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We did this for a family vacation we took for my moms 60th birthday. It was Her and her husband, her mother, me and my two sisters and our families (at the time each one kid). Here is what I did:

Breakfasts: 2 days "hot", most days make your own. Hot was a breakfast casserole and coffee cake one morning, the other was french toast casserole and fruit salad. For the make your own...we had LOTS of eggs, breakfast meats, cereal and milk.

Lunches: We kept these to mostly easy - but two days we did bigger lunches in place of a large dinner. Those days were ribs & spaghetti. The easy days were sandwiches and salads - we got the fixings, people could assemble as they wish. My brother in law grilled up about 20 chicken breasts the first day we got there, and us ladies stood around and prepped a bunch of fruits/veggies for easy assembly down the road. We also made a bit container of pasta salad and potato salad.

Dinners: we ate two three nights, ordered pizza one night, had a chef come in 1 night and cook for us, and did BBQ 2 nights. For BBQ we kept it simple - burgers/dogs, cheesey potatos, grilled corn, some veggies. The other BBQ night we did steaks, baked potatos and steamed broccoli.

I made a few desserts throughout. People also went out on a big alcohol trip when we got there - to get their own preferences. We didnt have any strict dietary issues in my fam but we had enough food and variety on hand I think it would have been ok.

I also got a LOT of snacks - I ordered from Jet.com and had them delivered before we arrived. We had leftovers and all just took some home with us.

I think our grocery bill for the week was around $800 if I am remembering correctly? And the chef was $400 on top of that. It worked out well. Some families did bring specific items they are particular about - but that was ok too!

We do theme nights for dinner.

- Greek night is a nice variation of taco night (shredded crockpot Greek chicken, salad greens, olives, tomato and cucumber, feta cheese, pita bread or chips, hummus). People can make Greek salads or gyros. Get carrots and some alternate carb for niece (rice, potato, GF bread or cracker).

- Spaghetti night with garlic bread and salad.

- Grill night.

Lunches are usually sandwiches and chips. Just have a large selection of meats and cheeses and bread and spreads. You can get a tub of macaroni salad or potato salad if you want. One day is going to be clean out the leftovers for lunch.

Breakfast is simple. Cereal, yogurt and granola, muffins. For that many people it's impossible to cook in the morning. Just add milk and fruit and coffee and call it a day.

I'd buy a huge sack of baby carrots and a tub of hummus, a bunch of salad greens, and some easy fruit like cuties, watermelon, apples, and grapes. They can be thrown on the side of anything to augment a meal.

When we do this we usually do a big breakfast or brunch around 11 and dinner in the evening. If people are hungry at other times we have lots of snacks (fruit, nuts, crackers and cheese, cereal, etc.)

For breakfast we usually alternate between pancakes and waffles served with eggs and either bacon or sausage. Then maybe a breakfast casserole one morning.

Dinners we have done lasagna, tacos, spaghetti, grill (hot dogs, burgers, pork chops). Now I can't remember what else!

@Mommy Finger: If that's the case I would either make giant hoagies on those big grocery store French bread loaves hollowed out and sliced into portions or make everyone make their own sandwich and pack it - we've done both. Just bring a cooler with condiments and sides.

We do a similar family vaca every summer and also one with friends. For both vacations we assign each family a dinner (or two) that they are responsible for (including doing the shopping too). If you are on beach or boat all day, you can have one family a night plan to head back early to prepare dinner. -Keep in mind that even the easiest dinners for that many people will take a surprising amount of time to make. - We also supplement with a couple easy BBQ, pizza or take out nights as well but our trips are a little longer.

Just something to think about, groceries for that many people even just for 3 nights could easily fill up a fridge so you might want to break up the grocery orders.

For breakfast and lunch people kind of just make their own but we have eggs, bread, bacon around and deli meats for lunch plus leftovers from dinners. Also usually a family will break off and go out to breakfast or lunch once or twice solo.

I have a whole weeks worth of meals that I use, it's nothing fancy, but I've noticed that what ends up happening is that I am usually missing the "extras" that you have in a fully stocked kitchen...that's what makes it complicated. And then there is the subject of planning and repeating so you don't have leftovers.

I basically did a spreadsheet and planned out, say using 6 eggs and half a package of bacon for scrambled eggs on one day, and 6 eggs the rest of the bacon for dinner for spaghetti carbonara a little later in the week. I planned specifically so I didn't need a ton of condiments and what not, and also in case I didn't have good utensils to prep.

When we do a big family vacation, we try to keep it suuuuuuper simple so no one has to slave away at meals (the mommies need to enjoy themselves too!)

Breakfast- cold cereal or individual yogurt cups served with fruit.

Lunch- variety of cold cuts, fancy breads and crackers, a veggie tray with ranch and hummus, salad mixes (like Asian, southwest, etc) and easy fruit sides like mandarins, bananas, apples. If we are out and about during the day I don't even make sandwiches- I just bring a pack or two of lunch meat/ cheese, a loaf of bread, and fruits and veggies and people can make their own on the go hahaha. No need to waste the morning making 20 sammies.

Dinner- Spaghetti with garlic bread and salad, Rotisserie chicken from the store with rice (you could sub cauliflower rice for GF) and veggies, grill out (usually burgers) with corn/ salad/ grilled asparagus, Beef roast in the oven with potatoes and veggies, tacos. A lot of these you could cook multiple in the oven at once on disposable trays if the kitchen is not well equipped.

@Mommy Finger: DH' side has a big reunion every other year - 36 people

Breakfast is on your own - we have cereal, bagels, toast, muffins, oatmeal, yogurt, etc

Lunch is also on your own - leftovers from dinner or sandwiches

Dinners were easy to prepare, a few I remember were: tacos and sides, baked spaghetti with salad and bread, burgers and hot dogs with sides

We also had snack foods and lots of fruit available

We do this with a bunch of friends every year (less drama, but more food allergies!). We do a hot breakfast for anyone who is up when it is served (usually around 10am), usually a crock pot casserole one day, eggs/bacon another, etc. Cereal, fruit and assorted breads are available before and after. We have one family manage breakfasts, and they aren't responsible for any other cooking on the trip.

Lunches are always what we call "MOM": stands for "make own meal." We have bread, cold cuts, cheeses, salads/cut veggies, chips and any leftovers available. Every family is responsible for managing their own family's needs from what is available (each comes prepared with empty tupperware/ziplocs for packing if necessary).

Dinners are generally all grilled items: hamburgers/hotdogs one night, grilled chicken the next, bratwurst and steak tips. Sides include grilled veggies, baked beans, salads, corn.

The key to making this work for us is loads of snack foods available for between meals - chips/crackers/cookies/marshmallows for toasting/breakfast bars.

This is great! We are doing a family vacation on the beach in 2 months and I'm saving these ideas!

We've done this exact thing the last 5 years:

Lunches we always do sandwiches, hot dogs, and then have pasta salad, potato salad, chips, fruit, veggies as sides.

Breakfast: I always make egg casseroles one morning, we do pancakes/bacon/eggs another, cinnamon rolls/muffins/fruit, and the last day before we leave is always donuts and leftover fruit.

Dinners: hamburgers/hot dogs/steaks, taco night, sloppy joes, chicken foil packs, with the same sides from lunch - veggies, chips, dips, pasta salad, etc.

Dessert - always smores