Valentine’s Day in Historic Downtown Sanford isn’t just about dinner reservations — it’s about experiences.
From waterfront strolls and wine walks to live music, craft cocktails, intimate dinners, and sweet treats, Downtown Sanford offers countless ways to celebrate love all week long. Whether you’re planning a full Valentine’s weekend, a classic date night, or something spontaneous, this is the place to do it.
Here’s your guide to lots that’s happening for Valentine’s Week and Weekend in Historic Downtown Sanford.
❤️ Special Valentine’s Events & Experiences
🍷 Sanford Valentine’s Wine Walk
Sip, stroll, and soak in the romance during the Sanford Valentine’s Wine Walk, hosted by Theater West End.
Taking place on Friday, February 13, this popular event features:
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Wine pours at participating downtown businesses
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Twinkling lights and romantic evening vibes
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A relaxed, walkable experience perfect for couples or Galentine’s groups
This is one of the best ways to experience Downtown Sanford at night. $20/pp
🚢 Valentine’s Weekend Aboard the Barbara-Lee
Romance meets river views aboard the Barbara-Lee with St. Johns Rivership Co..
From February 13–15, guests can enjoy:
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Valentine’s lunch and dinner cruises
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A special Valentine’s Week exclusive menu
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Cozy tables, full-course meals, and live entertainment
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Sweet extras like cherry mousse and heart-shaped ravioli
It’s a classic Sanford experience with an extra dose of romance.
🎬 Love Your Shorts Film Festival
Film lovers can add something truly special to Valentine’s Weekend with the Love Your Shorts Film Festival, happening February 12–15 in Historic Downtown Sanford.
Hosted at the iconic Ritz Theater, this annual festival showcases short films from Florida, across the U.S., and around the world. Since its founding in 2010, Love Your Shorts has become one of Sanford’s signature cultural events.
Attendees can enjoy:
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Curated short film screenings across multiple genres
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Filmmaker meet-and-greets and workshops
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A creative, arts-forward crowd and downtown energy
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A walkable location close to restaurants, bars, and dessert spots
It’s a perfect Valentine’s option for couples who love film, creativity, and experiences that go beyond the traditional dinner date.
🔥 Valentine’s Dinner Under the Stars at D’La Rosa Farm
For something truly unique, El Coqui Bakery partners with La Parri Grills for a live-fire parrillada experience at D’La Rosa Farm.
This intimate, ticketed event features:
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Traditional asado-style cooking over open flame
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A private outdoor farm setting
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Live music as the evening unfolds
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A full bottle of wine per couple
Designed for couples and small groups, this is one of the most memorable Valentine’s dinners happening anywhere nearby. $190/per couple
🍽️ Valentine’s Prix-Fixe Dinner at Buster’s
Buster’s Sanford is offering a Valentine’s Day prix-fixe dinner starting at 5pm.
Highlights include:
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A three-course prix-fixe menu
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Champagne included
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Multiple entrée and dessert options
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The regular dinner menu still available
Perfect for couples looking for a relaxed but elevated dining experience. $45/pp
🍺 Valentine’s Surf ’n Turf Dinner at Dee’s Brothers Brewery
For something fun and different, Dees Brothers Brewery is hosting a 5-course Surf ’n Turf Valentine’s Dinner for Two.
Details include:
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Two seatings at 5pm and 8pm
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An intimate event space
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$145 per couple with gratuity included
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Limited to 12 tables per seating
This is an excellent option for beer-loving couples who want a memorable night without the typical Valentine’s clichés.
🍣 Sushi, Sips & Valentine’s Vibes at Celery City Craft
Sushi & Seoul teams up with Celery City Craft for a Valentine’s Day special that’s playful and fun.
The “Whole Lotta Love” special includes:
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A heart-shaped avocado tower
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Two drinks to sip together
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Branded glassware to take home
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A single red rose
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Sweet treats to share
Available Valentine’s Day only, while supplies last. $40/pp
☕ Valentine’s Drink Specials at Palate Coffee Roasters
Date day counts too. Palate Coffee Roasters is rolling out a lineup of Valentine-inspired drinks, including:
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Cherry On Top espresso drinks
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Chocolate Covered Strawberry mochas
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Raspberry Cheesecake lattes
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Sakura Sweetheart Matcha
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Love in Bloom lemonade
Perfect for a casual coffee date, Galentine’s meetup, or a little self-love.
🍹 Valentine’s Weekend at Loggerhead Distillery
For couples who love craft cocktails and local flavor, Loggerhead Distillery offers a fun and laid-back Valentine’s experience right in the heart of Historic Downtown Sanford.
On Friday, February 13, book a distillery tour and tasting and enjoy an inside look at how Loggerhead’s small-batch spirits are made. The guided experience includes:
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An informative tour covering fermentation, distillation, equipment, and barrel aging
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Complimentary cocktail tastings
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Credit back toward an in-store bottle purchase
As part of Valentine’s weekend, don’t miss their festive craft cocktail Love Potion, made with:
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Loggerhead Key Lime Gin
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Butterfly pea flower
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Vanilla and lemon
The result is a beautifully colored, Valentine-themed cocktail that’s as fun to sip as it is to photograph.
Whether you’re starting your night here or using it as a relaxed pre-dinner stop, Loggerhead Distillery is a great option for couples looking to mix learning, cocktails, and local Sanford vibes into their Valentine’s plans.
🍫 Sweet Valentine’s Gifts at Wondermade
Wondermade is bringing the sweets just in time for Valentine’s Day with brand-new, in-house chocolate creations.
At the Sanford shop, you’ll find:
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Chocolate-covered marshmallows in multiple flavors
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Salted caramel, raspberry, maple, cannoli, and more
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Chocolate-covered pretzels, Oreos, and Biscoff cookies
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Food-focused Valentine’s gifts like chocolate bars, jams, honeys, candies, and teas
These chocolates are currently available only at the Sanford location, making this a perfect stop for a thoughtful local Valentine’s gift.
🎶 Valentine’s Night at The Capital Room Bar
Celebrate Valentine’s Day with cocktails and live music at The Capital Room Bar.
On Saturday, February 14, enjoy Decades of Love with live singing by Susie from 8pm–11pm.
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Free general admission
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Valentine’s-themed cocktails
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Classic lounge atmosphere
Private tables for two are available and include a bottle of champagne, savory treats, desserts, and premium seating — all for $35 per couple. Seating is limited.
❤️ Our Favorite Ways to Make It a Valentine’s Weekend
🌅 Take a Romantic Riverwalk Stroll
A sunset walk along the Sanford RiverWalk is simple, free, and genuinely romantic. Pair it with drinks or dessert afterward for an effortless win.
📸 Turn Downtown into Your Valentine’s Art Walk
Explore murals, sculptures, and historic streets while snapping selfies together. It’s a fun way to slow down and enjoy the atmosphere.
🍸 Make It a Full Night Out
Start with cocktails, enjoy your main event, then finish with dessert, wine, or live music. Downtown Sanford’s walkability makes this easy and stress-free.
❤️ One More Romantic Way to End the Night
If you’re looking for something casual but still special, head over to Henry’s Depot.
Grab handcrafted cocktails at The Basin, or share a sweet treat from Greenery Creamery.
It’s the perfect low-pressure way to:
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Keep the night going after dinner
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Enjoy dessert without committing to another reservation
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End the evening on a relaxed, romantic note
💘 Plan Ahead
Valentine’s Week and Weekend are some of the busiest days of the year in Historic Downtown Sanford. Many events are ticketed or have limited availability, so planning ahead is highly recommended.
Whether you’re celebrating big or keeping it simple, Historic Downtown Sanford offers endless ways to make Valentine’s Day special.
