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The price of a road trip south, Savannah, Georgia, offers wanderlust-y Midwesterners a taste of Europe—and a mild winter escape.

By Gary Thompson and Hannah Agran
Updated December 22, 2020
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Warm-weather getaway to Savannah, Georgia
Wormsloe State Historic Site
| Credit: Courtesy of Visit Savannah

History drips from Savannah, Georgia, the state’s oldest city, like its ubiquitous Spanish moss. Much of that history is sweet. Fairy-tale carriages roll past Gaston Street’s elegant, shoulder-to-shoulder homes. The brown-sugary scent of pralines wafts from shops. And in March, azaleas bloom beneath moss-laden oak limbs in a stunning pink display.

Savannah is one of the most romantic spots in the U.S. It’s like Europe, really, thanks largely to its Italianate, Georgian, Romanesque, Gothic and Greek Revival architecture. The iconic Cathedral Basilica of St. John the Baptist is a French Gothic pièce de résistance. The sense of being in another country—different accent, flora, flavors—is part of the fun.

So is discovering the squares. In 1733, Gen. James Oglethorpe planned Savannah with open squares for military drills; as the city grew, the squares multiplied. Today, 22 of these mini parks remain. Roads stop to wrap around them, maddening motorists but making the town a dream for pedestrians. And it’s easy to spot strolling Midwesterners— they’re wearing shorts when January high temps hit their 60-degree average. Some carry loaded beverages: Open containers (plastic) of alcohol are legal on the streets of the historic district, where it’s (almost) always happy hour.

So eat, drink and be merry here, but in a time of frank conversations about race, don’t shy from the more bitter flavors of local history. The African American Monument on Rousakis Riverfront Plaza shows a Black family with slavery’s chains at their feet. The inscription—poet Maya Angelou’s graphic account of slave-ship life—lands a gut punch. A half mile away at First African Baptist Church, once a stop on the Underground Railroad, air holes drilled in the floor mark where escaped slaves hid beneath the planks.

Like old European cities, Savannah has endured a lot. It was captured by the British in the Revolutionary War, spared by Gen. William T. Sherman in the Civil War, and fractured by segregation and the civil rights movement.

Survival has honed Savannah’s instinct for self-preservation. Decades ago, the city began protecting and restoring its architectural treasures, with part of downtown becoming a National Historic Landmark District. More recently, once abandoned properties have morphed into craft breweries, art museums and hotels.

There’s new construction too. The mixed-use Eastern Wharf development is adding homes, retail and rec near the historic downtown. As old live oaks and verdant squares share more of the city with chic boutiques and cutting-edge restaurants, Savannah evolves into equal parts traditional and pioneering. A new generation is writing its own chapter in city history, drawing from the bitter and the sweet.

Warm-weather getaway to Savannah, Georgia
Gaston Street
| Credit: Courtesy of Visit Savannah
Warm-weather getaway to Savannah, Georgia
Cathedral Basilica of St John the Baptist
| Credit: Courtesy of Visit Savannah

Do

Among the trolley companies, Old Savannah stands out with actors playing historical and cultural figures. Hop on to meet British architect William Jay, Haitian fruit sellers and Forrest Gump. FORSYTH PARK This lush 30-acre park on the edge of the downtown historic district attracts concerts and sports as well as strollers and sunbathers. The fountain at the north end is lit up at night.

Warm-weather getaway to Savannah, Georgia
Savannah African Art Museum
| Credit: Courtesy of Visit Savannah

Marvel at captivating ceremonial and spiritual objects from the 19th and 20th centuries. The collection of more than 1,000 West and Central African pieces includes beadwork, textiles, masks and wood carvings.

Warm-weather getaway to Savannah, Georgia
Tybee Island
| Credit: Courtesy of Visit Savannah

Day trip 30 minutes from downtown Savannah to this beach community with long stretches of natural coastline. A climb up the historic lighthouse gives a panoramic view of the island.

Snap a pic of a classic Savannah scene at the oldest of Georgia’s tidewater estates, established in the 1730s. Hundreds of stately oaks covered in Spanish moss line both sides of an avenue, forming a canopy more than a mile long.

Stay

Housed in a 19th-century cotton warehouse overlooking the Savannah River, this hotel has 56 rooms, many with water views. The Top Deck bar is one of the city’s few rooftop drinking spots.

A former Coca-Cola bottling plant pops with color and playful decor (like snaking lobby bookcases). Be pampered by seersucker-clad staff and a breezy courtyard.

Enjoy the intimate atmosphere of this converted private home. All 12 rooms in the main house showcase period artwork and furnishings; some include fireplaces and chandeliers.

Eat

A neighborhood spot in a former bank—the dining room retains the door to the safe. They take a loving approach to Southern cooking, elevating shrimp and grits with aged cheddar, bacon and tomato. Find inventive cocktails too.

An old Greyhound bus terminal now transports diners with contemporary Southern cuisine by chef Mashama Bailey. At lunchtime, sample her dishes at the Diner Bar in front. If you want dinner in the main dining room, better make reservations.

Warm-weather getaway to Savannah, Georgia
Cha Bella
| Credit: Courtesy of Visit Savannah

A day’s drive is the farthest that chef-owner Michael Lacy will go to stock the kitchen for a farm-totable American menu that tilts Italian. Favorites include rack of lamb, baked spaghetti squash and meatballs, and Gouda-and-duck ravioli.

Drink

Warm-weather getaway to Savannah, Georgia
Rocks on the Roof
| Credit: Courtesy of Visit Savannah

Atop the Bohemian Hotel, enjoy handcrafted cocktails, tempting tapas and river views—and maybe a ship or two passing in the night.

Though he was not on the 1860 ballot in Georgia (and other Southern states), the 16th president is all over this neighborhood bar. Come for beer and shots, stay for—and add to—napkin art.

A dock bar set on the outskirts of town, The Wyld is truly a local haunt with plenty of outdoor seating and a rustic feel that belies a menu of sophisticated small plates and cocktails.

Still in mourning for Sean Connery? Drown your sorrows James Bond-style with more than 300 takes on the martini, 007’s shaken-not-stirred cocktail.