How This Adventure Happened 🌴

Sometimes the best trips are the ones you don’t really plan.

This adventure started with our friends, Pat and Tashia Day. Tashia was attending a conference when she started bidding on a vacation package—and somehow, we won! 🎉

Of course, once we had the trip, the next challenge was figuring out when four adults could actually find a week that worked on everyone’s calendars. 😂 After a little calendar juggling, we landed on late August.

And as it turns out, we couldn’t have picked a better time.

We arrived in Hilton Head just as the busy summer season was winding down. The crowds were lighter, the pace was relaxed, and we were able to enjoy so much of what Hilton Head, Savannah and Charleston had to offer without fighting the peak-season crowds.

What started as a random vacation package turned into a week we absolutely needed—a chance to slow down, explore somewhere new, eat some amazing food, enjoy a few drinks, laugh a lot and spend time with great friends.

So that’s how four Hoosiers ended up packing their bags and heading south for a week of beaches, history, ghosts, distilleries, good food and questionable amounts of walking. 😂

And honestly… what a way to start this next chapter of life. 🌴🍷👻

🌴 Hilton Head Adventure — Day 1! 🌴

Our Hilton Head adventure officially started Saturday morning with a road trip full of the important stuff… food stops! 😂

First up: Parlor Doughnuts in Indy 🍩, then a very necessary stop at Buc-ee’s in Kentucky 🦫, and finally Smashburger for dinner. Because apparently road trips are just an excuse to eat our way to our destination. 😂

We arrived at our home for the week—a villa at Shipyard Plantation, right on the golf course. ⛳️🌴 And apparently, we had some local neighbors waiting to welcome us! A little alligator friend 🐊 and a few turtles 🐢 kept us company throughout the week. Because nothing says Hilton Head vacation quite like having wildlife casually hanging out in your backyard! 😂

Sunday morning we woke up to beautiful, sunny and HOT Hilton Head! ☀️🌴 And we were ready to explore!

We started the day at Harbour Town, checking out the iconic red-and-white-striped lighthouse and taking in the gorgeous views of the yacht basin. ⛵️

Then it was time for lunch at The Crazy Crab—fish and chips, fish and shrimp tacos, and absolutely no complaints from this crew! 🐟🌮

After lunch, we wandered through the shops before making our way to Honey & Thistle for a delicious wine tasting. 🍷 Because exploring is hard work, you know. 😂

Next stop: Coligny Plaza, where we did a little shopping and squeezed in another wine tasting at Carolina Tasting Room. We even brought home a few of our favorites! 🍷🛍️

We wrapped up the day at The Bank and Side Hustle Brewing, enjoying some dinner and drinks before calling it a night.

A pretty perfect first day on Hilton Head—beautiful views, good food, shopping, wine, and plenty of exploring. ❤️

And our little backyard friends were just the beginning… 🐊🐢🌴

Day 1 ✔️ — and plenty more adventure! 

👻 Hilton Head Adventure — Day 2: Savannah! 👻

Day 2 took us off the island and into Savannah, Georgia, for a full day of exploring, eating, drinking, history, and just a little bit of trouble. 😂

We grabbed a Savannah City Pass and were ready to make the most of it!

Our first stop was Old Savannah Distillery for a tasting. 🥃 Then we hopped on the sightseeing trolley and made our way to the Prohibition Museum, where we learned a little history and, naturally, had to visit the speakeasy for a delicious Old Fashioned. 🍹

Next up was the Pirate Museum, where we even got to meet Jack Sparrow! 🏴‍☠️😂

By then, we had worked up an appetite, so we stopped for lunch at Magnolias Cafe & Kitchen before jumping back on the trolley to explore more of Savannah’s historic streets, beautiful squares, and iconic landmarks.

Eventually we made our way down to City Market for more shopping and exploring—with a little gelato thrown in because vacation calories don’t count. 🍨😉

And then came the Savannah food crawl… because apparently one dessert is never enough! We had to try Byrd’s famous cookies, Kermit’s Key Lime Shoppe, and Savannah’s Candy Kitchen. 🍪🍋🍬

After all that walking (and eating!), we headed downtown to Churchill’s Pub for a drink and a few lessons in euchre. 🃏 The Days have been patiently trying to teach me… and I may finally be catching on. 😂

But the day wasn’t over yet!

That evening we started our Haunted Pub Crawl—a two-hour walking tour through some of Savannah’s most historic and supposedly haunted pubs. 👻🍻 We heard some great stories, explored some seriously old places, and may have wondered more than once if we were actually alone… 😂

And because apparently we hadn’t done enough for one day, we ended the night at a karaoke bar. 🎤

And we may or may not have sung a little karaoke… 😏😂

Another ridiculously fun day in the books. Savannah definitely knows how to show you a good time!

Day 2: history ✔️ food ✔️ shopping ✔️ cocktails ✔️ ghosts ✔️ euchre ✔️ karaoke ✔️

I’d say we’re doing vacation right. ❤️🌴👻

🌊 Hilton Head Adventure — Day 3: Beach Day! 🌊

Hoot hoot! 🦉😂 It was officially BEACH DAY… at least for Tashia and me! 🏖️☀️

The guys decided they had more “important” exploring to do… which apparently meant day drinking at Hilton Head Distillery and Island Winery. 😂🥃🍷

Meanwhile, we girls had the much better plan—sand, sun, waves, and absolutely nowhere to be. We spent the day soaking up the sunshine, listening to the waves, and chatting about life. ❤️ It was the perfect girls’ day and exactly what we needed!

Eventually, we reunited with the guys for dinner at The Smokehouse, where we enjoyed some seriously delicious BBQ. 🍖🔥

Then it was back to the villa for wine, games, and plenty of laughs. 🍷🎲

A little beach time, a little day drinking (for some of us 😂), good food, good wine, and even better company.

Day 3 ✔️ — 10/10 would do it all again! 🌴☀️🕶️

🌴 Hilton Head Adventure — Day 4: Charleston! 🌴

Up early and on the road because today was a BIG day in Charleston! We grabbed another City Pass and packed as much as humanly possible into one day. Spoiler alert: we succeeded. 😂

Our first stop was Fort Sumter, and we had to be on the ferry by 9:30 a.m. The two-hour visit was absolutely worth the early wake-up call. We learned so much about the Civil War, Charleston’s role in it, and the tremendous toll the war took on the city and its people. The first bullet that started the civil war was fired here.  And as if the history wasn’t enough, we spotted dolphins swimming alongside the boat! 🐬 What a sight!

After Fort Sumter, it was time for lunch and a pint at Holy City Brewing. 🍺🍔 Delicious! Then we headed to Firefly Distillery for a tasting—and WOW. What an experience!

Firefly is South Carolina’s largest distillery and the birthplace of the world’s first Sweet Tea Vodka, made with local plantation tea and Louisiana cane sugar. 🍑🍹 The property is HUGE and even hosts some pretty big concerts. But the best part? The staff. Absolutely amazing people who made the whole experience even better!

From there, we headed downtown for a walk through City Market and over to Waterfront Park to see the famous Pineapple Fountain. 🍍

Then it was time for one of the highlights of the day—we met up with Pat’s nephew, who is a cadet at The Citadel! 🇺🇸 He gave us a quick tour of the public areas of campus, including the library, chapel and bookstore, before becoming our very own private tour guide around downtown Charleston.

And what a tour it was!

We wandered through Queen Street, Market Street, Meeting Street and Rainbow Row, taking in the incredible architecture, historic homes, churches and buildings while learning about Charleston’s rich history along the way.

Both Savannah and Charleston have such a European feel to them. The cobblestone streets, historic architecture and beautiful buildings make simply walking around feel like you’re somewhere worlds away. ❤️

We stopped for a free treat from our City Pass at The Pineapple Hut—and WOW. 🤤 Definitely worth the stop!

Then it was time for dinner at Poogan’s Porch, a historic Southern restaurant housed in a restored 1891 Victorian home. The restaurant opened in 1976 and was named after Poogan, a neighborhood dog who was left behind by the home’s former residents and decided the porch was his new home. 🐶😂

The place is full of old Charleston charm with heart-pine floors, cozy dining rooms and those gorgeous front porches. And, of course, it wouldn’t be a proper Charleston restaurant without a little ghost story. 👻 Local legend says the building is haunted by former resident Zoe—and Poogan himself is buried out front!

After dinner, we walked down to The Battery, Charleston’s famous waterfront promenade and defensive seawall. The area has protected the city for centuries and eventually became the beautiful public park and promenade it is today. 🌊🌴

Then it was time to say our “see ya later” to Pat’s nephew. We loved getting to see a little bit of his world at The Citadel and having him show us around his beautiful city. ❤️

But… we weren’t done yet. 😂

Our next stop was The Blind Tiger, where we learned about the history behind the name and the illicit drinking establishments that popped up during the temperance era. And, of course, we had to try our first Espresso Martinis of the trip! ☕️🍸

Finally—because apparently we hadn’t walked enough—we ended our Charleston adventure with a Ghost & Graveyards walking tour through the historic city with Bulldog Tours, included with our City Pass. 👻 We explored one of Charleston’s oldest graveyards and heard some seriously creepy stories about the city’s past.

History, dolphins, distilleries, good food, beautiful architecture, family, ghosts and Espresso Martinis…

That’s a wrap on Charleston! 👻🍸❤️

And according to my step counter, we may have walked approximately the entire state of South Carolina. 😂