Clearwater, Florida is very much like a second home to me. Mainly because, it once was my home. For a brief period of my life between living in Memphis, Tennessee and living in Boston where I do now, I lived in Clearwater, Florida and it was truly the most magical time. And, yes, magical is the right word–I had dolphins in my backyard, the sun shone even when it rained, and Diagon Alley was just a mere one-hour away. Now, I make a weekend in Clearwater a normal part of my annual travel schedule.
Even though I typically just spent a couple of days here and there, I do still visit Clearwater at least twice a year. Some of my best friends still live there, it’s just an hour or so from Disney World (where I go every October), and, let’s face it, it’s just beautiful and perfect and a great escape from stiff New England life.
I haven’t written a lot about my time spent in Clearwater—primarily because I’m usually knee deep in piña coladas and/or neck deep in the Gulf of Mexico—but when Hotels.com asked me to share my favorite ways to spend a weekend in Clearwater, I jumped at the chance to talk about one of my favorite places like I’d just brushed up against a stingray. Tiny little squeal and all.
Obviously #1 on the list of amazing ways to spend a weekend in Clearwater, Florida is Clearwater Beach. Tripadvisor voted Clearwater Beach the #1 best beach in the country (again) in 2019… and, in case you’ve forgotten, that’s a country that includes the likes of Hawaii.
It really is pretty perfect though: powdery white sand so fluffy and soft you just can’t understand until you feel it, crystal clear turquoise water (I mean, it’s right there in the name!), and tons of space for beach activities (like, if you’re over the age of 30, napping). The area is full of great restaurants with amazing views, delicious food, Florida’s best sunset peeping (people literally applaud, every single night), and the best piña coladas this side of Puerto Rico. And so. many. dolphins.
You can spend an entire day of your weekend in Clearwater lounging on the beach, swimming in the warm, clear ocean, checking out Pier 60, eating all the fresh seafood, and laughing at the tourists as they’re borderline weeping as the sun goes down. Good times.
Even since I lived there in 2011/2012, they’ve done so much with Clearwater Beach. It’s used to be pretty much a total dive (don’t get me wrong, there’s still enough of the *local vibe* to have you questioning your life choices) but now it’s all bright, shiny, and just spoiled with parking.
CLEARWATER MARINE AQUARIUM
Just down the street from Clearwater Beach is the Clearwater Marine Aquarium, a really precious way to spend a weekend in Clearwater. You can get up close with dolphins, sea turtles, otters, hilarious giant pelicans, fish and other small sea creatures of all types, and my personal favorite, stingrays.
However, the Clearwater Marine Aquarium is not a typical aquarium—they specialize in the rescue, rehabilitation, and release of marine animals. The Clearwater Marine Aquarium is an animal hospital, rehabilitation facility, and serves as the permanent home for marine animals who’ve been so severely injured they can’t be returned to the wild. I’m not crying, you’re crying! Additionally, they’re dedicated to public education, research, and marine animal conservation.
But, the Clearwater Marine Aquarium is most famously the home of Winter, star of the movie A Dolphin’s Tale featuring Ashley Judd, Morgan Freeman, and Harry Connick, Jr. Now while it’s most well-known for the Atlantic bottlenose dolphin with a prosthetic tail, it’s lesser-known for being the place I used to work as a squid de-beaker for injured sea turtles. If you don’t know, now you know.
KAYAKING AT HONEYMOON ISLAND
Yes, technically Honeymoon Island State Park is in Dunedin, Florida but it’s damn-near the same thing so I’m still including this. After all, when I spend a weekend in Clearwater, this is what I do. So there.
I loooove kayaking in Florida and while Weeki Wachee Springs is probably my favorite, kayaking at Honeymoon Island is sooo much closer to Clearwater and a completely different experience altogether. This whole area is so gorgeous, interesting, and accessible from everywhere. There’s almost no one around, the waters are easily navigable and crystal clear, kayak rentals are reasonably priced, and there’s an endless list of awesome wildlife to observe in their natural habitats: dolphins, manatees, birds galore, jellyfish, sting rays that fly through the air (no joke), and maybe if you get lucky, even a couple of mating horseshoe crabs. (I mean, someone’s getting lucky.)
Besides the act of kayaking itself, there are tons of small islands here where you can shore up and explore (carefully, you can potentially do a lot of damage to both the natural ecosystem and the bottoms of your feet) and even more when the tide is low. You can explore nearby Honeymoon Island State Park (beware the abundant rattlesnakes, no joke again) and also stand up paddleboard here if that’s more your thing. Sitting is my thing.
TAKE IN A BASEBALL GAME
Yes, during a weekend in Clearwater I do, in fact, leave the beach every now and then.
Closer to the Tampa Bay side of Clearwater is Spectrum Field, home of the Clearwater Threshers—Single A affiliate of the Philadelphia Phillies. If you’re looking for an inexpensive way to spend a few fun hours in Clearwater (that don’t require a wet bathing suit or wondering what slimy creature just brushed up against your leg), check out a baseball game at Spectrum Field. You can still soak up your daily dose of vitamin D, but whilst holding a ridiculously cheap alcoholic beverage in one hand and a free matching alcoholic beverage in the other. (They have rrrreally great promotions here.)
During Spring Training, Spectrum Field is where you can see your big time Phillies players up close and personal, but gameplay here doesn’t stop in March. Like the rest of minor league baseball, the Clearwater Threshers play all summer from April – September.
EAT AND DRINK MY WAY AROUND THE CITY
When I spend a weekend in Clearwater, I admit most of my time is spent either in or on the water, but I do put on shoes every once in a while to eat and drink my away around town (which, admittedly, is usually at a restaurant or bar with a view of the water).
Clearwater, Florida has some of the best bars and eateries in the area and I make it part of my routine to hit up as many as possible. There are way too many to include here so I’ve got another post coming that will highlight all my favorite places to eat and drink in Clearwater (and St. Pete) so stay tuned! Be sure to subscribe at the bottom so you don’t miss it! In the meantime, do yourself a favor and go grab a piña colada at Palm Pavilion.
WHERE TO STAY DURING A WEEKEND IN CLEARWATER
Clearwater, Florida is so much more than just the beach… but why stay anywhere else? Here are my top picks for where to stay during your weekend in Clearwater, FL:
BUDGET: STA ‘N PLA MARINA RESORT
This. Place. Is. Adorable! Located on Clearwater Beach’s South Beach, Sta ‘n Pla Marina Resort is right on the water of Clearwater Bay and is just a 5-minute walk across the street to the beach and the Gulf of Mexico.
The property has 21 guestrooms and features an outdoor pool, free WIFI, beach umbrellas, self-parking, room service, and cute apartment-style rooms.
MID-RANGE: EDGE HOTEL
You’ll see the Edge Hotel featured in my post on my favorite places to eat and drink in Clearwater, but since it is a hotel, you might as well just go ahead and stay here.
The Edge is also located on the South Beach end of the island and features, among other things, an awesome rooftop bar and restaurant with amazing views (like this post’s featured image). They offer a couple of ocean-side pools, a 9/10 satisfaction rating, free WIFI, free buffet breakfast, 173 smoke-free guestrooms, and gorgeous ocean views.
LUXURY: WYNDHAM GRAND
Located smack in the middle of Clearwater Beach’s tourist district is the Wyndham Grand and my, oh, my is this place stunning. Those rooms! Those views! Those beach cabanas!
This hotel is just a 2-minute walk to Pier 60 and the most amazing Gulf sunsets (which you can see from your room, BTW). It offers three restaurants, a beautiful outdoor pool, a full-service spa, valet parking, free WIFI, and those views! Those rooms!
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