Trip Report | Hilton Head 2025
Overview
Every now and then, you take a trip that just sticks. The kind of week that makes your heart full and your camera roll overflow. That was Hilton Head for us this year - one beach house, seven families, 13 adults, 14 kids, and lots and lots of sunscreen.
We rented a huge house one row back from the ocean in Sea Pines, just a quick two-minute walk from the sand and steps away from our own private pool. For one glorious week, our crew - made up of my childhood girlfriends, our husbands, and all our kids - soaked up the sun, the memories, and the shared chaos of vacationing with a crowd!
Accommodations
We rented the house on VRBO and split the cost equally among families. Does it hurt a little to pay cash instead of using points and miles? Sort of! But well worth it in this case.
Six families stayed in the house, which was convenient given that most of the six bedrooms have a king or queen bed for the parents plus full-size bunk beds for the kids. The main floor is open and has several common spaces, which is essential for a group as big as ours! Add in several bathrooms, a private pool and backyard, and just steps from the beach, well…you can see why we loved this house so much. We actually stayed in the same house two years ago when we visited Hilton Head for the first time as a group.
The whole crew
The gals
The guys
Beach + Pool = The Daily Rhythm
Most days followed a simple formula:
Morning beach setup
Afternoon pool hangs
Evenings full of laughter and cocktails
The kids played for hours, rotating between digging in the sand, wave jumping, pool races, soaks in the hot tub, and cornhole on the lawn. Meanwhile, the grownups shared duties: setting up beach tents, keeping eyes on swimmers, applying sunscreen on repeat, and making lots of snack plates.
It felt a little like a modern-day commune, in the very best way!
Bikes, Ice Cream & Lowcountry Nights
One of our favorite nightly traditions was biking to Salty Dog for ice cream. Yes, basically every night. The kids loved it, and honestly, so did the grown-ups. When the weather cooled off enough in the evening, before getting the kids ready for bed, we’d take a 10-ish minute ride to Salty Dog to sample one of their many delicious flavors. My personal fave was Oreo, but the kids sampled vanilla, strawberry, cotton candy, cake batter, and mango throughout the course of the week. All crowd pleasers!
We also biked to Harbour Town, where you can wander through shops, watch boats dock, visit the lighthouse, and grab a bite or a drink at one of the many local restaurants. It’s the kind of spot that just feels like summer.
Dining Adventures: Big Group Edition
Feeding a group of 27 is no small feat, but somehow we made it work. We rotated cooking, cleaning, snack-duty, and grocery runs like a well-oiled machine.
We ventured out for a few meals:
Group dinner at Salty Dog - while we love the Salty Dog, it isn’t the best option for a group as big as ours. Plus, it was hotter than the surface of the sun the night we decided to go, and let’s just say they should invest in some shade structures and fans. Nonetheless, the service was good and we had fun despite almost getting heatstroke.
Small group lunch at the Harbourside in Harbour Town - gorgeous views and laid-back atmosphere. From the outside, this place doesn’t look like much, but the food was incredible, there’s a kids’ menu, and they have wine slushies on the drink list, so it was a win for me!
Another small-ish group lunch at the Tiki Hut in Coligny - beachy vibes, live music, and sandy feet were encouraged. Super casual and our waitress' name was Kitty Kat. It was a short drive from Sea Pines, but we enjoyed venturing out of our little bubble.
Girls’ night at Quarterdeck - because uninterrupted conversations with your besties and beautiful sunset views are priceless. This place is delightful and I’d love to eat there as a family next time!
The guys also snuck away for a fishing trip, after which they cooked their catches for lunch at Hudson’s Seafood - a repeat outing from our trip two years ago. They highly recommend.
Breakfasts and lunches were casual and go-with-the-flow. Quick stuff for breakfast at the house as the kids woke up, and lunches of chicken nuggets, PB&J, fresh fruit, etc. in between trips to the beach and pool. Pro tip: Place a grocery order ahead of time for delivery upon arrival. In preparation for the trip, we had a shared Google doc where everyone added their must-haves to ensure each family would have what they needed. Some of the dads did quick grocery runs (and booze runs) throughout the week when we ran out of specific things, which was super helpful.
For dinners, we ordered pizza our first night, grilled out another night, and ordered catering from One Hot Mama’s BBQ and Pomodori - both of which were delicious, and allowed us to press a much-needed “easy button” amidst the chaos. We also had enough food from both catering orders to provide leftovers throughout the week.
The Magic of Traveling with Your People
Many people might be scratching their heads trying to figure out how a vacation with a group this size could work logistically, and I can understand that. But there’s something really special about watching your childhood friends become the “aunts and uncles” in your kids’ lives. We all look out for each other’s children, help manage meltdowns, cheer on cannonballs, and pass around snacks without asking whose kid belongs to who. Us ladies grew up together, and now our husbands are friends in their own right. The kids generally got along swimmingly and made us grown-ups really proud.
The shared parenting, the teamwork, the way everyone just gets it - that’s what made this trip feel so easy and joyful. That’s why this group of friends is so special and so treasured.
Conclusion
Family travel doesn’t have to be fancy to be meaningful. Sometimes it’s the messy, sandy, loud, all-hands-on-deck kind of weeks that your kids will talk about for years.
These are the moments that remind me why our family travels in the first place: to connect, laugh, and slow down. To surround our kids with love and friendship.
Hilton Head, we’ll be back! Same crew, just a couple years older. 😉
Points & Miles Breakdown
Accommodations:
We rented a house for the week on VRBO. It was easiest to split the cost in cash, but don’t forget that Capital One Venture cards offer a “points eraser” tool. You can apply Venture Miles to erase any costs that code as travel on your statement. While we typically prefer to transfer our Venture Miles to airlines for free flights, since they are a flexible currency, they can be used in multiple ways.
Flights:
n/a because we drove! Stay tuned for a future blog post about road trip tips from yours truly.
Total Savings:
Since we didn’t use any points and miles for this trip, we don’t have any savings to report. For trips like this, I make sure to have a new credit card in hand, so at least the money we’re spending helps us meet another minimum spend!
If you are interested in learning more about racking up points and miles to take a dream trip, let me know! I’d love to help strategize credit card welcome bonuses with you and I’m happy to answer any questions.
