We had the perfect weekend in the South. Two destinations that are different enough to feel like a proper adventure, but close enough together that you don’t spend the whole weekend in a car. We actually planned a trip to Savannah, and Hilton Head was an impromptu decision — a day trip on a whim — but well worth it.

Exploring Savannah

Savannah was founded in 1733 and is Georgia’s oldest city and arguably its most atmospheric. The city is laid out as a grid of 22 park-like squares shaded by ancient live oaks dripping with Spanish moss, surrounded by beautifully preserved antebellum architecture.

The historic district is small and walkable, though there are plenty of ways to get around — the free SCAD buses run throughout downtown, and the hop-on hop-off trolley does a narrated tour if you want your history delivered with commentary, and there are plenty of walking tours. We decided to grab bikes from our hotel and explore that way, which turned out to be the perfect call.

We looped through Forsyth Park on a Saturday morning, which coincided with the farmers market. There were local vendors, fresh produce, flowers, and the kind of relaxed weekend energy that makes you want to slow down and people watch from a park bench. From there, we wound through the historic district past the beautiful houses draped in Spanish moss.

On our ride we passed the Owens-Thomas House, one of the finest examples of Regency architecture in America, completed in 1819. It’s now a National Historic Landmark operated by Telfair Museums, notable not just for its beauty but for its preserved urban slave quarters which are the only intact ones open to the public in Savannah.

We also rode past Colonial Park Cemetery, Savannah’s oldest municipal burial ground, established in 1750. It’s famous for having a history that ranges from Declaration of Independence signers to Civil War occupation to a yellow fever epidemic that claimed nearly 700 lives in a single year.

The Riverfront and a Detour Worth Making

Savannah’s riverfront is the obvious place to end up in the afternoon. We walked along the cobblestones, watched the ships move down the river, and took in the scene. But the real highlight was heading into the lobby of the JW Marriott Plant Riverside District.

The JW Marriott is housed in what was originally Savannah’s electric power plant, built in 1912 and operational until the mid-1950s. When it was converted into a hotel, the designers leaned hard into that fossil fuel history in the most unexpected way. The lobby, called Generator Hall, is part luxury hotel, part natural history museum. There’s a 135-foot chrome-dipped dinosaur skeleton named Miss Chromina Joule hanging under soaring glass ceilings. Massive geodes, fossils, a prehistoric tortoise shell, an Ice Age bear skeleton, and the world’s largest nugget of copper are displayed throughout the space. It’s completely unexpected and worth the walk-through.

Tybee Island: Beach Lunch at Snarky’s

We made a half-day trip out to Tybee Island, about 20 minutes east of Savannah. It’s a classic low-key beach town filled with sand, salt air, and a laid-back crowd. For lunch we stopped at Snarky’s, right on the beach. Casual, no-fuss, good music and pretty good food too.

Where to Eat in Savannah

Savannah is filled with great restaurants and we certainly ate our way through the city.

Collins Quarter

Collins Quarter is one of those Savannah restaurants that keeps coming up. We snagged a table outside, which was the right call: there’s something about watching Savannah street life from a patio on a warm night that feels like exactly where you’re supposed to be. Everything was well-prepared, and the atmosphere delivers. Book ahead. This one fills up, and walk-ins on a holiday weekend are a gamble.

11ten

Our other dinner was at 11ten, a sleek spot in the historic district. The standout of the night was the cauliflower appetizer — the kind of dish you keep picking at even when you’re full.

Breakfast at The Alida

Don’t sleep on breakfast at the Alida. The banana bread was a standout!

Ice Cream: Skip the Line, Go to Doki Doki

Here’s a tip I wish someone had given me: Leopold’s is not worth the wait. It’s famous and has been a Savannah institution since 1919, founded by three Greek immigrant brothers whose recipes are still used today. The famed Tutti Frutti flavor was apparently a favorite of lyricist Johnny Mercer, who grew up a block away and swept floors there as a boy. The history is genuinely charming, and the vintage parlor is worth seeing. But the 45-minute line wasn’t worth the wait. Also, there are two locations at the airport that didn’t have a line when we traveled, so that could be an option if you must try it.

Doki Doki, on the other hand, was genuinely good with nearly no line and is just next to Collins Quarter.

Drinks

The Alida’s rooftop bar is a solid option and convenient if you’re staying there. But Savannah has no shortage of good spots along the riverfront and throughout the historic district.

Day Trip: Hilton Head Island

We rented a car for a day and drove out to Hilton Head, about an hour from Savannah. It’s a completely different vibe — manicured, lush, more resort-town than beach town.

Coligny Beach

We spent the first part of the afternoon at Coligny Beach, the most accessible beach on the island. Wide, well-kept, backed by a small plaza with shops and restaurants. We parked in the free parking lot there and rented bikes nearby at Sharky’s.

Harbour Town: Bikes and the Lighthouse

From Sharky’s, we made our way to Harbour Town, the scenic marina area at the southern end of the island inside Sea Pines Resort. We biked out to the Harbour Town Lighthous, the iconic red-and-white striped landmark on every Hilton Head postcard. It’s a lovely ride through tall pines and live oaks.

We stopped at Quarterdeck for drinks and a light bite. The restaurant sits right next to the lighthouse with wraparound outdoor seating and a rooftop oyster bar overlooking Calibogue Sound. We ordered Aperol spritzes and a few small plates, watched the sailboats come in, and people watched – there were a lot of cute dogs around!

Summary

Savannah rewards slowing down. It doesn’t need you to rush through it. Pairing it with a day in Hilton Head gives the weekend a nice mix of history, culture, beach, and pure relaxation. I’d go back to both without hesitation.