2026 Valentine events in St. Augustine & St. Johns County, Florida

Artisan Gift Shop at the Peña-Peck House

Jan. 27-Feb. 14: Handcrafted Valentine gifts, including locally made jewelry, is available by local artisans at the historic Peña-Peck House, 143 Saint George Street, in downtown St. Augustine. The shop is open Wednesday-Saturday from 12-4:30 PM

I Love You, You’re Perfect, Now Change at Limelight Theatre

Jan. 29-Feb. 15: I Love You, You’re Perfect, Now Change is on stage every Thursday through Sunday at Limelight Theatre, 11 Old Mission Ave., in uptown St. Augustine. Tickets: limelight-theatre.org

Galentine’s at Blot Lip Lounge

Feb. 1-15: Gather your girls for a fun Galentine’s Special at Blog Lip Lounge that includes one custom lip gloss, bling bar, glass of champagne, and a special gift. Located on the fourth floor of the Treasury Building. Galentine’s Party event space also available for private rental. Please RSVP in advance at blotliplounge.com

Valentine’s Mini Vintage Flea

Feb. 5: Two Girls One Market will host the Valentine’s Mini Vintage Flea on February 5 from 5-9 PM at Muggsy’s in West Augustine, 213 West King Street. Local vintage vendors will offer Valentine-themed items.

904 Speed Dating for 55+ at Dick’s Wings

Feb. 11: If you’re 55 or better, celebrate love and friendship with us in person. Enjoy a fun, relaxed atmosphere filled with good vibes, great company, and maybe even a little dancing. Don’t miss out on this special 55+ Valentine Event — where the fun and laughter are always in full bloom! The event takes place from 4-5:30 PM on February 11 at Dick’s Wings, 4010 U.S. 1, St. Augustine. Tickets are available here

Valentine’s Day Special Love Tree History Tours

Feb. 12-19: Celebrate love in the nation’s oldest city with a charming and romantic journey through history! The Love Tree History Tour, a unique experience that combines fun, romance, and local history. Perfect for couples, friends, or anyone looking to enjoy a cozy, scenic tour. Departs from 134 Riberia Street, St. Augustine. Learn more at www.Rideandtour.com

Love Bites at Third Space Improv

Feb. 13: Laugh until your stomach aches while watching Love Bites—an unfiltered comedic look at modern dating. This stand-up comedy show dives headfirst into the highs, lows, and cringe-worthy dating apps, first dates, situationships, and everything in between. Third Space Improv, 200 Malaga Street, St. Augustine, Florida. More details at www.3rdspaceimprov.com

St. Augustine Film Society Valentine’s Party

Feb. 13: The St. Augustine Film Society will host a Valentine-themed party for you, your sweetheart and new friends! Snacks and treats will be provided. Admission: $10 for the public. Students and St. Augustine Film Society members are free.The event is set for Friday, February 13 from 7-10 PM, with doors opening 6:30 PM at The Waterworks, 184 San Marco Avenue in St. Augustine, next to the Main Branch Library.

Whetstone’s Mini Sweetheart Tour

Feb. 13-16: Treat your love to a special 30 minute mini tour to learn about these romantic treats while enjoying multiple free samples. The tours take place between 10 AM 3:30 PM at Whetstone Chocolates, 139 King Street, St. Augustine. Admission is $5 adults, and $3.50 for kids 4-12. More detaila at www.whetstonechocolates.com

Galentine’s Day Market at Coconut Barrel

Feb. 14: Grab your besties and shop local with 40+ vendors at this indoor market with additional pop-ups. A special gift (with purchase) and mocktails are served while supplies last. Admission is free. The event takes place on Saturday, February 14 from 10 AM to 3 AM at Coconut Barrel, inside Mall 2121, 21 U.S. 1 South, St. Augustine, Florida.

La Petite Kitchen at 36 Granada: Dumplings and Wontons

Feb. 14: Take an Appetizer Class and master the art of dumplings and wontons at 36 Granada in downtown St. Augustine. The class takes place at 11 AM Saturday, February 14. Enjoy a culinary experiences complete with fried wontons, spicy cucumber salad and jasmine rice. Reserve your spot: 36granada.com

The Art House: Heart Mug Workshop

Feb. 14: Sculpt a heart mug at this art studio, along with other class options throughout February. Located at 3920 A1A South Unit 8, in St. Augustine Beach. Details for all classes and workshops here: www.904arthouse.com/calendar

Galentine’s Day Party at Midnight Moon Books & Boutique

Feb. 14: Find your next good read with friends, and take advantage of the vendors onsite: charm jewelry, tarot cards, skincare, and crystals. Meet and greets with authors, wine, sweet treats, and complimentary gifts are featured. This event takes place from 2-5 PM Saturday, February 14 at Midnight Moon Boos & Boutique, 111 King Street, in downtown St. Augustine.

Sips and Serenades with First Coast Opera

Feb. 14: Join First Coast Opera on Saturday, February 14 for an intimate and elegant evening in support of the opera at the stunning home of Faith Tiberio Dougherty and Daniel F. Dougherty, overlooking the picturesque Matanzas River. Guests will enjoy heavy hors d’oeuvres and decadent desserts, wine, beer and bubbly. Enjoy live performances by The Mikado conductor, baritone Sean Christopher Stork and soprano Ali Molnar. The evening will also feature a curated silent auction.​ Tickets are $100 per guest. Space is limited for this celebration and we encourage you to make your reservations today. RSVP: www.firstcoastopera.com

Romanza’s Collage Concert: North Florida Jazz Quartet

Feb. 14: Listen to classic and modern jazz from a dynamic ensemble based out of Jacksonville, the North Florida Jazz Quartet. Dive into a night of energy and artistry, as performances of iconic music compositions from 1965 to the present day are explored. The concert takes place on Saturday, February 14 from 7:30-9 PM at The Waterworks, 184 San Marco Ave., in uptown St. Augustine. Admission: $30.00 per person. Purchase tickets in advance.

3 Blind Dates – an Unscripted Romantic Comedy

Feb. 14: An improvised romcom about holiday love stories inspired by YOUR real holiday love stories. 3 Blind Dates follows three single women navigating a round of speed dating—and the resulting dates. The twist? The audience gets to decide which speed dater each woman will go out with. Bring your dating stories along—they could become part of the show! Arrive 30 minutes early to enjoy a drink in the studio and share your tales with the 3 Blind Dates cast. The show starts at 8 p.m. Tickets are $20 in advance or $25 at the door. Third Space Improv, 200 Malaga St., St. Augustine. www.3rdspaceimprov.com/events

Boots & Bourbon: A Dutton Style Valentine’s at Ancient City Farmstead

Feb. 14: Enjoy a western-themed Valentine’s evening at Boots & Bourbon: A Dutton Style Valentine’s from 6-11 p.m. at Ancient City Farmstead, featuring live music, bourbon cocktails, and dancing in a ranch-house setting. Browse on-site vendors for custom western experiences, including Antler & Crown’s custom fittings for premium wool and beaver felt hats and the option for couples to create a custom brand. Tickets are $223.58. 395 St. Marks Pond Blvd., St. Augustine. www.eventbrite.com/e/boots-bourbon-a-dutton-style-valentines-tickets

Fury Valentine’s Day Live Music Champagne Cruise

Feb. 14: Cruise aboard a 45-foot Corinthian Catamaran for a 90-minute Valentine’s Day experience on St. Augustine’s Intracoastal Waterway. Guests travel past the city’s well-known landmarks after dark and enjoy complimentary drinks—champagne, beer, wine, margaritas, soda, and water—along with assorted snacks. Live music is provided throughout the cruise. Rates begin at $55.21 per guest ages 11 and up, $29.71 per guest ages 4–10, with free admission for children 3 and under. Fury Adventures, departing next to the Vilano Beach Pier, 250 Vilano Rd., St. Augustine. www.furystaugustine.com/live-music-sail

 

 

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