The Winter Park Old Fashioned Christmas Cruise

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Minimum purchase of 2

*12/28/20 Update* Our final sailing is on 12/31. Note that this leaves at 5:30PM.

Tour Overview

A new Orlando holiday tradition is born with the launch of The Winter Park Old Fashioned Christmas Cruise this December! Glide under the stars along the serene lakes and canals of world famous Winter Park while being immersed in the holiday spirit. Each sailing includes Christmas music and caroling, holiday trivia, and a reading of T’was the Night Before Christmas. Each guest also receives a gift bag with holiday treats, including a special item from ICON Park’s famous Shack Sweets Bakery!

Due to COVID, tours are very limited during this inaugural year and will sell out. All seats are $35; no discounts apply. Tours last approximately 90 minutes. Please check in by 6:15pm at the docks located at 312 East Morse Boulevard in Winter Park for loading. Cruises leave promptly at 6:30pm.

Tour Includes:

  • 80-Minute Nighttime Christmas Cruise Along the Canals and Lakes of Winter Park.
  • Christmas goodie-bags filled with treats and baked goods to be enjoyed by all.
  • A piping-hot cup of hot chocolate.
  • Christmas music, caroling, and trivia.
  • A beautiful reading of ‘The Night Before Christmas’ on the water.
  • Travel the lakes and canals of Winter Park to view magnificent mansions and local sites and see Christmas lights.
  • Children 6 and under must wear a life jacket on the boat.
  • Please reserve in advance.
  • Confirmations will be sent within 48 hours of booking, subject to availability.


The tour lasts approximately 80 Minutes.

Tours depart at 6:30pm SHARP from the Winter Park Scenic Boat Tour docks located at 312 E Morse Blvd, Winter Park, FL 32789. There is free parking around the docks and along the local streets in the area. If coming from the I-Drive or Orlando tourist zones, you may want to allow at least 45 minutes travel time depending on your departure location; check your GPS, Waze, Google Maps or other apps so you can be sure to join our tour in plenty of time.

This tour operates seasonally in December. Check the schedule on this page for exact details.

Please arrive at least 15 minutes before your scheduled tour to check in. There are no refunds or partial credits for guests who are late to the tour or no-shows. Tours depart regardless of weather!

Private and Large Groups:

A private tour (ten or more) can be designed for your group to deliver a customized, extraordinary evening! For groups of ten or more, please contact Sarah at or (407) 986-8687 to create your unforgettable visit!

Cancellation Policy:

You may receive a full or partial refund by notifying us via email at of the cancellation. No refunds shall be issued for cancellations not received at least 48 hours in advance of the starting time and date of your tour. Please review your Terms and Conditions document for other cancellation provisions.

Sunny’s Local Tips and Bits:

There are four towns named “Winter Park” in the United States. This one in Florida was the first. The other three are located in North Carolina, South Carolina and Colorado.


This tour is only offered in English. The majority of this tour is given on a boat over water and may not be suitable for all guests. Florida weather varies throughout the year, so you may want to check the forecast and plan to dress accordingly. We suggest wearing comfortable shoes and bringing an umbrella if there is a chance of rain. Consider bringing a jacket or windbreaker if the weather is chilly!

Not Available
Tour type: Specific Date
Maximum number of people: 15


100% of guests recommend

5 of 5 guest rating

based on 2 reviews

  • Caroline M

    1 Review
    "A Welcome New Holiday Tradition"
    My guests and I were on the 'pilot' cruise and I cannot overstate how much cheerful fun was created by this unique and new experience. In an otherwise depressed year, this is an amazing way to lighten the spirits and enter the holidays with a full heart. What made the night extra special was this immersive reading of Twas the Night Before Christmas and the little details put into making the experience special. This is a great new holiday tradition in Central Florida!
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  • Denise D

    1 Review
    "What a wonderful time we all had!!"
    What a wonderful time we all had!! The festivities were perfect!! Hot cocoa on a chilly night, trivia, carols, & good friends. And beautiful sights!! Thank you so much!! Merry Christmas ???????????????? Denise D & the rest of the group!!
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