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What do you look for in a Clearwater Beach Hotel? A beautiful private beach? Convenient access to all the fun things to do in Clearwater and beyond? How about award-winning on-premise restaurants and resort amenities? We chose Sheraton Sand Key for our anniversary weekend in Clearwater / St. Pete and put together a three-day/two-night romantic weekend itinerary based out of the spectacular Sheraton Sand Key Resort.

Sheraton Sand Key Lobby
Sand Key Beach in front of the Sheraton

Arriving at our Clearwater Beach Hotel

Clearwater Beach sits on a 25-mile long barrier island near Tampa and St. Petersburg on Florida’s west coast. Tampa sits at the back of Florida’s largest estuary, the 400 sqm Tampa Bay, while St. Petersburg was built near the mouth. Crossing over massive bridges on Tampa Bay and St Joseph’s Sound told us that we were entering a water world.

The city of Clearwater Beach repeatedly gets ranked as Florida’s best beach city because of beautiful beaches, high-rise Clearwater Beach hotels, and abundant activities. Clearwater is fun and happening, but we found paradise when we crossed the bridge to Sand Key, also known as the quiet side of the beach. The wide, empty beaches of Sand Key looked like the perfect home base for a romantic getaway.

As we checked in, our hostess told us about the Jolley Trolley and the Suncoast Beach Trolley that run up and down the coast from Tarpon Springs to St. Pete Beach. They both stop at the Sheraton Sand Key, and we could use them for free with our room key. We were all ready for our favorite type of romantic weekend, a car-free one!

Happy Hour and Sunset at Clearwater Beach

Clearwater Beach features sunset celebrations at Pier 60 that rival Mallory Square in the Keys. For two hours before sunset, and two hours after, music, movies, street performers, crafters converge on Pier 60 creating a festive atmosphere we didn’t want to miss. We could have taken the Jolly Trolley for free, but we brought our bikes, so we rode over Clearwater Pass to check out the party side of the beach.

It was still a little early, so we popped into Jimmy’s on the Edge rooftop bar for happy hour. We sipped piña coladas, ate discount appetizers, and let the stress of the week melt away. From our perch on the top of the Edge Hotel, we watched the activity in Clearwater Pass. The sunset dolphin tours found several pods hanging out by the jetty. There was even a scuba charter with their dive flag up anchored at the far end. We finished our drinks and headed down to Pier 60 looking for more things to do in Clearwater.

The Acro Maniacs were the first act that caught our attention. They are a team of concrete acrobats from Brooklyn that perform with no pads. They’ve been doing this act for 20 years and can still jump six small children in a single bound, which tell me the dangers of my office job. After the finale, we cruised the craft stands on Pier 60 itself until a rainstorm rolled in. While our evening got cut short by summer showers, there is plenty of fun to be had at Pier 60.

Edge Clearwater Beach Hotel

Exploring Dunedin

For our first full day in Clearwater Beach, we wanted to explore north of town. Jenn had been here before when she went diving with sharks at the Florida Aquarium, but this was my first visit. We rolled out of our hotel on bike, but this tour would be perfectly well supported by the Jolley Trolley or by bike. Our destination was Dunedin, a little Scottish town six miles away on the Pinellas Trail. The highlight of the ride was crossing the sound on the Causeway Bike Trail. The aqua blue water views stretched on as far as the eyes could see.

Dunedin in the summer was quieter than Jenn remembered over President’s Day Weekend. We popped into the Celtic Shop of Dunedin to see what’s up. The owner explained that Dunedin hosted festivals throughout the winter months, but things quieted down during the summer. I did pick up a pin with my Coleman family crest from Ireland. My lineage is probably more on the English side of the Colemans since my family traces back to the early settlers of Virginia, but that’s a story for another day.

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Even without bagpipers in the town square, we enjoyed Dunedin. The village itself is quaint and lovely with small mom and pop stores lining Main Street. Jenn insisted that we visit the Dunedin Brewery for wings. Dunedin Brewery is not only Florida’s oldest microbrewery, but they serve a wicked plate of wings. They get marinated overnight, deep-fried, served naked (no breading) with a choice of up to 2 dipping sauces. Delicious. We discussed our afternoon plans and checked the weather. We knew we wanted to go to Tarpon Springs, but incoming weather made us think twice about taking the Pinellas Trail the rest of the way up. Instead, we returned to the Sheraton Sand Key to see how the storms played out.

View of the Bay at Clearwater
View from Pinellas Bike Trail
Welcome to Dunedin
Dunedin Brewery- Florida's oldest craft brewery
Naked Wings in Dunedin

Soaking in Tarpon Springs

We made it back to our Clearwater hotel before the rain came, but it rolled in with a vengeance. Our windshield wipers could hardly keep up as we drove to Tarpon Springs. Tourism at Tarpon Springs centers around the historic sponge docks. It’s these docks that give this town a unique product and decidedly Greek feel. In the early 1900s, Greek divers began harvesting the prolific sponge gardens. Tarpon Springs became known as the Sponge Capital of the World, producing over one million dollars worth of sponges a year until a series red tide blooms devastated the sponge beds in the 1920s.

Large scale commercial sponging never returned, but Tarpon Springs retained its Greek heritage. We strolled the historic docks, ideally shopping for sponges and sampling Greek delicacies. We had our choice of pastry shops and mouth-watering gyros, but we want to give a special call-out to Hellas Restaurant and Bakery. They had to the best gyro we tasted this side of Athens!

Tarpon Springs Sponge Docks
Tarpon Springs sponge diver

Sunset at Sand Key Park

Between Sheraton Sand Key and Clearwater Pass sits Sand Key Park, a lovely county park that offers public beach access. Of course, it’s close enough to the Sheraton that we could just walk there down the beach.

We went at sunset, hoping to catch a glimpse of dolphins frolicking along the jetty like the night before. I’m sure this happens, and with a little luck and patience, you could get your dolphin on. On another trip, we might try snorkeling the jetty, especially during high slack tide so the visibility will be optimal. Since this was our anniversary weekend, we held hands watching the sunset and remembering our vows. “From this moment, I, Ed, take you, Jenn, as my best friend, my partner in life and crime, and my one true love.”

Sunset at Sand Key Park

Romantic Dinner at Rusty’s Bistro

Rusty’s Bistro is arguably one of Clearwater Beach’s finest restaurants and happens to be inside of the Sheraton Sand Key Hotel. We wanted to experience this local legend for ourselves and see why it won seven consecutive Golden Spoon awards for the best dining in Florida. We were not disappointed with its status as one of the most romantic things to do in Clearwater.

Jenn ordered the prime rib buffet, with tender prime rib and a rotating assortment of sides. The balsamic Brussel sprouts and sage dressing were to die for. I went for bay scallops that were succulent and popped with flavor.

Rusty’s exceeded our expectations, so we arranged to meet with Chef John, their award-winning head chef, to find out what his secret was.  He answered that it all started with the management staff, headed by Russ Kimball, who created a family atmosphere. Beyond that, it was the passion of the staff, high-quality ingredients, empowered employees, and keeping the menu fresh and current.

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Rusty's Bistro Sheraton Sand Key
Rusty's Bistro Sheraton Sand Key
Rusty's Bistro Sheraton Sand Key

Biking to John’s Pass Village

The beds at Sheraton Sand Key were so cozy that we wanted to stay and snuggle all day. If there’s one thing we learned about Florida is that if you’re going to bike in the summer, you’d better start early. We packed up our room, left our luggage with the bell desk, and started biking south on Gulf Blvd.

Just beyond the hotels of Clearwater Beach and Sand Key sits a series of small beach towns: Bellaire Beach, Indian Rock Beach, Reddington Shores to name a few. John’s Pass Village offered water sports, shopping, and waterfront dining. It was about 20 miles down Gulf Blvd, which was a perfect morning ride. We enjoyed lunch on the water and caught the trolley back to the Sheraton. Each trolley had a double bike rack on front that made it super easy.

A view of St John's Pass
The boardwalk at St John's Village

Leaving Clearwater Beach

We arranged for the bell desk to hold our luggage since we checked out earlier in the day and didn’t want it melting in our hot car. We came back the Sheraton hot and sweaty, so the front desk offered for us to shower off in the gym. Tell you what, nothing feels better after a Florida summer bike ride than a cool shower.

We had a couple of more things to do in Clearwater on the way out of town. First off, ice cream at Haze Ice Cream and then early dinner at The Bait House in Clearwater Beach Marina. Their signature drunken shrimp appetizer was as good as the views (which were excellent). We also had to visit a VR Dali popup that was just across the bridge. It was a traveling exhibit from the Dali Museum that allowed you to navigate inside a Dali painting with virtual reality. It made us really appreciate the artist and moved visiting the Dali Museum to the top of the things to do list next time we go to St Pete. With that, our adventure was officially over as we drove back to Orlando.

Drunken Shrimp and an amazing view at The Bait House
Haze Ice Cream
Dali Museum Popup

What Make the Sheraton Sand Key a Perfect Clearwater Beach Hotel?

Why did we choose to stay at the Sheraton Sand Key? For us, it had the best of both worlds. The on-site amenities like a large pool, private beach access, and fabulous restaurants, gave us an authentic beach resort experience. However, the fun and festivities of Clearwater were just a short hop away.

The rooms were large and comfortable. We never got tired of waking up and looking off our balcony to the ocean. We also loved the beds. They were the perfect firmness with remarkable pillows (we’re both kind of pillow snobs). We needed a good night sleep with all of the biking we were doing, and we slept like babies at Sheraton Sand Key.

Our trip took place over a special weekend for us too. It was our sixth wedding anniversary, and the Sheraton kept finding ways to make it special for us. From the beautiful grounds to the friendly staff, visiting Sand Key is one of the most romantic things to do in Clearwater.

Disclosure: A big thank you to the Sheraton Sand Key for hosting us and setting up a fantastic itinerary! For more travel inspiration check out their InstagramFacebook, and Twitter accounts.

As always, the views and opinions expressed are entirely our own, and we only recommend brands and destinations that we 100% stand behind.

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Clearwater Bay

Sheraton Sand Key

Sunset on Clearwater Bay

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