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Clearwater Retirement Guide

by Andrew Selby | Updated: February 21, 2025

Located west of Tampa and just north of St. Petersburg, Clearwater makes up the third leg of one of the most popular tourist destinations in all of Florida. Known for its white sand beaches and the fabulous Clearwater Marine Aquarium, this is the ultimate destination for those who want to feel like they are forever on vacation.

Because it is located so close to Tampa, Clearwater residents enjoy close access to a major international airport. They also enjoy some of the most beautiful beaches that you will find anywhere along the Gulf Coast.

Clearwater History

Originally home to the Tocobaga Native Americans, the area that would become Clearwater was first inhabited by settlers when Fort Harrison was built here around 1835. The town remained very small up until Peter Demens provided passenger train access to the area in 1888.

People began migrating to Clearwater in force a few years later, and the city was booming by the time the 1960s rolled around. Continued construction projects kept that growth moving all the way into the 2000's.

Clearwater Lifestyle

Everything about the Clearwater lifestyle revolves around the idea of an endless vacation. They were recently named TripAdvisor's #1 Beach in America, so there are an endless amount of ways to enjoy the sand and the water here!

In addition to things like relaxing on the beach, boating, fishing, and watching for dolphins, Clearwater also boasts an incredible amount of world-class golf courses, as well as all of the shopping and dining amenities you might expect to find filling your fantastic vacation retirement.

Clearwater Culture

Even the cultural elements come with a vacation-themed twist here in Clearwater. One of the most popular cultural attractions is the Clearwater Marine Aquarium, which happens to be the home of Winter, who you might remember as the star of Dolphin Tale.

If you are looking to catch a stage performance in a theatre that is chock full of history, then you will be happy to know that the Capitol Theatre offers precisely that experience. And there are always great shows on the calendar here!

Clearwater Shopping

Like most popular tourist towns in Florida, Clearwater has a unique collection of shopping options located in different parts of the city.

If you are looking for hip and trendy souvenir-style shops, head over to Mandalay Ave and Gulfview Boulevard. That is where you will find a Ron John Surf Shop, as well as Frenchy's Off the Hook and the Immortal Hulk Hogan's Beach Shop.

And for residents who need more of a mall-style shopping experience, Countryside Mall is the ultimate destination for those classic department and specialty stores.

Clearwater Dining

The best way to approach dining in Clearwater is to plan on grabbing something quick in between beach sessions. I generally can't go to Clearwater without eating at Frenchy's. They're known for their grouper sandwiches and have a few locations around the area.

A few more options we llike are Pearly's Beach Eats for fish tacos, and Crispy Cajun for a crawfish boil.

When you are ready to class things up a bit around dinner time, try Cesare's At The Beach and Bascom's Chop House is the place to go for a perfectly seared steak.

Where to Retire Near Clearwater

Valencia Ridge, the all-new community in the greater Tampa area, will offer contemporary home designs and world-class amenities for the ultimate 55+ luxury living. Nothing compares to the incredible 55+ lifestyle, as the world-class clubhouse will feature multiple pools, pickleball and tennis courts, fitness center, restaurant and bar, sports lounge, social hall and much more.

Fill out my online form.

With everything from beautiful white-sand beaches to delicious dining, everything about Clearwater is designed to make you feel like you are on an endless vacation. The only real difference is that you won't have to pack your bags and leave from this one!

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