleep, I highly recommend adding this to your itinerary. By arriving early you’re able to stare in awe and stargaze due to the pitch-black sky and you might be lucky enough to witness a shooting star like I did. Be warned though – the top of the summit is extremely cold so make sure you dress appropriately. Unfortunately both Kirsten and I had made a serious miscalculation as didn’t pack our winter parkas with us so we were both shivering. Fortunately for us however, sunrise did not disappoint and staring down at the clouds beneath us was an amazing experience.

Note: As of February 1st 2017, visitors now need to make a reservation beforehand, so be sure to check out their website if you plan on doing this.


Take a tour at the Haiku Mill
Sunrise In Haleakalā
Drive the Road to Hana
Visit the Ocean Organic Vodka Farm & Distillery Tour
Pick your own salad greens during a Lunch & Farm Tour at O’o
Go on a snorkel sail with Trilogy Excursions


On the last and final stop on our Hawaii adventure we took the Expeditions Ferry from Maui to Lana’i to spend three nights at the Four Seasons Lanai. The ferry only takes approximately 45 minutes and if you’re traveling here during the winter months, be sure to grab a seat on the top deck for some whale watching. Kirsten and I were amazed staring off in the distance as these magnificent creatures breached the surface of the water. I felt I had a front-row seat to a David Attenborough Nature special.

If the awesome whale watching experience wasn’t enough – we were both stunned by the amazing property at the Four Seasons Lanai. Kirsten has had the luxury of staying at various Four Seasons properties around the world said that the location in Lanai is on the top of her list and I was equally impressed. The island and the property are the very definition of serene, secluded and luxurious. Our only regret was that our stay here wasn’t longer.

The island is relatively small, so if you arrange to rent a Jeep you can drive around the island in only a few hours. Of course, you’ll want to stop off at various points, including wandering around Lanai City (they even have their own movie theatre!) and drive down to explore Shipwreck Beach.  We also both loved our horse back riding also arranged through the Four Seasons activity center, as we spent the morning with some great horses. Horseback riding is not an activity that I get to do often, so when i’m on a trip, I’m sure to always try to add it to our itinerary!


Horse Back Riding
Grab lunch at VIEWS at Manele Golf Club
Rent a Jeep for the day and explore the island
UTV Tour
Explore Shipwreck Beach
Dine at One Forty & Malibu Farm
Visit the Ho’okipa Cultural Center