Millions of visitors flock to Clearwater, Florida, each year for its pristine Gulf Coast beaches, which are ranked some of the best in America. With so much focus on coastal living, expect many activities centered around the water, from relaxing on the white-sand beaches to up-close encounters with stingrays at the aquarium.
Go inland and the laid-back vibes get a jolt in downtown Clearwater, a humming center of shops and restaurants serving world-class seafood. No matter where you are, you’ve got incredible views — and you’re never too far from those crystal-blue waters.
As always, check for travel restrictions and closures before planning your trip.
Friday: Explore Downtown
Though you may be eager to make a beeline for the beaches, start the trip with a day downtown. The first stop is breakfast at Clear Sky on Cleveland, an always-lively spot with decadent pancakes, biscuits and omelets — and, most crucially, build-your-own Bloody Marys.
Walk it off with a stroll through the Cleveland Street District, where you can pop into shops and break out of the Tampa Bay Escape Room before heading out onto the Downtown Clearwater Waterfront Pier for some excellent photo ops.
Grab lunch at Tequilas Mexican Grille & Cantina, where the portions are large and the queso comes highly recommended, followed by a 15-minute walk to the SimCenter Tampa Bay. Here, you can take a spin in life-size flight, space and Formula 1 race car simulators. With four different simulators, multiple virtual reality experiences, and a hydromassage option, this place will keep you busy all afternoon.
Alternatively, if you’re visiting during the spring months and you’re lucky enough to catch a ticket, head to BayCare Ballpark for some spring training baseball games.
All of that heart-racing excitement will get you hungry again. So make it an early bite at Roxy’s — a breezy American bistro where everything is made from scratch — before catching a show at the historic Capitol Theater.
The venue hosts something different every night, be it a Broadway tour or a multimedia music production, so take a look at the event schedule before traveling to time your visit. This will undoubtedly take you well into the evening before returning to your hotel for a good night’s sleep.
Saturday: Relax on the Beach
Experience the main draw of the Clearwater on day two — today is focused on the beach. Grab breakfast at the hotel before walking (if you’re staying nearby) or driving to Clearwater Beach. This stretch of white sand is the ultimate spot to set up your towels and umbrellas for some relaxation.
From here, spend a couple of hours reading books and taking a dip in the warm Gulf Coast waters before dining at Palm Pavilion Beachside Grill & Bar, set in a nearly 100-year-old open-air beachfront building. The low-key spot serves fresh seafood at picnic tables, making it ideal for a casual lunch — fried local grouper is the house specialty.
Afterward, hop in the car for a quick 3-mile drive to Sand Key for more beach time at a quieter stretch of shoreline known for its endangered sea turtle habitat (don’t worry — during nesting season, egg clutches are marked to protect hatchlings).
Wash up back at the hotel in time to go to Pier 60 for sunset. Snap some pics, then walk along the path to Crabby’s Bar & Grill for dinner, where you can order crab and conch fritters, plus one of the monthly drink specials.
Put a bow on your day of relaxation at the Tiki-themed Coco’s Crush Bar & Grillfor a nightcap. Be sure to order one of the popular frozen drinks while listening to live music and playing games.
Sunday: Meet the Wildlife
There are more water-related activities in the works today, but first: Breakfast. Pick up a blueberry-lemon scone or a cinnamon roll at Caffeinated Bakery and enjoy a leisurely morning by the bay. Then make your way to the famous Clearwater Marine Aquarium, which opens daily at 10 am.
You can easily spend a few hours here peeping the exhibits, listening to marine biologist talks and participating in hands-on animal encounters. Choose between petting a dolphin, taking care of a shark or feeding a stingray (all make for incredible photo opportunities). Island Way Grill is next door and is the perfect place to grab a burger and a beer for lunch.
After grabbing some grub, hop in the car and head 11 miles north to Caladesi Connection Ferry. There, catch a boat to the untouched Caladesi Island State Park for an afternoon of hiking along the Caladesi Island Wildlife Trail or kayaking through the mangroves (head to the café for kayak rentals).
Grab the ferry back and settle in for flame-grilled chicken sandwiches and clam strips at High & Dry Grill. And for one last hurrah, hop on over to the open-air Frenchy’s Outpost Bar & Grill, which is known for its daily live music and Tiki bar. Just be warned: The “Outpost Punch” goes down dangerously easy.
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