Location Independence: Hawaii Version

We’ve been back for a little more than a week now from Hawaii, and it’s time to evaluate another milestone in our location independence. We had easily accumulated close 100,000 points of various kinds using the Travel Hacking Cartel system over a few short months.  We also wanted to add a couple of lengthy flights to jumpstart some elite status redemptions planned for later. Hawaii was a natural fit. Here’s how it all happened, using a combination of statuses: Starwood Preferred Guest program points, Priority Club Rewards points, booking flights and excursions with our PassingThru Travel website, and keeping an eye out for “deals on the ground.”

A while back, as part of a Starwood Preferred Guest promotion, we were invited to take advantage of a very low cost opportunity with the Westin Maui Resort, just north of Lahaina on Ka’anapali Beach. We jumped on it, figuring a week’s stay in Hawaii would be just the ticket in January. As the date drew nearer, though, we began to have our doubts: one week in Hawaii just didn’t seem long enough, and with location independence, we didn’t need to be anywhere unless we wanted to be. So we added on to the first package with an Interval International timeshare exchange free-stay coupon for another week with Westin: at the Westin Princeville, on the north shore of the Garden Island of Kauai. This package included reciprocal privileges with the St. Regis Princeville Resort, a neighboring property that overlooked Hanalei Bay, where “The Descendants” with George Clooney was recently filmed. With one day’s overlap on the two packages, we had flexibility, and a more varied experience in our overall plan.

Using Priority Club Rewards points, we booked an almost-free hotel room at the Waikiki Beachcomber Resort. Upon arrival, we were warmly greeted as Rewards members, and given a room upgrade. Our combination of points plus $40 had bought us a terrific ocean view overlooking the vintage Royal Hawaiian hotel. A charming little candy gift with a personal welcome note was a very nice touch.

Consulting our PassingThru Travel website, we discovered there were hourly flights available from Honolulu to Kahului, giving us plenty of time to poke around the Waikiki area. We had breakfast, did a little shopping, and then jumped on our Go! flight to Maui.

The Starwood Preferred Guest promotion included some significant perks: an additional 7,500 Starwood points upon completion of the stay, and an economy rental car. Upon arrival in Maui, we upgraded to a jazzy red convertible. Nothing like seeing Hawaii with the top down and music blaring! When we arrived at the Westin Maui Resort, it was clear from the onset that Starwood Preferred Guest program members get top priority. We received a complimentary villa upgrade right upon check-in. Meanwhile, a smiling valet unloaded our bags, whisked away our vehicle, and met us at our villa with extra pillows and fluffy bathrobes! All rooms at the resort face the interior courtyard, with pool or ocean views.

Most villas, like ours, also have private lanais. It was later explained to us that the company doesn’t want its guests to overlook a parking lot or service area, and all resorts use this design feature. We could already see why Starwood Preferred Guest members view this resort and its sister on Kauai as two of the company’s most popular havens.

With location independence, we’ve learned to check internet connection quality immediately upon arrival. Throughout our stays with Westin, we stayed easily connected and paid no fees. Another requirement is a comfortable workspace. On this leg of the trip, Pete claimed the dining table in our villa, and I took a more casual approach: it was either the chaise longue in the living room, or out on the lanai.

We could have packed our stay on Maui with an assortment of activities, keeping busy and on the go all the time. Instead, we chose to schedule significant down time. We drove the Road to Hana, and went on a whale watching excursion. There were many additional opportunities to part with our money: zipline excursions, helicopter rides, luxury luau experiences with music and entertainment, and other adventures.

But for us, location independence also includes a reality check while traveling: we had to get a little work done almost each day while we were in Hawaii. Pete spent a good part of the morning (easy to do with the time change differences) working on adding items to our online stores, and  I continued with client responsibilities and researching for blog newsletter articles. We participated in a regularly-scheduled executive team conference call at 7 a.m. local time when it was the middle of the day back home. This was pretty easy on us as we’re early risers.

We used the same strategy for our second week in Hawaii: consult PassingThru Travel to island hop to Kauai from Maui, investigate opportunities to add dining points to our Priority Club Rewards account, schedule significant poolside time, and explore the island in our rented Jeep Wrangler with the top down. We found we preferred the more relaxed pace on Kauai, but the “island lifestyle” is alive and well everywhere. We tend to seek out places that the locals like to hang out, and we saved a significant amount of money eating and drinking where they do. This practice was validated at Tahiti Nui, in Hanalei, where a new photo of George Clooney and Jeff Bridges seated on our barstools is displayed! 🙂

We also double-dipped points programs by using Choice Rewards or Wyndham Rewards credit cards on purchases at the Westin Princeville and Maui Resorts for which we were also earning Starwood Guest Rewards points. So while we were relaxing and having fun, we were banking points for future benefits. This is a Travel Hacking Cartel strategy that we’ve made a habit. Join the Cartel and you can get information on how to incorporate tips like these as well as special promotions and rewards, too!

Many folks might dismiss an extended stay at places like the Westin Princeville and the Westin Maui Resort properties with a stopover in Waikiki as something they can’t afford. It’s true, Hawaii is an expensive destination, especially compared with prices on the mainland. But there are simple ways to keep costs in check, even while enjoying luxurious amenities. While our trip wasn’t completely free, it certainly was affordable, and the 4 and 5-star accommodations made us feel like rock stars. We had unforgettable experiences, didn’t sacrifice any work-related priorities, and proved to ourselves that location independence can work on a bigger scale when traveling to distant destinations.

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  1. says

    Hi Betsy and Pete – just read this as I’m sitting down to a cup of tea out of a mug – with the grey skies above and thinking quietly .. why aren’t I there?!! Sounds fantastic and you’ve worked it out so well – now who are your executive team that you need to have conference calls with at some unearthly hour in the morning?!

    It looks fantastic and am so pleased you had 2 weeks and were able to just be .. and enjoy the area … one day I shall get there – right now seems a very good idea!!

    Cheers and wonderful post to read … Hilary
    Hilary has an awesome blog post here: Valentine’s Day, Chocolate and Love Poems …My Profile

    • Betsy Wuebker says

      Hi Hilary – Sorry for the delay in responding to this comment! Yes, our experience was fantastic, and yes, you should get there right now! Our Exec Team call is actually with a client for whom we act in a variety of capacities. The morning hours worked well for us because we are early risers anyway. 🙂

  2. Elizabeth says

    I am happy to learn about your experience in Hawaii. It is great that you get to experience luxury without spending too much. I hope I can get an amazing deal just like yours. I especially want to try the helicopter ride. The view must have been breathtaking.
    Elizabeth has an awesome blog post here: DTS HomeMy Profile

    • Betsy Wuebker says

      Hi Elizabeth – Welcome to PassingThru! The helicopter rides are definitely very popular! We are saving this one for the Big Island, as we would like to go down into the live volcano based upon a friend’s description of her experience. We did hear from one friend who easily gets motion sickness; her experience was not enjoyable! Thank you for your comment. 🙂