The Court's Itinerary: A 3-Day Weekend in Seaside, Florida

Short on time but craving sand between your toes? Here’s exactly what to do in Seaside this weekend: settle into a bungalow at The Court, walk two to three minutes to the Gulf, and let the town’s pastel lanes, Central Square, and Timpoochee Trail fill the rest. This three-day itinerary is built for a Friday-to-Sunday escape, timed around real Seaside hours, real distances, and the kind of unhurried pace the town was designed for in the first place.

Seaside was born in 1981 as the birthplace of New Urbanism, a walkable town where homes, shops, and the beach all sit within a few blocks of each other. That means a weekend here doesn’t require a car, a packed schedule, or much planning at all. It just requires showing up.

Day 1 (Friday): Arrival and a Slow First Evening

Check-in at The Court opens at 4:00 p.m. A member of the concierge team will meet you on arrival to direct you to your reserved self-parking, and from there, your bags are the last thing you’ll need to think about. Each bungalow comes with a complimentary Nespresso bar, Peacock Alley linens, and a glass rainfall shower, so there’s no reason to rush back out.

Once you’re settled, walk the two to three minutes to the beach for a first look at the Gulf, or head straight into town. Central Square is the heart of Seaside and a good place to get your bearings before dinner.

• Dinner: Bud and Alley’s, Seaside’s longest-running restaurant, for seafood and a rooftop margarita with a Gulf view, or Great Southern Café for Chef Jim Shirley’s coastal cooking.
• After dinner: A walk through Ruskin Place, Seaside’s small artist enclave tucked just off the square, followed by dessert at It’s Heavenly Shortcakes & Ice Cream or Dawson’s Yogurt & Fudge.
• Nightcap: Airstream Row, Seaside’s line of vintage food and drink trailers, runs year-round and makes an easy first-night stop if you’re not ready to turn in.

Ask the front desk about your two complimentary bicycles through the Seaside Transit Authority while you’re checking in. You won’t need them tonight, but you’ll want them ready for tomorrow.

Day 2 (Saturday): The Full Seaside Day

This is the day to use everything Seaside and The Court put in front of you: the beach, the bikes, the shops, and the town’s Saturday rhythm.

Morning: Beach and Coffee

The Court arranges your beach chair and umbrella setup as a complimentary service, so your morning starts with a short walk to a spot that’s already waiting for you. Grab coffee and a pastry beforehand at Black Bear Bread Co. for tartines and specialty lattes, or Amavida for coffee and matcha.

If your weekend lands on a Saturday morning, walk over to the Seaside Farmer’s Market for local vendors and live music before the beach crowd picks up.

Midday: Bikes and Central Square

Pick up your complimentary bicycles and ride the Timpoochee Trail, the paved path that runs along Scenic Highway 30A and connects Seaside to neighboring beach towns. Even a short ride out and back gives you a feel for the coast beyond Seaside’s town limits.

Back in town, browse Central Square’s shops: Sundog Books for a beach read, Modica Market for gourmet snacks and picnic supplies, The Seaside Style for coastal apparel, and Anne Hunter Galleries or Art of Simple for local art. For lunch, Pickle’s Sandbar covers burgers and truffle fries, or grab a quick bite from Wild Bill’s Beach Dogs.

Afternoon: Pool or Beach, Your Call

Seaside’s three shared pools are open from 8:00 a.m. to dusk, an easy alternative to the beach if you want shade and a lounge chair. The Seaside Athletic Club also has pickleball courts if you’d rather stay active than horizontal.

Evening: Dinner and the Amphitheater

For dinner, Shrimp Shack for straightforward fresh seafood, or ‘drome for house-made dumplings if you want something different from the coastal-cuisine norm. Afterward, check what’s on at the amphitheater in Central Square. Seaside regularly hosts live music and events on its outdoor stage, and even an empty evening there, with the Tupelo Goods chairs and a warm night, is worth sitting in for a while.

Day 3 (Sunday): A Slow Morning Before Checkout

Checkout at The Court is 10:00 a.m., so keep this morning light.

• Breakfast: Daytrader for a lunch bowl-style breakfast, or Wild Nectar for an acai bowl to eat beachside.
• One last walk: Rose Walk or Lyceum Lawn for a quieter, greener side of Seaside before the town wakes up.
• If you have an extra hour: Grayton Beach State Park is a short drive west and home to Western Lake, one of only a handful of coastal dune lakes in the world. Even a quick look at the boardwalk is worth the detour.

Return your bikes, drop your beach chairs back with the concierge team, and check out by 10:00 a.m. Three days is enough to leave Seaside relaxed. It’s rarely enough to see all of it, which is usually the best reason to already be thinking about the next trip.

Good to Know Before You Book

• The Court has a 2-night minimum stay, which lines up naturally with a weekend visit.
• Check-in is 4:00 p.m. and checkout is 10:00 a.m.
• The Court is an adults-only property for guests 25 and up.
• Two bungalows welcome pets under 50 pounds.
• The closest airport is Northwest Florida Beaches International (about 25 miles, a 40-minute drive), with Destin-Fort Walton Beach and Destin Executive also nearby. See our Getting Here guide for directions.

Explore rooms and bungalows or check current offers and packages to start planning your weekend.

Frequently Asked Questions