Seven Squares, Seven Days: The Case for Staying Longer in Savannah
Savannah was designed to be explored in stages, via its 22 squares, each one a small world with its own gravitational pull. The plan that General James Oglethorpe drew in 1733 wasn’t merely a grid; it was a theory about how people move through a city, how neighborhoods cohere around public space, how a place sustains itself across centuries by giving people room to slow down and observe. Nearly 300 years later, the logic holds.
Three days here leaves you with the feeling that you’ve read only the first chapter. A week changes the relationship entirely. Seven days is long enough to stop navigating and start inhabiting: to know which café opens earliest, to have a walking route through the squares you prefer over the direct path, to understand why this particular city rewards people who plan for a week or more from the start.
Get to Know the Squares
Each of Savannah’s squares anchors a distinct neighborhood, and each has accumulated enough history to reward more than a single visit. Johnson Square, the oldest in the city and the first Oglethorpe laid out in 1733, is the civic anchor of the original plan; a monument to Nathanael Greene, Revolutionary War general, marks its center. Chippewa Square, shaded and central, has live oaks dense enough to break the summer heat and benches worth sitting on rather than passing.
Moving south and west, the character keeps shifting. Telfair Square fronts both the Telfair Academy and the Jepson Center for the Arts, one of the most complete concentrations of visual art in the region. Lafayette Square is quieter, facing the twin spires of the Cathedral of St. John the Baptist, with the Andrew Low House on its western edge. Madison Square is flanked by the Sorrel-Weed House, one of the more architecturally significant antebellum structures in the Historic District. Ellis Square, restored from a buried parking lot, anchors City Market and the surrounding blocks that come alive after dark.
A week gives you enough time to move between these worlds and let the city’s culture settle in: the architecture, the art, the buried history in every cornerstone.
Your Week Takes Shape
The weekday tempo. A morning that begins with espresso from your in-suite brewer and moves through a few hours of work at the ground-floor co-working table has a different quality to it. The Wi-Fi extends into the courtyard, which is quieter than the interior and better for long stretches of concentration. The complimentary bikes are a good option to stretch your legs, out through Forsyth Park, along the Starland District, or east toward the waterfront.
Thursday evening at Little James. The café and bar on the ground floor of The Ann Savannah deserves an evening of its own rather than a quick drink before heading elsewhere. Named for General James Oglethorpe, Little James runs a cocktail list with a Mediterranean influence rooted in southern soil. Order the Julep in Transit: bourbon, amaro sfumato, lemon oleo, mint.
Friday after dark. Ellis Square and the blocks around it fill with live music on weekend evenings. Jazz’d Tapas Bar, just below street level on the fringe of the square, brings in live blues, jazz, and swing six nights a week. Regulars outnumber visitors most nights, which gives it a real neighborhood feel.
Saturday morning. The Forsyth Farmers’ Market opens at 9 AM at the south end of Forsyth Park, with 60-plus vendors selling pastured meats, seasonal produce, craft bread, local honey, and prepared foods sourced from growers within 200 miles of the city. Buy something for dinner. The full kitchen in your suite means you can cook what you buy and actually enjoy doing it.
The weekend table. For your Saturday night, book The Grey. Occupying a 1938 art deco Greyhound Bus Terminal on Martin Luther King Jr. Boulevard, the kitchen works from regional produce, Gulf seafood, and the culinary history of a port that absorbed flavors from every ship that arrived. Reserve well ahead; it fills most nights.
Where You're Based
The Ann Savannah sits at 110 Ann Street, two blocks from the Savannah College of Art and Design and about a mile from Forsyth Park. The building itself is worth noting: completed in 2023, it is the first mass timber structure in the American Southeast, built from cross-laminated timber whose visible grain runs across the ceilings of every suite.
Suites run from one to four bedrooms, each with a full kitchen and in-suite washer and dryer, so the longer the stay, the more it settles into something that resembles home. Housekeeping comes weekly rather than daily, which means you can leave things where you left them. Laurel Market on the ground floor handles late-night cravings and forgotten sundries; and a fitness center there for when you need it.
The property works as a genuine alternative to short-term rentals: not by mimicking them, but by solving the same problem with more reliable means. The space of an apartment, the consistency of Marriott, and a building with enough architectural identity to justify staying inside as much as going out.
Explore suites and availability at The Ann Savannah.
