Anna Maria Island is, hands down, one of the best Florida beach towns to visit in fall.

You can start your morning on Pine Avenue, where you can grab a cinnamon bun from Ginny & Jane E’s and browse coastal home goods at Shiny Fish Emporium.

Then coast (literally) over to Bayfront Park for water views and pelican-watching, or loop around to Bean Point Beach for an uncrowded, quiet walk along the sand.

Fall also means local events like BayFest—a family-friendly street fair with live music, food vendors, and small-town vibes. And with fewer visitors, navigating the island by cart is even easier.

Kick things off where locals gather to toast the sunset: Jimmy’s Crows Nest, perched ten floors up with a panoramic view of Clearwater Marina and the beach beyond. It’s classy without being snobby, the kind of place where a cold rum punch tastes even better with sea breeze in your hair.

This is one of the best nightlife spots Clearwater Beach offers for low-key elegance. And yes, your golf cart fits perfectly in the hotel’s guest parking lot.

There are plenty of ways to explore Clearwater Beach: guided sightseeing tours, Segway rides, and boat excursions are popular options, but when you want to hit the streets your own way, nothing beats driving a golf cart. 

With a golf cart, you’re in control of the tour. Start your morning with coffee near Mandalay Avenue, swing past Pier 60, detour to the marina, and still make it in time for your dolphin encounter tour in Clearwater Beach. 

Want to grab tacos or catch a local art walk? Park right outside. No meters, no stress, and unlike in a Clearwater Beach Segway tour, here you march to the beat of your own drum and choose what and when to visit.

Not only that, but many of the best guided tours around Clearwater Beach, Florida, don’t include transportation—or if they do, it’s in a crowded van or tight trolley, so with a cart, you’re not squeezed next to strangers or stuck waiting on someone else’s schedule. You just roll where you want to roll.

The best things to do with kids in Clearwater Beach start with, well…the beach, and if you’re looking for safe shallow beach spots for toddlers or beaches equipped with everything for a family adventure, you’ve come to the right place. 

Clearwater Beach

Iconic, lively, and loaded with soft sand and clear, shallow water, Clearwater Beach is perfect for little ones still mastering their floaties. Better yet, this beach is close to all the action, so you’ll be able to spend some quality time with your kids and explore the city without any issue.

Want to make the trip even smoother? Hop on one of our 4-seater golf carts, and you’ll be able to go from Point A to Point B while enjoying the breeze and the sights! 

Sand Key 

If you’re looking for a quiet, more relaxed option just across the bridge, you can’t go wrong with Sand Key. Not only is this one of the most beautiful stretches of beach in town, but it’s also a big hit with the locals.

Better yet, Bay Park on Sand Key has some of the best picnic areas and playgrounds near Clearwater Beach, so you can spend the entire day here if you feel like it.

There are plenty of shops you can hit while around here, but if you’d rather travel with all of your beach stuff, consider choosing one of our 6-seater golf carts instead. The extra stuff lets you travel with coolers, flippers, floaties, umbrellas, and more, making the visit even more of a blast!

First up: Piertoberfest, St. Pete’s Oktoberfest on the Pier. Expect German beers, live bands, dancers, stein holds, and fun all day long at Family Park by the Pier. 

Rolling in with a cart means you dodge the parking battle, pull up close, and hop between tents with ease. Planning tip: arrive early, park the cart, then sample the brews and games without dragging bags around. 

Bonus: there’s also Oktoberfest Pinellas at the German‑American Society, with food, music, and dancing.

Start your getaway where the Gulf sparkles brightest. Clearwater Beach is a vibe all year, but in fall, it’s unbeatable. 

Think: a golf cart ride down Mandalay Avenue with the sea breeze in your face and no traffic jams in sight. From Pier 60’s nightly sunset festival to beach bars with live music, everything’s just a quick roll away.

At Beach Ride Rental, we see folks book carts here for everything from sunrise coffee runs to full-day family adventures. Street-legal means you can hit the hot spots and snag that golden-hour photo without worrying about parking meters.