Valentine’s Day in Orlando North is all about making memories with your favorite people. Whether you’re planning a romantic outing, a fun day with family, or an adventure with your bestie, we’ve got you covered. Here’s your guide to 20 can’t-miss experiences to share with someone you love.
Solve a Mysterious Escape Room
Mystique Escape Room (1125 Townpark Ave STE 1011, Lake Mary, FL 32746)
Escape Artists (115 N Oak Ave, Sanford, FL 32771)
Take your Valentine’s Day up a notch with a puzzle-solving adventure in one of Orlando North’s top escape rooms! At Mystique Escape Room in Lake Mary, you can dive into the world of swords and sorcery, unravel the secrets of Pharaoh Khaba’s tomb, or choose from two other thrilling escape games. Prefer something out of this world? Head to Escape Artists in Sanford, where you can break free from a high-tech space capsule or foil the plots of a mysterious secret society. These brain-bending challenges are packed with excitement, teamwork, and plenty of “aha!” moments, making it the perfect way to bond with someone you love.
Sneak into an Orlando North Speakeasy
Suffering Bastard (200 South Myrtle Ave, Sanford, FL 32771)
Crown Alley (7055 Co Rd 46ALake Mary, FL 32746)
Channel your inner Gatsby with a visit to one of Orlando North’s coolest speakeasies. Find the hidden door inside Tuffy’s Music Box to enter the funky, vintage-inspired Suffering Bastard tiki bar famous for their extra-strong “Suffering” cocktails, like the limit-two-per-guest “Zombie” cocktail, and immersive tropical decor. Or, step inside the red telephone booth inside Lake Mary’s Grafton Street Bar to enter Crown Alley, a British speakeasy where the craft cocktails are as refined as the vibe. Sneak in for their daily 5:30pm champagne toast and take advantage of 30% off beers, wines, and select cocktails from 5-7pm. Pair a “Lissy London” with Truffle Popcorn, Mini Lobster Rolls or Caprese Flatbread.
Hike the Econ River Wilderness Area
3795 Old Lockwood Rd, Oviedo, FL 32765
Disconnect from the digital world and immerse yourself in nature at the tranquil Econ River Wilderness Area. A hidden gem in Orlando North, this 240-acre retreat offers an oasis of pine flatwoods, sandhill, and river swamp. Whether you’re strolling along the shaded trails or quietly watching the wildlife—such as white-tailed deer, great horned owls, and bobcats—you’ll experience a rare moment of peace. The beauty of the wilderness offers a perfect setting for reflection, intimate conversation, or just appreciating nature together, making it an ideal way to unwind and truly connect with someone you love.
Create a Valentine’s Bagel Board with Jeff’s Bagel Run
1351 Alafaya Trail #1013, Oviedo, FL 32765
Turn breakfast into a Valentine’s Day adventure with a bagel haul from Jeff’s Bagel Run in Oviedo. Choose from hand-rolled favorites like Sesame and Everything or try unique flavors like Cacio e Pepe or Blueberry Frost. Add house-made spreads—think Cookies and Cream or Whipped Garlic Herb Butter—and pair them with specialty drinks like their viral Lavender Honey Oat Milk Cold Brew. Grab a variety to set up a DIY bagel board and share a fun taste-test with someone you love. Whether it’s a family brunch or a cozy morning with your Valentine, Jeff’s Bagel Run makes breakfast unforgettable. Pro tip: Order ahead on their app to skip the lines!
Time Travel to the 19th Century at The Old Jailhouse
113 S Palmetto Ave, Sanford, FL 32771
Arrest your Valentine’s heart with a dinner at The Old Jailhouse in Sanford, a dining experience steeped in history and charm. This beautifully restored 19th-century building, once home to the Seminole County Jail, now dazzles as a unique restaurant featuring original brickwork, arched windows, and historic details. Share starters like crispy Brussels Sprouts or Smoked Fish Dip, and savor mains like the Belly Up Burger with mustard BBQ pork belly or Buttermilk Chicken with white bean cassoulet. After dinner, extend your date next door at Brix and Mortar Urban Winery, where you can sip on handcrafted wines in a cozy, intimate setting.
Catch Next to Normal at Theater West End
115 W 1st St, Sanford, FL 32771
Celebrate Valentine’s Day with a dramatic evening at Theater West End in Sanford. Catch the opening performance of the critically acclaimed musical Next to Normal (showing Feb. 14–March 2), a deeply moving story about a family navigating love, loss, and mental health with resilience and heart. With its intimate setting and high-quality productions, this is live theater at its best—perfect for an evening that will inspire connection and conversation with someone you love.
Score a BINGO at Dees Bros Brewery Trivia Night
210 Magnolia Ave, Sanford, FL 32771
Celebrate Valentine’s week with laughs, drinks, and a little friendly competition at Dees Brothers Brewery’s Wednesday trivia night in historic downtown Sanford. Housed in a 100-year-old building, this family-run brewery serves up creative craft beers like the Merry Men’s Porter and Bröllop öl IPA with lingonberries, plus vegan-friendly bites. Their themed Trivia Nights are the perfect chance to test your knowledge, sip on small-batch brews, and win free swag with someone you love.
Paint Your Partner at Calliope Street
1280 Oviedo Mall Blvd, Oviedo, FL 32765
Add a splash of humor and creativity to your Valentine’s Day with the cheeky Paint Your Partner event at Oviedo’s Calliope Street on February 14. Perfect for couples with a sense of humor, best friends, or even first dates looking to break the ice, this guided painting class invites you to create your own artistic rendition of your special someone—no experience required! For pet lovers, their famous Paint Your Dog event on February 16 offers the chance to turn your furry friend into a masterpiece.
Wine and Dine at Enzo’s on the Lake
1130 S US Highway 17 92, Longwood, FL 32750
Up the class this Valentine’s Day with an unforgettable night at Enzo’s on the Lake, a Longwood institution renowned for its authentic Italian cuisine and enchanting lakeside setting. With over 40 years of history, Enzo’s combines old-world charm with exceptional dining, featuring favorites like Fettuccine al’Aragosta e Gamberi and the signature Bucatini alla Enzo. Pair your meal with a selection from their curated wine list or a handcrafted cocktail like the Limoncello Spritz. Finish the evening on a sweet note with their heavenly spiced after-dinner cookies—an oft-overlooked gem.
Catch a Flick at AMC Altamonte 18
433 E Altamonte Dr, Altamonte Springs, FL 32701
Share the magic of the wizarding world with someone you love this Valentine’s season as the first four Harry Potter films return to the big screen at AMC Altamonte 18. Showing February 13-16, 20-23, and 27-March 2, this is the perfect opportunity to relive the enchantment with your kids, your partner, or a fellow fan. Whether you’re introducing the story to a new generation or rediscovering the wonder yourself, watching Harry’s journey unfold in a theater is an unforgettable way to bond and create new memories together.
Bird, Alligator, and Manatee Watch at Caffe Di Riverwalk
225 W Seminole Blvd #106, Sanford, FL 32771
Start your Valentine’s Day with a cozy coffee date at Café Di Riverwalk, a charming spot overlooking the tranquil waters of Sanford’s Lake Monroe. Sip on warm coffee or indulge in a house-made sweet treat as you take in the breathtaking lakeside views. Keep an eye out for the wildlife that calls the area home—you might spot osprey nests, manatees, alligators, or fish jumping in the water.
Shape Molten Glass at Orlando Glass Center
130 Bomar Ct STE 130, Longwood, FL 32750
Engage your creative side with fire and creativity at the Orlando Glass Center in Longwood, where their Valentine’s Special invites you and your partner to craft a glowing glass heart together. Under the guidance of expert instructors, you’ll shape molten glass into a unique keepsake. Perfect for adventurous couples, this hands-on workshop offers the chance to bond, explore something new, and create a lasting memory.
Score a Hole in One at Topgolf
1010 Greenwood Blvd, Lake Mary, FL 32746
Switch up your Valentine’s Day with an evening at Topgolf Lake Mary, where fun, food, and a little friendly competition come together. Whether you’re aiming for the high scores in Topgolf Signature or smashing virtual targets in Angry Birds Golf, there’s a game for every skill level—no golf experience required. Perfect for couples, families, or group dates, Topgolf offers a playful way to connect and share laughs. And with their Tuesday half-price deal, you can swing the night away without stretching your budget.
Get Cozy with Cheese Fondue at Colorado Fondue Company
1016 Semoran Blvd, Casselberry, FL 32707-3535
Nothing says “Valentine’s Day” like fondue, and Casselberry’s Colorado Fondue Company delivers a cozy, interactive dining experience perfect for celebrating love. Share their signature Swiss Chalet Cheese Fondue with fresh bread and veggies or try the Filet Mignon cooked on a sizzling hot rock for a fun, hands-on meal. Finish the night with their Rocky Mountain Avalanche Chocolate Fondue, a decadent treat. With its ski lodge vibes and welcoming atmosphere, it’s perfect for couples, families, or even Galentine’s Day. Book ahead and make it a night to remember!
Paint Pottery at Pottery U Paint
2632 West State Road 434, Longwood, Florida, 32779
Bring your creativity to life at Pottery U Paint in Longwood, a fun and welcoming studio perfect for couples, families, or friends looking for a unique way to celebrate. Choose from a wide variety of pottery pieces—like coffee mugs, vases, or whimsical figurines—and customize your creation with vibrant paints and techniques like sponging or marbling. Enjoy complimentary snacks and drinks while you work, and take your time crafting something truly special with someone you love.
Ride Swan Boats at Center Lake Park
299 Center Lake Lane, Oviedo, FL 32765
Experience Center Lake Park from a whole new perspective with an Oviedo swan boat ride, perfect for a romantic date or a fun activity with the kids. For just $5 for two people or $10 for up to four, you can paddle across the calm waters in whimsical swan-shaped boats that add a playful twist to your outing. Kids will love the excitement of being on the water and navigating their very own swan, while couples can enjoy a lighthearted and unique way to connect. Rentals are available Saturdays and Sundays from 11 a.m. to 7 p.m., weather permitting. After your 20-minute ride, take a stroll along the boardwalk or relax at one of the park’s charming outdoor spaces for a memorable day out.
Pamper Yourself at Koi Nail Spa
2111 WP Ball Blvd, Sanford, FL 32771
Treat yourself and someone special to the ultimate pampering experience at Koi Nail Spa in Lake Mary this Valentine’s Day. Whether you’re celebrating a mother-daughter day or a quiet escape with a friend, indulge in luxurious treatments like the Collagen Spa Pedicure or the Organic Spa Pedicure with Dead Sea salts and delightful fruity aromas. The serene atmosphere, complete with massage chairs and complimentary beverages, makes it the perfect setting for relaxation and rejuvenation.
Experiment with a New Art Form at Hawaii Fluid Art
1425 Tuskawilla Rd #209, Winter Springs, FL 32708Are you an experienced crafter? Try something completely out of the ordinary at Hawaii Fluid Art in Winter Springs. Unlike any other art experience, fluid art combines science and creativity to produce mesmerizing, one-of-a-kind masterpieces. Whether you’re swirling paints on a canvas, crafting a romantic resin beach scene, or designing colorful glass art, the process is as thrilling as the results. Every piece is unpredictable and unique, making it an unforgettable way to connect with someone you love.
