Moving to Clearwater, FL? Here’s 15 reasons why you’ll be thankful that you did

February 27, 2018 by The727Team


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Clearwater, Florida

There’s a world of opportunity out there for those that choose to embrace adventure.  As you meet people in Pinellas County, you’ll find that many of them are not natives, and at some point of their lives they decided to venture here to live in what some call a tropical paradise.

Clearwater Beach is a well-known beach throughout the U.S. and needs little introduction.  When you hear the city of Clearwater and Clearwater Beach you might think they are two different cities, but that is not the case (learn more here).  Clearwater Beach is only a title and is part of the city of Clearwater jurisdiction.

As you read our article you’ll discover Clearwater is much more than a tourist destination.  We’ll dive into the intricacies of what makes Clearwater so special with a list of the top 15 reasons you’ll be thankful you moved here!

1. The Beach

Clearwater Beach has frequented many top beach lists for years!  One of the better known is the annual list put out by Trip Advisor.  For the year 2018, Clearwater Beach was listed as the #1 Beach in the United States and #7 in the World.  There are two ways to access the beach by land.  You can travel on Gulf Blvd which runs along many of Pinellas County’s western beaches or you can choose to take the Clearwater Memorial Causeway.

Although both routes are impressive, if you’ve never visited this beach before I would recommend you take the Clearwater Memorial Causeway for your first experience.

The view could be described as somewhat magical as you take in Clearwater Bay from both sides which is usually filled with boats, jet skis, the occasional pirate ship and dinner cruises. Anywhere you go here you will see happy people truly having the best times of their lives in this tropical playground.

As you cruise past the palm trees you’ll see colorful florida-style buildings, shopping centers, restaurants, bars and much more.  If your first stop is the beach, there are plenty of parking options available.

The Pier 60 parking lot might be my favorite place to park because it’s in the center of the action and just a few feet from touching the sandy beachfront.  Other places that may be available depending on the time of day you go and the season include: The Hyatt Regency Parking Garage, North Beach Parking Plaza and many more! (Find more parking choices and directions here)

When I first set foot on the beach many years ago I would best describe the feeling as euphoric.  Being in a place that was so relaxed yet had so many choices was a welcoming escape from the complexities and challenges life can bring us.  Here you could choose to truly be alive, appreciate, and experience a world of no worries.

Of course Clearwater Beach although not always #1 has been a popular beach for decades.  Although there are plenty of beaches through Pinellas that are less crowded, many won’t have nearly the amount of amenities due to sheer size and appeal towards tourists.  Everyone’s appetites for crowds is going to be different, but if you want to visit and have a little more beach real estate separating you and the next person, I’d recommend visiting during these times:

Year round you’ll always have more luck on weekdays especially earlier in the day (think early morning 7-11am).  Spring break and summertime like most beaches will usually bring your largest turnouts so be prepared for difficulties with parking and personal space during those periods. It might be smart to just have an Uber drop you off if you’re planning on having a few drinks anyway. Many people choose to get much of their beach time in during September and October when the weather is still warm and school is back in session. 

The good news is you’ll be able to enjoy visiting the beach most of the year without freezing to death. 

2. Restaurants

I hope you like seafood cause that’s all you’re gonna get.  Shrimp stew, shrimp sandwiches, shrimp on a stick, shrimp in a shrimp…

Just kidding… but we are in a beach area and the known staple of Clearwater is actually grouper.  If you don’t like seafood you’re in luck because Clearwater is a pretty big city so there’s a myriad of choices both on and off the beach.

I’d first like to address my fellow seafood lovers and then we can jump into many of the alternatives.  In no particular order here’s some of my favorite seafood places you’ll want to consider:

Frenchy’s Rockaway Grill – Whether you see them advertised on a bus or signs throughout, it’s hard not to mention Frenchy’s due to it’s viral-like popularity.  Known for their grouper sandwich, they really know how to entertain with live music every night.  

Island Way Grill – If you’re not hanging out with the likes of Morgan Freeman and Hulk Hogan (both who have been spotted here on numerous ocassions), you can get your car valeted and enjoy fine dining with options such as fresh shrimp, scallops, oysters and more!  Their Sunday brunch buffet is also a great option if you are looking to experience a little of everything.

Crabby Bills – Don’t be thrown back by the caricture of an older gentleman scowling at you.  That’s just Bill and he is one of the founders of this great establishment.  With a little quirkiness and a laid-back vibe, Crabby’s offers many great choices including grouper sandwiches, crab, lobster, shrimp, scallops and more for the seafood lovers!

If you’re taking someone that doesn’t appreciate seafood as much as you, you’re in luck because all of the restaurants above feature plenty of non-seafood options as well.

Im my opinion there’s so many restaurant options in Clearwater it’s hard to do it justice.  The beauty of the area is it gives you the opportunity to explore, find hidden gems and establish your local favorites you share with your friends and family.

For non-seafood here’s some places I’d recommend visiting:

Watercolour Grillhouse – 

Located inside the Marriott Suites if you want a fine-dining experience, I can’t recommend this place enough.  I first tried this place on my wedding day and my wife and I have revisited on several special occasions.  Although I think you really can’t go wrong with anything on their menu, the highlight is they have the best filet-mignon I’ve ever had in my life.  Give it a shot, and let me know what you think!

Cafe Ponte – Another high class experience, this is a fine dining journey you’ll want to try out.  Don’t forget to put your monacle on and top hat, but honestly this place is not only about dining but presentation so you’ll want to dress nice when you visit.  They have a mushroom soup that is out of this world, breads that you won’t feel ashamed to keep waiving down the waitress for and a variety of entrees and appetizers that will leave you happy.

Hamburger Mary’s – Although this restaurant isn’t unique to Clearwater with several locations across the states, it’s definitely a worthy experience if you’ve never been to one.  This LBGT-friendly burger restaurant is famous for their hilarious drag-queen bingo nights and great food.


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3. Boating

If you don’t own a boat, don’t worry because there’s plenty of options to experience the open water.  At some point you’re going to want to get yourself on a boat to truly appreciate the paradise we live in.

Chris and I hold a membership at Freedom Boat Club where we have the ability to take people on the water.  If you’re in the market for a waterfront home, don’t hesitate to reach out to us for your specific needs.

Let’s jump into many of the options you’ll have to explore Clearwater Bay and the Gulf Of Mexico on the water.

The Tourist Approach –

Clearwater, FL has many vendors ready to show you the area in style.  Some of the most popular options are:

Captain Memo’s Pirate Cruise – Around since 1993, this famous cruise has become part of the Clearwater culture.  If you spend a day at Clearwater Beach it’s very likely you’ll see the pirate ship sailing off in the distance.

Starlite Cruise – With daytime and evening options, this dining cruise has been something I’ve experienced multiple times.  It’s a great and cost-effective way to get on the water.  *Tip – If you book during a weekday evening, you’ll have a greater chance of having most of the yacht to yourself*

Encounters With Dolphins – This cruise specifically goes through paths where dolphins have previously been spotted.  It’s your best shot to experience wild life in their native environment in Clearwater Beach.

Renting and Memberships – 

If you’d like to avoid sharing the experience with people you don’t know, you can always rent a boat or jet ski or even sign up for a membership:

Clearwater Boat Rentals – 

This company allows you to choose from a variety of Pontoons and experience the water on your own.  They offer 1/2 day, 3/4 day and Full Day (8 hour) rentals.

Clearwater Beach Jet Ski Rentals – Offering rentals and guided tours, this could definitely be a highlight of your Clearwater experience!

Freedom Boat Club – As noted earlier in the article, we are members of Freedom Boat Club.  In our opinion this is the best way to experience boat life if you frequently go out on the water but don’t want to deal with the maintenance and cost of owning your own.  They offer a variety of boats to choose from and offer great deals throughout the year.

Owning and Storing –

If you choose to own (if you don’t already) there’s a variety of methods to store your boat:

Your Backyard – Doing real estate for a living, we’ve seen many people who choose to store their boats in their backyards.  If you are house shopping you may find looking for a bigger back yard may be advantageous.  (We can also help you avoid neighborhoods that may have deed-restrictions preventing this, or finding a condo with boat slips available for purchase or rent.)

U Stor N Lock – If you are looking for a storage unit for your boat and don’t mind hitching it and taking it to the water, this can be a great cost-effective option to protect your boat from weather.

Clearwater Beach Marina – You can dock your boat directly at Clearwater Beach so all you have to do is jump right in and explore the sea.

Boating is a way of life here and we hope that you get to experience it at some point and time.  If you have any specific questions, please don’t hesitate to reach out to us (click here).

4. Weather

On average Clearwater, Fl experiences 240 sunny days per year.  There’s a stigma that comes with Florida that it’s too hot here.  I think this depends on where you are coming from.  I was born and raised in Columbia, South Carolina and it definitely got hotter there than Florida most of the time.  The reason why this part of Florida is different is we have the coastal breeze that really helps manage the temperature.  A good half of the year, we experience those perfect days in the 70’s.  Just to give added perspective, these were the average high and lows (fahrenheit) over the course of 2017.

January 66° / 56°
February 66° / 57°
March 71° / 62°
April 76° / 68°
May 80° / 73°
June 84° / 78°
July 86° / 79°
August 87° / 80°
September 85° / 77°
October 80° / 71°
November 73° / 63°
December 70° / 60°

5. Homes

There are plenty of choices for everyone due to the massive size of Clearwater.  Looking for a waterfront mansion? There are several along the beach, harbor and bay.  Need something more in the suburbs? We’ve got plenty of neighborhoods that are well-maintained within 5-10 minutes of the Causeway.  We even have a neighborhood where wild peacocks roam the neighborhood if you’re into experiencing some unique wildlife.

If you’re looking for low maintenance there are condos both on and off the beach that will make you feel like you are on a permanent vacation.

Over the past 5 years from 2013 to 2018, the appreciation has been strong for Clearwater in residential sales.  The average price was $166,603 in February of 2013 and is $240,486 for January of 2018 which is averaging over 7.76% appreciation a year.

Appreciating Homes In Clearwater
As more people realize what a great area this is to live, with the limited land on our peninsula, there is a higher chance of increased demand with limited supply.

If you’re interested in starting your journey to purchasing your next home or condo in Clearwater, FL, feel free to reach out to me for any questions you may have: Ryan Eisenhower (Licensed Realtor) – Remax Realty Unlimited – #727-777-3797 or by email at

6. Pier 60

If you’re looking for a great place to capture Clearwater Beach’s beautiful sunsets or to fish at night, Pier 60 is your spot.

If there was a heart for Clearwater, it would be Pier 60.  From entertainment and street performers, to local artisans selling local crafts and even a playground for children, it’s a great location to unwind.

The pier is well kept and it’s likely you’ll see photographers out there taking pictures of people because it’s a very photogenic location.

There’s an event called Sunsets at Pier 60 that operates 364 days of the year.  The event time changes based on the season, but it usually starts 2 hours before sunset and ends 2 hours after.

It’s a really nice touch for the area because it shows how involved the community is coming together and celebrating where they live.


7. Walkability

The most famous walking and biking path in the area is The Pinellas Trail.  The trail runs through from the southern part of the county to the most northern, from St. Petersburg to Tarpon Springs.

The trail cuts through Clearwater and offers easy access to branch off from the trail and take the Causeway to the beach.

Clearwater offers many walking paths not only in downtown but throughout many parts of the city.  Whether you choose to walk on the beach or on the many trails (many which are located in parks), you’ll have plenty of choices!

Here’s a few local favorites:

Beach Walk – A clean winding path that borders the beach and offers a safe way to view the beach and local restaurants and hotels across the street.  There’s many pedestrian crosswalks, washing stations, artwork and more!

Ream Wilson Clearwater Trail – If you like to run or bike and want to experience a little bit of nature, check out this trail that takes you both through Clearwater and Safety Harbor.

Clearwater Memorial Causeway – 

The Causeway is one of the two routes to Clearwater beach.  With paths for walkers and runners on the sides, you can take in all the beauty of Clearwater (this is a very popular path for walking groups in the area).

Along with St Petersburg, FL, Clearwater offers some of the most scenic walkability in the county and is definitely worth experiencing!

8. Tourism

The tourism industry is a major part of the Clearwater economy.  If you are looking for work in entertainment and services that let you experience the culture of the area, this may be the place for you to pursue it.

So you may be thinking, why is tourism a good reason to move here?  There’s a huge benefit to living in an area many only get to experience on their family vacations.

Have friends or family that you’ll want to visit?  You won’t have too difficult of time getting most people to want to come to a beach town.

Clearwater and more specifically Clearwater Beach isn’t just recognized in the states, it’s known to foreigners around the world as well.

By having a strong tourist economy, Clearwater has to keep the creativity going offering many forms of entertainment to keep people coming back from year to year.

As mentioned earlier, Clearwater Beach was already named the #1 beach in the United States so the people of the community have been doing an excellent job keeping up the reputation.

9. Events

Just about every week there’s a special event or festival happening in Clearwater.  While we won’t be naming all of them, I did want to share a few favorites with you so you can get a better idea of the experiences you would have living here.

The Clearwater Sea-Blues Festival – Every year this festival takes place with a mixture of Blues music from artists around the world and amazing seafood.  As you explore the festival you’ll see a variety of art and food vendors, you can choose to rent a chair, lay in the grass or walk around viewing the acts far away from a large video screen.

Fun ‘n Sun Clearwater – Going on for over 60 years, this annual festival amps up the activities in the area with more attractions including live music, beach events, tournaments, cultural events and more!  This event has helped the area especially in bringing more local tourism to the city.

Downtown Clearwater Craft Beer & Music Fest – If you love craft beer this is definitely an event you won’t want to miss.  Each year several dozen Florida breweries come together to represent and showcase their fine brews.  There’s also local food, art, and usually wine and sangria too!

Cooters Stone Crab Fest – Do you love crab? Well if you live in or are visiting Clearwater you may be in luck.  Every year the Cooters Restaurant located in Clearwater Beach hosts a 4 day celebration for the start of stone crab season.  Everything is usually at a generous discount and you’ll have a variety of crab to choose from.

Oktober Fest – Both Clearwater and St Petersburg are known for their Oktober Fest celebrations.  There’s usually a variety of mini events and activities during this time and many restaurants and bars that will offer specials.

Sugar Sand Festival – Are you ready to be blown away by works of arts made out of sand?  I’ve truly seen some of the most impressive and thought provoking pieces of art at this festival that takes place every year.

When I first moved to the area in 2009, I would always see tons of activities and events to do.  You’ll always have options if you choose to live in this area and if you’re looking to network as well, we also are the creators of three social groups: The Pinellas County Meetup with almost 3000 members, The Pinellas County Young Professionals, and The Pinellas County Parents Social Club.  We’d be happy to introduce you to several people and help you get out and explore the area.

10. Nightlife

Although there are plenty of great establishments around Clearwater, the best of the nightlife in my opinion is on Clearwater beach.  Want to start your night with a great view of the area?  Check out Jimmy’s Crow’s Nest rooftop bar that gives you a clear view of Pier 60 and the beach.

Want to get really wild and listen to some amazing music?  Shepard’s Tiki Bar is located right on the beach and is part of the Shepard’s Resort.  The times I’ve been I’ve never been disappointed.  They book DJ’s, and even from time to time will book famous musicians you may remember from the past.

The Brown Boxer is another local favorite that features an in-door and out-door seating area, live music (depending on the night), pool tables, darts and more.

If you’re looking to dance check out the Wave Nightclub.  Clearwater Beach stretches about 2.5 miles so it is very possible to walk anywhere but most people will take Ubers or taxis when they are traveling from the far east and west side of the beach.

Clearwater Beach is a popular spot for tourists and bachelor/bachelorette parties.  Don’t be surprised on any given night to see soon-to-be grooms and brides with their parties running around doing wild activities and checking off lists their friends have put them up to.  This comes from no personal experience of my own… ok well maybe that one time I got married… 

11. Legendary Sunset

I’m sure you’ve witnessed a sunset or two in your life.  But have you witnessed a Legendary Sunset?  That’s right… even on a bad night Clearwater doesn’t let you down.

When you witness your first sunset at Clearwater Beach, it’s best to be near Pier 60 to truly experience the people-watching opportunity.  You’ll see all sorts of things happening.  Couples both young and old holding hands, photographers snapping pictures away, fishermen with their lines out gazing off in the distance and a sense of happiness in the air.

At that one moment in time, you get to capture a large group of people coming together celebrating another day being alive.  You might even hear some cheers and applause as the sun sinks below the horizon.

Although there are multiple spots to catch the sunset, do yourself a favor and add this experience to your bucket list to stand on the beach near Pier 60 and live the moment.

12. Lifestyle

The lifestyle in Clearwater can best be described as laid back.  People come here to have a good time and that requires a lot of people behind the scenes pulling the strings to make it happen.

Although Clearwater is larger in size compared to most of the other Pinellas cities, it’s not uncommon after you establish roots here to run into people you know.

There’s also a bond here with the locals.  Whether you gather at Pier 60 park at sunset and watch movies outdoors, participate in tours with your family and other locals or root on some of the local sports teams like the Clearwater Threshers (minor-league baseball team), I feel there’s a vibe of good energy here that can be appreciated.

So what does the lifestyle look like of the average Clearwater local?  It depends on the person but I have many friends in Clearwater that enjoy playing volley ball, swimming and sailing, fishing, and hanging out the beach.  There’s a good mix of philosophies, personalities, and there’s no barrier between someone that lives in a mansion or someone that rents hanging out at the same establishments.

With that being said, we hope if you get to experience the Clearwater culture, you’ll find a variety of lifestyle choices to suit your needs and build your life by design.

13. Location

Clearwater and Clearwater Beach located in the northern part of Pinellas County offers convenient access to US-19, Alternate 19, and Gulf To Bay Boulevard that leads to and from Tampa.

If you look at the map of the boundary lines cited earlier in the post, you’ll notice Clearwater stretches all over the place.  The location encompasses lots of parks, great accessibility to restaurants, shopping, and local ammenities.

Some great places you’ll want to check out are the Clearwater Marine Aquarium, Ruth Eckerd Hall, Clearwater Mall, and Countryside Mall.

If you or someone you known plans on attending college, Clearwater includes popular colleges such as USF (The University Of South Florida) and SPC (St Petersburg College).

Clearwater alone is estimated to be over 39 square miles.  Happy exploring!

14. Hulk Sightings

Are you READY for Hulkamania brothers and sisters?  Are you ready for the 24 inch pythons?!  Well you are in luck because, the one… the only… Hulk Hogan lives in Clearwater. 

Terry Bollea aka Hulk Hogan has lived in Clearwater for a very long time even during his wrestling career.  Hulk not only lives here but he’s sort of the city’s unofficial mascot.  You’ll see a statue of him right in front of Hogan’s Beach Shop located in Clearwater Beach.

The Hulkster doesn’t shy from making public appearances and if you live here long enough, you’ll probably have your share of Hulk Sightings.

The first time I ran into Hulk was at Island Way Grill.  I had just left a wedding and was at the outdoor bar with my wife and brother-in-law.  I remember looking at a man directly across from me at the bar and I thought his resemblance to Hulk Hogan was uncanny.  I told my brother-in-law “don’t point, but that guy across from me looks a lot like Hulk Hogan” to which he replied that is “Hulk Hogan.”

I chose not to bother the Hulkster but took a few quick pictures for my memories.  I could tell the guy was just trying to enjoy a drink and relax and even though a few people came up and asked for pictures, he remained relatively unbothered during his time there.

I imagine it must be hard for celebrities like Terry to enjoy the area without being harassed but he always seems to take it like a champ.  Many people will spot Terry driving around on his boat through the Clearwater area and he has built a reputation for staying in his wrestling persona of Hulk Hogan for all this time.

While there are other big celebrities living in surrounding areas including Tampa, the Hulkster is the undisputed big celebrity for the city of Clearwater.

15. The Community

If you are looking for a community-oriented place to live, you’ve found the right spot.  As you walk around, there isn’t an immediate indication of who are tourists and who are locals… you just see people enjoying the sights and experiencing the culture.

Locals tend to be friendly and there’s strong support to keep the community safe and clean.  Few words can describe this as it’s something that has to be experienced.

Final Thoughts

We do real estate in the area and primarily do most of our business in Pinellas County.  Clearwater is one of my real estate specialties because not only have I lived there but I’ve sold in Clearwater and experienced many of it’s amenities.  We write these blogs to help people understand the areas they are interested in living in whether they are looking to buy now or years from today.

Clearwater is special, it is a place you can truly enjoy and appreciate as you familiarize yourself with the area, and we are happy to answer any questions you have to help you with your real estate needs or desire for local knowledge.

Are you looking to learn more about real estate in Clearwater, Florida? Here are a few of our popular blogs and pages that might be helpful to you!

Frequently Asked Clearwater Relocation Questions

Real Estate In Clearwater Beach, FL

The Clearwater Community Page

The Clearwater Beach Community Page

Email us at for any Real Estate inquiries or if you just want to say hello.

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As your go-to real estate experts, we are happy to provide you with detailed property information and schedule a showing even if the home is listed through another agent or brokerage.  

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