How to Take the Best Vacation in Clearwater Beach, Florida

Take A Break is your definitive guide to the perfect trips to recharge, rediscover yourself and your relationships, and reconnect with the world. We’ll cover shopping stops, great bars, restaurants worth your money, photo opportunities, memorable trips and experiences, and other important details you need before you book.

Here, we chat with Lindsay Holmes, senior travel and wellness editor at HuffPost, about why you’ll want to put Clearwater Beach, Florida on your bucket list.

What attracted you to Clearwater Beach as a place to visit or explore?

I grew up nearby so I spent a lot of time at Clearwater Beach. In high school, our classes ended around 1 pm and we all went straight to the beach. It felt like a vacation in my own backyard. The sand is powder soft, the Gulf of Mexico is a sight to behold, and there are tons of great restaurants and activities nearby – whenever we went in the evening or on weekends, I never wanted to leave.

What are the best times of the year to visit?

April and May along with September or even early October are ideal. The heat and humidity are brutal in summer, especially in July and August, so I recommend avoiding that time of year. You are also at risk of encountering thunderstorms in the afternoon, especially on the beach, during the summer months.

If you’re from a state that really has seasons, I recommend going after the cold has passed or you’re not ready for colder temperatures. The winter months can be warm, but you also run the risk of hitting your 50s. (I know, tragic). If you’re really looking for beach weather, late spring or early fall are often your best options.

What’s your best advice for getting there? How can you make travel as stress-free as possible?

Clearwater/St. Petersburg has a small airport, but Tampa International Airport probably has the most options if you’re flying. From there it is only about a 40 minute drive to the main beach area. You can book a transportation like Super Shuttle or you can easily take Ubers or Lyfts. Setting up all of your transportation beforehand will make everything as easy as possible.

If you drive, be prepared to deal with bridges and traffic, especially in the most popular travel months. Basically there is a path that goes to the beach and it fills up quickly. There is also a large roundabout that a lot of drivers get nervous about, especially when there are a lot of cars. Patience is key when navigating Clearwater Beach by car.

The soft sand and blue water of Clearwater Beach will leave you feeling relaxed and refreshed.
The soft sand and blue water of Clearwater Beach will leave you feeling relaxed and refreshed.

Where do you recommend staying when you go?

There are so many hotels along the beach that are worth a visit, especially if you want direct access to the water or a pool. Some of the most popular include the Sandpearl Resort, the Wyndham Grand Clearwater Beach, and the Hyatt Regency Clearwater Beach.

Also, there are cute boutique hotels, like the Hotel Cabana. Airbnbs are also an option, and you can often find some great ones within walking distance or by Uber or Lyft.

What are your favorite restaurants or foods to eat while you’re there?

Frenchy’s Rockaway Grill is a must visit if you are ever in Clearwater Beach. It is an initiation rite; I don’t make the rules. It is situated right on the water, with a large patio that runs out onto the sand. It is the perfect place after a long day in the sun. Order the halibut sandwich and crab fries and I promise you will never be the same. My mom loves her crab soup too.

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 Palm Pavilion or Crabby’s Bar and Grill if you’re looking for something low-key with a beach bar vibe. And for all you buffalo 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 Publix supermarket. There is absolutely nothing like eating a Pub Sub on the beach. It is one of the greatest pleasures in life.

What bars or entertainment venues do you make sure to go to? What is good to drink there or what else should people know?

Frenchy’s and Palm Pavilion are good places if you want to have a drink on the beach. They have great affordable frozen cocktails (if you’re from a major city, the prices will blow your mind). My favorites are the pina coladas, which I know are extremely basic. But after a hot day of swimming and sunbathing, it really hits the spot. They also have rum runners, lime coladas (another favorite), coconut margaritas, and more.

Many restaurants, including Frenchy’s and the Palm Pavilion, often have live music. I recommend going during sunset if you can get a table. Entertainment, a refreshing drink and unspoiled landscapes. What more could you want?

What are your favorite stores and what do you look for when you are there?

There are plenty of local souvenir shops along the beach, which are great for window shopping or finding a trinket to commemorate your trip.

A pina colada from Frenchy's Rockaway Grill in Clearwater Beach.  The perfect gift after a sunny day at the beach.
A pina colada from Frenchy’s Rockaway Grill in Clearwater Beach. The perfect gift after a sunny day at the beach.

What is your favorite place to take photos and why?

The entire beach is ready for photos! If you walk north along the beach, past all the hotels, you’ll definitely get good shots without a group of people in the background or pushing alongside you. Pier 60 is also a great photo spot if you want panoramic views of the Gulf (you might also see some dolphins if you’re lucky).

Which tourist attraction should people skip and what should they do instead?

Personally, I’d say skip the pirate-themed boats that go out on the water and opt for a dolphin-watching boat, or even go parasailing. Some people enjoy pirate cruises, but most locals say they’re really not worth the price. If you are a fan of water sports, many people are also enthusiastic about renting jet skis.

Where do you feel most relaxed, calm or happy?

I feel so comfortable when I am walking or sitting on the north side of the beach. We always parked there during 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 that path, 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 tourist areas, so you get a level of tranquility that you can’t really find in the busier parts.

What picturesque places do you recommend visiting?

For 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 change the day. Try visiting Sand Key Beach or Caladesi Island State Park, which offer another slice of Gulf paradise.

The view from the patio at Frenchy's Rockaway Grill.  Sunset is a popular time, but the wait is worth it.
The view from the patio at Frenchy’s Rockaway Grill. Sunset is a popular time, but the wait is worth it.

What are some specific planning tips to know before you go so you don’t get stressed?

There are some: First, expect to be exposed to UV rays and plan accordingly. The sun will catch you if you’re not careful. Wear sunscreen, even if it seems cloudy in the summer.

You should also expect afternoon thunderstorms if you go in the warmer months. (I personally love them, but they can be annoying during the holidays.) Storms usually arrive around 3 p.m. and can last anywhere from 20 minutes to over an hour, depending on the forecast. It is useful to plan any beach days or excursions around it; you are likely to have better weather the earlier you get out.

Finally, get familiar with the stripe shuffle. If you visit anytime between April and October, it’s typically stingray season. Put 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 life going to Clearwater Beach. Just be careful, don’t stress!)

What do you make sure to pack if you go and why?

To state the obvious, swimsuit and sunscreen. Some people prefer to bring water shoes for stingray season and beach t-shirts because, as mentioned, the sun can be very strong.

Anything else visitors should know?

Make. No. Food. He. Gulls. They are everywhere and they want your food. Feeding them only makes them more needy (and could be dangerous for them), not to mention that you’ll annoy all the other swimmers around you. Keep your sandwiches, snacks, and anything else to yourself. Trust me.

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