Hilton Head Travel Guide: 6 Days on HHI

hilton head beach view

In September, my family and I went to Hilton Head! Today, I’m going to share our Hilton Head Travel Guide, after spending 6 days on Hilton Head Island. It was actually the first time that Liam and London had been to the ocean, so in our Hilton Head itinerary, you will notice that we tried to spend as much time as we possibly could at the beach.

name in the sand 2020

Also, I need to mention that I was SO EXCITED to be able to travel! COVID-19 has been an absolute pain in my ass. I had a trip booked to Hawaii in March that ended up getting canceled. Instead of traveling, I was spending my time creating graphics for travel quotes.

Moving on…

While on Hilton Head Island for 6 days, we ate at a lot of different restaurants. We tried to visit all of the most popular restaurants on Yelp, and I’ve wrote a separate blog post that lists my Top 5 Places to Eat in Hilton Head.

view from sea cloisters hilton head

There are tons of fun things to do in Hilton Head in September, so if you’re looking for some great Hilton Head vacation ideas, you’ve come to the right place!

Hilton Head Travel Guide

  • Day 1: Sea Cloisters Villas, Folly Field Beach, Kroger, Giuseppi’s Pizza
  • Day 2: Coligny Plaza, Flatbread Grill & Bar, Salty Dog Cafe, Folly Field Beach, Night Walk on Beach
  • Day 3: Hudson’s, Salty Dog Tshirt Shop, Shelter Cove Community Park, Pool
  • Day 4: A Lowcountry Backyard, Harbour Town, Drive Around & Explore
  • Day 5: Hilton Head Diner, Pool, Bella Italia Pizza
  • Day 6: Folly Field Beach

Hilton Head Travel Guide: Day 1

Sea Cloisters Villas

Originally, when we decided to go to Hilton Head, I made a spreadsheet of all the best places to stay in Hilton Head and how much each of them would cost. I almost booked one, but I’m glad I didn’t.

sea cloisters interior view

A friend of mine goes to Hilton Head every year, and she told me about the Sea Cloisters Villas. For less than a hotel, we got a 2 bedroom, 2 bathroom condo that had a huge balcony with a beach view. 

It also had a full kitchen with stove, microwave, fridge, dishwasher, blender, toaster oven, dishes, everything you could possibly want in a kitchen, etc. Our villa had 3 TVs, a washer and dryer, and the condos have their own private pool.

sea cloisters living area

We had way more space than we ever would have needed. The other bathroom and bedroom were barely even used, but it didn’t matter because it was still less expensive than a regular, tiny hotel room and it was WAY BETTER.

If you’re ever going to Hilton Head, I highly recommend Sea Cloisters Villas. It was the best. 

Plus, if you go with a bigger group of people, where you actually need another bathroom and bedroom, you’ll save loads of money!

father and son at beach

I could go on and on about Sea Cloisters, but I won’t. If you have questions, just ask me.

Folly Field Beach

Our condo was right on Folly Field Beach, so that is the beach that we always went to. 

Not sure if it was because it was right in front of our condo or if it was because of COVID-19, but it was never “packed” like most popular beaches are.

little boy on folly field beach

Again, I’m definitely glad we stayed at Sea Cloisters, because after driving around Hilton Head Island, I think it would’ve been a huge pain to go to any of the beaches if you weren’t staying within walking distance from them.

A lot of places have “no beach parking,” so I assume you’d have to walk further than I would have liked to if you stayed somewhere else, drove, and parked.

This also saved us from getting sand all over my car, so that was even better.

We didn’t go to any other beaches, but Folly Field Beach was perfect, so we didn’t need to.

little girl on beach with sunglasses

And yes, Liam and London loved the beach!


We went to the grocery on our vacation! I bet you won’t see this on many Hilton Head Travel Guides.

It wasn’t for fun or anything, but like I said, we had a full kitchen. Being able to get groceries saved us from having to go out to eat for every meal, which is always a plus.

kids eating breakfast in hilton head

At Kroger, we were able to get things like bagels and fruit for breakfast, hot dogs and frozen pizza for lunch, cookies and Cheetos for snacks, and alcohol to drink while we sat on the balcony. 

They also have souvenirs inside Kroger, which are probably cheaper than the ones at the regular souvenir shops. 

Giuseppi’s Pizza

My friend recommended Giuseppi’s Pizza, too, and I’m glad she did!

hilton head pizza giuseppi's

If you know me at all, you know I love pizza, and this pizza was incredible. Read more about it on my Top 5 Places to Eat in Hilton Head blog.

Hilton Head Travel Guide: Day 2

Coligny Plaza

This is basically the souvenir shop area of the island. There are also restaurants, ice cream shops, booths advertising Hilton Head attractions, etc.

I got a Hilton Head sweatshirt that is super comfortable.

Liam was obsessed with this treasure chest inside one of the shops, so we got him that.

And can you BELIEVE we found a keychain with London’s name on it? London’s name is never on anything (except for London, England things), so obviously, we had to buy that.

There was also a shop somewhere around there that sold Vineyard Vines t-shirts, so Cameron and I got Hilton Head VV shirts. I actually forgot I had it until just now, so I guess I should probably wear that soon.

Flatbread Grill & Bar

This isn’t one of the places that I found on Yelp, but it was at Coligny Plaza and we were hungry.

The food wasn’t that memorable, but I did get a Blue Hawaiian. I think that was the first Blue Hawaiian I’ve ever had, and I will be getting them more often now. They are delicious.

blue hawaiian drink

The kids barely ate any of their food, and this is where we learned to start letting them split a kids meal wherever we go. It saves money and there’s less food on the floor afterwards!

The Salty Dog Cafe

Can you even create a Hilton Head Travel Guide without suggesting The Salty Dog Cafe?

kids in front of palm tree

Well, you probably shouldn’t, but I elaborate more on that in my Top 5 Places To Eat in Hilton Head blog.

Folly Field Beach & Sunset Walk On The Beach

Another beach day! We also went for a night walk on the beach at sunset.

kids on beach at sunset

I was hoping to get some great sunset photos, but that didn’t happen.

family on beach at sunset

I did finally get a picture of me with the kids, though. That never happens!

Hilton Head Travel Guide: Day 3

Hudson’s Seafood House on the Docks

Yet again, another recommendation from my friend, Tara!

hudson's fish n chips

This is a great place to go if you love seafood and want to have lunch or dinner near (or practically on) the water. You can read more about it in my Top 5 Places To Eat in Hilton Head Blog.

Salty Dog T-shirt Shop

I don’t know what it is about The Salty Dog, but their shirts are trendy. Everyone has them! I started seeing Salty Dog t-shirts like 20 years ago, so I knew about Salty Dog Cafe long before I’d ever been anywhere near one.

salty dog koozies

Obviously, this means that we had to buy some. Cameron, Liam, London, and I all got one. We also got some cups and koozies.

parrots at the salty dog

There are a few parrots outside the t-shirt shop, so the kids got to look at them and try to get them to talk!

Shelter Cove Community Park

Every time we walked past any playground, Liam begged to go on them. 

boy at shelter grove park

This is probably one of the more unique things to do in Hilton Head, because most people don’t go to playgrounds during their vacations.

girl at shelter grove park

Finally, I looked up “parks near us” on Google, and Shelter Cove Community Park looked like the best one. It was a good park, but I wouldn’t go out of my way for it or anything. Only go there if your kids are really passionate about playgrounds.

Sea Cloisters Pool

The ocean was actually pretty rough most of the time we were in Hilton Head. There were several days where they had a yellow flag posted, which according to google, a yellow flag “indicates potentially high surf or dangerous currents and undertows.”

A yellow flag was posted on the beach during our third day, so we used that time to go to the Sea Cloisters pool!

In our experience, the Hilton Head weather in September was always around the upper 70’s to mid 80’s, but usually pretty cloudy.

girl with floaties in pool

Because the Sea Cloisters pool is only available to people who live at or are vacationing in the Sea Cloisters Villas, it was never very packed. The regular pool goes from around 3 feet – 8 feet, and there’s also a kiddy pool.

kids on beach with towels

We brought along some floaties for the kids that we bought on Amazon, and they loved the pool!

Hilton Head Travel Guide: Day 4

A Lowcountry Backyard Restaurant

I believe Cameron said that this was the “best meal he’s ever had in his life.” If you want to find out what he ordered, my Top 5 Places to Eat in Hilton Head blog pairs perfectly with this Hilton Head Travel Guide.

fried green tomato blt

Harbour Town

Like The Salty Dog Cafe, Harbour Town is also back in Sea Pines Resort, so you have to pay to get into it. I think the cost was $9.00.

It’s where the lighthouse is that you always see on those HHI stickers that people have on their cars.

harbour town hilton head

There’s also a lot of touristy shops in Harbour Town, which is great if you’re looking for souvenirs. It started to rain while we were there, so there weren’t many people.

Drive Around & Explore Hilton Head

Because it was raining, we decided to drive around and explore Hilton Head Island. There are actually a lot of celebrities that have (or once had) homes on Hilton Head. We tried to see some of those, but when doing that, you will find that a lot of places are gated.

We actually drove right up to the gate of one because we didn’t know what we were doing. Cameron told the security guy that we were “just driving around,” and he said “this is a private community!” So we had to turn around.

Then, we went through the Cookout drive thru to get milkshakes because the kids were asleep in the car. Brilliant.

Hilton Head Travel Guide: Day 5

Hilton Head Diner Restaurant

I loved this place!! They give you looooots of food. I could not leave this place off my Hilton Head Travel Guide.

hilton head diner french toast

See the photos and read more on my Top 5 Things To Eat in Hilton Head blog.

Sea Cloisters Pool

Day 5 was another windy, yellow flag day on the beach, so we went to the pool again.

kids in hilton head pool

At this point, Liam was acting like he liked the pool more than the beach, but I think he may have changed his mind by the last day. Maybe? I’ll have to ask him again.

Bella Italia Pizza

Honestly, we wanted Giuseppi’s again, but for some reason we couldn’t get the order to go through on Door Dash.

It was fine, though. Not as good as Giuseppi’s, but still okay.

Hilton Head Travel Guide: Day 6

Folly Field Beach

Finally, on our last day, Poseidon, the great god of the sea, gifted us with a beach day with no yellow flag! FINALLY.

The kids really loved playing with the boogie boards and sand toys. 

kids on beach with boogie board

I don’t know if it was because of the rough water from the few days before it, but LOTS of things were washing up on the beach. While we were there, I noticed several kids with starfish, and Liam even held a sand dollar.

Then, I went over to pick up a shell and realized it was jellyfish.

jellyfish at folly field beach

It was at that point that we left the beach. I googled different jellyfish breeds and found out that this one apparently doesn’t sting people.

siblings at hilton head beach

But I still didn’t want any of them touching us! There were probably other kinds out there, too.

Time To Go Home

The next morning, we woke up and left for Cincinnati! It takes 10 hours to get from Cincinnati to Hilton Head, but it’s still one of the closest ocean beaches to us.

On the way there, we stopped in Asheville, NC to sleep for one night, but on the way home, we just drove straight home.

Have you ever been to Hilton Head?! If so, what was on your Hilton Head itinerary? Give me ideas, because we definitely want to go back!

If you have your own Hilton Head Travel Guide, feel free to leave that in the comments, too!

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