Take A Break is your ultimate guide to the perfect trips to recharge, rediscover yourself and your relationships, and reengage with the world. We’ll cover shopping stops, great bars, restaurants worth your money, photo opportunities, memorable drives and experiences, and other important details you need before you book.
Below, we chat with Lindsay Holmes, senior wellness and travel editor at HuffPost, about why you’ll want to put Clearwater Beach, Florida, on your bucket list.
What drew you to Clearwater Beach as a place to visit or explore?
I grew up nearby, so I spent a ton of time at Clearwater Beach. In high school, our classes would end around 1 p.m. and we’d all beeline straight for the beach. It felt like a vacation in my own backyard. The sand is powdery soft, the Gulf of Mexico is a sight to behold, and there are tons of great restaurants and activities nearby ― whenever we’d go for an afternoon or on the weekends, I never wanted to leave.
What are the best times of year to visit?
April and May along with September or even early October are ideal. The heat and humidity is brutal in the summer, especially in July and August, so I’d recommend avoiding that time of year. You also run the risk of encountering afternoon thunderstorms during the summer months.
If you’re from a state that actually has seasons, I highly recommend going when you’re over the cold or not quite ready to endure chillier temperatures. The winter months can be warm, but you also run the risk of it getting into the 50s. (I know, tragic.) If you’re truly looking for beach weather, late spring or early fall are often your best bets.
What’s your best tip for getting there? How can you make the travel as stress-free as possible?
Clearwater/St. Petersburg has a small airport, but Tampa International Airport will likely have the most options if you’re flying. From there, you’re only about a 40-minute drive away from the main beach area. You can book transportation like a Super Shuttle or you can easily take Ubers or Lyfts. Getting all of your transportation set up beforehand will make everything as seamless as possible.
If you’re driving, be prepared to deal with bridges and traffic ― especially in the more popular travel months. There’s essentially one road that goes into the beach and it’ll get packed quickly. There’s also a large roundabout that many drivers get flustered by, especially when there are a lot of cars. Patience is key when navigating Clearwater Beach in a car.
Where do you recommend staying when you go?
There are so many hotels right along the beach that are worth checking out, especially if you want direct access to the water or a pool. Some of the most popular ones include the Sandpearl Resort, the Wyndham Grand Clearwater Beach and the Hyatt Regency Clearwater Beach.
Additionally, there are cute boutique hotels, like Hotel Cabana. Airbnbs are also an option, and you can often find some great ones within a short walk or Uber or Lyft ride.
What are your go-to restaurants or foods to eat while you’re there?
Frenchy’s Rockaway Grill is a must-visit if you’re ever in Clearwater Beach. It’s a rite of passage; I don’t make the rules. It’s situated right on the water, with a large patio that empties out onto the sand. It’s the perfect spot after a long day in the sun. Order the grouper sandwich and the crab fries and I promise you’ll never be the same. My mom also loves their she-crab soup.
If you’re looking for something a little more “upscale” one night, the Beachcomber and the Island Way Grill are solid options that have been around for years. There’s also the Palm Pavilion or Crabby’s Bar and Grill if you’re looking for something low-key with a beach bar atmosphere. And for all you chicken wing fans, the city of Clearwater is also home to the original Hooters. (There’s also a location on Clearwater Beach.)
I also have to plug a stop at the grocery store Publix. There’s absolutely nothing like eating a Pub Sub on the beach. It’s one of life’s greatest pleasures.
What bars or entertainment spots do you make sure to hit? What’s good to drink there or what else should people know?
Frenchy’s and the Palm Pavilion are good spots if you want to grab a drink on the beach. They have great, affordable frozen cocktails (if you’re from a major city, your mouth will drop at the prices). My favorite are the piña coladas, which I know is extremely basic. But after a hot day of swimming and sunbathing, it really hits the spot. They also have rum runners, key lime coladas (another favorite), coconut margaritas and more.
Many restaurants, including Frenchy’s and Palm Pavilion, often have live music. I recommend going during sunset if you can get a table. Entertainment, a refreshing drink and pristine scenery. What more could you ask for?
What are your favorite shops and what do you look for when you’re there?
There are tons of local souvenir stores along the beach, which are great for window shopping or finding a trinket to commemorate your trip.
What’s your single favorite spot to go for photos and why?
The entire beach is ripe for photos! If you walk north along the beach ― beyond all of the hotels ― you’ll definitely get good shots without a bunch of people in the background or pushing alongside you. Pier 60 is also a great location for photos if you want sweeping views of the Gulf (you might also get a glimpse of some dolphins if you’re lucky).
What tourist attraction should people skip and what should they do instead?
I’d personally say skip the pirate-themed boats that go out in the water and opt for a dolphin sightseeing boat, or even go parasailing. Some people enjoy the pirate cruises, but most locals say they’re not really worth the price. If you’re a water sport fan, many people really rave about the jet ski rentals as well.
Where do you feel the most relaxed, calm or happy?
I feel so at ease when I’m on a walk or sitting on the north part of the beach. We’d always park there for the day when we were in high school. I have fond memories of lounging in the sun with my friends, gossiping about what happened in class or who was dating who at the time.
Every time I go back, I make sure to walk up that way, which ends up being about a mile or so away from Pier 60. It instantly makes me feel like a teenager again. It’s also nice because it’s further away from the touristy areas, so you get a level of quiet that you’re not really afforded in the more crowded parts.
What scenic spots do you recommend checking out?
For some good people watching, I definitely recommend walking along the pier or in some of the more populated areas. There are also other beautiful beaches nearby if you want to switch it up for the day. Try checking out Sand Key Beach or Caladesi Island State Park, which offer another little slice of heaven of the Gulf.
What are some specific planning tips to know before you go so you’re not stressed?
There are a few: First, expect to be exposed to UV rays and plan accordingly. The sun will get you if you’re not careful. Wear sunscreen ― even if it seems cloudy during the summer.
You should also expect afternoon thunderstorms if you’re going in the warmer months. (I personally love them, but they can be annoying on a vacation.) Storms typically roll in around 3 p.m. and can last anywhere from 20 minutes to over an hour, depending on the forecast. It’s helpful to plan any beach days or excursions around it ― you’ll likely get better weather the earlier you go out.
Finally, familiarize yourself with the stingray shuffle. If you visit anytime between April and October, that’s typically stingray season. Shuffle your feet in the water so they know you’re coming. (For what it’s worth, I’ve never had a problem with them in my lifetime of going to Clearwater Beach. Just be aware, don’t stress!)
What’s one thing you make sure to pack if you’re going and why?
To state the obvious, a bathing suit and sunscreen. Some people prefer bringing water shoes for stingray season and beach shirts because, as mentioned, the sun can be very strong.
Anything else visitors should know?
Do. Not. Feed. The. Seagulls. They’re everywhere, and they want your food. Feeding them just makes them more needy (and it could be dangerous for them) ― not to mention you’ll annoy all the other beachgoers around you. Keep your snacks, subs and anything else to yourself. Trust me.
