Pass‑a‑Grille Sightseeing Guide: Explore Old Florida in One Perfect Loop
At Beach Ride Rental, we make it easy to explore Clearwater by golf cart and catch every new attraction 2025 has to offer. From luxury resorts to beach festivals, our street-legal carts turn the trip into part of the fun.
Book yours todayand cruise straight to the coast’s best new spots.
Clearwater Beach
If you love a mix of speed and sunshine, September’sClearwater Offshore Nationalsis pure adrenaline. Picture it—90 powerboats thundering past Pier 60, rooster tails flying, crowds cheering.
It’s one of those weekends where the whole beach hums with energy. And because our carts are street-legal, you can explore Clearwater by golf cartand roll right up to the action without the stress of big-event parking.
Need a place to crash? The brand-new Opal Sol Resortopened this February, bringing 248 beachfront suites, a skybridge to its sister property, and the largest ballroom in Pinellas County.
Come November, the vibe shifts from roaring engines to smooth melodies at the Suncoast Jazz Festival.Three days. Three stages. Dozens of artists serving up everything from New Orleans brass to late-night blues; all with the Gulf as your backdrop.
Stay steps away at the waterfront ChartHouse Marina Hotel, which debuted in spring, then wander down to Jimmy’s Island Grill for fresh seafood and sunset cocktails.
With one of our street-legal carts, you can explore Clearwater by golf cart from your hotel to the festival, the beach, and beyond without ever hunting for a parking spot.
St. Pete’s
September kicks off with the roar of the St. Pete Powerboat Grand Prix. Massive Class-1 boats tear across the Bay at speeds up to 160 mph, while AquaX jet skis race closer to shore. The whole waterfront, especially the Pier District, turns into a giant viewing party.
Fast-forward to November and the music takes center stage with the all-new St. Pete Country Festat Vinoy Park.Three days, three stages, and more cowboy boots than you can count.
This is where aSt. Pete golf cart rentalreally shines: you can roll from your hotel to the park, then over to dinner or some other St. Pete hidden gems on a golf cart.
The month wraps with the holiday shopping spree that is Shopapalooza Festival, also at Vinoy Park. We’re talking 350+ local vendors, live bands, food trucks, and even Santa sightings. Load your cart with gifts, grab a bite, then cruise the few blocks to the Pier District for a nightcap or a sunset stroll.
Downtown St. Pete
Downtown St. Petemakes it easy; we just make it more fun.
The iconic Don CeSar Hotel,standing proud in all its rosy glory after storm repairs, is back in full swing. This “Pink Palace” is more than a photo op; it’s home to upscale dining, beachside cocktails, and a spa you’ll want to melt into after a day in the sun.
Come November, theTaste of the Beachesreturns, tempting you with bite-sized flavors from dozens of local restaurants.
Instead of wrestling for parking at each stop, a golf cart lets you hop between eateries with the Gulf breeze in your hair. It’s the perfect way to turn “dinner” into a progressive food tour, and one of the easiest golf cart friendly attractions in Florida to check off your list.
Treasure Island
November turns Treasure Island into a living art gallery during the Sanding Ovations Master’s Cup(Nov. 20–23, with an Encore Nov. 29–30).
Master sculptors from around the globe transform the beach behind Bilmar Beach Resortinto towering, intricate sand masterpieces; the kind you have to see to believe.
Add in beachside concerts, a craft market, and a Saturday night fireworks finale, and you’ve got one of the family attractions accessible by golf cart you’ll be talking about long after the tide comes in.
Treasure Island’s cart-friendly streets mean you can roll right from the art displays to a sunset dinner, making it one of the most golf cart friendly attractions in Florida this fall.
Madeira Beach
Every November,Madeira Beachreels in one of the biggest fishing events in the U.S., and 2025 is no exception.
From Nov. 6–8, the King of the Beach Kingfish Tournament & Festivalturns the Madeira Beach Recreation Complex into a lively hub of music, marine vendors, and sizzling seafood smells you can catch from blocks away.
Arriving in one of our street-legal carts means you can slip into neighborhood parking without battling the main lot crunch, then stroll right into the action. And when the sun sets over Boca Ciega Bay, it’s hard to imagine a better way to end a Gulf Coast fall evening.
Speaking of Boca Ciega Bay, it is by far one of the most unique places to visit in Pinellas County, so make sure to add it to your itinerary.
Indian Rocks Beach
In 2025, Indian Rocks Beachgave its beloved 17th Avenue Beach Access Parka fresh start, reopening in January with new amenities and dune walkovers.
It’s a favorite local spot to roll up in a street-legal cart, park just steps from the sand, and enjoy a quieter stretch of shoreline.
Come fall, the town’s signature music series, Rock the Rocks, hits its November groove. On Nov. 8, Crabby Bill’sbeachfront stage will fill the air with island rock and blues from noon to 10 pm, with craft vendors offering early holiday shopping in between sets.
The venue’s location right on Gulf Blvd makes it a breeze to reach in a golf cart, and locals take full advantage, cruising over for seafood, sunsets, and songs by the shore.
Gulfport Beach
Gulfport kicked off 2025 with its newly branded Gulfport Night Market, turning the town’s historic waterfront district into a twinkling mix of art, music, and late-night bites.
By fall, the vibe only gets better, and in November, the market weekends come with a holiday twist. On Nov. 7 and Nov. 15, Beach Boulevardfills with live bands, artisan booths, and shops staying open well past sunset.
Gulfport’s small-town waterfront charm and cart-friendly streets make it a perfect evening outing for both locals and visitors, and the place to be if you want to travel on a sightseeing golf cart.
Dunedin
Dunedin started 2025 with a big win for golf lovers, the grand reopening of the historic Donald Ross, designedDunedin Golf Club.
While the fairways are the main draw, Dunedin’s walkable, cart-friendly downtown is where you’ll want to spend your fall evenings.
November brings one of the city’s biggest street parties: Dunedin Wines the Blueson Nov. 8. Multiple stages light up Main Streetwith all-day blues performances, while food and wine vendors keep the glasses full.
The festival’s open-street setup makes arriving in one of our golf carts a breeze. You can park close to the action, then hop between music stages and wine tastings without missing a beat.
Anna Maria Island
Anna Maria Islandstarted 2025 with the reopening ofBayfront Park, a bayside gem perfect for picnics, beach strolls, and sunset views over the water that has more than earned its place in many Florida gulf coast travel tips blogs.
In September, theGreg LaPensee Bowling Tournament(Sept. 6) brings the community together for an evening of strikes, spares, and friendly competition at Bowlero Bradenton.
Palm Harbor
Palm Harbor’s walkable downtown sets the stage for some of the season’s most flavorful and festive gatherings.
In November, food lovers can sip and stroll during Taste of Palm Harbor(Nov. 13), sampling signature dishes from more than 20 local restaurants. A week later, the streets fill again for the Palm Harbor Craft Festival (Nov. 22–23), where artisan vendors line Florida Avenue with handmade jewelry, pottery, and unique décor.
While Palm Harbor isn’t as golf-cart-saturated as some neighboring towns, there are pockets, like nearby Ozona, where you can really make the most out of this eco-friendly beach transportation.
Safety Harbor
Safety Harbor’s waterfront charm meets lively street festivals each fall, and November brings two of its biggest draws.
First up is the Safety Harbor Wine Festival (Nov. 1), where more than 100 wines, multiple music stages, and a waterfront sunset create a night worth savoring.
Later in the month, the town’s beloved Third Friday Street Celebration (Nov. 21) takes over Main Street with food trucks, artisans, and live bands filling the air with music.
Thanks to Safety Harbor’s golf-cart-friendly downtown, our golf cart rentals make it easy to cruise in, park in a designated spot, and join the fun without circling for car parking. It’s the kind of place where locals wave as you roll past; and you might just end up making a few new friends along the way.
Explore Florida on a Golf Cart!
Florida’s Gulf Coast is buzzing with ways to make 2025 unforgettable and at Beach Ride Rental, we want to make your trip even easier with one of our golf cart rentals in Clearwater Beach and other destinations.
Whether you’re in the mood for music, markets, or a lazy afternoon at a newly opened waterfront park, these towns are ready to welcome you.
So, what are you waiting for? Book your golf cart today, and let’s turn this year’s “things to do” list into “things you did, and loved.”
FAQ'S
Sorry, no joyrides on the sand. Most Florida beaches don’t allow carts directly onshore. But we’ll get you close enough that the walk to the waves is just a flip-flop stroll away.
Farther than most people think. Our carts are perfect for exploring nearby neighborhoods, hopping between restaurants, and cruising scenic coastal routes. Just remember, stick to roads 35 mph or under.
Yes, and we encourage it! We’ve seen everything from pirate flags for Gasparilla to twinkle lights for holiday parades. Just make sure decorations are secure and don’t block your view.
If you’re a sunrise person, start early for quiet streets and glowing skies. Night owls? Evening rides mean cooler temps and maybe even fireworks over the water. Either way, the Gulf knows how to put on a show.
Of course, safety comes first. Let us know when booking, and we’ll make sure your cart is set up with a child seat.