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Hilton Head, South Carolina Family Vacation

April 26, 2021

Hilton Head, South Carolina Family Vacation

April 26, 2021

Our two good friends, Cortney and Emily, recently took a trip together with their families to the Hilton Head, South Carolina area. We thought it’d be fun to have a completely different take on a family vacation and share their recap to provide some new content and ideas for travel! This post will be written from their point of view.

A bit about them…

Cortney, Katie, Sara, Amy, and Emily

Cortney and Emily have been our good friends for a long time, dating back to high school and early college but our husbands have been friends for even longer – back since middle school!

Cortney and her husband Kurt live in a suburb of Chicago, Illinois with their two kids, a 1 year-old daughter, Reese, and 4 year-old son, Clark. A recent lifestyle change for them, they hired an au pair named Sabina from Germany to help out their family at the start of the pandemic, who also joined them on the trip.

Emily and her husband Drew live in a suburb of Milwaukee, Wisconsin with their 1 year-old daughter Mila. Drew and Emily have done a lot of traveling together on their own, but this was their first trip with their daughter.

Why did you choose Hilton Head, SC?

My husband and I wanted to plan a long trip as a family of three for the first time. With our 14-month old daughter, we thought driving would be best, knowing we would want to pack all the baby essentials. With this in mind, we searched the internet for warmer weather and not too far of a drive from Milwaukee, WI. Weather in Hilton Head can vary throughout the day in March/April – meaning mornings and nights are chilly and the afternoons are perfect with a high of 80!

Our must-haves for this particular trip included: 2 bedrooms, kitchen, local amenities, golf (for Drew), and nearby pool/beaches. We knew Florida would be warm in late March but didn’t want our first road trip with a young toddler to be that far so we looked to the southeast. We were told by people to check out Hilton Head, South Carolina for many years. My husband knew there was lots of golf in this area so that wouldn’t be a problem for his time away. 

My brother, his wife, and their 4 kids have vacationed there several times before and always talked about how amazing it was. Drew and Emily told us, randomly one day, that they were planning a trip there at the end of March, and we thought – why not? Kurt and I can still do some of our work remotely and we thought it would be a great place for our kids to visit. Also, Kurt and I had never been to the Carolinas! We thought a road trip with the fam sounded exciting – even with a car-sick kiddo. 🙂 

Transportation and Travel Logistics

We drove 15 hours in our VW Atlas SUV. We also bought a Thule roof rack to fit all of our stuff. On the way down we took 3 days, driving about 5 hours each day. We did this initially so we could stop in Columbus, Ohio the first night and visit my family. The drive went remarkably well. Clark was glued to his iPad and only needed to stop for gas and bathrooms. On the way back to Illinois, we woke the kids up at 6 a.m. and hit the road, and honestly, it was the best decision. The kids were still groggy and Reese even went back to sleep for a little over an hour. And, the best part, is there is no traffic at that time so we just zoomed out of there.

We packed up our SUV drove to Hilton Head with plans to stop 2 times to stay overnight as we didn’t know how our 14-month old would do. Due to bad weather, we drove from our home in Milwaukee to Indianapolis for our first overnight, then onto Greenville, SC for our second (this was actually a super cute downtown I would like to check out again!) In total, with some bad traffic and weather, we got down to Hilton Head from Milwaukee in 18 hours. We planned on 15-16 on the way there.

Road Trip Tips for Traveling with Young Kids:

  • Getting to and from HH reminded me of going to Lambeau Field, as there are just 2 lane roads to get there and it can get really congested when everyone is trying to arrive or depart at the same time. So, expert tip, LEAVE EARLY to avoid sitting in traffic. 
  • Also, for any car sick kids, we had peppermint essential oil to reduce nausea, hospital-grade puke bags (just in case), and a change of clothes in the car. Clark also took 1/2 a pill of Dramamine every day we drove and NEVER got sick. Not even during the winding mountain-y parts. 
  • Another tip for when you have kids and adults and have to make stops on your drive – pack away all the clothes in your suitcases/bags for the vacation, but bring a separate, small bag just with overnight stuff. That way, we only had to carry in two small bags into the hotel each night that had pajamas, toiletries, and clothes for the next day, rather than bringing in all the luggage each time. 
  • Sabina made “busy bags” before we left for Reese. They included different types of activities to keep her occupied, and we found most of them off of Pinterest.
  • Lastly, and this is based on personal misfortune, don’t drive your vehicle into a parking garage when you have a roof rack that you’ve forgotten about….

Where did you stay in Hilton Head, SC?

We stayed in the Sea Pines area of Hilton Head. Which was… amazing. It has everything you need and we never felt the need to leave Sea Pines. If you stay outside of the Sea Pines “area”, you have to buy a day pass to enter the grounds. Our 3 bed, 3.5 bath condo was the perfect location, size, and well-maintained/clean. We would 100% stay here again.

Here is the link to our condo rental:
VRBO Condo in Sea Pines

There are condos and villas all over to rent but there are also mid-size to mansion size homes to rent and own! We landed a 2 bedroom villa in the Racquet Club area of Sea Pines and we decided to rent it for 14 days. We rented through the resort vs. a third party like VRBO. By doing this, we got $100 credit to the resort to use on anything during our stay (this was a promotion they ran at the time). Our total stay came to about $200 per day for a large two-story unit. Would I stay there again? Sure! A different unit or area of Sea Pines for sure to check out another area.

About Sea Pines and Harbour Town

  • Harbour Town is within Sea Pines and a prime destination on the island.
  • A historic lighthouse has a nice view of the harbor, with a small fee to visit the top
  • Shops and restaurants, and live music at night
    • The Salty Dog Cafe is the most popular (probably the best shrimp and lobster po’boy sandwich I’ve ever had).
    • Coast had amazing seafood and much more. We ate there on Easter and 2 other times.
  • Sea Pines fitness center is free for anyone staying at the resort can use this facility. With COVID, you have to sign up online ahead of time to claim your time and slot.
  • Large wooden play area & park for the kiddos.
  • Petting zoo for the kids at Sea Pines
    • Free to attend but pony rides cost $15 and a couple of dollars for food pellets. Here, people could feed farm animals and walk around the little farm.
  • Across the street was a pubic pool. It was never too crowded, despite not being a super large area.
  • Tennis courts and golf courses
  • Sea Pines also has its own beach – which was perfect, never too crowded, 5-7 min drive from our condo , and has a restaurant right there where you can go up to order apps and boozy drinks to take back to your beach area.

Best Kid-Friendly Things to Do:

  • The Sea Pines beach really was the best part!
  • Petting zoo and pony rides
  • Walks around the grounds looking for gators, the parks and having picnics
  • Walking to Harbour Town for coffee and pastries in the mornings
  • Venture out of Sea Pines and explore – some of the places we went to included:
    • Shelter Cove town center
      • has a nice park that overlooks another inland harbor and then has outdoor dining and shopping on the other side. A little more upscale I would say!
    • Hudson’s Restaurant
      • the place to go for food. It was about 20 minutes away from Sea Pines. They don’t take reservations and expect to wait a while. The first night we tried to go was a 2 hour wait. So then we went at 4:30 and it was a 40 min wait! It has a beautiful view of the water as well. Great oysters, hush puppies, and shrimp! Shrimp is the food to get in Hilton Head from what we were told!.
    • Island Winery, Hilton Head Brewing Co, and Hilton Head Distillery
      • all in the same area which is nice to hop between them. All have tastings and some food options at the brewery
    • All the restaurants are essentially kid-friendly as they had kid’s menus, high chairs/etc. We didn’t have a bad meal anywhere! The food was really great everywhere.
      • My biggest tip for people traveling there with little kids during peak season is to not even attempt to try and sit down at a restaurant unless your kids are old enough to occupy themselves for an extended period of time. Many places don’t take reservations and you end up going for a table only to be told it’s a 1-2 hour wait – everywhere. We learned that the hard way the second night we were there and didn’t have a good plan B, with screaming crying hungry kids. So from then on we just ordered ahead and picked the food up to either eat outside nearby or back at our condo. Best decision we ever made because then the kids could eat on time and not have meltdowns. 
    • take a day trip and drive into Savannah, Georgia about an hour away. It’s a cute city but would be more enjoyable for families with older kids, couples, or a girl’s trip!
Day trip to Savannah, Georgia, about 1 hour drive from Hilton Head
Reilly’s Plaza, just outside of Sea Pines

Thanks Cortney and Emily for sharing all about your trip — it looks like a great vacation destination for kids of all ages and a place the adults would enjoy too! If you’ve got any questions we can pass to them, please send us an email or DM and we’re happy to get it answered! Adding Hilton Head, South Carolina to the neverending list of future travel spots….

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