Shell combing on Nokomis Beach
Venice Sail into the sunset

A Memorial Weekend Itinerary in Casey Key

Heading south for Memorial Day weekend? Slow it down by staying off-the-beaten trail in the island paradise of Casey Key

Casey Key is a predominantly quaint and quiet residential island with sprawling properties and waterfront mansions that will make your jaw drop –  all along scenic Casey Key Road. In contrast with the palatial homes, however, are a handful of mid-century beachside motels, just a stone's throw from the Gulf of Mexico. 

Check in to your Digs

On the Beach in Casey Key
On the Beach in Casey Key

If you’re looking for a truly private stay on Sarasota’s most exclusive island, check out these quaint island escapes on Casey Key or nearby Nokomis: 

Rent Jet Skis, Paddleboard & Parasail

Once checked in, don't waste a second away from the crystal-blue waters and white sand shoreline. No matter your speed, you can find a water sport or activity to your (or your group's) liking. 

For water fun and a fast-paced adventure, sign up for a Cool Breeze jet ski tour. Their guides will start by taking you along the mangroves as you speed along toward Roberts Bay. See what the beautiful shorelines of Casey Key look like from a different vantage point on the water. Make sure to grab a GoPro or waterproof camera before heading out. You're going to want pictures!

Grab a couple of paddles and your companions to head back out on the water for some standup paddleboarding on the Gulf of Mexico. You can rent SUP equipment from Silent Sports Outfitters at Blackburn Point. They also offer tours and rentals if you'd prefer a local guide to show you around the blue waterways.

If paddleboarding isn't your thing. Perhaps soaring over the water in a parasail is. Built for four people, you can see the water from a seagull's point of view. Venice Parasailing will take you on a tour of Casey Key, where you can try to spot manatees and dolphins as you glide above the Gulf. The captain may even throw in a dunk or two if you're hoping to get a bit wet!

Ring Toss & People Watch

There's arguably no better place to watch the sunset, and the people, than at Casey Key Tiki Bar. This bar will make you feel like you're on spring break year-round. The large tiki hut is outdoors and almost entirely on the soft sand of a small beach and boat launch. Providing shade from a long, sun-filled day, many boaters, beachgoers and paddlers wash up ashore here for the energy and refreshments like delicious daiquiris and margaritas – making it often crowded. There's also a ring toss and a giant Captain Morgan statue there, which always keeps things interesting.

When hungry for some dinner, just walk over to the neighboring Casey Key Fish House for fresh-caught seafood – including Peel & Eat Gulf shrimp, Conch Fritters, Smoked Mahi Fish Dip, Grouper Sandwich, Diver Scallops and so much more. And don't think about leaving until you try a slice of the Key Lime Pie, its famous cheesecake topped with caramel sauce and fresh whipped cream.

Grab a Healthy, Hearty Brunch

The Healthy Omelet at Cafe Evergreen
The Healthy Omelet at Cafe Evergreen

In Nokomis, start your day by grabbing a great breakfast at Cafe Evergreen. Featuring fresh juices and smoothies, draft kombucha, organic coffee, probiotic drinks, matcha lemonade and many more morning beverages, this health-forward cafe is a great spot to fill your tank before a full day of play. The food menu offers many vegan-friendly options along with locally pastured raised beef. Find a variety of salads, sandwiches, omelets, bowls, burgers and more.

Beach It Up or Go Sailing

Spend the rest of your day sunbathing, shell combing or body surfing on Nokomis Beach, Sarasota County's oldest public beach and located right off Casey Key Road. The beach provides the safety of lifeguards while you or the kids swim, a boardwalk to stroll, fishing, a canoe/kayak launch, picnic shelters, a playground, volleyball nets, beachside restrooms, free parking and showers to wash off the salt and sun. 

If you've got the budget to spend the day starboard, check out Sail Venice, which lets you create a customized sailing trip around you. They'll even sail to the dock at Pop's Sunset Bar and Grill if you'd like to drop anchor for dinner and drinks.  Located at Crow's Nest Marina, Sail Venice also teaches sailing lessons for those of you who want to take your sailing adventure to the next level. 

Grab a Tiki Drink & Enjoy Live Music

Spend all evening by the water and under the hanging lights at Pop's Sunset Grill, a Gulf Coast's favorite Old Florida landmark – well loved by locals and tourists alike for its island-like atmosphere and fresh local fare. The waterfront outdoor dining area is open year-round with fire pit tables, a courtyard with daily live music and three different bars – the main being outside under a giant tiki hut overlooking the Intracoastal Waterway.

Frozen daiquiri, piña colada or rum punch in hand, pair your island-inspired cocktails with snacks from the Raw Bar Menu or Pop's Fry Baskets for some truly good Florida eatin'. The Bou-Tiki is also a great place to shop and grab some branded merch before you leave.

Celebrate Memorial Day

Catch one more Gulf Coast sunset and take a moment to remember why we celebrate Memorial Day in the first place. Thank a veteran and enjoy the feeling of your toes in the sand as the colors of the sky turn orange-pink before it's time to pack up and head back home.