Winter Park Historic Village and Scenic Boat Tour

Welcome to one of Florida’s best-kept secrets, the lovely city of Winter Park!
Chartered in 1887, Winter Park is more than 100 years old and has the pedigree to prove it. Home of the first college in Florida, host to multiple U.S. Presidents swapping the chills of Washington for a tropical paradise, and the southern magnet of many celebrity visitors, Winter Park has a rich history just waiting to be explored and discovered!

This tour will give you a look at Winter Park from street level as well as from the beautiful lakes and canals surrounding this historic village. Your guide will share the fascinating history of this southern resort town, and the stories of the celebrities who have passed through.

Then view the stunning mansions of past and current town leaders and natural wildlife as your view Winter Park its magical waterways.

Whether you are a visitor or a seasoned Central Floridian, you will have a great time while learning about the storied history of this beautiful hamlet!

Meeting Point

401 S Park Ave

401 S Park Ave, Winter Park, FL 32789, USA

Tours which depart after 5:00pm or on Sundays originate from the benches in front of the City of Winter Park Administrative Building, located at 401 South Park Avenue (southwest corner of South Park Avenue and West Lyman Avenue), Winter Park 32789.

151 W Lyman Ave

151 W Lyman Ave, Winter Park, FL 32789, USA

Tours departing before 5:00pm, Monday – Saturday meet in the lobby of the Winter Park Chamber of Commerce Building, located at 151 W Lyman Avenue, Winter Park 32789.

What's included:

• Fun facts about the buildings, historical figures and celebrity connections to Winter Park.
• 10% discount for your next Original Orlando Tours adventure (valid for 30 days).
• Earn Sunny Perks Reward Points for gift cards or other discounts.
• 90 Minute Guided VIP Tour of Key Locations in Winter Park.
• Travel the lakes and canals of Winter Park to view magnificent mansions and local sites.

What to expect:

Duration: 3 hours, 15 minutes

Winter Park

Winter Park, Florida

On this fascinating Winter Park history tour, you’ll learn why this picturesque village became (and still is!) a mecca for wealthy businessmen, politicians, celebrities and their families over the years, as you wander along with the shops, restaurants, and historic buildings along Park Avenue, the thriving center of town. Wandering under the treed canopies and passing European-styled cafés, we’ll recount the personal stories of this Central Florida treasure and share the intriguing history behind the walls you see.

1 hour, 30 minutes

Scenic Boat Tour

312 E Morse Blvd, Winter Park, FL 32789, USA

You’ll also enjoy a boat cruise on the Winter Park Scenic Boat Cruises as part of your visit where you’ll see awe-inspiring mansions and estates of past and current business leaders and celebrities, including many references to the people and stories that you heard on the land portion of the tour!

1 hour • Admission Ticket Included