BlogJanuary 2023

How to Plan a Boat Trip in Winter Park FL

How to Plan a Boat Trip in Winter Park FL

By Debbie Hanson

Jan 19, 2023

Basic information that covers how to plan a boat trip Winter Park, FL. Boating on Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, launch access

Winter Park is a city close to Orlando, Florida that is known for family freshwater fishing and boating opportunities. If you’re wondering how to plan a boat trip in Winter Park FL, you’ll find it easier if you learn a little about the four most popular and accessible lakes in the Winter Park Chain of Lakes.

While there are six lakes total in the Winter Park chain, the best lakes based on access are Lake Virginia, Lake Mizell, Lake Osceola, and Lake Maitland. Certain lakes are better suited for different types of boating or paddlesports than others and only boats under 21-feet are permitted (except for pontoon boats and sail boats, which shall not exceed 24 feet) on the Winter Park Chain, so this basic information about four of the lakes in the Winter Park Chain of Lakes can help you plan your Winter Park FL boat trip.


Lake Virginia

Lake Virginia is a 223-acre lake that is best known for water skiing and watersports. Public boat ramp access to the lake is from Dinky Dock at Ollie Avenue. Dinky Dock Park (situated on Lake Virginia’s shoreline) provides the ideal spot for an afternoon family picnic and for families to fish from the pier. Lake Virginia is known being home to some of Winter Park’s most famous historical homes and estates. If you search “boat trip Winter Park” online, you’ll also find scenic boat and kayak tours that depart from Lake Virginia and take area visitors through a few of the largest lakes in the Winter Park Chain of Lakes.


Lake Mizell

Since 62-acre Lake Mizell is much smaller and quieter than Lake Virginia, it’s the ideal lake for planning a paddling trip. If your favorite type of boating is kayaking or canoeing, Lake Mizell is a good place to do it. There is no direct access to Lake Mizell, but you can launch a kayak or canoe at Dinky Dock on Lake Virginia and make the short paddle over to Lake Mizell if you want to take in the lush scenery, private homes, and historic estates. If you want to fish from your kayak, you can target largemouth bass while fishing on Lake Mizell.


Lake Osceola

Lake Osceola covers 156 acres and is located just two blocks from Park Avenue in downtown Winter Park. For those who want a scenic Winter Park boat trip, there are boat tours that operate from this lake and take visitors through the three of the largest lakes in the Winter Park Chain to catch glimpses of the Albin Polasek Museum and Sculpture Garden from the water. Boating access to Lake Osceola is provided by the ramp at Dinky Dock Park. If you decide to plan on paddling trip on Lake Osceola, be aware of the tour boats as you navigate through the canals.


Lake Maitland

As the largest of the lakes in the chain at 449 acres, Lake Maitland spans portions of Winter Park and Maitland to the north. There is a series of canals that connect Lake Maitland to Lake Virginia and Lake Osceola. Lake Maitland is one of the most popular lakes in the Winter Park Chain for boating and watersports; however, the Fort Maitland Park public boat ramp is currently being renovated, so check with the City of Winter Park or a “plan my boat trip” app before trailering your boat to Lake Maitland.


Permits are required for all boats on the Winter Park Chain (available through Winter Park City Hall and the Winter Park Library). Before planning any boat trip, it is always a good idea to check a boat trip planning app. Boat trip planning apps can provide you with updated information on boat ramp access, lake depth, and navigation hazards to be aware of.

Debbie Hanson
Debbie Hanson
Debbie Hanson is an award-winning outdoor writer, women’s sport fishing advocate, IGFA world record holder, and freshwater guide living in Southwest Florida. Hanson’s written work has appeared in publications such as Florida Game & Fish Magazine, BoatUS Magazine, and USA Today Hunt & Fish. To learn more about her work, visit or follow her on Instagram @shefishes2.