Waterway Adventures: Exploring Winter Park Chain of Lakes by Paddle
- Savvy Single Mama
- Nov 13
- 8 min read
Updated: 18 minutes ago
If you’re looking for a fun, affordable day outdoors that your whole family will love, grab your kayaks, or couple of paddle boards and head to the Winter Park's Chain of Lakes. Just a short drive north from Orlando, this series of peaceful, connected lakes is perfect for beginner kayakers and paddleboarders — calm water, friendly locals, and plenty of wildlife to keep us entertained and inspired. Waterway Adventures give a different perspective than those on land. Exploring picturesque lakes separated by canals that go under bridges and through tree tunnels will make you feel rainforest delight!
See the map below to help navigate. All underlined text will link to that website. I am not in affiliation with any of these businesses, just sharing for your planning purposes.
Chain of Lakes? 🔗🔗🔗
Because Central Florida is dotted with several lakes that connect, let's clarify which chain we are focusing on here. Warning, Chat GPT and online searches may send you all over. This one connects Lakes Osceola, Virginia, Mizell, Minnehaha, Nina and Maitland. This is where you'll find the ever-photographed Venetian Canal. It's a specific set of Lakes that connect and create this vibe of nature meets a foreign escape!
Note: The Winter Park Chain of Lakes is made up of 20 - 25 interconnected Lakes where more water sports take place. This is not the Chain I am referring to today.
We launched from Dinky Dock Park, one of the easiest (and free!) places to park and get on the water, and spent the day exploring hidden canals, spotting turtles, and soaking in the sunshine — all without spending more than a tank of gas. Don’t own your own water vessels? That’s okay, I’ll share how to rent some to make this budget day trip easy and fun!
While we did this adventure as a girls day out, this is a great family fun day as well. This will help you plan and adapt to meet the needs of your crew. It could as easily be done solo! Strong swimmers recommended as the water can be deep in certain areas!
Details:
When wandering, it’s still good to know the logistics, and be aware of your surroundings.
*Distance: Varies. 3 miles between Dinky Dock in Winter Park and Fort Maitland in Maitland. At any time, you can reverse your trail and double back to return to your starting point. These are the two public parking sites with launches. Expect a 6-mile round trip if you are going all the way through, and back.
Dinky Dock has restrooms, a fishing dock, small beach area, picnic tables and grills.
The Winter Park Scenic Boat Tour is a popular choice for visitors, or those who don’t have access to a water vessel. Scenic narrow canals connect the lakes. When the boats come through the canals, there is a very tight squeeze. For this reason, increased boat traffic, there are less people finding this as a viable day trip.
If you are up to the adventure, and ready to pull into small dock areas or back up if a larger boat comes through while you are rolling through, plan this day!
🌿 Paddling Through the Chain of Lakes: My Day Paddling the Winter Park Waterways
There’s something magical about being on the water before the rest of the world wakes up. The air is cool and soft, the surface of the lake still like glass, and the only sounds are the gentle dip of your paddle and the distant call of an egret. That’s exactly how my morning started on the Chain of Lakes near Winter Park, a stretch of connected waterways that feels like stepping into a slower, wilder Florida.
☀️ Setting Out from Dinky Dock Park
We launched from Dinky Dock Park on Lake Virginia in Winter Park. The mist still clung to the edges of Lake Virginia, and the water reflected the pink and gold of the sky like a mirror. There’s a small dock here that’s perfect for kayaks and paddleboards, and the view alone is worth waking up early for. We actually just walked our boards in along the grassy edges. We arrived early, and snagged the last two parking spots in the smaller lot. There was a party setting up for a family barbeque, so I strongly recommend arriving early.
Two of us blew up our inflatable boards lakeside we could hear the soft hum of morning — fish jumping, ospreys calling overhead, and the gentle lap of water against my board. One of us bought over the hard board, and we were all ready fairly quickly. The lake is huge, but that early morning, it felt completely ours. We didn’t see many other people out on the water at first. Later we’d see the tour boats cutting through canals, jetskiis, tons of kayakers and even more on boards.
Fern Canal leads to Lake Osceola. This is a lovely introduction to the waterways.
Venetian Canal connects Lake Osceola with Lake Maitland which is the longest canal.
In Lake Maitland there’s a park with azalea gardens where weddings are held. We passed a wedding party taking gorgeous photos on our ride. We actually pulled off into the shade of the larger trees and sat just relaxing for a bit here.
A canal off Lake Maitland runs into Lake Nina, which is the smallest of the Lakes.
The next canal takes you by a bike trail (part of the Maitland Bike Route) and goes into Lake Minnehaha.
🌾 Through the Canals and Cypress
What makes this area so special isn’t just the lakes themselves — it’s the canals that connect them. As you glide through, the world changes around you. The open water gives way to winding, shaded passages lined with aged cypress trees draped in Spanish moss. The light filters through the branches, turning everything a soft, green-gold glow.
We passed by a family of turtles sunning themselves on a log, and a great blue heron took off right beside me, its wings nearly brushing the water. It’s quiet here, but not silent — the kind of quiet that hums with life. We found all of nature to be in bloom in April and the weather was very cooperative! (Florida can be known for Afternoon thunderstorms and excessive heat).
You will see a lot of wildlife! And some yard/ tree decorations as well!
🦩 Wildlife Around Every Corner
If you love wildlife, this area is pure paradise. I spotted ospreys, egrets, herons, and other fun birds. I did not see gators but know there are a few curious alligators lounging in the distance. Reminder to keep your distance and your hands in/ on your own vessel! I could’ve spent hours there just floating and watching the sky.
At one point, a soft breeze rippled through the water lilies, sending their white blooms dancing like tiny boats. Moments like that make you forget how close you are to busy towns — it feels like pure, untouched Florida.
🧺 A Pause and a Picnic
You could pull ashore at Kraft Azalea Park in Lake Maitland to stretch your legs and grab a snack. It’s shaded, peaceful, and has picnic tables right by the water. If you’re planning your own paddle, this is a great halfway point to rest, refill your water, or just soak up the scenery.
🍽️ Ending the Day in Winter Park
You are centrally located to take a short drive to a cute downtown area. A variety of restaurants, cafes, and eateries await!
After a few hours exploring, we headed back toward Winter Park, tired but happy — the good kind of tired that comes from sun and water and miles of paddling. We packed up and drove into town for lunch at BoVine Steak House where we just drove down Park Ave, found a place to park and walked around. We all wanted real food after working up an appetite paddling, and sat outside with a nice cold drink and downtown vibe.
The historic downtown is full of charm — brick streets, bike paths, and cheerful locals who don’t seem surprised to see someone wander in with saltwater hair and a sunburned smile. This is a cute area with pretty parks, tree lined streets, shops and lots of outdoor markets.
💬 Why I’ll Be Back
Kayaking the Winter Park Chain of Lakes is more than just a day trip — it’s a reminder that Florida’s beauty isn’t only found on beaches or theme parks. Out here, surrounded by water and wildness, you get a glimpse of the state as it once was — peaceful, untamed, and full of quiet wonder.
Our friend Jen, who was with us, has been coming been for years and led the way for us! Next time we return, I'll be better directed having done this the first time. The first time always helps you get your bearings and figure out your place in space, then see what you could or would do differently next time. Hopefully, this helps make your day easier to plan!
🚣♀️ “When You Go”
Best Time to Visit: Go early in the morning (to secure parking) or late afternoon for calm water and cooler temps. Spring and fall offer ideal weather, but warm days make this a year-round family outing. We went in April, and found the perfect Florida Day for this adventure.
Launch Spots:
Dinky Dock Park – 410 Ollie Avenue, Winter Park, Fl 32789 - Family-friendly, with free parking, restrooms, and a gentle sandy launch. Perfect for beginners or anyone bringing kids.
Fort Maitland Park – 900 S. Orlando Ave, Maitland Fl 32751- Parking fee paid by online system by scanning QR codes posted.
Don't have a paddle board or kayak? Peace of Mind Kayaks rents boards, connect with James at 407-733-8338.
Want to go with a tour group?
Get Up And Go Kayaking leads guided tours with clear kayaks for fun exploring with a guide.
~Wherever your travels take you, be sure to keep your presence in the moment.
~Nature is healing, grounding and living. Tune in.
~Enjoy where you are.
~Be a little flexible with people and their navigation of time.
~Let go of things you can't control.
~Remember to put your people above things, and cherish the memories.
~Do things that will make you proud of yourself when you remember the scenario.
~Live more, in abundance and walk in your own footsteps.
~Breathe fresh air, feel the flow of water, and find your own level.
I specialize in helping families and individuals spend more time enjoying their quality time and less time having to figure it all out. My four children have been my test subjects of how to plan a great adventure for many years and now that my youngest is 21, many of my travels are work related, or grandma related! As time has changed, I've evolved but I still LOVE TO TRAVEL, explore, wander, visit, discover, learn and love. If nature is there, I can find my happy place. I use the term single not to emphasize my status but to signify that if I can manage some family fun on a limited teacher's salary with four children, anyone can do it. I am very intentional in how I spend my time and earnings. I typically seek out budget friendly ways to enjoy my time, but will occasionally splurge for the right reasons :-)
Happy Travels!!
God Bless every road you travel on. xo
Mz. Savvy
A note from the editor:
The information in this article was accurate when published but may change without notice. Confirm details when planning your trip. I hope this makes it easier for your planning process.
Thank you for stopping by today! Please share your thoughts and experiences, we are all on this journey to live and love together. I welcome your travel tips & tricks :-)
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