Savannah has 22 squares. The average visitor sees six of them, and sees most of those through the side of a moving trolley while someone reads a script over a loudspeaker. A proper Savannah squares walking tour fixes that.
That is not a knock on the trolley. It is a knock on the itinerary. Oglethorpe did not lay out this city in 1733 so people could drive through it. He laid out a grid of wards, each one built around a public square, on a footprint that runs roughly two and a half square miles and is flat the entire way. The whole thing is a walking machine. You are standing inside a 293-year-old piece of urban design and the correct way to experience it is at three miles an hour.
Here is the route. It costs nothing, it takes about two hours at a walking pace and four hours if you stop for coffee and a cemetery, and it will show you more of Savannah than any ticketed tour on the board. Four steps: walk the Bull Street spine, step off it to the east, loop back through the quiet western half, and — the part almost nobody gets right — do it at the correct hour of the day.
The Problem With How Most People See Savannah
Savannah hosted 12.9 million visitors in 2025, who spent $4.1 billion and generated $506 million in state and local tax revenue. That is a lot of people moving through a very small footprint. And the volume concentrates: the riverfront, Broughton, City Market, Chippewa, Forsyth. Five or six nodes absorb the overwhelming majority of the foot traffic, and everything the tour operators sell is optimized to move groups efficiently between them.
So you get the highlight reel. You see the fountain, you hear the Forrest Gump bit, you photograph the Mercer-Williams House from the sidewalk, and you leave with the strange feeling that you skimmed the city rather than read it. Your camera roll looks exactly like everyone else’s camera roll.
Here is the part worth sitting with. Savannah’s design is not decorative. Each ward was laid out with the square at the center, trust lots on the east and west for public buildings, tything lots on the north and south for houses. The pattern repeats twenty-two times. You cannot perceive a repeating pattern from a vehicle moving through it once. You perceive it on foot, around the fourth or fifth square, when your body starts predicting where the next one will be before you see it. That moment is the actual attraction of any real Savannah squares walking tour. Nobody sells a ticket to it.
Who’s Telling You This
I have been investing in Savannah since 2004 and operating rentals here through every version of this market — the 2008 collapse, the COVID shutdown that emptied River Street, and the short-term rental consolidation of 2024 and 2025. Sid Was Here manages properties across the Historic District and the neighborhoods around it, which means I have answered the “what should we actually do tomorrow” text message a few thousand times. This is the Savannah squares walking tour I hand them, and it is the same one I give my own family.
Now stop reading about me and go look at the map.
Step 1: Walk the Bull Street Spine — Five Squares, One Mile
The Savannah squares walking tour starts at City Hall on Bay Street, at the top of Bull. Walk south. Do not deviate. You are about to hit five squares in one straight mile, and they are arranged in near-perfect chronological order, which is the single most useful accident in Savannah’s layout.
Johnson Square (1733). The first one ever laid out. Nathanael Greene is buried under the monument in the center — a Revolutionary War general interred in a bank plaza, surrounded at lunchtime by people in suits eating salads. Christ Church sits on the east trust lot, where a trust lot is supposed to sit.
Wright Square (1733). Two monuments, and the smaller one matters more. The large boulder on the southeast side marks the grave of Tomochichi, the Yamacraw chief without whose cooperation Oglethorpe’s colony does not survive its first winter. His original monument was removed in 1883 to make room for the one honoring a railroad executive. The boulder was the correction, placed later.
Chippewa Square (1815). Oglethorpe’s statue stands in the center facing south — deliberately, toward Spanish Florida. Two things people get wrong here: this square is named for a War of 1812 battle, not anything colonial, and the Forrest Gump bench was a movie prop. It was never a real bench. It lives in the Savannah History Museum now. Visitors stand at the north end photographing empty ground every single day.
Madison Square (1837). Sergeant William Jasper, mortally wounded in the 1779 Siege of Savannah, stands mid-charge. The Green-Meldrim House on the west side is where Sherman headquartered in December 1864 and wrote the telegram offering Lincoln the city as a Christmas gift.
Monterey Square (1847). Pulaski’s monument, Congregation Mickve Israel, and the Mercer-Williams House. The most photographed square in the city and, unsurprisingly, the one where you will wait longest for a clean shot.
Walking time, end to end, without stopping: about 25 minutes. Budget 90.
Step 2: Take the Savannah Squares Walking Tour East, Where Nobody Is
This is where the tour stops being a tour and starts being a city. Cut east from Madison or Monterey and the crowd volume drops by an order of magnitude within one block.
Lafayette Square gives you the Cathedral Basilica of St. John the Baptist — the twin spires you have been seeing over the rooftops all morning — and the Flannery O’Connor childhood home on the north side. Go inside the cathedral. It is free, it is open to the public most of the day, and the interior does something to people who thought they were done being impressed by buildings.
Troup Square has the armillary sphere on six turtles and a cast-iron dog fountain on the corner that exists purely because someone in 1897 thought dogs were thirsty. This is a residential square. There are people reading on the benches who live here.
Whitefield Square is the one with the white gazebo, which is why it hosts more weddings than any other square in the city. It is also the southeasternmost square, which makes it a natural turning point.
Then walk Jones Street for a few blocks. It is the street every “prettiest street in America” list means when it says Savannah — brick and tabby sidewalks, live oaks meeting overhead, and residents who have made a quiet peace with being photographed. Walk it west, back toward Bull.
If you have appetite left, Calhoun Square sits just east of Monterey and the Massie Heritage Center on its edge is the last standing building from Georgia’s oldest chartered public school system. It is the best thirty minutes of context available in the district for the price of a museum ticket.
Step 3: Loop Back Through the Quiet Western Half
This is the half of the Savannah squares walking tour almost nobody does. That is the entire reason to do it.
Pulaski Square and Chatham Square sit west of Bull in the lower district, and Chatham gives you Gordon Row — fifteen attached Greek Revival townhouses built in 1853, still standing in a single unbroken line. It is the most architecturally coherent block in Savannah and there will be four people on it.
Orleans Square carries the German Memorial Fountain, honoring the immigrants who built a substantial share of what you have been walking past. Telfair Square anchors the museum district — the Telfair Academy and the Jepson Center face each other across it, a Regency mansion and a Moshe Safdie glass building, and the argument between them is more interesting than either one alone.
Crawford Square, up in the northeast quadrant, deserves its own sentence. It is the only square with a basketball court and a playground fenced inside it, and it served as a gathering place for Savannah’s Black community during segregation, when access to the other squares was restricted. That history is not on the trolley script.
Finish north at Ellis Square, which is the one that proves the whole system is fragile. It was demolished in 1954 for a parking garage and stayed a parking garage for fifty-six years before the city tore the garage down and rebuilt the square in 2010. Two of Oglethorpe’s original twenty-four — Liberty and Elbert — were not so lucky. They were lost to the interstate ramp and never came back. Twenty-two is what survived.
Step 4: Walk It at the Right Hour, or Don’t Bother
This is the step that separates a great morning from a miserable one, and it is the one visitors ignore.
In summer, walk between 7:30 and 10:00 a.m., or after 6:00 p.m. Savannah in August routinely runs a heat index above 100 by early afternoon, with humidity that makes the shade under the live oaks feel like a different climate zone than the sun twenty feet away. The route is roughly three miles with the detours. Three miles at 2:00 p.m. in August is not a walking tour, it is an endurance event, and people quit at Chippewa and call a car.
The light is better anyway. Bull Street runs north-south, which means early and late sun rakes down it lengthwise through the oaks and Spanish moss. Midday sun comes straight down and flattens everything.
Sunday morning before nine is the quietest the Historic District ever gets. You will have Madison and Monterey essentially to yourself.
Two practical notes. The sidewalks are brick, tabby, and cobblestone, frequently uneven and occasionally hostile — flat shoes with real soles, not sandals. And the squares hold mosquitoes at dawn and dusk, so if you are walking the evening version, treat that as a known cost of doing business.
One Savannah-specific detail worth knowing: within the Historic District, you may carry one 16-ounce plastic cup of your beverage of choice on the sidewalk. Glass and cans, no. Cup, yes. It is legal, it is normal, and it makes the western loop considerably more pleasant.
What a Bad Savannah Squares Walking Tour Costs You
You buy four tour tickets, see six squares through a window, and never once feel the pattern of the grid. Or you book a stay fifteen minutes outside the district because the nightly rate looked better, and then pay for parking every day, drive in, circle for a spot, and walk half the route before quitting because getting back to the car is another mile. Whatever you saved on the nightly rate evaporates into garage fees and lost hours, and the trip becomes about logistics instead of the city.
If the walk leaves you wondering what one of these Historic District buildings actually costs, that is a different conversation and we have that one too — Team 912 works with investors buying in Savannah.
What It’s Worth When You Get It Right
Two hours. Zero dollars. Fifteen-plus squares instead of six. And by the fourth one, you stop needing the map — you know a square is coming because the grid told you so, and you can navigate a city you have never been to before by pattern recognition alone. That is a thing you get to keep. You will also have seen Crawford, Gordon Row, and Troup, which means when someone asks about your trip you have something to say that isn’t “we saw the fountain.”
The Savannah Squares Walking Tour, One More Time
Walk the Bull Street spine from Bay Street to Monterey. Cut east to Lafayette, Troup, and Whitefield, then take Jones Street back west. Loop north through Pulaski, Chatham, Orleans, Telfair, and Crawford, and finish at Ellis. Do it early or do it late. Wear real shoes.
Stay where the route starts. Sid Was Here manages fully furnished homes and apartments inside and around the Historic District — the kind where you walk out the front door and you are already on Step 1. Booking direct at vacationrentalsavannahga.com means you deal with the people who actually operate the property, not a call center in another time zone.
Not ready to book? Grab the free Savannah Neighborhood Guide — it breaks down which parts of the district are quiet, which are loud, which are walkable to what, and where the parking actually is. Useful whether you stay with us or not.
About the Author: Julie Gates has been investing in Savannah real estate since 2004 and operates Sid Was Here, a full-service property management company handling short-term, mid-term, long-term, and commercial rentals across the Savannah region. She is a published BiggerPockets author (The 30-Day Stay, 2023) and a Forbes Business contributor. Reach the team at sid@sidwashere.com or (912) 525-0042. Local investors can also join us at the Cashflow Savannah meetup.
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