May 7-11 St . Augustine Food + Wine Festival Enjoy over 400 varieties of unlimited wine , beer and spirits , live music , celebrity chef dinners , cooking demos , and a variety of tasting events . Renaissance Resort at World Golf Village , 500 S . Legacy Trl ., St . Augustine . www . staugustinefoodandwinefestival . com
May 9 St . Augustine Orchestra Spring Concert The performance begins at 8 p . m . at Tocoi Creek High School . 11200 St . Johns Pkwy ., St . Augustine . www . staugustineorchestra . com
May 9-10 Drake ’ s Raid Witness a reenactment commemorating the attack of the land and naval forces of Sir Francis Drake against Spanish San Agustín in 1586 . The encampment takes place at the Fountain of Youth . Drills , demonstrations , and living history interpretations from 10 a . m . -5 p . m . on Saturday , then beginning at 7:30 p . m ., a battle between the town ’ s defenders and Drake ’ s English privateers takes place from the City Gate on Orange Street and proceeds down St . George Street to the Governor ’ s House Cultural Center and Museum at the Plaza de la Constitución . Fountain of Youth , 11 Magnolia Ave ., St . Augustine . hfm . club / event / drakes-raid-3
May 9 – 25 “ Fly By Night ” at Limelight Theatre Enjoy this darkly comic rock-fable ; a melancholy sandwich maker ’ s humdrum life is intersected by two entrancing sisters . Tickets are $ 30-35 . Performances are Thursdays – Saturdays at 7:30 p . m . and Sundays at 2 p . m . 11 Old Mission Ave , St . Augustine . www . limelight-theatre . org
May 10 2025 Masterworks Concert presented by St . Augustine Community Chorus The St . Augustine Community Chorus collaborates with The Bel Canto Singers of Daytona presenting “ Hope Eternal .” The concert takes place at the Cathedral Basilica of St . Augustine from 7:30-9 p . m . 38 Cathedral Pl ., St . Augustine . www . staugustinecommunitychorus . org
May 11 Red Boat Tours Mother ’ s Day Special Celebrate Mom with a relaxing Dolphin Odyssey and Sightseeing Tour at noon or the B . Y . O . B . Sunset Cruise at 6:30 p . m . The Captain shares history and humor with popular songs . Dolphin Odyssey tickets are $ 29 for adults , $ 15 for ages 3-12 . Sunset Cruise tickets are $ 39 . Departs from the Vilano Pier – the ramp on the left past the Blue Bird . 260 Vilano Rd ., St . Augustine . www . redboattours . com
May 12 Full Moon Sail on Schooner Freedom Enjoy a moonlit evening aboard the Schooner Freedom as it sails through St . Augustine ’ s Matanzas Bay . This sailing excursion departs at varying times from the St . Augustine Municipal Marina . Tickets are $ 55 and include complimentary beer , soda , and wine . 111 Avenida Menendez , St . Augustine . www . schoonerfreedom . com
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