Continuing with our beach day trip series, we bring you Clearwater Beach – a haven for laid-back beach lovers. Some of you might remember an email I sent out while I was visiting Clearwater earlier this year.
Voted one of the top 25 best beaches in the WORLD, Clearwater Beach is a little more than two hours southwest of The Villages. Just hop on I-75 to Tampa, then cross the bay on Memorial Causeway. The road ends right at the beach.
If you’ve seen the recent hit movie Dolphin Tale, you’ve already seen parts of Clearwater and Clearwater Marine Aquarium (CMA). Filmed in the area, Dolphin Tale is based on the true story of one of Clearwater’s most famous residents, Winter, a bottlenose dolphin. When Winter was only three-months old, she got caught in a crab trap and injured her tail. She came to CMA for rehabilitation, but her injuries were too great and she lost her tale and two vertebrae. However, a marine mammal veterinarian and CMA trainers worked with Hanger Prosthetics to build Winter a prosthetic tail. Winter plays herself in the movie and stars alongside Harry Connick, Jr., Ashley Judd, and Morgan Freeman. Winter shares her home at CMA with Panama, another bottlenose dolphin.
Of course there are more animals at CMA than Winter, and there is a lot more to do. You can learn about turtles, otters, and sharks and you can even interact with the dolphins. There is also kayak tour or a two-hour sea safari. The more adventurous can take a behind the scenes tour or even be a trainer for a day.
When you cross the causeway into Clearwater Beach, the road ends at Pier 60. Pier 60 might sound like a nightclub but it’s actually a 1,080-foot fishing pier. You can walk out mid-point, or for a small fee, you can stroll all the way to the end. If get inspired, you can even try your hand at fishing. The pier bait house can hook you up (no pun intended) with a rental rod and reel. The park near the pier has a snack bar, the all-important restrooms, and, if you’re with the grandkids, a pretty good playground.

Though you’ll pass the pier as soon as you enter Clearwater Beach, be sure to come back in the evening (6 to 9 pm), to experience “Sunsets at Pier 60,” a daily mini-festival with vendors, street performers (buskers), and of course, an awesome view of the sunset over the water. As a bonus, on Friday and Saturday nights, around 8:15ish, pull up a beach towel and catch a family-friendly movie. The flicks are free, but bring a little cash for popcorn and soda.
For the true Florida beach experience, check out Caladesi Island State Park, just a few miles north of Clearwater Beach. Proclaimed the #1 beach in America (2008) by “Dr. Beach” (Dr. Stephen Leatherman), the 600+-acre park is one of the few undeveloped barrier islands left in the state. It’s rich with sea oats and oystercatchers (a wading bird), a mangrove forest, and other Florida flora and fauna. On Caladesi, take a swim, kayak along the mangroves, fish, go shelling, or read a book on the beach. There’s also a three-mile nature trail through the interior of the island. Public showers are available on the island and Café Caladesi offers casual beach food, a gift shop, beach chair and umbrella rentals as well as kayak rentals.
There is no car access to the island, but you can get there via ferry. The ferry is $14 for a round-trip (plus $8 per vehicle to get onto Honeymoon Island State Park, where the ferry departs), but think “un-crowded” and “unspoiled,” and it’s worth the fee. Just a note, no pets are allowed in Caladesi, but Honeymoon Island has a dog beach.
Many Clearwater visitors (and locals) make it a point to stop at the Clear Sky Café. About a block from the beach, the restaurant serves from breakfast to late-night. The menu is versatile, and offerings range from burgers and pizza to steaks and local seafood.
For something a little different, try breakfast on the patio, and forego the traditional eggs Benedict, and try a version with crab or salmon. We hear the French toast is good too.
Clear Sky has a weekday happy hour from 2:30 to 6:30 p.m., with food and beverage specials. Late-night drinkers can catch another happy hour from 11 p.m. to 1 a.m. but the specials at that time are drinks only. However, the kitchen is still serving pizzas, flatbreads and paninis.
Another popular restaurant on the beach in Clearwater that my wife and I fell in love with is Frenchy's. While we frequented the Rockaway Grill location because it was right by our hotel, Frenchy's actually has four locations in Clearwater, and they are best known for their blackened grouper sandwich. Do not miss it!
When you’re ready to move off the beach and onto the water, Classic Cruises is the answer. The tour and charter company operates The Enterprize, a 1965 37’ Chris Craft Roamer, and the Tradewinds, a 60’ three-masted schooner. The Enterprize is available for one-and-a-half-hour trips, or it can be charted for the day. Tradewinds sailing trips are limited to six people, and word has it that the sunset cruises can’t be beat for relaxation and romance.
If you plan on making your Clearwater Beach trip an overnighter, the area has the usual hotel offerings (Doubletree, Holiday Inn, etc.), but the smaller properties could be a good choice. Several motels participate in the Superior Small Lodging Program. To be included, properties undergo independent review, and proprietors must commit to the quality, comfort, congeniality, cleanliness and safety standards of the program.
Also, the aforementioned Frenchy's has a “retro boutique motel” that they own and operate called Frenchy's Oasis Motel. We took a drive by and it looked pretty nice.
We stayed at the Sandpearl Resort. The place is amazing. We would definitely stay there again if we ever get back over to Clearwater. It was first class all the way. While it's a resort, many of the units are owned by private owners. We actually found the one we stayed in on VRBO.com, so my advice if you go there is try both the main Sandpearl website as well as VRBO.com and see what makes the most sense for you.
Anyway, if you head over to Clearwater, let me know how it goes.
In case you missed it, you might also like the first of our beach series articles: Sanibel Island
Be sure watch for our upcoming “Day Trip” post on St. Petersburg, a culturally diverse beach town just a few miles from Clearwater Beach.
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