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 your 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: Arrival and a Slow First Evening

Check-in at The Court begins at 4:00 p.m. A concierge will meet you when you arrive and show you to your reserved parking, and after that you won’t need to think about your bags again. Every bungalow has a complimentary Nespresso bar, Peacock Alley linens, and a glass rainfall shower, so there’s no need to hurry back out. Ask the front desk about your two complimentary bicycles through the Seaside Transit Authority when you check in. You won’t need them tonight, but you’ll want them ready for tomorrow.

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

• Dinner: Bud & 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: Walk through Ruskin Place, Seaside’s small artist community just off the square, then get dessert at It’s Heavenly Shortcakes & Ice Cream or Dawson’s Yogurt & Fudge.
• Nightcap: Have dessert at It’s Heavenly Shortcakes & Ice Cream or Dawson’s Yogurt & Fudge, or take a cocktail back to your porch and end the night there.

Day 2: The Full Seaside Day

Today is the day to enjoy everything Seaside and The Court have to offer: the beach, the bikes, the shops, and the town’s weekend energy.

Morning: Beach and Coffee

Start with coffee and a pastry at Black Bear Bread Co., known for tartines and specialty lattes, or Amavida for coffee and matcha. Then head to the beach, where The Court has already set up your complimentary chairs and umbrella.

On Saturday mornings, stop by the Seaside Farmers Market for local vendors and live music before the beach gets busy.

Midday: Bikes and Central Square

Take your bikes out on the Timpoochee Trail, the paved path along Scenic Highway 30A that links Seaside to the neighboring beach towns. Even a short ride gives you a feel for the coastline beyond Seaside.

Back in town, browse the shops around Central Square. Pick up a beach read at Sundog Books, snacks and picnic supplies at Modica Market, coastal apparel at The Seaside Style, or creative finds and local art at Art of Simple. For lunch, Pickle’s is known for its burgers and truffle fries, and Wild Bill’s Beach Dogs is good for a quick bite.

Afternoon: Pool or Beach, Your Call

Seaside’s three shared pools are open from 8:00 a.m. to dusk, which makes them a good option if you want shade and a lounge chair. If you’d rather stay active, the Seaside Athletic Club has tennis and pickleball courts and a fitness center.

Evening: Dinner and the Amphitheater

Have dinner at Shrimp Shack for fresh, simple seafood, or at ‘drome for house-made dumplings if you want a break from coastal cuisine. Afterward, see what’s happening in Amphitheater, which hosts live music and events throughout the year. Even on a quiet night, the Tupelo Goods chairs are a pleasant place to sit for a while.

Day 3: A Slow Morning Before Checkout

Checkout is at 10:00 a.m., so keep the morning easy.

• Breakfast: Grab house-made tacos from Amavida, or an acai bowl from Wild Nectar to eat on the beach.
• One last walk: Rose Walk or walk the Lyceum Lawn, two of the quieter, greener corners of Seaside.
• If you have an extra hour: Grayton Beach State Park is a short drive or bike ride west. It’s home to Western Lake, one of the world’s few coastal dune lakes.

Return your bikes and check out by 10:00 a.m. Three days is enough time to leave Seaside relaxed. It’s rarely enough to see everything, which is the best reason to start planning your 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 or check current offers and packages to start planning your weekend.

Frequently Asked Questions