Hellobee Boards

No experience, but Mrs Turtle just went to Hawaii with the family/has lived there and kaohinani has lived there too

Have you been there before so you know what stores there are? Do you know if you will have grill access at your condo?
We have gone to Maui several times as a family (with ILs, my parents, alone) and stayed in condos. We finally figured out the best food shopping options. We found that food was very pricey at the grocery stores, but getting a rewards card for the supermarket helped a bit. We are costco members, and their prices were SO MUCH CHEAPER. Even for fruit, fish, but especially for alcohol. The Maui costco is right next to the airport, so it's not easy to get to from where we stay.
It's worth doing a little online or condo-network digging to find out the best grocery stores.
FWIW, here's what we did:
off plane, straight to costco where we bought wine and beer, eggs, veggies, fish, fresh pineapple, a few meals worth of food, lunch fixings, favorite snacks.
Takeout for first night dinner - someplace cheap but yummy that a friend recommended
Assess the condo situation with respect to spices, condiments, pots and pans, grill utensils, grill condition and how crowded the communal grills get (note: we made friends with other vacationers at the grills, so don't worry if they are busy. It's a nice way to meet people!)
First day AM: got straight to having fun, ate breakfast at condo, either brought lunch to the beach or ate out and had something easy planned for dinner.
Second day: made a plan for the rest of the week and planned to stop at a grocery store on our way back from the beach.

Things that we do now, as "veterans"
-Identify our fave restaurants where we want to eat out so we know we will likely only have to cook X number of dinners at the condo.
-make our own cocktails every night to enjoy at sunset.
-leave one or two additional meals open for impromptu dinners out
-have simple snacks on hand to take with to the beach, for day trips, to avoid the "hangries"
-hit the farmer's market if we can
-Bring our favorite spice blend from home so we don't have to hunt for it at the grocery store
-bring a collapsible soft-sided cooler from home so we can pack lunches for the beach and road trips. We purchased it on a Maui trip and now bring it with us on lots of trips
-check out the knives at the condo and buy one sharp knife if necessary
-don't buy too much early in the week! Short run-in shopping trips take much less time away from your beach time. Now I would even shop alone during nap time to get it done more quickly!
-we ask folks at the condo (especially at the grills!) for suggestions on new restaurants to try, and for suggestions on where to buy more local foods to prep ourselves. That's how we found out about a tiny little shop that sells the best ribs in the world as well as fresh fish
-we focus on what we like that HI does best: fish and fruit! Every breakfast and snack is fruit-based and we look for local specialties when we can find them. We try to find local coffee too

@BUNBUN: agree about food being SO EXPENSIVE. We stayed in a rental on the Big Island and were shell shocked by grocery prices, and we lived in NYC at the time!

I don’t enjoy cooking on vacation because it feels like work, but I would try to have meal ideas in advance and see what you find at the grocery store. I agree about having a short list of restaurants to try. Also, when we are on vacation we will typically try to eat out at lunch since it’s generally cheaper than dinner and do easy dinners at home, or picnics.

@Mrs. Pajamas: Aloha, Mrs. Pajamas! You are so lucky to have the opportunity to vacation in HI. I have lived there twice in my life and it is my favorite place in the world. I am not certain which island you will be staying on (I lived on Oahu both times but have island-jumped for short 1-3 day trips) so I may be limited to help. Since the cost of living is so expensive there (tourist spot, island living, having to import goods - of course a gallon of milk is over $6 and gas is astronomical!), I have a few ideas for getting delicious food, as well as, being able to add some island flair to your dishes... Here goes:

(1) Buy locally or at superstores. There are farmers' markets everywhere, meat markets that sell fresh meat and fish, fruit stands galore, and people selling eggs and nuts at every turn - TAKE ADVANTAGE of having them around. The food is organic/fresh and super cheap! We always had avocados, fresh fruit (pineapple, dragonfruit, citrus, watermelon), veggies of all sorts, nuts (macadamia is huge), raw sugar cane, kelp, local coffee blends, fresh fish and chicken, and Kobe beef from one vendor. I LOVED cooking in HI.
Another idea is maintain a club card. Sam's and Cosco were on Oahu. Buying in bulk (Bread, cereal, raw baking needs, TP, paper towels, and napkins) is huge help in keeping costs down (as well as one's sanity).

(2) While out, take advantage of food trucks for a cheap way to celebrate local tastes - there are Shrimp trucks (Giovanni's is famous), Korean BBQ food trucks, wahoo fish trucks (fish sandwiches, tacos, fries with an amazing dip), Chicken and pork Hawaiian cuisine trucks (spam and egg on rice, musubi bites, quartered chicken, pulled pork, white rice, poi, and haupia [coconut] rice pudding), and Japanese food trucks (sushi and sashimi to go).

(3) Go fishing as part of your experience- fishing tours exist in which people can fish off of the beach. The tours will show you the best spots for fishing, crabbing, and sightseeing and one can pick one and do that activity. I never did it but friends of DH and mine did. They had a blast. Bringing home a fresh supper from the sea is always amazing.

(4) Ethnic stores are a treasure trove of decently priced goods. There are many small (mom and pop) Korean, Japanese, and Indian food marts that afford a foodie so many options for cooking while vacation.

I hope my advice was even remotely helpful. If you have any questions, please, feel free to wall me. A hui hou koʻu hoa and have a spectacular vacation!

I have a spreadsheet for this, it contains a menu plan for the days (Breakfast, lunch, dinner, snacks) and it details where we will be that day. I design the meals, then I make a grocery list.

My biggest tips are to make things that don't require a lot of extra ingredients and special equipment. As an example, I will buy a container of fresh pico de gallo and use that in my corn and bean salad, as the veggies in omelets and as a topping for tacos.

I will also bring some items with me, like a enough tea bags, laundry detergent and dishwasher detergent packs, a few dryer sheets and a small bottle of dishsoap because I like my products best. This way I dont have to buy big ones at the location, or buy super expensive small sizes.

I also bring stuff to do, every vacation I buy a new board game for us to play as a family. I always bring few art supplies and other small boredom busters. I will also bring a small collapsible cube to store it all in so it's not all over the condo.