We are finishing up our week at Bay Club and thought I'd update this thread on what has worked so far.
We did pack a check bag which cost us $30 to check and saved us about $100 in food costs. We packed some extra canned goods in part because we are clearing out our pantry at home as we are gearing up to move, along with a box of cheerios, oatmeal, Pam, olive oil, frozen hot dogs for my brother, non-scented laundry soap pods and dryer sheets, seasonings, with chili seasonings and believe it or not Jello. (Note: The jello didn't jell correctly and wasn't great.)
We ate in almost exclusively for the first five days. We spent $200 at Costco and purchase a package of steaks, corn, eggs, buns, a package of chicken breasts, muffins, a pineapple and tangerines, a salad kit, tortillas, Kona coffee, a gallon of milk and a Britta. (Note: the corn was bad). At the local market we purchased butter, shredded cheese, OJ and sunscreen. We also hit the farmers market and picked up some local bread and artists wares. In a day trip to Hilo we ran into a Walmart to get an OTC med my wife needed and she noted that many of the touristy bags and trinkets found across the island were available there too.
Finally we got tired of our own cooking. We ate at a couple of places that were OK, but mostly provided change of pace and provided left overs for lunches. I should note the Brita is a grand success although keeping track of the reusable water bottles has been a challenge at times.
Tomorrow we leave for Gardens of West Maui, we have half the chicken left which we will pack frozen, the seasonings, and things we brought with us from the mainland along with the Brita. We will stop again at Costco for more steak & a few things, and likely the Safeway for the remainder.
Our checked bag has a bad wheel from a previous trip and we hope to abandon it in Maui and avoid the check bag fee. Was it a hassle? (a bit). Did it save us money..? Definitely. If we were a little more flush we might have just cast $$ to the wind but this trip we needed the savings to pay for other things, including moving expenses to our new home in Texas! (more on that later).