The Jolly Trolly is exactly what it sounds like – a breezy community streetcar where people occasionally burst into song with a view of the coast. Truly! I’ve seen it happen more than once!

Something quite like this.

If you are visiting the area or are a nearby Floridian, definitely take a day trip on the Jolly Trolley. You can begin at any point on the route, and it has stops in Tarpon Springs, Dunedin, Safety Harbor, and Clearwater Beach.


You can have breakfast alongside the lively sponge docks of Tarpon Springs. Enjoy strong Greek coffee and baklava while shopping for shells and luscious olive oil soaps. It almost feels like you’re cheating somehow when the $4 trolley pass takes you away on a Mediterranean vacation.

Next stop, Dunedin [LINK DUNEDIN ARTICLE]

The Florida-Scottish seaside town has 3 amazing breweries within walking distance of each other, and it is difficult to keep oneself from walking in to Strahan’s Ice Cream when its smell beckons. The brewery walking tour:

Dunedin Brewery

Sventh Sun Brewery

Dunedin House of Beer


After quenching your thirst at a few of Dunedin’s breweries & strolling its downtown, it’s onward, to Clearwater Beach. This is one of the more touristy spots on the tour but it’s a nice change of pace from the quaint daytime stops.

For sunset, find a spot on the beach to see Florida’s greatest show.

A pirate ship travels out every night at sunset and fires its cannon. Welcome to Florida!