Let’s set one thing straight. Clearwater Beach is amazing on its own, make no mistake. You can spend a whole week just on our little island paradise and be spoiled with pristine beach conditions, top-notch drinking and dining, shopping, water activities and evening entertainment to your heart’s content. Nevertheless, for those of you who tend to get a little restless and generally like exploring, we are including an outing to the southern beaches for a change of scenery and a beach for every mood. 

Tuck into Breakfast at Ryan’s Cafe (9:30 am – 11:00am)

Head to Ryan’s Island Cafe for today’s breakfast intake. Ryan’s is technically “newer” to the beach, but is actually one of the better breakfast spots around and has garnered glowing online reviews. This locally owned café is a must-visit on your trip. Everything is excellent on the menu, honestly. Choose from the Morning Monster, Belt Breaker and Boss Stacked pancakes, or opt for the leaner Athena’s Cali Benedict followed by the Healthy Choice Parfait.

Then catch the trolley from Pier 60 or the boardwalk direction south.

Chill-out at Sand Key (11:15 – 1:30pm)

Digest your breakfast at Sand Key, the quieter little sister of Clearwater Beach, by lodging yourself in a beach cabana and enjoying the views. Or, you could walk around the park along the intracoastal and keep a lookout for dolphins.

Lunch in Indian Rocks or Redington Shores (1:45 – 3pm)

Next, jump on the trolley and continue south. The shoreline is dotted with amazing beaches, and you’ll be passing Belleair Shore, Indian Shores and Indian Rocks, where you could make a lunch stop at Crabby Bill’s to get involved in some succulent oyster action. Or, continue south for lunch at Seabreeze Island Grill over in Redington Shores. Grab something lighter, like crispy zucchini fries or a salad to save yourself for dinner, as we’ve got something special in mind.

Stroll along the quaint North Redington Beach to take in the local vibe before catching the next trolley south toward’s Madeira beach.

Explore Madeira Beach and John’s Pass (3 – 5pm)

Get a feel old for the Old Florida charm and stroll around the rustic John’s Pass Village, a turn-of-the-century fishing village with a plethora of unique shops (including Zeno’s with the World’s Most Famous Taffy), restaurants, fishing and water activities. It was created by a hurricane in 1848 and is named after pirate John Levique, who was the first to cross it – avast ye landlubbers!

If you haven’t tried parasailing yet, this is an excellent opportunity to try it. And if you prefer something closer to land, you could also get a Waverunner from Woody’s.

Quench your thirst on Treasure Island (5 – 7:30pm)

After all this excitement, you’ll probably feel thirsty. We got you covered! Catch the next trolley and continue further south. Get off where Treasure Island and Sunset Beach meet and stop at Sea Dog Brewing Co. This two-level brew pub sits right on the intracoastal with ample seating and a generous menu with local craft beer and beer-infused cocktails.

Feeling invigorated from your pit-stop, walk back onto Gulf Blvd direction south, where you could stop at Caddy’s right on the beach for further refreshments (they have some great specialty drinks) and to catch the sunset. Right next door you’ll also find Ka’Tiki with reasonably priced drinks, a buzzy vibe and live entertainment 7 days a week running until 10pm most nights. Consider stopping here before heading to dinner, or you can tick this one off on your way back after dinner!

Dinner at Taco Bus / or RumFish Grill (8 – 9:30pm)

Now for dinner, we’ve got two options in store for you, totally depending on your vibe. If you prefer a budget-friendly, more casual bite, then you’ll find our beloved Taco Bus just in front of Sea Dog! You could grub down authentic Mexican flavors and then head back to Ka’Tiki to cap off the day.

But if you are up for an experience, you could backtrack, hop on the Suncoast Beach Trolley and continue south towards the ever-so-popular RumFish Grill. The trolley stops right outside! When this place hit TradeWinds Beach Resort, back in 2014 it was the talk of the town, and it still is – at least for out-of-towners, much owing to its huge fish tank. You are basically sat in a 33,500-gallon aquarium, immersed in an under-the-sea atmosphere, with the occasional shark swimming past while you’re tucking into cutting-edge fish dishes. Just remember to book in advance to secure your seats at this place.

Once you are done exploring the southern beaches, you know what to do – trolley it, or haul a free ride back home.