Southern Squares & Ghostly Tales: A Long Weekend in Savannah with Milo & Beck

If you’ve ever wondered what it’s like to explore a city draped in Spanish moss, layered in ghost stories, and brimming with historic squares with two lively nephews, let me set the scene: Savannah, Georgia, a perfect mix of quirky, charming, and just the right amount of spooky. With Milo (10, adorable and curious) and Beck (14, all legs, baseball stats, and mischievous charm) as my travel crew, this long weekend was one for the memory books.

Friday: Pool Tables, Park Benches & a Hint of Hollywood

We checked into Aloft Savannah Downtown around 3 PM – sleek, modern, and just edgy enough to impress a teenager. 

Within minutes, the boys discovered the hotel pool table and initiated a friendly (read: very competitive) game. Beck, naturally, tried to show off his “top spin” shot and missed the cue entirely. Milo giggled, then casually made the shot.

After settling in, we set off on foot to Chippewa Square, home of the legendary Forrest Gump bench scene. Milo lit up. “That’s Beck’s favorite movie right now!” he said with wide eyes. We reenacted our best “Life is like a box of chocolates” moments, then strolled past the Independent Presbyterian Church, featured in the film’s opening feather sequence.

Dinner was at Huey’s on the River, with a view of the hulking container ships gliding by. Milo was fascinated by their size, while Beck timed each one to see how long they took to pass (a new sport, apparently). We feasted on shrimp and grits, catfish, Cajun rice, and fried green tomatoes, Southern comfort in every bite. They loved trying new flavors!

Heels to Hikes Hint: Share with one of the kids – you don’t want leftovers while traveling…

As the sun began to set, we sat on the brick steps near Rousakis Plaza, soaking up the golden light while a street musician played trumpet. Beck got caught in a hilarious skit after tossing money into the tip jar and tried to moonwalk away coolly, only to trip over his own shoelace. Savannah, you never disappoint.

Back at Aloft, the boys faced off again at the pool table, determined to impress a guy named “Noah” who had become their unofficial coach. Milo played with laser focus. Beck, still buzzing from his street performer cameo, dramatically called his shots like a pool hall legend. Eventually, bedtime came and we settled in with a glass of water each and Forest Gump on the t.v. 

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Saturday: Scavenger Hunts, Savannah Squares & Ghostly Whispers

Saturday was mission day. We set out to explore all 22 historic squares of Savannah, but not just to see them. Oh no, we were on a mission to find out why each was named and who they honored.

Savannah Square Trivia: (Or as Beck called it, “History with Swagger”)

• Madison Square: Named after President James Madison, but also the site where Union troops camped during Sherman’s infamous “March to the Sea.” Beck insisted Sherman “definitely would’ve been a left-handed pitcher.”
  
• Pulaski Square: Honors Casimir Pulaski, a Polish nobleman and Revolutionary War hero who died in Savannah. Milo asked, “Did he come with a sword?” Probably, buddy. Probably.
  
• Telfair Square: Celebrates Edward Telfair, Georgia’s governor. His daughter founded the Telfair Academy, now a stunning art museum. Milo wanted to know if she painted anything with ghosts in it.
  
• Oglethorpe Square: Named after Savannah’s founder James Oglethorpe, the visionary behind the city’s genius grid of squares. Beck thought the layout was “like Minecraft, but fancy.”
  

Our self-guided trivia walk turned into a hilarious blend of ghost hunt, history lesson, and improv comedy routine. 

Beck kept score. Milo kept notes. I just tried to keep up!!

We cooled off over lunch at Collins Quarter, where we rehydrated, devoured short rib hash, and watched Milo make friends with the waiter by asking, “What’s your favorite menu item, like personally?”

Back at Aloft, a quick swim hit the spot, followed by clean clothes and a casual dinner at B&D Burgers. Then we braced ourselves for the main event…

The Ghost Tour: Shadows, Stories & Shivers

At 7:30 PM, we met Julianna from Genteel & Bard for her Savannah Dark History Tour. From the very first eerie tale, she had us hooked. Beck leaned in, hanging on every gruesome detail. Milo? He was wide-eyed, gripping my hand, asking softly, “Do you think they’re still here?” (Narrator: They probably are.)

From haunted inns to tales of cursed staircases, Julianna spun her stories like a Southern Scheherazade. By the time we reached our last stop, the boys were sufficiently creeped out, in the best possible way.

No shame in calling an Uber for the ride back. Milo whispered ghost questions all the way. Beck recapped the entire tour like a true crime podcast host. We were haunted, delighted, and completely done.

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Sunday: Brunch Goals & One Final Horn Blast

Sunday morning meant brunch and one last wander through the cobblestones.

Here are a few family-friendly brunch gems to keep in mind:

• The Collins Quarter at Forsyth – Park views and killer coffee.
  
• B. Matthews Eatery – Cozy and classic with a Southern twist.
  
• Goose Feathers Café – Quick bites and sweet pastries for early risers.
  
• The Funky Brunch Café – Cook your own pancakes at the table. Milo would’ve stayed all day.
  

After brunch, we went ship chasing. Yep, we drove along River Street’s cobblestones, hoping to catch one last container ship. And just as we rolled down the windows…

HONNNNNK!

Beck whooped. Milo waved wildly. The ship saluted us back. Our own cinematic farewell.

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Heels to Hikes Hint:

Traveling with kids of different ages? Let each one “lead” a part of the trip, whether it’s choosing lunch, narrating history, or picking the next destination. With a little freedom, their personalities shine, and the memories multiply.

Tote Bag Tips:

1. Comfortable Walking Shoes or Espadrels/Wedges – NO high heels here
Savannah is best explored on foot. Cobblestone streets and long walks through historic squares call for sneakers or cushioned sandals to keep everyone happy.

2. Lightweight, Breathable Layers
Summer heat and humidity can be intense, but some indoor stops (like museums or cafes) may have strong A/C. A light jacket or wrap can help balance the temperature swings.

3. Water Bottles for Everyone
Keep teens hydrated as you explore. Refillable bottles are eco-friendly and easy to refill at parks or cafes throughout the city.

4. Snacks on the Go
A small stash of Byrd’s cooler cookies, “a bar” – protein bar, or jerky can prevent mid-tour hunger meltdowns, especially during long walking routes or ghost tours in the evening.

5. Small Bills for Treats
Whether it’s grabbing pralines at River Street Sweets or tipping a street performer, having a few dollars in cash makes for a fun way to experience “street-smosphere” by interacting with talented artists along the way.

6. Phone Chargers or Portable Battery Packs
Between taking photos, navigating maps, and keeping in touch, phones drain fast. A portable charger is a lifesaver for you and your teens.

7. Rain Ponchos or a Compact Umbrella
Savannah weather can change quickly. A lightweight poncho or umbrella keeps you dry without weighing down your bag.

8. Sunscreen and Bug Spray
Historic squares are beautiful but often sunny and full of greenery where mosquitoes love to linger, be prepared.

9. Notebook or Small Sketchpad
For teens who love journaling, doodling, or noting their favorite stops, a compact notebook is a fun keepsake of the trip.

10. Extra Space for Souvenirs
Between t-shirts, saltwater taffy, and quirky boutique finds, you’ll want a little extra room to bring home mementos from the adventure.

Download our custom Itineraries – loaded with hints, trivia, and detail