Back to the Beach: Seaside

The coastal cottage getaway

Cottage Rental Agency - Seaside, Fla.

I’ve been meaning to get back to the Florida Panhandle for ages. Growing up, I spent several vacations in Panama City and Destin, but I never visited the much-talked-about South Walton coastal communities dotting Scenic Highway 30A. Of course, I’d heard all about these locales that sounded like they’d sprung from a painter’s palette—WaterSound, Seagrove, WaterColor, Miramar— and when the opportunity to discover the area for myself arose, I started packing my bags. After a call to Cottage Rental Agency, the premier provider of rental properties in Seaside, I was ready to hit the road.


Cottage Rental Agency - Seaside, Fla.

When I walked into my cottage, I understood why it was named “This Side of Paradise.” Everything was perfect but not precious or pretentious. The ceilings are high, the floors hardwood, and the home entertainment state of the art. The great room and three bedrooms convey a coastal-chic aesthetic without a hint of beach kitsch, and the well-equipped kitchen is outfitted with modern appliances with a lovely vintage feel.

On the screened-in porch off the second-floor master suite, I found a hammock just begging to be used for an afternoon nap and was happy to oblige. The top floor features two tower decks, which afford alternate views of sunrise and sunset, as well as Seaside’s distinctive roofline. It’s also great for counting stars deep into the night.

Many first became aware of Seaside when it served as the location of the 1998 film The Truman Show, starring Jim Carrey as a man aware that his life is a reality TV show. Although the friendly residents, beautiful homes, well-mannered children,sunny skies, and unique shops were part of the movie’s script, the real town is strikingly similar—and that’s by design.


Cottage Rental Agency - Seaside, Fla.

Robert Davis and his wife Daryl began developing Seaside, the first New Urbanist town in the country, in the early eighties on eighty beachfront acres his grandfather had purchased decades earlier. Robert had spent his boyhood summers building sandcastles on the beach and knew it was something special. The community he envisioned would also be one of a kind: easy to get around, with plenty of places for people to gather. The cottages would be harmonious but distinct and offer Gulf views unobstructed by high-rise condominiums.

Bicycles are the preferred method of transportation, and as I meandered up and down the tree-lined streets, I admired the pastel and jewel-tone homes that range from one-bedroom bungalows to mansions that sleep twelve. Many have clever, pun-heavy names like Cow Bella, Whatcha Dune, Sea Ya, and License to Chill.

Nine pavilions, each with its own distinctive architectural style, offer access to the sugar-white sands of the Gulf, and the beach is lined with Cabana Man’s royal-blue beach umbrellas and chairs, offering shade and solace to the sun-weary. After beach-combing or bodysurfing the clear-blue water, head back to 30A and indulge at one of the vintageAirstream food trucks. Grab a grilled cheese at The MeltDown on 30A, a pulled-pork sandwich at Barefoot BBQ, or a shaved-ice treat from Frost Bites. Once you’ve refueled, try your hand at bocce ball or croquet, take a dip in one of the three pools, or check out the totally renovated fitness center.

While sun and fun are always on tap, fall and winter are great times to visit this idyllic area. Seaside’s Seeing Red Wine Festival features alfresco tastings, seminars, and vintners dinners at several restaurants. And the popular 30A Songwriters Festival will bring more than 100 musicians to venues up and down the highway for a weekend of outstanding performances. That’s all the encouragement I need to begin planning a return trip to Seaside and future getaways to the other coastal towns of South Walton.

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