The Winter Park Old Fashioned Christmas Cruise (Only Available Here!)

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Minimum purchase of 2

Tour Overview

Most bookings are currently filled at this time, if you do not see a slot for your booking please join the waitlist for updates on additional slots should they become available, as well as priority access to next years cruise bookings.

Experience an Orlando holiday tradition with 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 and The Christmas Story. Each guest also receives a gift bag with holiday treats, including a special treat from DOLCE restaurant baked by Master Baker Jillian Hopke from Holiday Wars on The Food Network.

Tours last approximately 80 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. $65 per person; no discounts, passes or certificates apply due to limited capacity.

Tour Includes:

  • 80-Minute Nighttime Christmas Cruise Along the Canals and Lakes of Winter Park.
  • Travel the lakes and canals of Winter Park to view magnificent mansions shining with dazzling Christmas lights!
  • A piping-hot cup of Italian supreme hot chocolate greets you upon arrival.
  • Your favorite Christmas carols to set the mood for the evening.
  • A beautiful reading of “T’was The Night Before Christmas’ and “The Christmas Story” while gliding along the serene waters.
  • Christmas trivia.
  • Christmas goodie-bags filled with treats and baked goods to be enjoyed by all.
  • Children 6 and under must wear a life jacket on the boat.

Upgrade to VIP!

VIP seating includes the unobstructed first row seating for the best pictures, gift certificates to a free 2021 or 2022 Original Orlando Tours Explorer Walking Tour (up to a $75 value each), and a special gift. There are only two VIP seats available for each sailing. VIP pricing is $99 per person.


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 can be designed for your group to deliver a customized, extraordinary evening! For group information, 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:

A Winter Park tradition for the beautiful homes along the 5 main Winter Park lakes is to decorate the backs of the house with lights for Christmas so that you can view these spectacular light displays from the water!


This tour is only offered in English. The majority of this tour is given on a boat over water and may not be suitable or accessible 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! Booking groups will attempt to be sat together, but due to capacity and vehicle layout groups may be split up.


100% of guests recommend

5 of 5 guest rating

based on 3 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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  • Kylie Evans

    1 Review
    "A "Must-Do" Tradition for Us!"
    This is our favorite Christmas tradition and for good reason! You sail on a modified pontoon boat along the Winter Park lakes where the mansions decorate their backyards. Meanwhile there is Christmas music playing on the boat with Christmas treats. The Christmas story and the Night Before Christmas are played, along with some trivia and some quiet time to just soak it all in. We had a delightful time and this is on our regular holiday list now. Splurge for the VIP seats if available on your boat for the front row and some great pictures!
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