St. Augustine Group Trip-Hosted by Sheri Rosa

The St. Augustine Ghoulies Weekend was a three-day, thoughtfully curated trip organized by Sheri Rosa, blending history, hauntings, local food, and relaxed exploration in one of Florida’s most atmospheric cities.

Friday evening began with a group dinner at Crabby’s Beachside, followed by an optional beach walk along St. Augustine Beach. Guests then had the option to experience St. Augustine’s darker side through evening activities such as the Dark of the Moon Ghost Experience at the St. Augustine Lighthouse or the immersive Spectral Sip: A Haunted Tea Room Experience at The Local Refillery. The night wrapped with free time to return to accommodations or explore Old Town nightlife.

Saturday focused on a walkable exploration of Historic Downtown St. Augustine. The day included breakfast at Maple Street Biscuit Company, followed by stops at Second Read Books, The Spice & Tea Exchange, and free-roam time along St. George Street. Additional highlights included visits to My Cauldron Too and cocktails at The Tipsy Duck Parlor, with time built in for guests to choose their own lunch spot in the historic district.

The afternoon offered optional activities such as the Medieval Torture Museum, regrouping at St. Photios Shrine, and a flexible activity block that allowed participants to explore landmarks like Castillo de San Marcos, the Colonial Quarter, local museums, shops, or waterfront views. The evening concluded with dinner at Mill Top Tavern, followed by a private Booze & Boo Ghost Tour hosted by ghoulie Heather Feather in partnership with Nightly Spirits.

Sunday closed out the weekend with brunch at The Blue Hen Café, with an optional outing to Sykes Family Farm Crop Maze, featuring seasonal activities and a vendor market.