A week of fun things to do in Hilton Head Island

My family has been visiting Hilton Head every year since I was an infant. We usually visit during Easter week, in addition to other times during the year. And I LOVE that we have that tradition because Hilton Head is a place filled with so many memories. I know it may be cooler to travel the world… but we just love coming back to the same spot. We always stay at our family’s Hilton Head Villa, which is available for rent! It’s so cute & comfortable.

What’s your opinion? Do or don’t: vacation at the same place?

I really REALLY love that my kids are experiencing the same memories with their cousins – and me – that I have as a child. So much love there. I know my grandparents were grinning ear to ear from heaven watching over us the entire week. They bought the villa in 1979 (coincidentally, the year I was born) to bring the family together. Here’s our week…

For the photo curious – Photos taken with the Fuji x100f, iPhone, and a GoPro

Things to do in Hilton Head: Day One

Dinner at Old Oyster Factory

The first night, the “young” cousins had dinner at the Old Oyster Factory. The restaurant is a Hilton Head establishment and has been serving guests with views of the water for more than 25 years. The menu has popular seafood items like crabcakes, steamed shrimp, calamari, and fried seafood in addition to a great selection of oysters and steaks. Most importantly, the wine list is surprisingly FANTASTIC with wines I’d expect to see on a fine dining wine list. When I saw the Ferrari-Carano Fume Blanc on the wine list at a great price, I knew someone had good taste because that wine is made for seafood. Yay.

Things to do in Hilton Head | Day Two

Work out at Cyclebar Hilton Head

CycleBar is a beautiful facility and not a horrendous workout if you love spinning. I don’t love spinning. I was ready for the class to be over at the six-minute mark. Then, I got distracted with the Maroon Five video playlist which made the workout slightly more tolerable. However, they don’t always show concerts/videos. Usually, it’s a leaderboard ranking everyone in the class.

Grocery shopping in Hilton Head

Hilton Head has a Publix, Fresh Market, and a Whole Foods. If Trader Joes were in the mix, it would be a grocery store heaven. But Mount Pleasant is grocery store heaven, and that’s two hours away. Whole Foods. I love going to Whole Foods, but since I don’t visit often, I walk around like a kid overwhelmed at Disney World. I was on a mission for Gluten Free, Dairy Free snacks (a story for another blog post) and found a lot of options including Chocolate Power O’s, which pretty much sustained my 4-year-old for the week.

Hilton Head Beach

Rash guards, huge beach hats, a good dose of sunscreen (I used Hint spray sunscreen which smells like grapefruit!) and we headed to the sand with a large sandcastle kit from The Kangaroo Pouch in Myrtle Beach. Water was freezing, kids had a blast anyway. Sandcastles were built and immediately stomped to ruins.

Dinner at the villa

Happy hour commenced with Gordon’s Ceviche, Dry Creek Chardonnay and Stag’s Leap Wine Cellars Karia Chardonnay. We had dinner with the family at the villa. My son (9) talked my dad (72) into a poop emoji pinata for the celebration of my aunt’s birthday. The poop emoji is not in my dad’s texting repertoire. Do you see the joy on my son’s face? 💩 Fun night for all.

Things to do in Hilton Head | Day Three

Orange Theory Hilton Head

A workout at Orange Theory won’t kill you but will make you think you’re about to die. This is the day I took my cousin Liz’s place at Orange Theory, a ridiculously expensive but also ridiculously addictive workout chain. After one class earning 20 splat points, I am hooked.

Orange’s theory, according to science and algorithms so it MUST be factual, the color-coded zones indicate how much fat you’re burning and you earn splat points. Staying in the orange/red and earning between 12 – 30 splat points became a goal I HAD TO CONQUER. I worked out harder than I usually work out, which consists of a slow saunter while listening to a podcast and trotting in intervals when Couch to 5k tells me to run. Make working out a game, and I’m apparently a lot more motivated to burn calories. Bring it, Orange Theory, I’m seriously considering paying your exorbitant monthly fee.

Shelter Cove

The playground at Shelter Cove Town Centre has great views and is located in a cool shopping center. The former interior Shelter Cove mall was renovated a few years ago and turned into a gorgeous lifestyle center, anchored by marsh views and a gigantic park and playground. I don’t think you can find a prettier view from a playground. If you aren’t toting around kids, the shops are fantastic – from outdoors stores to boutiques. With a 4 year old and 9 year old… I window shopped.

Dinner at Frankie Bones

Frankie Bones is a cool Italian spot with an excellent wine list. The atmosphere and decor were not what I expected: modern Rat Pat artwork and steak-housey modern decor was cozy and cool. The Italian menu had a million things I wanted to order, always a good sign. The wine list. WOW. I tried to encourage the table to drink red wine so we could take advantage of the excellent deal on Rodney Strong Symmetry – but alas, none would commit to a 1.5 liter of fancy wine (even though it was a great price.)

Things to do in Hilton Head | Day Four

Family Photo Op About 100 photos, and a handful we could print. Sound about right?

Sandbox Children’s Museum

This is a bike ride from our place in Shipyard, just off of Pope Avenue. Sandbox Children’s Museum is the sweetest Children’s Museum packed with cool areas for toddlers and young kids. Both of my children (4 and 9) LOVE it. I have to give my husband credit for discovering this place, which has become a new tradition for us. When my kids talk about Hilton Head, the Sandbox is always mentioned as the place they want to visit.

Marley’s Island Grille for lunch is hands down, one of the best places on the Island. The menu is fantastic – and it’s counter service so you can order and then do your thing. It’s outside. The play area is filled with cool yard games like Connect Four and Cornhole. The food is FABULOUS. I had the shrimp burger and just thinking about it makes me want to go back. My daughter was pumped about the large shrimp souvenir cup, typically reserved for cocktails. (They let us order one with water.)

The RBC Heritage Golf Tournament is a Big. Deal. The 51-year-old tournament dresses the famous Harbour Town Lighthouse in red plaid, takes over the golf course, and brings celebrity golfers like Dustin Johnson to the area to drive around in tournament SC-manufactured BMWs. My husband scored us VIP passes, and we spent the afternoon with Gloria Ferrer sparkling, walking the course, and even managed to shop in the Southern Tide tent. I’d never been to a PGA tournament, and even though I am not a sports fan, I love a good tailgate – and that’s pretty much what a golf tournament is. Two thumbs up.

Dinner at Shelter Cove

Dinner at Bucci & Murray’s Pub in Shelter Cove happened by accident. We went to Shelter Cove (the one with the Poseidon statue, not the new shopping center) for a food and music festival. It was a great little festival, but with 20 people and young kids… the set-up was not going to be accommodating for dinner. So, we stumbled into Bucci & Murray’s to see if they could squeeze us in. They did. Plus, the kind hostess didn’t murder me with her eyes when I changed the reservation several times. They took our orders, brought out our food, and divided up the check without a lot of drama. Kids loved dancing to the band. Adults enjoyed drinks and conversation. Food was fantastic. It was an unplanned visit but I’d be back – the service and food and drinks far exceeded expectations.

Things to do in Hilton Head | Day Five

The best lunch in Hilton Head

The Best Greek Restaurant on the Planet is It’s Greek to Me located next to Coligny Plaza. I go for the dips. The feisty feta, hummus, eggplant, and tzatziki served with bright red tomatoes, crisp cucumbers, peppers, chunks of feta, kalamata olives plus warm pita bread is the best appetizer available to humankind. I ordered the chickpea salad as my entree, which sparked a new obsession for chickpea recipes. If you’re visiting, GO. The salmon is also a favorite. And the greek salad. The soups are always delicious. Basically, anything you order is fantastic. The kids love it, too!

A Rainy Afternoon could have ruined the day, or we could have piled into a crowded movie theater… instead, we opted to just stay inside, dye Easter Eggs, and play Slamwich. It was a nailbiter of a game with two lawyers, marketing professional, and a 9-year-old. My 9-year-old beat us all.

Poseidon Restaurant at Shelter Cover

Dinner at Poseidon was made possible by Aunt Susan who had the foresight to make reservations weeks in advance. If you want to go to this place (and trust me, you do!), make a reservation on Open Table or call. This trendy seafood spot is open and airy and buzzing with people in khaki pants and pastel colored shirts and ladies in Lilly Pulitzer. (It’s Hilton Head, the preppiest destination on the planet. We clearly played the part, as evidenced in the above photo.) The seafood menu is fantastic and so is the wine list. This is a cool spot for cocktails but even better for dinner.

Things to do in Hilton Head | Day Six

Tanger Outlets Hilton Head (there are 2!)

Shopping at Tanger was the typical experience with kids – telling the little one to stop hiding in the clothes racks and the older one he couldn’t buy every single item he laid his eyes on – but then I turned the corner. And staring back at me was my BFF from college!!!! She lives in Beaufort and runs an uber-cool event planning company – we made plans earlier in the week but canceled due to the flu… and that excursion was her first venture out into public. So we went to lunch!

Hudson’s on the water

Lunch at Hudson’s on the Water is always delightful. I love friends you know so well, you’re just totally comfortable, the conversation picks up where you left off a year ago, and it’s just like coming home. That was lunch for me. 💕

Our last night with the family was a fun, relaxed evening with pizza (although, ordering pizzas for 20 different preferences was interesting) followed by a game of Heads Up. My son LOVED IT SO MUCH. And so did everyone else – we all got really into it. The game is a free app on your phone – you place the phone on your head and a word pops up – everyone yells clues at you until you guess the answer and then flip to the next word. The best part? It records the crowd yelling clues (unless you don’t want it to!) It is hilarious and perfect for a group!

Final Hours

Breakfast at Plantation Cafe is always a great way to kick off the day. After coffee and crabcake benedict, we headed back to pack up and get on the road.

Hope y’all enjoyed some fun things to do in Hilton Head!!

More recommendations for fun things to do in Hilton Head:

• Where we stay: a Happy Hilton Head Villa
• We loved the Dolphin Seafari Cruise with our kids
• Best Hilton Head restaurants – from donuts to seafood!
• Go kayaking! Kayak Hilton Head has plenty of fun options
• Go to the Salty Dog Cafe in Sea Pines for a fun night with your family