WINTER PARK SUP FIELD GUIDE
Glide Winter Park: A Guided SUP through the Chain of Lakes
A two-hour, guided paddleboard tour launching from Dinky Dock that moves through Winter Park’s canals, waterfront homes and open lake views—essential prep for meeting point, duration, gear and participant rules.
Glide Winter Park: A Guided SUP through the Chain of Lakes.
Float under Florida skies as guides from Otter Paddle Orlando lead a relaxed, family-friendly paddle through Winter Park’s scenic lakes and lush canals. The POP UP SUP Guided Paddle Tour from Dinky Dock is paced for all levels, with on-land instruction, premium inflatable boards and continuous guide support so you can watch for wildlife, study waterfront homes and take in open-lake panoramas.
Highlights
Outing Highlights
Chain of Lakes & Quiet Canals
The guided outing threads peaceful canals into open-lake views, offering a gentle route past waterfront homes and habitats where wildlife is often visible.
Premium Inflatable Boards; Optional Kayaks
The operator supplies all equipment, including premium NIXY inflatable paddle boards and an optional kayak setup, so you can arrive ready to paddle without gear hassles.
Beginner-Friendly, Guide-Led
Each tour begins with a short on-land orientation and keeps guides alongside participants on the water, designed to build confidence for newcomers while remaining family-friendly.
What the day feels like
What the Outing Feels Like
Expect a relaxed, two-hour paddle led by expert guides: a brief land-side skills session, then steady progress through canals and across open water at a welcoming pace suitable for varied abilities, with guides staying nearby throughout the tour.
Suitability
Who it's for
Who this outing is for—and who should reconsider.
Practical planner
Details to review before reserving
The signature guided outing departs at 11:00 AM and runs approximately two hours.
All paddling equipment is included; participants should bring sun protection, a water bottle and any personal items they want on the water.
Meet at Dinky Dock Park, 410 Ollie Ave, Winter Park, FL 32789.
Advance reservations are recommended to secure a board; walk-up bookings are accepted while boards last.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
Are beginners welcome on the Winter Park Guided Tour?
Yes. The tour is designed for all levels and includes a short on-land overview before launching; guides remain with participants on the water.
How long is the tour?
The guided paddle is approximately two hours in duration.
Where do we meet the group?
The meeting location is Dinky Dock Park, 410 Ollie Ave, Winter Park, FL 32789.
Can I bring children?
Children are welcome provided they exceed the minimum age; minors aged 3 years and under are not permitted.
Can I bring my dog or other pets?
No—pets are not allowed on the tour.
Is alcohol or smoking allowed on the tour?
No—alcohol and smoking are not permitted during the outing.