A 5-Day Seaside, Florida Vacation Itinerary

Five days is the sweet spot for a Seaside Florida vacation: enough time to fall into the town’s rhythm, and enough time to venture beyond it. This itinerary bases you at The Court, a two-to-three-minute walk from the beach, and spreads your days between Seaside itself and the neighboring towns along Scenic Highway 30A. No hour-by-hour schedule, just a loose shape for a slower kind of trip.

Seaside is the birthplace of New Urbanism, a walkable town designed so homes, shops, and the beach all sit within a few blocks of each other. That’s part of what makes longer Seaside Florida vacations work so well: the town itself never feels like it runs out, and everything nearby is a short bike ride or drive away.

Day 1: Arrival and Settling In

Check-in at The Court is 4:00 p.m. The concierge team meets every guest on arrival to direct you to reserved self-parking, and each bungalow comes stocked with a Nespresso coffee bar and Peacock Alley linens, so there’s little reason to leave the property tonight beyond dinner.

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

• First dinner: Bud and Alley’s for seafood and a rooftop sunset, Seaside’s longest-running restaurant.
• A short walk: Central Square and Ruskin Place, Seaside’s artist enclave, to get oriented before the busier days ahead.

Day 2: Beach, Town, and Central Square

Spend your first full day close to home. The Court arranges your beach chair and umbrella setup as a complimentary service, so mornings start with a short walk to a spot that’s already waiting for you.

• Breakfast: Black Bear Bread Co. for tartines and specialty lattes, or Amavida for coffee and matcha.
• Late morning: Browse Central Square: Sundog Books, Modica Market for gourmet snacks, The Seaside Style for coastal apparel, and Anne Hunter Galleries for local art.
• Lunch: Pickle’s Sandbar 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 It’s Heavenly Shortcakes & Ice Cream.

If your trip lines up with a Saturday, save this morning for the Seaside Farmer’s Market instead: local vendors and live music before the beach crowd arrives.

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

This is the day to use your bikes or a car and head west on Scenic Highway 30A toward Grayton Beach and WaterColor.

Grayton Beach State Park is home to Western Lake, one of only about fifteen coastal dune lakes on the entire Gulf Coast and one of a small number found anywhere in the world, alongside a handful in New Zealand, Australia, and Madagascar. Spend the morning on the boardwalk or out on the water; paddleboarding and kayaking on Western Lake are the classic way to see it.

• Morning: Western Lake and the Grayton Beach State Park boardwalk.
• Midday: Lunch in Grayton Beach or WaterColor, then a walk through WaterColor’s boat club and marina area.
• Afternoon: Back to Seaside by bike along the Timpoochee Trail, which runs the length of 30A and connects the towns without ever needing the highway itself.
• Dinner: Shrimp Shack for fresh seafood back in Seaside, or ‘drome for house-made dumplings.

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

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

• Morning: Eastern Lake near Seagrove for kayaking, a local favorite with easy access to the water and, on a good outfall day, a paddle straight from the lake out to the Gulf.
• Midday: Alys Beach, known for its white Bermuda-style architecture and courtyard gardens, worth a slow walk even without an agenda.
• Afternoon: Rosemary Beach for boutique shopping and a coffee break in the town square.
• Dinner: Back in Seaside at 87 Central Square if your evening lands on a Tuesday or Thursday for their paella night, or Pizza Bar for something simpler.

Return your bikes for the evening, or keep them one more day. Either way, the beach chairs are still yours until checkout.

Day 5: A Slow Morning and Departure

Checkout at The Court is 10:00 a.m., so let this last morning be as unhurried as the rest of the trip.

• Breakfast: Daytrader for a lunch bowl-style breakfast, or Wild Nectar for an acai bowl.
• One last walk: Rose Walk and Lyceum Lawn, a quieter, greener side of Seaside before the town wakes up.
• Before you go: A final stop at Modica Market for something to bring home, or 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