Wandering Boldly: My Solo Trip Through Savannah & Bluffton, SC
There’s something transformative about traveling alone. For me, it came after a major life shift, a breakup with someone who had introduced me to the world of travel. I didn’t want that chapter of my life to end just because our relationship had. So I decided I would continue on; just me, myself, and my carry-on.
I’m Tiffany, a Realtor based in Tulsa, Oklahoma. I’ve lived in Tulsa most of my life, but a few years ago, I found myself asking some big questions. What does Tiffany really want now? Could a new city bring healing and inspiration? Could I maybe even move? I decided it was time to test those waters. Whether it’s a beach town, a historic cottage, or just a home where the trees sway a little differently, I was open. Curious. And ready for a little Southern inspiration
So, first up: Savannah, Georgia, and Bluffton, South Carolina — two Southern gems that kept calling my name. This was more than just a vacation; it was research, rest, and maybe the start of something new.
Freedom to Travel: Solo Trip, Realtor Edition
The beauty of my job is that I can work from anywhere. Give me my laptop, phone, Wi-Fi, and my trusted team back in Oklahoma, and I’m good to go. While I travel, deals still close, clients are still taken care of, and I don’t miss a beat.
Planning starts online, I’m always using tools like:
- Tripadvisor (to see what’s really worth visiting)
- Instagram tags (for visual inspiration)
- Wikitravel (for history and tips)
- Facebook travel groups (like Girls LOVE Travel)
- TikTok
- Expedia (to find the best spots & read reviews of areas and places to sleep)
When you’re traveling solo, the planning becomes even more personal. You’re curating every experience to fit you. If you don’t have a partner who loves to travel, it’s okay. Not everyone has to share the same interests in a relationship. But that doesn’t mean you give up the things that light you up. Find friends to join you. Or get comfy going alone. There’s real power in that. (And freedom too!)If you’re not quite there yet, consider joining groups like “Girls Love Travel“ on Facebook. With over a million members, it’s filled with women coordinating trips, sharing safety tips, and offering encouragement. Be safe, vet your travel companions, and trust your gut, but know you’re not alone in wanting to see the world. You just need to be brave enough to start. There are groups, forums, and safe ways to meet fellow travelers, or, like me, you can get comfortable doing it solo.
Arriving in Bluffton: Cozy, Quiet & Quirky
I had flown American Airlines first class because… why not? I’ve worked hard, and comfort matters. From Savannah’s airport, Bluffton was just a 40-minute drive, which was perfect for me to easily check out both cities in one visit! So I picked up my Alamo rental SUV (via Expedia) and headed out. Nowadays, I prefer the Turo app for booking cars. It’s quick, easy, and the owners typically have the car waiting for you with keys locked in a keybox at the airport. So much simpler sometimes than waiting in the long rental car pickup lines.
I found the cutest Airbnb in Bluffton, a charming little carriage house at 7 Hickory Trace. It was around $120 a night, and adorably decorated with Southern flair: a mosquito-net-draped bed, full kitchen with coffee pods and creamer, complimentary wine, and handwritten local guides. A perfect solo setup. Bluffton itself is a quiet, picturesque town centered around a little square. Think: mossy trees, family-owned shops, and evenings that wind down early. It’s peaceful, but don’t come here if nightlife is a top priority. That said, I did find a fun local hangout one night: Old Town Dispensary. Firepit outside, friendly locals inside. I ordered my usual, Jack Daniel’s with pineapple. (It’s strange enough that some bars have started calling it “The Tiffany.” 😂) Bluffton may be sleepy, but it has soul.
Exploring Hilton Head & Daufuskie Island
I love horses, so naturally, I booked riding lessons at two different barns. First up:
- Deep Sigh Farm in Seabrook, SC: A rustic, intimate 13-acre farm. I had a Western-style lesson with Barb, the lovely owner. It was peaceful and soulful
- Lawton Stables in Hilton Head: Gorgeous and polished, but the trail ride was slower-paced since I was grouped with beginners. Still a scenic, relaxing ride through protected forests.
It’s key with your solo travels to find what you love and just book it! It’s up to no one but yourself to find things you enjoy and do what brings YOUR SOUL happiness. For me, a lot of that happiness is also eating. So, lunch at Red Rooster Café after riding? That Gobbler sandwich with strawberry jam and a S’mores coffee might have been the best surprise of the whole trip. That first night, I headed to Old Oyster Factory in Hilton Head Island. I bellied up to the bar solo and treated myself to a Southern feast: oysters labeled by their rivers (May River, James River, Single Lady), hush puppies, clam chowder, and a Tito’s sweet tea, my other signature drink. I was present. And I was proud. Also, now extremely full from all of my delicious Southern meals. Yum!
Since I was exploring relocation possibilities, I decided to check out Daufuskie Island. I met up with a fellow Realtor for a good old-fashioned tour. To get there, you hop on a ferry from Hilton Head; there are no cars allowed on the island, only bikes, horses, and golf carts. It felt like something out of a novel. The island is quiet and absolutely beautiful, with:
- Secluded beaches
- Golf courses and country clubs
- Clubhouses and pools
- Beautiful homes ranging from quaint cottages to multi-million-dollar retreats
I toured a $400,000 duplex with views of the golf course. Although charming, the club memberships can cost upwards of $24,000 per year, depending on the community.
It gave me a lot to think about — and definitely scratched the “what if” itch.
A Day at Magnolia Plantation
One of my favorite days was spent at Magnolia Plantation just outside Charleston:
- Founded in 1676 by the Drayton family
- $35 for the full tour package (home, gardens, slave quarters, swamp)
- Guided by someone who’d worked directly with the Drayton family
The gardens were sprawling and poetic, but also layered with the complex history of those who were enslaved there. The slave quarters remain, and the tour does a thoughtful job honoring both the beauty and the weight of that legacy.
In the Audubon Swamp Garden, I wandered through shaded paths and boardwalks, and yes, I spotted two sunbathing alligators near the water. Shoes with good tread? Highly recommended.
Hello, Savannah: History Comes Alive
Now onto Savannah — one of the most historic and haunted cities in America. I was instantly captivated.
I downloaded the Tour Buddy History app for a self-guided walking tour focused on the historic district. Savannah was the first planned city in America, originally built around 24 squares (22 remain). Each square is filled with stories — from Yellow Fever to Civil War legacies.
One of the highlights was my visit to the Thomas-Owens House and Slave Quarters. It gave me a true glimpse into 18th- and 19th-century life, and the contrast between privilege and pain was sobering. The gardens between the house and slave quarters were once used for livestock and produce — now beautifully manicured and peaceful.
Favorite Stops:
A TripAdvisor favorite and absolutely worth it. I had bacon-wrapped shrimp rolls, collard greens, cornmeal oysters, and a perfectly dressed Caesar salad. The building is reportedly haunted, according to both the app and the staff, but the atmosphere was warm and welcoming.
Right on the Savannah River, where cotton ships once docked. I visited Savannah’s Candy Kitchen, where I picked up sweets for my dad and granddad. The area is steeped in history: cotton prices dropped drastically during the Depression, triggering massive economic shifts. From 28¢ per pound to just 5¢, the collapse of this port was a key piece in the puzzle of the Great Depression.
This home took five years to build and was a portfolio piece for the builder, Isaiah Davenport; he built one home on nearly every square in the city to showcase his versatility. Each room showcases a different style, and the haunted tales (especially of his pet cat!) are part of the charm.
Stylish and intimate with velvet seating and expertly crafted cocktails. A wonderful spot to wind down and take in the energy of the city without the noise.
A Solo Night Out in Savannah
The Haunted Pub Crawl with Spooky Steve
This was a highlight: I joined a haunted pub crawl led by Spooky Steve, a storytelling savant in a top hat.
Stops included:
- Moon River Brewing Co. – Ghost photos encouraged
- Abe’s on Lincoln – Napkins cover the ceiling
- 17Hundred90 Inn – Haunted journals and chilling tales
- Six Pence Pub – Classic British feel, layered with spooky stories
The group vibe was amazing; travelers, locals, and first-time visitors all swapping stories and raising glasses to a city that never sleeps (literally — thanks, ghosts).
Afterwards, the Peacock Lounge was the place to be. A packed, speakeasy-style dance bar full of energy and charm.
A Morning in Forsyth Park & the Sorrel-Weed House
Before heading home, I made time for two more essentials:
- Forsyth Park: A 30-acre space filled with fountains, gardens, and ancient oak trees. Civil War soldiers once camped here, and you can still feel the history in the soil.
- Sorrel-Weed House: A solemn, haunted beauty. Bricks bear the fingerprints of the enslaved who built them. The proximity of the surgical table to the kitchen is both eerie and powerful.
Travel Tools I Love
Looks like jewelry, acts like a lifeline. Two quick presses alert my emergency contacts and local police to my location. I wear it when I travel solo or go on dates. (Just don’t shower in it — learned the hard way. 😅)
📱 Apple Maps & Extra Battery Pack
You’re gonna walk a LOT. Backup your phone, charge your chargers, and bring the cords!
📱 Tour Buddy App
Perfect for self-guided explorations, especially in cities with rich histories.
✈️ American Airlines First Class
Because comfort matters, and when you work hard, you earn your little luxuries. This helps me arrive rested and not in pain, but also the ease of getting work done when in flight, so that when I land, I don’t feel behind or stressed. Worth every penny!
Final Thoughts: Traveling Solo with Purpose
Traveling alone doesn’t mean being lonely. It means you get to do what you want, when you want. You discover who you are outside the expectations of others. For me, this trip was healing, invigorating, and full of clarity. I set my own pace, followed my curiosity, and met some incredible people along the way. I got four homes under contract while on this trip, proving once again that real estate doesn’t have to be tied to one place.
Would I move? I don’t know. But I saw enough to know that my options are wide open, and the world is waiting.
Until next time…
Tiffany 🥂🌸✈️
