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Peacocks, Presidents and Puzzles - The Winter Park Walking Tour + Boat Tour

Original Orlando Tours

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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!

About This Deal

This is a typical itinerary for this product

Stop At: 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.

Duration: 1 hour 30 minutes

Stop At: 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!

Duration: 1 hour

Additional Information

  • Confirmation will be received at time of booking
  • Infants must sit on laps
  • Not recommended for travelers with back problems
  • No heart problems or other serious medical conditions
  • Not recommended for pregnant travelers
  • Near public transportation
  • Stroller accessible
  • Surfaces are wheelchair accessible
  • Transportation is wheelchair accessible
  • Wheelchair accessible
  • Most travelers can participate
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 30 travelers
  • Face masks provided for travelers
  • Hand sanitizer available to travelers and staff
  • Paid stay-at-home policy for staff with symptoms
  • 90 Minute Guided VIP Tour of Key Locations in Winter Park.
  • Fun facts about the buildings, historical figures and celebrity connections to Winter Park.
  • Travel the lakes and canals of Winter Park to view magnificent mansions and local sites.
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days).
  • Earn Sunny Perks Reward Points for gift cards or other discounts.
  • Entry/Admission - Scenic Boat Tour

  • Gratuities

3 hours 15 minutes

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

Voucher Info
You can present either a paper or an electronic voucher for this activity.

The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Original Orlando Tours in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.

This offer is not eligible for promo codes.

Fine Print

  • Voucher valid only for date and time listed; may not be exchanged or redeemed for other dates.
  • Purchaser name and phone number must be provided at checkout; this information will be shared with Viator and the tour operator for purposes of order fulfillment.
  • Groupon promo codes may not be used for this offer. Groupon voucher Terms of Sale and Extraordinary Event Policy do not apply.
  • See Viator voucher terms under "Viator Vouchers" here.
  • Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts.