Winterfest Pensacola is a spectacular event that illuminates the picturesque Downtown Pensacola, spanning from Historic Seville to the vibrant Palafox Business District. As a brand, Winterfest offers a range of exceptional products and services that cater to families and groups of all sizes. Embark on one of our three exciting holiday memory tours, perfect for creating lasting memories.

With our Vintage Style Five Flags Trolleys, operated by the renowned Five Flags Trolley Co, you can explore the beauty of Pensacola in style. Our hand-restored Red Trolleys exude elegance and opulence, featuring solid wood contoured seating and brass fixtures. Accommodating up to 34 guests, our trolleys provide panoramic views of the captivating scenery.

For special occasions such as weddings, engagements, or parties, our trolleys with dance floors and party lights enhance the celebratory ambiance. Additionally, we go beyond trolley services, offering shows and entertainment with our talented actors, historians, and local guides. Whether it's a historic neighborhood tour, a military reunion, or any other event, Winterfest Pensacola guarantees an enchanting and memorable experience