Your Guide to a Loved-Up Valentine’s Day
Valentine’s Day is right around the corner, and whether you’re a hopeless romantic, a last-minute planner, or firmly on team self-love, one thing is certain: this is the perfect excuse to celebrate love in all its forms. From candlelit dinners and cozy nights in to thoughtful gifts, sweet treats, and even a chance to win big, we’re here to help you plan a Valentine’s Day that feels special, meaningful, and totally you!
To make things even easier, we’ve put together a Valentine’s Day Guide packed with ideas, inspiration, and local gems to help you plan every detail. And don’t forget, you can also enter our Valentine’s Day Contest for a chance to make this year’s celebration even sweeter.
Romantic Valentine’s Date Ideas
Whether you’re planning something low-key or going all out, romance is all about creating moments you’ll remember long after the roses fade.
Sip, Savour & Celebrate at EPIC Wineries
A winery date is a Valentine’s Day classic for a reason. Our EPIC Wineries offer stunning views, intimate vibes and delicious local wines that set the mood perfectly. Spend the afternoon sipping, strolling, and soaking up the romance. It’s relaxed, elegant, and effortlessly romantic. A few wineries offering special Valentine’s Day events and promotions include:
- Cooper’s Hawk Vineyard – Make Valentine’s Day extra sweet with their Love The Wine You’re With – Custom Valentine Labels. Paired with a decadent Dutch Boys chocolate and a set of wine charms this is a thoughtful, personalized gift that’s equal parts heartfelt and delicious—because the best way to say “I love you” is with wine, chocolate, and a touch of charm. Order online until February 12th.
- Muscedere Vineyards – Indulge in a thoughtfully curated sensory experience at Muscedere Vineyards with your Galentine or loved one on Saturday, February 14th at 1pm. Enjoy a one-hour guided tasting featuring four Muscedere Vineyards wines, each expertly paired with a selection of handcrafted artisan cheeses and chocolate.
- North 42 Degrees Estate Winery – celebrate your love with a 3 course Valentine’s Day Dinner Feature: Indulge in a classic dinner feature of spaghetti and meatballs, made timeless by those romantic dogs in Disney’s Lady and the Tramp, or select from the regular menu options all made with love.
- Paglione Estate Winery – Valentine’s Day Wine Pairing Dinner – Romance the night, celebrate family or friendship, or simply treat yourself with a 4-course candlelit wine pairing dinner.
Dinner Dates Worth Dressing Up For
If Valentine’s Day had a love language, it might be: reservations made in advance. Treat your special someone to a memorable meal at one of these local favourites:
- Maiden Lane Wine & Cocktail Bar – With a creative seasonal cocktail menu and an extensive wine list curated by passionate hosts, you and your partner can sip on beautifully balanced beverages while enjoying relaxed conversation and romantic vibes.
- Sawyer’s Craft BBQ – Reserve you space for Steak & Date nights February 13th and February 14th! Three seating times available for dinner for two and 30% off all bottles of wine.
- River Room Restaurant – Book your table now and indulge in a romantic evening with exquisite cuisine and enchanting ambience and live music.
- Gladstone Commons – will be featuring a 4 course Lover’s Prix Fixe for you and that special someone! They’re spreading the love and the special Valentine’s Day menu will be running Friday(13th), Saturday(14th) AND Sunday(15th).
- Antonino’s Original Pizza – it’s time for everyone’s favourite Valentine’s Day tradition: heart-shaped pizzas! The perfect time to treat yourself to a delicious and on-theme treat all while supporting a great cause.
Remember to make reservations early. Valentine’s Day tables book up fast, and nothing kills the romance like a long wait.
You’ll find even more date-night inspiration in our Valentine’s Day Guide.
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Music, Shows & Date-Night Entertainment
Add a little culture to your celebration with a show or concert:
- Celebrate a couple of days early by experiencing the legendary sounds of The Beatles with ultimate tribute band, The Fab Four live for an ALL AGES show on Thursday February 12th at The Colosseum at Caesars Windsor
- Make your Valentine’s Day date night unforgettable with an evening at the Windsor Symphony Orchestra’s “Lee Siegel Sings Broadway” concert on February 14th at the historic Capitol Theatre. Featuring dynamic Broadway favorites performed by acclaimed vocalist Lee Siegel alongside students from the St. Clair College Music Theatre program, this two-hour show blends passion, theatre-style energy, and live orchestral magic—perfect for sharing a cultured, romantic night together.
- Dinner and a Show: Pretty Woman — a perfectly paired evening of romance and nostalgia! Start the night with a three-course plated dinner in the elegant skyline ballroom before moving into the Chrysler Theatre to watch the classic love story on the big screen.
- Take a trip back to the golden age of rock ‘n’ roll with The Dreamboats—a high-energy quartet breathing new life into the sounds of the 1950s and ’60s. The Dreamboats deliver an electrifying live show that blends vintage charm with youthful swagger. Friday February 13th at the Chrysler Theatre.
There’s something magical about sharing a live performance together, whether it’s music, theatre, or comedy.
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Winter Fun for Two PLUS family-friendly fun
Lean into the season with:
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Turn a winter skate into a Valentine’s Day memory with a skate-date (or family skate day!). The City Hall Square Ice Rink, where the lively atmosphere, twinkling lights, and convenient skate rentals make it an easy and fun stop for couples or families with kids. Or take things at a slower, more scenic pace at The Loop at LaSalle Landing, a beautiful waterfront skating trail that feels downright magical in the winter. Whether you’re holding hands, pushing a skating aid, or laughing through a few wobbly laps, it’s a perfect way to enjoy Valentine’s Day together.
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Celebrate Valentine’s Day with a splash of fun at Adventure Bay Family Water Park — the perfect way to turn your day of love into an unforgettable adventure!
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Celebrate Valentine’s Day with a day of color, beauty, and sunshine at Colasanti’s Tropical Gardens — a romantic escape that feels like a mini-adventure together. Wander hand-in-hand through lush gardens, enjoy cozy moments in vibrant greenhouses, and treat your sweetheart(s) to fresh local eats and sweet treats (donuts!) along the way.
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For a Valentine’s Day that feels peaceful, profound, and perfectly memorable, consider a nature-filled escape to Point Pelee National Park, Ojibway Park, or Holiday Beach or any of the parks and trails that enhance our region. Each one offers a refreshing way to connect with your special someone(s). Whether you’re strolling shorelines, watching birds in flight, or sharing quiet moments among towering trees and open skies, these scenic spots invite you to slow down, breathe deep, and enjoy the kind of togetherness only the great outdoors can inspire.
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Make Valentine’s Day extra cozy and fun by stopping by the S’mores & Cocoa Festival at WindsorEats Food Hall! This free, festive event is all about gooey s’mores, rich hot cocoa, and warm vibes—perfect for couples, friends, or families looking to share sweet treats and snuggle up around fire pits while you sip and savor together.
Cold hands, warm hearts, right?
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Thoughtful Valentine’s Day Gift Ideas
The best gifts don’t have to be flashy. Thoughtful, meaningful, and personal always win.
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Looking for a Valentine’s Day gift that’s thoughtful, fun, and actually used? The Barrels Bottles and Brews Flight Log is a unique and unforgettable present for the beer lover, and craft beverage explorer in your life. Plan “flight dates” where you both taste new brews, compare notes, and reminisce about favourites. Whether they’re a seasoned connoisseur or just enjoy trying something new, the Barrels Bottles and Brews Flight Log is a gift that keeps delighting long after Valentine’s Day. The best love stories are filled with good times and great drinks.
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Valentine’s Day is just around the corner, and our W.E. Made It program is here to help you find the perfect, most unique, made-with-love gift for that special someone in your life. From handcrafted jewelry to indulgent local treats, shopping W.E. Made It means supporting local makers while giving a gift that truly comes from the heart. Head to yqgmade.ca to start your shopping today. W.E. Made It is your exploration guide to the hundreds of creatives that design, stitch, build and brew amazing products here in Windsor Essex. Shop local and support the businesses that embody our region’s true creative spirit. Discover locally crafted products like pottery, jewellery, apparel, art and furniture – or sip & savour with locally created culinary delights to enjoy at home as well as local coffee, teas, wine, beer and spirits.
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Get ready for Valentine’s Day with What’s Poppin’ Popcorn Factory’s Lovestruck pink and red kettlecorn. Single serving bags are perfect for a little addition to a box of chocolates or diamonds!
You’ll find even more thoughtful gift ideas inside our Valentine’s Day Guide.
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Plan a Valentine’s Day Getaway
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Looking for the perfect Valentine’s Day idea? Book the Valentine’s Day package at Hyatt Place Windsor and surprise your loved one with a stylish overnight retreat, complimentary dessert and late checkout, comfy accommodations and easy access to romantic Windsor Essex activities — making it a stress-free celebration you’ll both remember.
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Treat your love to a unique Valentine’s weekend escape at Lungovita Beach Retreat. Unwind together in a cozy geodesic dome, soak in lake-view hot tubs, relax in cedar saunas, and enjoy peaceful strolls along Lake Erie for the perfect mix of romance and rejuvenation.
Even planning the trip together can feel like a date!
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Self-Love Valentine’s Day Ideas
Memories last longer than chocolates (though we love those too). Consider gifting or enjoying an experience from:
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Celebrate Valentine’s Day with a playful, hands-on pottery experience at SKETCH Clay + Pottery
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Explore partner stretches and massage at Estate of Health
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A peaceful visit to the Art Windsor Essex, Museum Windsor – Chimczuk Museum or Leamington Arts Centre
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Plan a unique and rejuvenating Valentine’s Day weekend getaway to Wilderness Retreat and Nordic Spa, where you can unwind in your own private Nordic spa cabin surrounded by tranquil forest.
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Sweet Treats to Share (or Keep for Yourself)
No Valentine’s Day is complete without something sweet. Luckily, we’re spoiled for choice:
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Iron Kettle Commissary – Cozy comfort treats made for sharing.
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Lakeside Bakery Deli Cafe – Sweet, small-town baked-with-love indulgences.
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The Twisted Apron – Elevated flavours for a sweet Valentine’s splurge.
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Cookie Bar – Decadent cookies your Valentine will adore.
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Evelyn’s Candy House – Beautiful sweets made to impress your sweetheart.
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Walker’s Fine Candies – Timeless chocolatey treats for classic romance.
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Ruscom North Shore Maple Farms – Naturally sweet maple gifts straight from the farm.
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Hawksview Honey – Local honey for a truly sweet Valentine.
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Café Amor – Coffee, treats, and love in every bite.
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Red Lantern Coffee Co. – Handcrafted beverages and pastry made in-house.
Pick up a box to share, create a dessert crawl, or enjoy a quiet moment with your favourite treat and a hot drink.
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Enter Our Valentine’s Day Contest
Just in time for Valentine’s Day we have your chance to win a DELUXE Valentine’s prize package valued at $350, packed with swoon-worthy, locally made goodies from our W.E. Made It Partners. Shop local, gift with love, and make this Valentine’s Day unforgettable.
Enter TODAY and enter DAILY for your chance to win our W.E. Made It Valentine’s Day of Love Giveaway! Contest will close on Sunday, February 8th.
Plan Your Perfect Valentine’s Day with Our Guide
No matter how you choose to celebrate, planning ahead makes all the difference. Our Valentine’s Day Guide is filled with even more ideas, local spots, and inspiration to help you create a day that feels personal, joyful, and stress-free.
From romantic dates and thoughtful gifts to self-care and sweet treats, everything you need is in one place. Happy Valentine’s Day!
