Holiday Boat Parade Paddle & Toy Drive
Schedule
Sat Dec 13 2025 at 05:00 pm to 08:30 pm
UTC-05:00Location
Dinky Dock Park | Winter Park, FL

About this Event
All is merry and bright on our Holiday Boat Parade Paddle!
Sunset Meet and Greet: We'll meet at Dinky Dock Park at sunset to enjoy the gorgeous lake view from the oak-lined park with a white sandy beach. Your guide will assign you to quality and fitted stand up paddleboard gear and give a 10 min safety and paddling technique briefing on land.
Ugly Sweater Contest: Before we launch, you'll get a chance to walk the runway, showing off your ugliest Christmas sweater. The winner gets a $100 gift certificate for a Wave of Wellness Adventure Trip (including the Florida Springs Houseboat Adventure, Punta de Mita Adventure, or Maui Adventure)!
Toy Drive: We'll collect all toy donations for Toys for Tots, spreading joy to needy children during the holiday season. One toy gets you $10 off your entry (see ticket options below), but please bring as many as you want!
Paddle: Then we'll launch into Lake Virginia and paddle to the best viewing location for the Winter Park Boat Parade!
Boat Parade: From our up-close, floating VIP seats, we'll view the parade of brightly decorated boats, lighting up the night and reflecting off the water.
Tour of Lights: Following the parade, we'll paddle the shoreline for a close look at the festively-decorated estates surrounding the lake.
What's Included:
- 3-hour Guided Tour
- Boat Parade Viewing
- Ugly Sweater Contest - win a $100 gift certificate
- Toy Drive
- Stand Up Paddle Instruction
- Stand Up Paddleboard Rental Gear
- Tour Photos
- Paddle Tribe
- Holiday Glow Stick
Other Ticket Options:
- BYOPaddle Craft for a discount
Get $10 Off either entry when you choose the " & bring a toy" option.
Stand Up Paddle Skill Level: Beginner to Advanced - Instruction included, No Experience Necessary. Must know how to swim. Kids 12 years old and under may ride along with an experienced adult for free - please bring your child's life vest.
Paddle Distance: about 1.5 mi at a leisurely pace, including stops and breaks along the way.
Bring: Water, towel, snacks, dry change of clothes, beverages, toy for Toy Drive. If you're bringing your own paddle craft, a light, life vest and whistle are required by law. Holiday board decorations are highly encouraged!
Wear: Holiday apparel that is easy to move in and can get wet (like dry wicking workout clothes or swimwear). Ugly Christmas Sweaters encouraged for a chance to win our contest!
Parking: There is a parking lot at Dinky Dock Park. It usually fills up early on the weekends so overflow parking may be found in the garage just behind it toward Aloma Ave, or in the library parking lot across Aloma.
Time: Meet at 5p. Ugly Sweater Contest at 5:30p. Launch at 5:45p. The parking lot fills fast so arriving early is recommended. If bringing your own gear, please arrive as early as you need to prepare (especially inflatables).
IMPORTANT: In the event of inclement weather (rain/lightening/high winds), you will be notified of a reschedule via email at least 2 hours prior to your scheduled paddle. We only reschedule so that your SUP experience will be the most safe and enjoyable one possible!
Guide: Jessica Cichra is a SUP enthusiast that has been actively paddle touring, racing, surfing, and instructing since 2009. She is the founder of Wave of Wellness, a company with a mission to empower clients through adventurous activities that enhance all areas of well-being with a focus on travel, SUP, yoga, and community. Jessica guides paddle tours in Central Florida and internationally on adventure travel retreats.
Tips are highly appreciated if you believe your instruction, service, and experience to be exceptional!
*Due to the uncontrolled nature of our outdoor environment, our route and launch site/time are subject to change. We do our best to keep to our schedule but due to the pace of the group, our end time is subject change.









Where is it happening?
Dinky Dock Park, 410 Ollie Avenue, Winter Park, United StatesEvent Location & Nearby Stays:
USD 33.85 to USD 60.54
