Your Ultimate Guide to a 20-Person Kiteboarding Trip to the Outer Banks

The plan is to gather 20 of your favorite kiteboarding comrades for a week-long, wind-fueled adventure in the Outer Banks of North Carolina. You envision epic downwinders, flat water, strong winds, sunset beers on a deck, and enough shared meals to feed a small army. It sounds incredible. It also sounds like a logistical nightmare but fear not, this is not only possible, but it’s also the recipe for one of the most memorable trips for you and your crew.  

The Outer Banks, with its excellent selection of rental homes and world-class kiteboarding spots, is practically designed for this kind of large-scale pilgrimage. You need a solid game plan. Consider this your playbook for pulling off the ultimate group kiting trip without losing your sanity or your friends.

Part 1: Timing is Everything - When to Go

Your first major decision is choosing your week. The Outer Banks offers a long kiting season, but two windows stand out as the absolute prime time for wind, weather, minimal crowds, and availability of home rentals.

Spring (Mid-April to Early June): This is the season of glorious southwesterly thermal winds. As the mainland heats up, it consistently pulls cooler air from the ocean, creating a reliable 15-25 knot breeze that often kicks in like clockwork in the early afternoon. The water is warming up, the summer crowds haven’t yet descended, and the air is that perfect combination of warm sun and cool breeze. You’ll likely need a full wetsuit (a 3/2mm or 4/3mm), but the trade-off is session after session of consistent, beautiful wind.

Fall (September to October): Many locals will tell you this is the true golden season. The water is at its warmest from the summer sun, the crowds have vanished, and the wind patterns shift. You’ll get a mix of late season southwesterlies and the first powerful northeasterly cold fronts. These fronts can bring several days of strong, punchy winds, making for incredible sessions. The vibe is mellow, the sunsets are spectacular, and you can often get away with a shorty wetsuit or even board shorts well into September. For a large group, this is arguably the best time to go, as you’ll have wide-open spaces on the water.

Part 2: The Windy Playground - Where to Ride

Make your home base in Salvo, this places you in the heart of the "Tri-Villages" (Rodanthe, Waves, Salvo) on Hatteras Island. This is the promised land for kiteboarders. While the Atlantic Ocean offers amazing wave riding for the advanced crew, the real gem for a group with varying skill levels is the Pamlico Sound. The sound is a massive, shallow body of water on the west side of the island, offering miles of waist-deep, flat water and secret butter-flat spots in the grass.

• Salvo Day Use Area: This will be your backyard. It's a public access point with a large sandy beach, restrooms, cold water showers, and plenty of space to launch and land kites. The shallow water extends for hundreds of yards, making it an ideal and safe learning and progression environment. When the wind is blowing from the south or southwest, this spot is pure perfection.
• The Slicks: Just a bit north of Salvo, you'll find various access points to outstanding flat water. These areas are slightly shielded by marsh grass, which grooms the water into a glassy surface perfect for freestyle tricks. Launch at Kitty Hawk Kites and downwind to this spot.
• Canadian Hole (Haulover Day Use): A short drive south, this legendary spot is a must-visit. It’s a massive rigging and launching area that can handle huge crowds. It works best on a south or southwest wind and is a fantastic social hub for kiters from all over the world.
• Sandy Bay (The Wash Out): About 40 minutes south from Salvo just before Hatteras Island, this spot has lots of parking, shallow water and a small launching area. It’s ideal for when those strong northern cold fronts blow down. Small slicks are just north of the launch area. Those who like wave riding should pop over the dunes and give the ocean a try here.

With so much shallow water, the sound is incredibly safe, but it's always wise to have a designated person on the beach keeping an eye on the crew and to help with launch and landing kites.

Part 3: The Command Center - Booking Your Mega-Mansion

This is where the OBX shines. The island is famous for its enormous "event homes" that are practically built for groups like yours.  Depending on the group size, you’ll need one or two homes. For a group of 20, count on two homes.

Start your search 8-12 months in advance, especially for a prime season week. The best houses get booked early. Your go-to resources will be the large, local realty companies that specialize in these properties:

• Surf or Sound Realty
• Midgett Realty
• Sun Realty
• Outer Beaches Realty

When searching their sites, filter for homes in Salvo that sleep 10+ people. Look for key amenities that turn a good trip into a great one: a swimming pool and hot tub for post-session relaxation, a game room with a pool table for no-wind days, and most importantly, a kitchen with two refrigerators and two dishwashers. Trust me, with 20 people, only one of each is a recipe for disaster. If you can find one, a home on the sound side with direct access to the water eliminates driving and is the crème de la crème of spots.

Part 4: Herding Cats with Kites - Mastering Group Dynamics

Getting 20 people to live together harmoniously for a week requires a bit of structure. The goal is to minimize friction and maximize fun. Setting expectations before the trip is key.

The Social House and the Chill House

Not everyone wants to stay up late, have multiple drinks, and talk about their epic jumps and tricks, so set one house as the place where things can go late, and most, if not all, of the meals take place.  Ensure that the crew in this house is of a like mind. Set the other house as a place for people who enjoy reading, relaxing, and napping.

Group Events

Trying to round up everyone to go somewhere is difficult, but one tried-and-true event (if it's not windy one evening) 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, easily available online.

The Meal Plan: The single biggest source of group-trip chaos is food. Who’s cooking? Who’s cleaning?  Solve this with a structured plan.

1. Divide and Conquer: Create a sign-up sheet one week prior to the trip that breaks the group into dinner teams
2. Assign Nights: Team A is responsible for Monday dinner, Team B for Tuesday, 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.
3. Create a pizza night: That way no one has to cook.
4. Make Thursday night left over night. You’ll be shocked as to how much food is still available.
5. 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.
6. Fend for Yourself: For breakfast and lunch, everyone is on their own. 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.

The Chore Chart: Your rental house isn’t a hotel. A simple system keeps the place from devolving into a frat house by day three. Create a small chore chart for daily tasks: taking out the trash and recycling, loading/unloading the dishwashers (a constant job), and doing a quick sweep of the main living area. Rotate these simple duties daily. A little effort from everyone keeps the communal spaces livable and pleasant.

Part 5: The Money Talk - Keeping Finances Friendly

Talking about money can be awkward, so make it transparent and simple from the very beginning. Send out notice of the trip at least three months in advance.

1. The Deposit: The moment you find the perfect house, you need to collect a non-refundable deposit from every single person. This is non-negotiable. It secures their spot and, more importantly, confirms their commitment. The total cost of the house divided by 20 is their share. Require 50% of this as a deposit to book the house, with the final balance due a month or two before the trip. As the organizer, you are the bank.
2. Tracking Expenses: Ask everyone to keep their receipts for the food they buy for the communal meals. Appoint a person who is good with numbers to add it all up and divide it accordingly. Some people will owe, some will be owed money and it can be distributed accordingly. My meal expenses on the most recent trip were $45 (excluding the dinner out).
3. Alcohol Expenses: This is definitely not communal, it’s BYOB all the way!

Part 6: No-Wind Adventures

It’s bound to happen. You’ll get a day or two with no wind. Don’t despair! The Outer Banks is an adventure playground.

• Surf Session: The other side of the island is the Atlantic Ocean. Even on a non-windy day, there are often fun, gentle waves perfect for learning to surf or for a longboard session. Head to the Cape Hatteras Lighthouse area for one of the best breaks on the East Coast.
• Climb a Lighthouse: You’re in a historic area. Both the Bodie Island Lighthouse (to the north) and the Cape Hatteras Lighthouse (to the south) are stunning and offer incredible panoramic views of the island.
• Play on a Sand Dune: Drive 40 minutes or so north and explore the massive sand dunes at Jockey’s Ridge State Park.
• Day Trip to Ocracoke: Take the free vehicle ferry from Hatteras Village to Ocracoke Island. This remote, charming island feels like it’s a world of its own. Rent a golf cart, explore the village, visit the Ocracoke Lighthouse, and grab lunch at a waterfront restaurant.
• Go Fishing: Try your hand at surf fishing from the beach, or book a half-day inshore fishing charter out of a local marina to explore the fish-rich waters of the Pamlico Sound.

Organizing a trip of this magnitude is a big undertaking, but the payoff is immense. Watching 20 of your friends share a perfect sunset session on the sound, laughing around a giant dinner table, and creating memories that will be retold for years is an incredible reward. With a little planning, you won't just be the trip organizer; you'll be a legend. Now go rally the crew. The wind is waiting.