Vintage Style from

Five Flags Trolley Co.

Our hand-restored Red Trolleys have solid wood contoured seating and brass fixtures that evoke the opulence of an earlier age. Polished and refinished by our volunteers and trolley experts, our trolleys are the most stylish way to bring up to 34 guests to any Northwest Florida or South Alabama event, from Destin and Pensacola to Fairhope and Mobile.

Service with a Smile

Our trolley drivers are decked out in the style of your choice, and always happy to see you. A warm, enthusiastic greeting and a ring of the hand-pull bell and you're on your way!

The Finest Appointments

Our large, slide-open windows and clear rear deck provide excellent views of the scenery along your route. Love your music with our great sound system, and stop off at the service bar to mix up a drink or pour a glass of champagne. Whether it's an elegant wedding, a historic neighborhood tour, or a military reunion, you’ll ride in style on the Red Trolley.

Decorate with Flair

Interior and exterior decorative options are available for your rental. We have special packages for wedding charters and proms as well as custom banner and signage options. Ask about our services when you're making your reservation, or reserve some time to decorate it yourself.

Guaranteed to Deliver

Five Flags Trolley is so confident of our service, we’ll even warranty our competitors! Getting the right transportation for your event is important. Don’t let delays, problems, and low standards interfere with your perfect day. Just sign up for our Trolley Cavalry service, and we’ll ride to the rescue with a simple phone call.

We do More

Charter trolleys are just the beginning of our services. With Red Trolley Repertory Theatre you can enjoy a show along the way! Our actors, historians, and local guides can bring your trip to life with pirates, aliens, or heroes of the past. If you’re coming to town with a tour group, we offer receptive operator services to make your stay in Pensacola splendid!