We returned from our first big vacation as a family of four just over a week ago. We travelled over 11 hours to get to Hilton Head Island, South Carolina, where we met up with my mom and dad (Mimi + Poppy), and my sister and her family. So there were 6 adults, two babies, and one Ari. 🙂

I had never before been to HHI, and neither had my husband. And, to be honest, I did very little planning (if any) whatsoever! I meant to plan out some adventures ahead of time, but Summer got so busy with all of the normal day-to-day stuff… it just never happened! My sister, on the other hand, had done some planning. But life with babies rarely — if ever! — goes as planned.

One thing that was set well in advance was our condo for the week. We stayed at Seacrest Villas, directly on the North Forest Beach, and just steps away from Coligny Plaza.

Our condo was beautiful. It was three-bedrooms, 3-baths, and had a full kitchen and dining room — plus TWO balconies! It was truly gorgeous! And part of me — the super mom part of me — could have had just that and nothing else for an entire week. No responsibilities; not our house; no laundry and cleaning — just that for a week.

But there was so much to do!

Annie O’s Kitchen. We discovered this place by pure chance. We found ourselves upon a child-free evening and had not at all planned it out. Where would we go alone!? Well, a google search later and the results… showed a bunch of other places. But I happened to see the description of this restaurant — their meats, dairy, and eggs, are all-natural and cruelty-free. There are no antibiotics, no preservatives, no pesticides, and sustainable. Basically, totally our wheelhouse.

I had the Chicken and French Toast (what a fun play on chicken + waffles!) and Chad got the flash-fried whole flounder with collard greens.

We absolutely loved the atmosphere and the vibe from the staff. They were incredibly hands-on — the chef even came by to deliver our meals to the table. The cornbread? Bomb. The sweet tea? SO bomb. The desserts?! OMG I can’t even!

After our dining experience, we convinced the whole family to join us for a ‘last hurrah’ dinner at Annie O’s. And the whole family — Mimi, Poppy, my sister and brother-in-law — we all said, hands down, best food we had during the whole trip!


If you dine between 3:00 – 6:00 PM, the majority of their entrees are 50% off!

And make reservations!



The atmosphere is less appealing to children, but the waitstaff and other employees were super friendly to the kids.

Coligny Splash Pad. The beach, the pool… they can be… exhausting for parents. There’s just so much sand and ‘stuff,’ that kids need. This splash pad was a perfect break for all of us. Located near Coligny Plaza, the splash pad is just off the beach and easily accessible.

Our kids had a blast running in and out of the fountains — and even made a couple of friends! I suggest hitting the splash pad first thing in the morning, before the sun really starts beating down on the kids. But, in case you find yourself there a little later, just know that it does have a little overhead shade, thanks to the awesome trees!


Have the kids where some sort of water shoes to avoid stubbed toes.

Arrive first thing in the morning for the least crowding.



Skull Creek Boathouse. My sister insisted that we go here. We were having a rough day with the kiddos and I didn’t have even a second to check out the menu ahead of time. But I’m so happy that I put all of my trust in her with this restaurant decision!

When we arrived shortly after 5PM, the place was already packed with an hour wait for outside seating. As much as we wanted to sit outside, we were also dealing with a time limit thanks to the kiddos bedtimes! Instead we opted for an immediate high-top table inside. Believe it or not, they have highchairs for the high-top tables, so they could easily accommodate two infants.

Our meals were delicious! I ordered the fried fish and chips and a big side of hush puppies (because, yum!). And Chad ordered a lobster rice bowl that tasted amazing.

My sister and her husband loved the lowcountry boil — and I had some serious food envy of them!

After our meal, we headed to the dock to check out the views. On the other side of the dock there is a beautiful outdoor beer garden with picnic tables, sandboxes for kids, and giant connect four games. The live music was a young guy playing guitar and singing up on stage. It was the perfect way to spend an evening!


Arrive early and be prepared to wait if you are looking for outdoor seating.

But also enjoy that time in the beer garden while you wait!
The restaurant will text you when your table is ready!


Really family-friendly! Each child will get to pick a prize from the treasure box after the meal.

The outdoor beer garden is the perfect place for parents to spend a relaxing evening with young kids.

Java Burrito. We stopped here, first and foremost, for the Java. But I was so impressed by the food setup that I had to come back later in the week to try it out. It’s nestled in a business park on William Hilton Parkway, so you almost have to go searching for it; but I promise it’s worth it!

Their coffee bar is definitely high-end, specialty coffee, with a huge clientele that prefer a pour over (hello!? LOVE pour overs!). But they also offer cocktails for those customers who are going to hang out in the cool café for a bit!

As far as the food, they offer Mexican-style burritos and bowls with ingredients that are locally sourced, for breakfast, lunch, and dinner. Yep – they do breakfast burritos with farm-fresh eggs!

I opted for a burrito with chicken, rice, beans, queso and guacamole. As someone that frequents other fast-casual burrito places, I can tell you that this was far superior to the rest of them. The freshness is something that you can taste!


Take a look at the menu online ahead of time so that you have an idea of what you want to order.

Definitely order coffee, too!


Yes, for a quick family meal. But not for lounging around.

Duck Donuts. So I realize that this is a franchise location and not a native Hilton Head Island thing… but for those of us who do not live near a Duck Donuts, checking this out while we’re on the island is KEY.

See, I have a love affair with donuts. I like them fancy and I like them plain — I don’t discriminate! Ha!

These donuts are served up fresh out of the fryer! We customized our order of a dozen and a half so that we could basically try all of them. Somehow a single plain old fashioned donut ended up in our pack. And I swear to you that is the best darn old fashioned, plain ol’ donut, I have ever had!

(Good news, Ohio friends — there is a Duck Donuts on Polaris Parkway in Columbus!)


Prepare to wait in line.


Very! The kids have fun watching the donuts being made.

Frosty Frog. This little dive of a frozen cocktail bar is located in Coligny Plaza and features about 25 different frozen daiquiri combinations such as a Hurricane, Grape Danger, Sex on the Peach, Piña Colada, and Jungle Juice! Real Talk: They put all of their drinks, daiquiri or not, in styrofoam to-go cups — whether you’re eating in or taking food to go. Also, you’re allowed to walk with the open container anywhere within Coligny Plaza.

We took our daiquiris to go and walked around the plaza a few nights. They were so delicious! My favorites were Jump Start and Grape Danger.

After several visits, we decided to give their pizza a shot. And OMG it’s delicious! Like, really good and the slices are, as Ari would say, GINORMOUS! 🙂


If there are more than 3 of you ordering daiquiris, save yourself a few bucks and order a gallon to-go.
It’s the most cost-effective way to sip some frozen yummies!


Not very.
We saw a lot of children there with their parents, but it’s really more of a bar than anything else.

A Lowcountry Backyard. Located in Palmetto Dunes, this gem of a restaurant serves up local cuisine with some serious lowcountry flair! We arrived just before 4:30PM, which is when they open for dinner service. We were quickly greeted with two other families awaiting the dinner ‘bell’! Great minds (and early bedtimes for babies — likely)!

The atmosphere in the outdoor seating area is awesome. There’s giant Jenga, a hillbilly golf set, a giant porch swing, and a stage for the nightly solo performances.

Our food did not disappoint. Between the fried green tomatoes, the shrimp and grits, crab dip, and grilled pimento cheese sandwiches, we left… satisfied very full.


Arrive right when they open to avoid a wait.

Sit outdoors.


There is so much to keep the kids entertained, between the games, the music, and the mason jars with lids as sippy cups!

Pirates of Hilton Head. Chad took Ari on this adventure without me and Remy Bea, which was fine. The Pirates of Hilton Head is an excursion in Harbour Town (near the lighthouse!) on The Black Dagger! The kids, which range in age from 3-10, in groups of about 20 children (max), learn to speak like pirates, get tattoos, and take down Stinky Pete with water cannons! Ari had such an amazing time and came home with enough gold doubloons to last him a lifetime! We will definitely be hitting this up with every visit.


Check Groupon to see if they have any deals first (they did for us!).

Make sure you plan to spend some time in Harbour Town because there’s a $6 fee to be in the area,
but you have in-and-out privileges all day.

Wear a small backpack and bring plenty of water and snacks.


Very much so! Especially for kids 3 and up!

We will certainly be making Hilton Head our go-to vacation spot from hereon out. I can’t wait to visit all of these places again! Make sure you pin this for later! xo




{ 26 comments… read them below or add one }

Blondedlights September 4, 2017 at 7:09 pm

I love this area, we visited on our honeymoon back in May!


tammigirl September 4, 2017 at 10:59 pm

Hilton Head is my favorite place to go on vacation. Well, tied with a cruise. 🙂


Sarah Althouse | Pretty Simple Ideas September 5, 2017 at 7:19 am

I’ve been wanting to go to Hilton Head with my husband! Also, love that mermaid bathing suit. so cute.


Amanda September 5, 2017 at 8:35 am

Somehow with the exception of Charleston, South Carolina has not been a place I’ve spent much time. I have friends who’ve gone to Hilton Head every summer for 30 years, but I’ve never been. Will have to remedy that after reading your post!


Johnnielynn Rios September 5, 2017 at 10:33 am

Wow this place looks Amazing!!! And it sounds like you all had a great time.


Virjinia Harp September 5, 2017 at 12:51 pm

All that delicious food! Chicken and french toast sounds awesome. It sounds like you had a blast!


ChristineSaltyMama September 5, 2017 at 1:25 pm

I LOVE this write up!! And those donuts have me drooling 😉 Looks like an amazing place to visit!


Kate @ GreatestEscapist September 5, 2017 at 1:49 pm

My mom has an annual timeshare in Hilton Head, & my aunt & uncle own a rental beach house there, so we’ve been going my whole life. I love it there & love that there’s always still so much new stuff to discover. As I told you on Instagram, Skull Creek Boathouse is one of my faves & managed by a high school friend, so we always go there – but I’m going to suggest a few of these other spots to my mom for our trip later this month!


Celeste September 5, 2017 at 1:54 pm

Oh wow this place looks so amazing! I want to visit so badly!


Meli September 5, 2017 at 2:00 pm

This trip looked fabulous! I seriously could eat at the places you did! I will be adding this to my travel list for sure!
Thanks for sharing! XXX


Jenny September 5, 2017 at 2:36 pm

Looks like a great place for a family vacation! And those donuts look delicious!! Thanks for sharing!
Mom Insane Fit


Brittany September 5, 2017 at 6:32 pm

Wow, great post! Sounds like you guys had an amazing trip! I’ve never been to South Carolina, but would love to visit, I’ll have to keep this in mind!


Heydy Lopez September 5, 2017 at 9:04 pm

I’ve never heard of Hilton head before!! Thanks for sharing all the great things about it <3


Lauren September 5, 2017 at 10:09 pm

Looks like you guys had a great time and the food looks so yummy too!!



Katherine Fox September 7, 2017 at 8:21 am

My hubby and I recently went to Charleston, SC so I immediately added Hilton Head Island to our list! This post has some amazing tips and OMG THOSE DONUTS. YES. Pinning this for our future travels to HHI! I’m so excited to go there now!


Amanda September 7, 2017 at 11:31 am

Wow, this sounds like a great place to go! All of those restaurants look great! And looks like your bub had a blast in the fountains! Glad to see you enjoyed your time there! 🙂


Corey | The Nostalgia Diaries September 7, 2017 at 12:32 pm

It looks like you had a great time! I grew up in South Carolina and it holds a special place in my heart — especially the coast!!


Keri September 7, 2017 at 9:16 pm

We love Hilton Head, I will keep this post for future!


Ashley September 7, 2017 at 10:14 pm

Wow! What a fun place! I would love to visit and stay there!


Amanda September 7, 2017 at 10:44 pm

I’ve never been to Hilton Head Island, but now I want to go! There are so many fun things to do, and all that food! What a dream vacation!!


Sarah September 9, 2017 at 11:17 pm

Your vacation there looks SO fun! I’m hungry looking at all the good food you found along the way!


Stephanie Gilbert January 30, 2018 at 8:02 pm

This sounds like a great vacation spot! I love places with AmAzInG dining options… sounds like there are!


jaclyn January 30, 2018 at 8:57 pm

We went to HHI 5 years ago and this makes me want to go back. The drive was a bit challenging for us…but maybe now that the kids are older. It is such a fun place!


ashley peavey January 30, 2018 at 11:10 pm

Wow this looks like a fun place to visit!


Jennifer from Maune Legacy January 31, 2018 at 3:26 pm

This trip looks amazing! Thank you for including all the family ratings for your activities!


Aly Funk January 31, 2018 at 4:31 pm

I love Hilton Head! It’s been years since I’ve been there and this makes me want to go back!


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