Clearwater Beach Itinerary: How to Spend the Perfect Weekend on Florida’s Gulf Coast

Sugary white sand? Check. Serene water? Check. Epic sunsets? Check. 

If all of these sound like your dreamy beach getaway, Clearwater Beach will check all of your boxes. 

On Florida’s west coast, Clearwater Beach’s soft, sugary sand melts into the tranquil Gulf waters. The water is calmer than what you’ll find on Florida’s best east coast beaches, and along this section of the state’s coast, you also tend to find some of the prettiest white sand in Florida. Clearwater Beach even celebrates this honor every spring with the Pier 60 Sugar Sand Festival. 

Even if you don’t get to visit Clearwater Beach during their renowned festival, this is a great beach to visit anytime. This beach is bustling and has lots of restaurants, shops, and things to keep you busy. You’ll also notice one cute and quirky thing about Clearwater Beach: it’s full of dolphins, both in, and out of the water. As you stroll around, be on the lookout for the colorful, six-foot dolphin statues all around town— each is unique in its own way. Searching for the dolphins around town is actually an experience in itself, and is just one of the fun things you can experience during your “fintastic” weekend in beautiful Clearwater Beach. Here’s a few of my other personal suggestions:

Clearwater Marine Aquarium was home to a very famous dolphin that you may have heard of: Winter. She’s kind of a celebrity in these parts, and if you’ve seen the Dolphin Tale movies you’re likely familiar with her story (If not, watch before your trip). It’s a touching story about a dolphin who gets injured and ends up with a prosthetic tail, thanks to the genius folks at Clearwater Marine Aquarium who were able to save her life. She lived there for many years and has created a legacy. 

In addition to seeing their resident dolphins, you’ll also get to see a variety of fish, turtles, stingrays, and more. Your ticket gets you access to a lot, but there are also some cool add-ons for those who want to get up-close-and-personal with some of the animals. If you’ve never painted with a dolphin, you can even do that. You’ll get to hold a canvas while a dolphin gets creative and creates a masterpiece you can take home. 

A couple of hours before sunset head to Pier 60. Clearwater Beach is known for having some amazing sunsets and they celebrate it every night with a family-friendly party at the pier. You’ll find local artists selling their wares, and this is a cool spot to find some unique souvenirs to take back home. The street performers will be keeping you entertained as well, and there’s games for the kiddos. Of course, the main event is the sunset itself, and this is a great spot to see it. If you want to keep the fun going a little while longer, head over to one of the beach’s most popular restaurants, Crabby’s Bar and Grill, where you’ll find yummy food and live music. 

After you’ve learned about dolphins at the aquarium, get ready to see them in the wild. Clearwater Marine Aquarium conducts boat tours, but there are several other companies that offer other options, too (one is even shaped like a giant shark). To see the Mega Bite Boat, you’d think it might scare off the dolphins, but they seem to love it. 

Keep in mind, this is a little different than seeing dolphins at the aquarium—these are wild animals. They don’t show up on cue, and with nature, you can never guarantee anything. However, I can assure you that the dolphins absolutely love hanging out in Clearwater Beach. The Tropics Boat Tours feels so confident about seeing dolphins on their tours that they do guarantee it. If you don’t see one, you can come back for another tour at no charge. 

 As your day comes to an end, get ready for another jaw-dropping sunset. Every sunset is a little different, so they never get old. If you see enough, you may even get lucky and see the “Green Flash” that occasionally happens for a split-second just as the sun is setting. It’s pretty rare to see this phenomenon, but I did see it last time I was in Clearwater Beach. It happens so quickly, though, so just be ready. 

To mix things up and get a different sunset view, walk across the street from the beach near Pier 60 and head up to SHOR American Seafood Grill. It can be easy to miss, but there are stairs that lead to its location on the second level of the Hyatt Regency. You may want to make a reservation in advance to make sure there’s a table with your name on it at sunset. This is the perfect spot to grab a couple of cocktails and gaze across the horizon as you watch the setting sun. I’m a big fan of their Espresso Martinis, but their food is equally as good. Try the whipped feta, and if you love seafood, order the Florida Grouper. It’s served with a unique carrot ginger sauce which I totally love. When you’re begging the server to give you the recipe, you know it’s that good. 

The public beach area around Pier 60 in Clearwater Beach is popular and has ample room to spread out and make sandcastles. It’s great, but who doesn’t love a private beach? My little tucked away, secret beach is at the Hampton Inn and Suites, positioned at the southern end of Clearwater Beach. They’re also a pet-friendly hotel, which is good news for us pet parents. They share a quiet stretch of private coastline with another notable hotel, the Dolphin Sands—which is Clearwater Beach’s first eco-friendly hotel. The Dolphin Sands also has an interesting artifact in its lobby: one of Winter’s prosthetic tails. 

This private beach has the same sparkling white sand you’ll find at the public beach area, but with a much more laid-back, exclusive setting. You can lounge in a chair and have drinks brought to you while you watch the shorebirds play and wave at the boats sailing by. It’s a really scenic spot that overlooks the bridge, and you can just step right outside of your hotel and have your toes in the sand. Having easy access to just run up to your room whenever you need to is always something I like when looking for a beach hotel. The oceanfront pool and hot tub is a nice touch as well. 

Another thing I love about the Hampton Inn and Suites is the rooftop bar. Evy’s Terrace Bar and Bistro is a hidden spot that has some great views (especially at sunset), and you can visit even if you aren’t staying there. If you go, make sure to try the Spinach and Artichoke Rockefeller Dip. You’ll thank me! 

It takes me about two and a half hours to get to Clearwater Beach from the Orlando area, but if you’re flying in, you can get there much quicker. You can fly into the St. Pete-Clearwater International Airport (PIE) or Tampa International Airport (TPA), rent a car, and drive there in about 30 minutes. If you don’t want to rent a car, you’ll be happy to know that taxis and ride-shares are easy to use in this area. Those flying into TPA also have the option of riding the PSTA Grouper Airport Express to Clearwater Beach. 

Once you’ve made it to the beach, you also have options for getting around. If you have a car, you may opt to leave it parked for your time on the beach, as you’ll have to pay to park at most places, and finding parking can be a little challenging. You’ll see the Jolley Trolley making its way through the streets of Clearwater Beach though, and this is a great option to get you around town while you’re there. 

I know it sounds a little broad to say Clearwater Beach has something for everyone, but it really does. It was named as one of the best beaches in the United States for families—and for good reason. With little swimmers, you of course want to take extra safety precautions. There are public beach areas with lifeguards on duty, which of course adds a little security. But the water in Clearwater Beach is pretty calm, too. This makes a safe setting for the little ones to get out and splash around. 

I’ve also traveled there solo, with my significant other, and with my pets and all have been great experiences. This is a developed piece of coastline that has many places to stay, play, and eat. There’s an abundance of activities, and plenty of shops as well. It is a busier beach, but if you’re looking for a beach that has all you need within easy reach, along with calm water and white sand, this is your beach— no matter your age or who you’re traveling with.