Sharky's Beachfront Restaurant (Walking right along the shoreline — about a 20 to 30-minute beach walk)

One of our absolute favorite traditions is taking a gorgeous stroll right along the shoreline straight down to Sharky's Beachfront Restaurant. There is nothing quite like walking on the beach to work up an appetite, grabbing something tasty and cold on their beachfront patio, and then taking a relaxing walk back to burn off your meal. It is an amazing way to experience the coast! Click here for more information.

Beach tip: Bringing a drink onto the sand is allowed 11 months out of the year (strictly banned in March), provided you carry a valid photo ID and use plastic or cans instead of glass.

Angry Tuna Seafood Company (Right inside Pier Park — a 5-minute walk from the Calypso tower)

Head down to Pier Park and check out Angry Tuna. It's a super relaxed spot with great food right in the middle of everything. You'll definitely want to try their smoked tuna dip, the seared tuna bowl, or the tuna nachos and BLT. They are also known for having $1 drafts on select beers like Yellowfin and Outlaw. Summer happy hour times can change a bit, so just double-check with your server when you get there! Click here for more information.

The Back Porch Seafood & Oyster House (Right in the Pier Park area — about an 2-minute walk from Calypso)

This is a go-to spot right in the Pier Park area. It’s perfect for a classic, reliable waterfront seafood meal. Our guests and family always love their baked oysters and their famous chargrilled Amberjack sandwich. Click here for reviews and additional information.

Dusty’s Oyster Bar (Heading southwest down the beach — about a 15-minute walk right along the sand)

If you want a quick and easy beach walk in the opposite direction of Pier Park, strolling right along the sand brings you to this legendary, old-school local landmark. Dusty's is famous for its totally unpretentious, rustic dive-bar vibe where the walls and ceilings are completely covered in signed dollar bills. It is an absolute haven for oyster lovers—whether you prefer them fresh and raw, steamed, or baked and chargrilled with rich garlic, butter, and cheese toppings. Pair them with some of their fantastic fried seafood baskets and cold drinks.

Beach tip: Bringing a drink onto the sand is allowed 11 months out of the year (strictly banned in March), provided you carry a valid photo ID and use plastic or cans instead of glass. Click here to read reviews.

McGuire’s Irish Pub (Located on Front Beach Road — about a 4-minute drive)

If you're looking for an incredible atmosphere, live music, and massive portions, McGuire's is an absolute must-visit landmark in PCB. The interior is wildly cool—the ceilings and walls are completely covered in millions of signed dollar bills left behind by guests over the years. It’s famous for its lively pub energy, in-house brewed ales, and incredible food. Whether you go for their legendary steak and mushroom pie, fish and chips, or a giant soft pretzel with beer cheese, you definitely won't leave hungry! Click here for more information.

Diego’s Burrito Factory (Located on Front Beach Road — about a 4-minute drive or a short walk from Calypso)

When you want something fast, fresh, and fully customizable, Diego's is a fantastic nearby spot. It’s super convenient to pop over to build your own massive burritos, tacos, or bowls piled high with fresh ingredients. It's a great, casual go-to when everyone in the family wants something a little different! Click here for reviews and directions.

Zollo’s Pizza (Located in Pier Park — about a 5-minute drive)

Zollo’s is fantastic when you just want to grab a quick, delicious slice or a whole pie. Keep in mind it's not a sit-down restaurant, so it's best for grabbing food to take back to the beach, the pool, or up to the room to enjoy. Click here for reviews and directions.

Great White Pizza (Right in the Pier Park area — about an 2-minute walk from Calypso)

If anyone in your group is avoiding gluten, this is a fantastic spot to keep in mind. They offer great gluten-free options so nobody has to miss out on pizza night. Click here for reviews and directions.

The Donut Hole (Located about a 15-minute drive from Calypso)

You can't visit PCB without a trip to The Donut Hole! It’s a local institution. The Bavarian cream donut is an absolute crowd-pleaser and everyone's favorite, but get there early because the best ones go fast. Click here for reviews and directions.

Kilwins Ice Cream & Chocolate Fudge (Right in Pier Park — a 3-minute walk from Calypso)

When you have a sweet tooth after dinner, Kilwins right in Pier Park is hard to beat. Walking through the door to the smell of freshly made waffle cones and fudge is half the fun. Their chocolate fudge and artisanal ice cream are the ultimate vacation treat. Click here for reviews and directions.

Firefly (Located on Richard Jackson Blvd — about a 10-minute drive from Calypso)

If you're celebrating a milestone, an anniversary, or looking for an unforgettable date night, Firefly is the premier spot for upscale dining in PCB. While it is definitely on the pricier side, stepping inside feels like entering an enchanted, magical forest. The dining room is centered around a breathtaking indoor replica of a grand oak tree canopied with thousands of twinkling fairy lights. The kitchen delivers an exceptional, creative menu featuring high-end steaks, fresh seafood, and incredible attention to detail. It is an absolute showstopper of a restaurant when you want to get dressed up and make a night truly special!
Click here for reviews and directions.

1. Airstream Row (Located in Seaside, FL — about a 35-minute drive from Calypso)

This is a famous, nostalgic row of vintage silver Airstream trailers converted into permanent, gourmet food trucks sitting right on the beautiful town square of Seaside. You can stroll around, grab food from different trailers, and sit under the shaded trees. Local favorites include:
The Meltdown on 30A: Legendary gourmet grilled cheese sandwiches (the Brie and Bacon melt is a must-try).
Frost Bites: Famous for massive Hawaiian shave ice injected with rich, homemade frozen custard.
Crêpes du Soleil: Made-to-order sweet and savory French crepes, along with refreshing cold Frosé.

To learn more click here.

2. The Big Chill 30A (Located in Watersound, FL — about a 25-minute drive from Calypso)

This spot is a bit closer and features a massive open-air entertainment district. It's a large, family-friendly plaza surrounded by local food windows and bars, all centered around a giant lawn with a massive LED jumbotron screen and a live music stage. It feels like a giant backyard party. A few famous stops there include:
Macho Taco: Famous for "Mexican-inspired soul food" like loaded street tacos and chorizo quesadillas.
Duo’s All-American Eats: The go-to spot for premium, juicy burgers and crispy hand-cut fries.
Local Smoke: Excellent Southern barbecue, highly praised for its slow-smoked pulled pork and piled-high BBQ Nachos.
Click here for reviews and directions.