Date night ideas in Winter Garden

Guest post with the City of Winter Garden

No matter how long you have been a couple, it’s been said that the most memorable Valentine’s Day gift is time spent together.

Historic downtown Winter Garden has a number of romantic ways to celebrate the occasion to create a lasting impression. Here are the best date night ideas Winter Garden has to offer couples.

Date night ideas in Winter Garden: image of a couple hugging in historic downtown Winter Garden near Orlando

Visit Historic Winter Garden for a romantic evening. Image: Cricket’s Photo & Cinema

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DATE NIGHT IDEAS
DOWNTOWN WINTER GARDEN

Take a Horse-Drawn Carriage Tour
February, 12, 13 & 14, 6pm – 10pm
Nothing is more romantic than a carriage ride under the stars and twinkling lights. 20-minute tours depart at Downtown Pavilion, 104 S. Lakeview Ave. Make reservations in advance.

Watch a Romantic Movie at the Garden Theatre
Sunday, February 14 at 6:30 pm
Garden Theatre, 160 W. Plant St.
The ultimate romance movie, Casablanca, has a special showing on Valentine’s Day. What better way to watch the classic than surrounded by the elegance of the historic single screen cinema. Limited tickets available for advance purchase.

Visit your Local Brewery…Aphrodisiac Ale on Tap
Crooked Can Brewing Company, 426 W. Plant St.
Sample a selection of local brews, including holiday special release aphrodisiac ale “Barrel Aged Cherry Cheeks,” and compare favorites. Relax to the live music in the outdoor patio on select days. Take a Brewery Tour for a sneak peek at the fermenting process, offered hourly, 12pm – 4pm on Feb. 14 (advance reservations required).

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Date night ideas: image of downtown entrance with bike trails and brick lined streets in downtown Winter Garden

Welcome to Winter Garden. Image: @officaldowntownwintergarden

Take a Romantic Stroll
February 12, 13, and 14
Enjoy the sights and sounds of Valentine’s Day while strolling through the twinkle-lit tree-lined tunnel of love path while marveling at majestic City Hall lit-up red and stop by the Splash Pad lit up purple for the holiday. While strolling, hum along to the romantic tunes broadcasted through the streets, perhaps even prompting a serenade.

Visit Your Local Bookstore
Writer’s Block Bookstore, 32 W. Plant St.
Head over to the new local independent bookstore, Writer’s Block Bookstore, to pick up a secret wrapped book with a clue to see if this blind date is a perfect match. Or play matchmaker for friends to gift a fun surprise!

Browsing a bookstore is also a fun date activity. Select a book to read together (perhaps a romance novel), and take turns reading each other passages. While there, pick up a fun trivia or board game to play at home.

Go for a Bike Ride
February 12-14
Winter Garden Wheel Works, 101 W. Plant St.
Perfect weather and the West Orange Trail, which runs through quaint downtown, are the perfect combo for a great date activity. Special offer of “Two-for-One Bike Rentals” at Winter Garden Trailhead or discount on purchase of tandem bike.

Go out to Dinner
Spend time reconnecting over dinner, enjoying your favorites or trying something new. Downtown restaurant offerings run the gamut from multi-course prix fixe dinners, artfully created cuisine, and steak houses, to pizza parlors, burger joints, and delis. Eat in, or on expansive outdoor patios, or take to-go for home or a picnic.

Indulge in Chocolate & Dessert
It wouldn’t be Valentine’s Day without chocolate and sweets and Downtown’s chocolate shops, bakeries, coffee houses and ice cream and custard parlors are the perfect places to indulge. Options available for all dietary preferences, plus even treats for your furry friends. Here is a list of sweet shops in Winter Garden.

Make a Toast over Drinks
Although this Valentine’s Day will look different from the last, take a moment to toast to having each other during some trying times with custom crafted cocktails, beer, wine or your favorite beverage. Enjoy drinks indoors or at outdoor patios under the stars, or even take your beverages to go for a private celebration at home. Check out this list of complete list of drink venue options in Winter Garden.

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Go Shopping with Your Special Someone for Something Special
Shop hand-in-hand along the charming historic streets and pop in the one-of-a-kind shops to select the special something for your special someone. The unique boutiques and stores are ideal for finding the perfect gift, including fine jewelry, chocolates, fresh flowers, apparel, home décor and furniture, and so much more. Here is a complete list of shopping options in Winter Garden. v

The array of date ideas all within historic downtown Winter Garden make it easy to check all Top 10 off your list to truly make this Valentine’s Day memorable. Since small businesses are the heart of downtown, visiting these shops and restaurants during Valentine’s Day weekend supports “Love Local,” a campaign initiated by the City of Winter Garden to help local businesses affected by the pandemic, so why not spread your love this Valentine’s Day.

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