Winter Garden, FL

Great spot to see the sunset. Grab a bottle of wine and to go dinner.

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Photo by Jon Burket Photography

Tim’s Wine Market
Windermere, FL

Feb 6

4 - 8PM

$5 glasses of wine, barkuterie & charcuterie, Woofie’s Mobile Grooming Van services, and a photographer doing on-site mini-sessions for $20 - Valentines themed photos with your pup! Sip, pamper, & celebrate puppy love.

Southern Hills Farms
Clermont, FL

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Feb 13 

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Ditch the hustle and bustle of your typical Valentine’s Day plans and join us for a romantic evening at Southern Hill Farms! Experience the beauty of our sunflower fields, enjoy a romantic movie under the stars and create lifelong memories with your special someone.​

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$39.95 per person

Swalty Sisters

Winter Garden, FL
 

Feb 14
10 - 4PM 

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Drinks, Refreshments, and giveaways!​​

Home State Brewing

Winter Garden, FL
 

Feb 15

11:30AM

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90-minute, all-levels class for anyone looking to meet new people, make new friends, and maybe share a laugh.

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$20 per person

Winter Garden, FL

A great place to learn about the history of Winter Garden

Winter Garden, FL

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Bike Rental  via Wheel Works.

Southern Hill Farms
Clermont, FL

Feb 7

9AM

 Where wellness meets Galentine's!

Join us for a Sculpt Galentine’s workout at Southern Hill!

Think: a feel-good barre class, then stay and sip + snack with some of our favorite local vendors – permanent jewelry, fresh sourdough, açaí bowls, and charcuterie to name a few - and of course Southern Hill strawberries 

Grab your girls + a yoga mat, make a morning of it, and celebrate strength, movement, and friendship.

Spots are limited – grab yours now.

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$15 entry

FREE for PB members

Gymnastic USA
Winter Garden, FL

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Feb 14
5 - 9PM

Parents Night Out allows you to have some "me or us time" while the children have a blast! Enjoy dinner and a movie while the children enjoy pizza and cartwheels (not at the same time of course!).
 

Members: $34.00
Non Members: $40.00
Siblings $24.00
Day of Drop Ins: $45.00

5K + Kids Races

Southern Hills Farms
Clermont, FL
 

Feb 14

8AM

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This will be the sweetest race you’ve ever run! Join us for a Valentine’s Day themed 5K featuring your favorite sweet treat - chocolate!

All 5K participants will receive a chip timed race, t-shirt, finishers medal and sweet treats at the finish line!
 

Kids race will include a race medal and bib plus some fun Valentines Chocolate treats!

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$40 per person

Winter Garden, FL

Sundays

12 PM, 1 PM, 2 PM, 

3 PM, 4 PM

$5 includes a free 9 oz pour

Clermont, FL

Feb 13-15

During Wine Fest enjoy full range of award-winning table wines, from dry to sweet. Local Artists and Crafters display their work. Enjoy live music on our outdoor stage. Lakeridge wine, beer, soft drinks and a variety of food is available for purchase, along with Winery tours and tastings.

Tours & Tasting
Monday-Saturday 10- 5PM
Sundays 11- 5PM

Winter Garden, FL

Enjoy learning bout history of railroading in Central Florida 

Call us Feb 9-16 to redeem

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4 weeks free couching membership! Just mention this Valentine's Guide.

West Orange Dream Center
Winter Garden, FL

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Feb 14
12 - 4PM

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Sweet Valentine’s celebration where love, inclusion, and connection come together. ASL Valentine Family Day welcomes Deaf, signing, and disability-inclusive families for a joyful time filled with activities, signing, and community.

Home State Brewing

Winter Garden, FL
 

Feb 15

10AM

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Come bend, balance, laugh, and flow together in a playful partner-style yoga class designed to connect. Open to all pairs- romantic or not! No experience necessary! Just bring a mat, a buddy (or not!), and an open heart

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$10 per person

Winter Garden, FL

Tuesday-Friday: 11–5PM

Saturday 10-4PM

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See local art from 

paintings to sculptures

Winter Garden, FL

Thursdays Singers Open Mic 7-10

Fridays and Saturdays Live Music 8-11

Sundays Jazz Jam 5-8

Order food and drinks while enjoying a variety of talent.