A 5-Day Seaside, Florida Vacation Itinerary

Five days is the right length for a Seaside, Florida vacation. It’s long enough to settle into the town’s pace and still leave time to explore beyond it. This itinerary bases you at The Court, a two- to three-minute walk from the beach, and splits your days between Seaside and the neighboring towns along Scenic Highway 30A. There’s no hour-by-hour schedule, just a loose outline for a slower trip.

Seaside, founded in 1981, is the birthplace of New Urbanism, a walkable town designed so that homes, shops and the beach are only a few blocks apart. That’s why longer Seaside vacations work so well. The town never feels used up, and everything nearby is a short bike ride or drive away.

Day 1: Arrival and Settling In

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. 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 from the Seaside Transit Authority when you check in. You’ll use them most days of the trip. Pick up your two complimentary bicycles through the Seaside Transit Authority after you check in. You’ll use them most days this trip.

• Dinner: Bud & Alley’s, Seaside’s longest-running restaurant, for seafood and a rooftop sunset.
• After dinner: Walk through Central Square and Ruskin Place to get your bearings
• Nightcap: Have dessert at It’s Heavenly Shortcakes & Ice Cream, or take a cocktail back to your porch and end the night there.

Day 2: Beach, Town, and Central Square

Spend your first full day close to The Court. Your complimentary beach chairs and umbrella are set up for you each morning, just a short walk away.

• • Breakfast: Black Bear Bread Co. for tartines and specialty lattes, or Amavida for coffee and matcha.
  • Late morning: Browse the shops around Central Square. Pick up a beach read at Sundog Books, gourmet snacks at Modica Market, coastal apparel at The Seaside Style, or creative finds and local art at Art of Simple.
  • Lunch: Pickle’s for burgers and truffle fries.
  • Afternoon: Back to the beach, or one of Seaside’s three shared pools, open 8:00 a.m. to dusk.
  • Dinner: Great Southern Café for Chef Jim Shirley’s coastal cooking, followed by dessert at Dawson’s Yogurt & Fudge.

If this day falls on a Saturday, start the morning at the Seaside Farmers Market for local vendors and live music before the beach gets busy.

Day 3: West Along 30A, Grayton Beach and the Dune Lakes

Take your bikes or the car west on Scenic Highway 30A toward Grayton Beach and WaterColor. Grayton Beach State Park is home to Western Lake, one of the rare coastal dune lakes found along this stretch of the Gulf Coast. Similar lakes exist in only a few other places in the world, including New Zealand, Australia and Madagascar. Spend the morning on the boardwalk, or get out on the water by kayak or paddleboard.

• Morning: Explore Western Lake and the Grayton Beach State Park
• Midday: Lunch in Grayton Beach or WaterColor, then a walk around WaterColor
• Afternoon: Bike back to Seaside on the Timpoochee Trail, which runs the length of 30A and connects the towns without using the highway.
• Dinner: Shrimp Shack for fresh, simple seafood, or ‘drome for house-made dumplings. Afterward, see what’s happening at the amphitheater, which hosts live music and events year-round.

Day 4: East Along 30A, Rosemary Beach and Alys Beach

Head the other direction today, toward Seagrove, Alys Beach, and Rosemary Beach.

• Morning: Kayak on Eastern Lake near Seagrove, a local favorite with easy access to the water. When the lake is open to the Gulf, you can paddle straight out to the beach.
• Midday: Walk through Alys Beach, known for its white Bermuda-style architecture and courtyard gardens.
• Afternoon: Shop the boutiques in Rosemary Beach and stop for coffee in the town square.
• Dinner: Back in Seaside, try paella night at 87 Central Square on a Tuesday or Thursday, or keep it simple at Pizza Bar.

Day 5: A Slow Morning and Departure

Checkout is at 10:00 a.m., so keep your last 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 Lyceum Lawn, two of the quieter, greener corners of Seaside.
• Before you go: Pick up something to take home from Modica Market, or have one more coffee at Black Bear Bread Co.

Return your bikes, drop your beach chairs with the concierge team, and check out by 10:00 a.m. Most guests fly out through Northwest Florida Beaches International Airport, about 25 miles and a 40-minute drive from Seaside, or Destin-Fort Walton Beach Airport, about 27 miles away. See our Getting Here guide for full directions.

Good to Know Before You Book

• The Court has a 2-night minimum stay.
• 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.
• Rates vary by season and demand; check current availability directly through the booking system.

Browse rooms and bungalows or see current offers and packages to start planning your Seaside Florida vacation.

Frequently Asked Questions