Explore the storybook streets of America’s oldest town, St. Augustine, for an electrifying display of holiday cheer.

By Lisa Roberts
November 11, 2009
Thayer Gowdy

St. Augustine, Florida, greets holiday visitors with a megawatt smile. Every year, beginning midsummer, city crews start stringing up more than 2 million white lights at 100-plus locations. Businesses and individuals add to the glow with light displays of their own. But you’ll have to turn to local personalities for color: A city ordinance limits holiday lights to white or clear bulbs in the historic district.

Spain’s first settlement in the continental United States, this is the oldest European town in the country. (Sorry, Jamestown, Virginia, and Plymouth, Massachusetts.) The Spanish traditionally mark Christmas by placing a simple white candle in their windows, and this city took that practice to the max. The area struggled through pirate attacks, epidemics, and the threat of English occupation before the construction of Fort Castillo de San Marcos in 1695. After decades of fighting, Spain traded Florida to England in 1763 in exchange for Cuba. However, England’s rule was short. After the American Revolution, the victorious colonies gave Florida back to their Spanish allies―for a while. In 1821, Florida became a U.S. territory.

By land: Pick a horse-drawn carriage from the bayfront stand, then tuck yourself under a plaid throw and clip-clop into the night. Narrated trips last from 45 minutes to an hour and cover more than two miles. Sights include the Lightner Museum, St. George Street, the Castillo de San Marcos, and the light-strewn Plaza de la Constitución. Rates are about $20 for adults and $10 for children; a private ride for two runs about $85, plus tip.
By sea: Catch the full effect of all the wattage from the schooner Freedom (904/810-1010, schoonerfreedom.com). The sailing ship pushes away from its Matanzas Bay dock late each afternoon for two-hour sunset tours that are capped by a panorama of the glittering waterfront. Tickets cost $45, which includes beer and wine.
By air: See incredible views of the glowing city from a helicopter (904/824-5506 or oldcityhelicopters.com). Night tours begin at $170 for up to three passengers and cover 17 miles. Or, if you’re not up for a ride in a chopper but still want a bird’s-eye view, you can honor the city’s nautical tradition by climbing the 219 steps to the observation deck of the St. Augustine Lighthouse (staugustinelighthouse.com), which is across the bay on Anastasia Island.

Even though Spain founded the city, the English spent time here, too. You’ll see them during the British Night Watch and Illumination, St. Augustine’s best-known holiday event. On December 4 and 5, visitors can mingle with re-enactors, who parade by torchlight and keep guard as a holiday proclamation is read to the crowd. Then, with church bells ringing, thousands of candles are lit. Accompanied by fife and drum, the costumed British soldiers make their way through the streets, singing carols and firing muskets.

Magically, snowfall appears twice every night for Winter Wonderland at the St. Augustine Amphitheatre. Families flock to the play area, with an outdoor ice rink and a 100-foot ice slide. After getting the wiggles out, children love to explore Elf Village and the lighted nature trail. There’s also a nightly bonfire, with s’mores kits available from vendors. Don’t miss out on the mini-blizzards at 7:30 p.m. and 9 p.m.; they’re the only ones Floridians are likely to see. (Northerners can enjoy the beauty without worrying about shoveling!)

St. Augustine celebrates from Thanksgiving through January, with everything from a one-time regatta to nightly trolley tours. On December 6, historic residences opulently decked out by St. Augustine Garden Club members will open their doors for the Christmas Tour of Homes. On December 12 and 13, more than 20 historic inns―displaying lavish trimmings including greenery, red satin bows, and, of course, twinkling white lights―offer tastes of signature dishes from local restaurants.

After starting your day with a cup of joe and a pastry at Crucial Coffee Café (26 Charlotte St.; 904/810-2080), you’ll work up an appetite for more. The dining’s casual at restaurant/microbrewery A1A Ale Works (1 King St.; 904/829-2977 or a1aaleworks.com), which has a balcony overlooking Matanzas Bay and much of the holiday street scene. The accent is on seafood: Choose from dishes like grouper piccata, mango barbecue shrimp skewers, and sesame tuna.

At Opus 39 Restaurant and Food Gallery (39 Cordova St.; 904/824-0402 or opus39.com), guests can create their own four- or five-course dinner, or select the seven-course tasting menu that emphasizes organic ingredients. A dedicated wine room features a collection of fine vintages.

O’Steen’s Restaurant (205 Anastasia Blvd.; 904/829-6974) isn’t shy when it comes to the big flavors of seafood. Its fried fish, oysters, clams, and shrimp earn raves; a casual family atmosphere and reasonable prices keep the love affair alive.

Spice things up New Orleans style at Harry’s Seafood Bar and Grille (46 Avenida Menendez; 904/824-7765 or hookedonharrys.com). From the po’boys to the crawfish étoufée, the menu is pure Louisiana. Opt for the courtyard seating under the lit shady trees, start with crab cakes, and save room for chocolate bread pudding.

Ward off the evening chill with a steaming cup of cocoa at Tedi’s Olde Tyme Ice Cream (65 St. George St.). Try the spiced Minorcan version made with 47 percent chocolate and lavishly topped with whipped cream. To take the taste home, buy a tin
at Whetstone Chocolates (42 St. George St.; whetstonechocolates.com).

Go seaside Sunday morning at The Reef Restaurant (4100 Coastal Hwy.; 904/824-8008 or thereefstaugustine.com). With a carving station, crab legs, salmon, and shrimp, the buffet has something for everyone. Wash it all down with Champagne. Reservations are suggested for the brunch, served from 11 a.m. to 2:30 p.m. Adults eat for $30; kids 12 and under, $13.

Within the San Marco Avenue antiques district’s three blocks―San Marco Avenue north from Castillo Drive to Pine Street―you’ll find dozens of stores to browse for treasures. Must-sees include A Step Back in Time (60 San Marco Ave.; 904/810-5829), Jena’s Antiques & Art (56 San Marco Ave.; 904/823-3456), and Antique Emporium (62 San Marco Ave.; 904/829-0544). And this time of year, it’s hard to resist the Christmas Shop (12 Castillo Dr.; 904/824-9898), which features dozens of collectibles.

Browse along quaint Aviles Street, south of King Street in the downtown historic district, for art galleries and boutiques selling everything from souvenirs to leather goods to antique books. See artist Gayle Prevatt create vivid paintings and memorable jewelry at Moultrie Creek Studios (9C Aviles St.; 904/829-2142 or moultriecreek.com), or pick up a vintage gift at Bouvier Maps & Prints (11 D-E Aviles St.; 904/825-0920), which has historic charts, antique botanical prints, and maps. This area is no doubt why Good Morning America called St. Augustine the No. 1 place in the United States to feel as if you’re in Europe.

The AAA four-diamond Casa Monica hotel (rates from $200, 95 Cordova St.; 904/827-1888 or casamonica.com), built in 1888, offers sumptuous elegance complete with a tapestry-draped lobby and crystal chandeliers. Each of its 138 guest rooms and suites has feather pillows, a Bose sound system, and WiFi.

At just 72 rooms, Hilton Historic Bayfront Hotel (rates from $169, 32 Avenida Menendez; 904/829-2277 or hiltonhistoricstaugustine.com) claims to be the smallest Hilton property in the world. Guests are treated to old-world decor, luxurious bedding, and a panoramic view of the city’s bayfront.

The oldest lodging in the oldest city, St. Francis Inn (rates from $169, 279 St. George St.; 800/824-6068 or stfrancisinn.com) stands out for its homey comfort and individual guest attention. Each of the 14 rooms and suites has private baths, and some offer whirlpool tubs, fireplaces, and balconies. Furnishings are traditional with a dash of gingham romance.

(Published December/January 2010)