So, you’ve found your dream house on the Outer Banks of North Carolina for your family. It’s a stunning 10-bedroom place, and everyone is looking forward to a week of sun, sand, surf and good times. Well done, it's an experience worth savoring, but first, make sure you have a good plan to execute the rest of the trip. Let me tell you a quick story to explain why.
One year, for my father-in-law's 75th birthday, his three kids, along with their partners and the grandkids, decided to throw him a surprise birthday week at a cottage with everyone there. With my mother-in-law's help, we all pulled it off. He was surprised and it went well, but at the end, they both said, “thank you, this was fun, but please don't ever do this again.”
These are exactly the feelings that can come about from a well-meaning but poorly thought-out family trip. You can end up with too much work falling to a small number of people, different expectations around what the group will do and when they'll do them. The idea of we'll all pitch in or we'll just sleep wherever sounds good but doesn't always work out.
On future group trips, we came up with a much better plan and one that left everyone saying, let's do this again. So how did we transition from disaster to success? Here’s our hard-won advice.
Money.
These fabulous homes, with their private pools, game rooms, and acres of deck space, aren't cheap and getting the money issue solved is always tricky. A simple solution is best. Make sure everyone knows the price and agrees to it. Give people the due date for the deposit and the final payment date.
We’ve found that a “per bedroom” cost is the easiest way to assign everyone their fair share. A simple group email outlining the cost and payment for everyone (i.e. everyone sees what everyone else is paying) and firm deadlines works wonders. Sometimes parents may want to kick in additional funds for family members who are in a different financial situation and that’s fine.
Collect a non-refundable deposit from everybody. This is non-negotiable. It secures their spot and, more importantly, confirms their commitment. Divide the total cost of the house by the number of attendees to get the deposit figure. Attendees must then send you a 50% deposit to book their space in the house immediately. One month out, the final balance is due.
Who sleeps where?
Don’t assume people are going to be happy on a pullout couch or a mattress on the floor. Try to make sure everyone has space when choosing a home. Make sure people who want to turn in early have the quietest room. Parties and night owls should not ruin others' sleep.
Assign rooms accordingly. With these homes, things are upside down. Think of the top floor as the noisiest (that’s where the kitchen is) and the bottom floor as the quietest. Consider putting the families on the main level (first living floor). There’s generally more room down here, with a secondary quasi-kitchen; it’s also closest to the pool.
If you have anyone with mobility issues or older adults, ask them where they would like to be and work around their needs. Consider who gets along with whom and assign accordingly. Put the night owls on the top floor by the kitchen.
The vacation starts!
Upon arrival, set up your house with zones.
Once you’ve arrived, the goal is to minimize friction and maximize fun, so carve out special “zones”.
- Set a social floor zone: Not everyone wants to stay up late, have multiple drinks, and listen to music, so set the top floor of the house as the place where things can go late. This should also be the same spot where most, if not all, of the meals take place, as this is where the kitchen is.
- Set a quiet room: Most homes also have a TV room on the main floor. Set this as the chill-out area for watching movies, reading and relaxing.
- Designate the games room: Some homes have a pool table and video games on the main floor, perfect for adults and teenagers to hang out and relax.
- The pool area: Many homes also come with private pools and hot tubs; designate this as the noisy fun area for everyone.
- Main Balconies: These are free for all. Remind people that each bedroom generally has its own balcony, and they can retreat there any time they like.
The Meal Plan:
Meals can often fall to the planner, or, if it’s extended family, to the matriarch, or just to a couple of people. Make sure everyone gets a turn – in pairs or groups.
Use a structured plan that includes group dinners. Breakfast and lunch are handled on an individual basis. This hybrid model provides a fantastic, social group dinner each night without the burden of planning a ton of meals. It also allows people the freedom to eat what and when they want during the day.
- Give people jobs to do: Create a sign-up sheet one week before the trip that allows people to create their own dinner teams. Someone may have a specialty that everyone loves. In our group, we have a BBQ pit master who makes the best ribs, so we let him have a whole dinner night to himself (with assistants, of course). Perhaps on another night, Mom wants to make her famous slow-cooker pot roast that everyone loves.
- Assign Nights: Team A is responsible for Saturday dinner, Team B for Sunday, and so on. This means that for one night of the trip, your team is responsible for everything: planning the meal, shopping for ingredients, cooking, and cleaning up afterward.
- Make Monday pizza night: You’ll have had two nights of cooking, now it's time for an easy meal that everyone loves, and no one has to cook.
- Make Thursday night leftover night. You’ll be shocked at how much food is still available.
- Set Friday to go out for dinner: I’ve found that the last night of the trip is best for this, and Waterman’s Grill is a large spot that can handle big groups. You can get the iconic group shot here with the sun setting in the background.
Meal Expenses. When you buy for a group, it may seem expensive at the time, but after you divide it up by person, the cost is surprisingly low. On one of our recent trips, our meal expense for the entire week (6 dinners) was only $90 per person.
- Assign a condiment controller. Get this person to bring the condiments, paper products, spices, and other communal items from home to avoid duplication.
- Tracking Expenses: Ask everyone to keep their receipts for the food they buy for the communal meals. Appoint someone good with numbers to add it all up and divide it accordingly. Some people will owe, some will be owed, and the money can be distributed accordingly.
- Alcohol Expenses: This is not communal; it’s BYOB all the way!
Trash & Tidy: This is often overlooked! Designate a "trash master" who ensures the bins go out on collection day and that recycling is separated. Quick tidies of common areas (living room, game room) can be done by whoever is using them, but a general 15-minute "power clean" before dinner each night can prevent things from getting out of hand. On the Saturday morning of checkout, ask volunteers to help with a light cleaning. Make sure you review the checkout list provided by the house rental company.
Plan a Group Event that Everyone will Like
Trying to round up everyone to go somewhere is difficult, but one tried-and-true event (that everyone generally shows up to is a beach fire. Usually, a few people have 4WD vehicles, and they can transport the wood, chairs, and coolers to the spot. Just make sure you have a beach-driving permit, which is easily available online.
Now you have the logistics sorted, how do you manage the personalities?
In every large family or group gathering, you'll find a cast of characters, each bringing their own distinct energy, needs, and potential for conflict. Even the most agreeable people in the group can seem problematic if they don’t know what expectations you have for them. Recognizing these types and having a diplomatic strategy prepared is crucial for a smooth week.
In a family setting, the personalities will be well-known. Engage with those people on a one-on-one basis to find a role that suits them. Perhaps there’s a musician who likes to play, get them to perform one night. For the early riser, give them an honorary designation as the “official coffee guru” responsible for getting the coffee on. For the watersports enthusiast, get them to bring all their gear and oversee the beach activities. For the partier, make them the official bartender and ask them to create a special cocktail for the trip. For the bookworm, ask them to compile a list of books for the group to try.
The options are limitless; it depends on the quirks of the group. The key is to make it fun and not onerous.
In Summary
The secret to an Outer Banks group vacation lies in proactively establishing an upfront financial plan, dividing the house into social and quiet zones, structuring communal meal duties, managing the mix of personalities, and managing expectations. With a bit of preparation, your dream house rental becomes the setting for an effortless and truly unforgettable collective experience you’ll want to do over and over again.