Expert Advice

How I Redefined “Work From Home” And Spent An Unforgettable Month In Hawaii

One Hilton Grand Vacations Owner used her vacation ownership to work (and play) from Oahu

Raeanne V

Imagine you’re working remotely on the East Coast, and while on your 10 a.m. virtual meeting, you look out your kitchen window. You see the dreary, gray skies and leafless trees. Maybe there’s a light snowfall that’s pretty at first but immediately turns into rain. All of it is a bleak reminder that you could be somewhere sunnier. Does this sound familiar?

This happened to me, and I was over it. I decided to pack my bag for a month and a half and give a new meaning to the “WFH” acronym we all know and love — "work from home” became “work from Hawaii.” 

A Hilton Grand Vacations Owner poses on the beach of Oahu at sunset 

“Isn’t that a big time difference?” you ask. Yes, it is — Eastern Time is six hours ahead of Hawaii. But when you’re on a tropical island in the Pacific Ocean, with the vast blue ocean to your right and lush green mountains to your left, it’s totally worth it.

I’m here to walk you through my average day working from Hawaii while on East Coast hours to help you decide if the new WFH is for you.

Things To Consider While Planning

Which Island?

My family grew up vacationing in Hawaii, so I’m familiar with the islands of the Aloha State. I love the otherworldly vibe of the Big Island, Kauai’s lush greenery and Maui's diverse terrain. However, I’m a 20-something from New York; going from beach to mountain to city intrigued me. So I picked Oahu. Oahu is budget friendly since I never had to rent a car. Waikiki is completely walkable; rideshares and public transportation can take you around the island.

Where to Stay?

I had enough ClubPoints to cover the entire stay, so I booked a Studio with a kitchenette in Lagoon Tower, a Hilton Grand Vacations Club. It’s about a 10-minute walk from central Waikiki to the Ala Moana Shopping Center, and Hilton Hawaiian Village has plenty of restaurants. Plus, there are tons of activities available at the hotel, like nighttime luaus, Friday night fireworks, morning yoga and hula classes. Bring a friend so you have a work buddy to make the early mornings more pleasant.  

My Average WFH Day

A Hilton Grand Vacations Owner enjoys a breakfast acai bowl while in Oahu, Hawaii 


4–5 a.m.: Get up, sign on to Slack and catch up on emails.

5–5:30 a.m.: Join a team meeting via Zoom.

5:30–6:50 a.m.: Complete my work projects, with the occasional meeting.

6:50–7:00 a.m.: Grab Starbucks coffee and breakfast.

7:00–7:10 a.m.: Walk around the lagoon during sunrise.

7:10 a.m.–noon: Continue to work on projects in my queue and attend meetings. Aim to sign off by noon to start the day’s playtime.


Island Vintage Coffee has multiple locations. My go-to order is the Island Latte, Liliko’i Moana Acai Bowl and Kimchi Fried Rice. If you’re in Waikiki, check out Maguro Spot for poke bowls and Kono’s. (I love their Kalua pork sliders.) Head to Hank’s Haute Dogs for a Hawaiian hot dog. I also love the Korean fried chicken and loco moco from The Food Company and Waiahole Poi Factory’s Hawaiian plate lunches on the East Side.

A Hilton Grand Vacations Owner on a hike of Olomana Trail in the lush greenery of Oahu, Hawaii 

Afternoon Activities

In the afternoon, I usually chose from one of the following activities. Venture to a different part of the island, including the North Shore to watch the pros surf killer waves during the winter, snorkel Electric Beach on West Side or chill on the beautiful beaches on East Side.

There are some amazing hikes on the island. My favorites are Ma’ili Pillbox, Koko Head Crater and Olomana Trail. Please read the reviews on AllTrails for the hike’s difficulty, as some may be outside your comfort zone. Olomana was incredible but a difficult hike on my own, even though I’m very active.

For an afternoon snack, I recommend Musubi Cafe IyasumeLappert's Ice CreamMatcha Cafe MaikoLeonard’s Bakery and Waiola Shave Ice.

A Hilton Grand Vacations Owner surfs while on a working vacation in Oahu, Hawaii 

Sunset Activity

Learning to surf in Hawaii was my ultimate goal for my one-and-a-half month adventure. It took me three weeks of trial and error to read the waves, paddle hard enough to catch them and get up on a board, but it was totally worth it. Surfing at sunset was my favorite activity in Hawaii, so I always rushed back to Kuhio Beach in Waikiki to make my sunset surf session, even if it was only 30 minutes.

For surfboard rentals and lessons, my favorite place to go to is Moku Surf Shop on Kuhio Ave. The people who work there are super friendly, and a two-hour board rental is only $10.

If surfing isn’t your thing, everyone will love watching the sunset from China Walls, Kuhio Beach and Sunset Beach.

A Hilton Grand Vacations Owner and her friend at the beach at sunset on Oahu, Hawaii 


Aim to have dinner by 7 p.m. to get home early for work the next day. Many restaurants in Waikiki have long wait times, so try to make a reservation in advance or order takeout. Some of my favorite restaurants are Eating House 1849Roy’s WaikikiMarugame Udon and Highway Inn.

Working remotely from Hawaii was an incredible experience, where hard work and play coexisted daily. Working early hours was a challenge at times. However, I felt like I was in Hawaii for twice as long because not a minute was wasted. It takes dedication, creativity and a few beach naps to make it work. But if you want your remote job to take place somewhere as beautiful as Hawaii, it’s possible.

Read more stories of other Hilton Grand Vacations Owners and how they’ve used their vacation ownership to create unforgettable adventures.

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Hilton Grand Vacations Owner Raeanne surfing while on vacation in Hawaii

Raeanne V

Raeanne’s been an Owner since 2019. One of her highlights of ownership was using her ClubPoints to WFH (work from Hawaii) for three nonconsecutive months. Follow Raeanne to satiate your travel bug for adventurous vacations.

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