We're Dreaming of a Coastal Christmas

Even Seaside's slogan, "a simple, beautiful life," reads like a refuge from holiday chaos. Located just off Scenic Highway 30A on Florida's Emerald Coast (think white sand and shimmering emerald green water), this town is known for its gorgeous coastline, stunning architecture, bounty of fresh Gulf seafood, and shopping that goes way beyond shark-tooth necklaces. It's also famous for being the too-pretty-to-be-real setting for the movie The Truman Show.

During the summer, vacationers (including occasional celebrities) flock here, seeking tan lines and frozen cocktails. But in the winter, it's quieter. And there's a special kind of restorative beauty to a pristine beach in the wintertime.

Seaside and nearby destinations along the Gulf celebrate Christmas with coastal flair. "Christmas in Seaside evokes a simpler time," says Phil McDonald, the chef at Bud & Alley's Pizza Bar, a popular restaurant near Seaside's bustling downtown. "It feels like being in a Norman Rockwell painting." From the quaint post office decorated in artful bows and natural wreaths to the iconic Coleman Beach Pavilion wrapped in over 4,500 white lights, it's an ideal setting for getting into the holiday spirit.

The best way to appreciate Seaside's character is to experience it from the comfort of your own rental cottage. (That's also your only option; there isn't a chain hotel in sight.) Most are a short stroll from the town center, providing proximity to all you need to eat, drink, and be merry.

Start your day like a local with a creamy latte from Amavida Coffee and Tea (amavida.com) near the Central Square, where you can also find biscuit sandwiches, baked pastries, and espresso drinks from freshly ground single-origin beans. In the afternoons, Amavida serves beer, wine, and Latin American-inspired snacks.

Take a few quiet moments on the beach to soak up the sounds of your holiday: the rushing tide and rustling sea grass. Afterward, it's hard to imagine anything more enjoyable on a brisk winter morning than exploring streets framed with picket fences and wandering the countless footpaths that wind through town. Stop and admire candy-colored homes with whimsical names like Key Lime, Surf Lodge, and Shore Is Fun. Along the way, you'll pass lots of vine-covered arbors, sculpture installations, and gorgeous wraparound porches decked out with garlands and wreaths. Nearby, a tranquil path leads to a hidden gazebo. Overhead, you'll see a canopy of limbs speckled with pinecones still clinging to the bare branches.

Nine of those charming streets lead to Seaside's renowned beach pavilions, which stretch over the dunes to offer breathtaking views. Each one is designed by a different architect and provides a distinct perspective on the coast.

Don't miss 15-year-old Seaside Interfaith Chapel (seasidefl.com), designed by architect Scott Merrill. It's one of many celebrated landmarks in the community and an inspired space for a holiday service or concert—or just a little quiet time to reflect on the season.

Rimmed with palm trees that glitter with twinkling lights, Seaside Amphitheater is the heart of downtown and a prime location for the best dining and shopping. The annual Turn On the Town celebration on November 26 includes a Christmas parade, the arrival of Santa Claus, and the lighting of a Christmas tree at the amphitheater.

Don't be surprised to hear laughter emanating from the bar at Great Southern Café (thegreatsoutherncafe.com), chef Jim Shirley's acclaimed restaurant and the town's unofficial living room. "Seaside at Christmas has a magical feel," the chef says. "All around town, neighbors—and occasional neighbors—reconnect for their families' Seaside Christmas tradition." Open from sunup to last call, the restaurant is a fantastic spot for a festive holiday meal. At breakfast, think mimosas, pillowy beignets, Fried Green Tomato Benedict, Eggs Sardou Benedict with creamy collards and artichoke sauce, and smoked Gouda grits. Later in the day, try Apalachicola oysters on the half shell and Grits and Grillades (slow-roasted beef in a rich Shiraz stew).

Chef McDonald at Bud & Alley's Pizza Bar (budandalleys.com/pizza_bar.php) can serve you a Negroni and excellent seasonal salads (such as grilled eggplant with seasoned yogurt and chile pepper or pear and arugula with hazelnut) and inspired pizzas like Brussels Sprouts & Pancetta or a white pizza with clams, Parmesan, and chili. Just across the sidewalk, The Shrimp Shack (sweetwilliamsltd.com/shrimp_shack.asp) serves Apalachicola oysters on the half shell, lobster rolls, and steamed shrimp to go; or you can grab a table at their own pavilion—one of the prettiest perches on the beach.

What's a beach trip without ice cream? Pop into Heavenly Shortcakes & Ice Cream (sweetwilliamsltd.com) for a few star-shaped brownies and some yummy coconut gelato.

If you still need last-minute gifts for friends, relax—Seaside's stylish boutiques offer options for everyone on your list. And what's better than crowd-free alfresco shopping?

Perspicasity (perspicasityseaside.com) is an open-air beachside bazaar with boho-inspired apparel such as cowboy hats, sundresses, batik sarongs, and espadrilles. The Seaside Style (theseasidestyle.com) is an essential souvenir stop for pastel T-shirts, hoodies, and accessories. To buy splurge gifts for special names on your list, visit La Vie Est Belle (lavieestbellegallery.com), which has an exquisite collection of pearl necklaces and other designer jewelry. You'll find stocking stuffers galore at Duckies Shop of Fun (shopduckies.com) and gifts for book lovers (including first editions and photo essays about the area) at Sundog Books (sundogbooks.com). Music geeks should wander upstairs to browse the vintage vinyl collection at Central Square Records (centralsquarerecords.com).

You can start there to curate a no-cooking-required holiday feast, with steamed shrimp and lobster rolls accompanied by a bottle of wine from The Seaside Wine Project (seasidefl.com/theseasidewineproject). Modica Market (modicamarket.com) is Seaside's neighborhood grocery store and your go-to for excellent rustic breads, such as smoked rye with seeds or cracked corn country, as well as wine and cheese, vintage candies, and homemade pastries. Here, you can also pick up the necessary beach house treats like Southern Craft Creamery's handmade ice cream in seasonal flavors like cranberry-satsuma and dried plum and rum.

It's a point of pride in this nature-loving beach burg that bikes are the preferred mode of travel, so rent a beach cruiser (think balloon tires, a cushy upright seating position, and vintage styling) from the Seaside Transit Authority (seasidetransitauthority.com). Adult rentals include combination locks, quick-release wicker baskets, bike bells, and helmets. Tandem bikes, carriers for kids, and cargo trailers for beach gear are also available.

Fuel up for your ride with a smoothie from Raw & Juicy, a popular Airstream trailer selling a menu of fresh and raw vegan food (rawandjuicylife.com). Owner Jenifer Kuntz also helped develop the year-round Seaside Farmers Market held at the amphitheater every Saturday morning.

Now choose your direction. Take a 40-minute bike ride southeast along paved trails to Rosemary Beach, another adorable town that offers alfresco lunch options and holiday shopping. For a slice of Old Florida, pedal northwest to Grayton Beach. Along the way, pass tranquil coastal dune lakes, which are made of both salt water and fresh water. That should give you an appetite for lunch at The Red Bar (theredbar.com), a beloved local favorite and a convivial spot for a killer Bloody Mary (with enough pickled vegetables to call it a breakfast salad) and a flawless fried shrimp po'boy.

Picturesque drives along Scenic Highway 30A make for festive road trips and deliver a broader sense of the area. Design buffs should head to Alys Beach, a luxurious resort town featuring brilliant white homes that are modeled after the traditional houses of Bermuda. While you're there, swing by Alys Shoppe to pick up some last-minute stocking stuffers, and treat yourself to a cup of cheer at NEAT (alysbeach.com/dining), a beautiful new bottle shop and tasting room. It's an easy spot to settle in for a glass of bubbly or local craft beers. (Try Oyster City Brewing Company's Hooter Brown Ale.)

Families with kids should hit The Village of Baytowne Wharf (baytownewharf.com) for serious holiday sparkle. Located inside the gates of Sandestin Golf and Beach Resort, Baytowne Wharf hosts an annual 12 Nights of Lights that includes an ice-skating rink as well as plenty of boutiques, art galleries, casual restaurants, and photo ops with Santa. On the way back, stop at Goatfeathers Seafood Market and Restaurant (goatfeathersseafood.com) in Santa Rosa Beach for beach-house provisions like smoked tuna dip and steamed shrimp.

As the newest rental company in Seaside, the Homeowner's Collection (homeownerscollection.com) offers dozens of premier cottages from owners who are participating in the program.

Take advantage of high-quality amenities, special touches, and personalized service throughout your vacation. All stays include perks like passes for parking, swimming, and fitness centers.

Rental costs span from $172 to $736 per night or $1,204 to $5,152 per week. Accommodations range from Secret Garden (a two-story cottage in a beautifully landscaped area near Central Square) to Lucky Charm (located across from the chapel and featuring five porches to soak up the gorgeous coastal scenery). You can also rent quaint guest cottages such as Dreamboat, a one-bedroom gem directly across from the beach.

Wherever you stay, you'll never forget Christmas in this very special town. With lots of fresh local food to feast on and a mountain of locally inspired presents underneath your (palm) tree, you and yours will feel right at home for the holidays—but in a whole new way. Before you leave, enjoy a sunrise stroll on the beach so you can take the ultimate souvenir—a little Seaside serenity—back home with you. Consider it a gift to yourself.