Old World Winter Park with Boat Tour

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Tour Overview

You’ll marvel at how a touch of Europe and old Southern elegance merge to form the Orlando suburban village of Winter Park during your visit with Original Orlando Tours!

Home and destination for celebrities of the arts, sports and politics over the ages, from Mister Rogers (yes, that Mister Rogers!) to FDR and Barack Obama, this little urban hamlet boasts some of the most expensive real estate in Florida, snuggled around quaint shops, cafes and fabulous restaurants.

You’ll see breath-taking mansions and local wildlife among natural settings as your tour starts with an hour-long guided cruise through two, narrow man-made canals and three of the seven lakes on the tranquil Winter Park chain.

Once your guided cruise has ended, you’ll be ushered to Park Avenue, the main street of Winter Park, to explore the village’s shops and cafes on your own, a destination for many of Orlando’s local residents looking to experience a bit of European cachet in Central Florida.

With a vast assortment of high-end boutiques and local cafes, Park Avenue will be a slice of Florida worth experiencing first hand!

Old World Winter Park with Boat Tour Includes:

  • Round-trip transportation from your hotel
  • Parking and admission ticket for a one hour boat tour and guided cruise of Winter Park
  • Shopping/Dining time on your own on Park Avenue
  • Assortment of cold drinks
  • Professional guide with local commentary
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days)
  • This Original Orlando Tours Explorer Tour includes an Orlando discount booklet for each guest
  • Confirmation will be sent within 48 hours of booking, subject to availability
  • A minimum of 3 people per booking is required
    • Children Ticket: 4-12
    • Adult Ticket: 13+
  • The minimum age of all our guests is 4 years old

Exclusions and Extras:

  • Lunch is not provided
  • Gratuities
  • This tour is not wheelchair accessible


Approximately 5 hours total. Please note that Orlando traffic conditions can vary widely while I-4 is under construction. This tour typically operates all year.

Cancellation Policy:

You may receive a full or partial refund by notifying us via email at info@originalorlando.com of the cancellation. No refunds shall be issued for cancellations not received at least 72 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:

The world famous “Temple” orange was discovered in Winter Park and developed in the surrounding groves. The original tree still stands on private property within the city. Mr. Rogers met fellow music student and his future wife, Sara Joanne Byrd, on the campus of Rollins College in Winter Park.


This tour is only offered in English. Florida weather is unpredictable and may impact the tour. If the tour boats are closed, a visit to the Winter Park History Museum, the Casa Feliz Historic Home and Venue, the Albert Polasek Museum or other activity may be substituted. If our guide deems weather conditions for this tour potentially unsafe due to weather conditions prior to commencement of the tour, Original Orlando Tours will offer a substitute tour at the original day and time, offer a credit to be used on any future Original Orlando Tours adventure, or fully refund the tour fee, the choice of which is at the option of our special guests impacted by the weather disruption. There are no refunds once the tour has commenced (i.e., the vehicle has left your departure point). This tour also includes an Orlando discount savings booklet. We suggest wearing a hat, comfortable shoes and sunscreen to make your tour an enjoyable one in warm months as well as a jacket in cooler weather.

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Not Available
Tour type: Daily Tour
Duration: 5 Hours
Maximum number of people: 12


100% of guests recommend

5 of 5 guest rating

based on 2 reviews

  • "Boat Tour Was Incredible"
    Incredible boat tour with scenic views - lots of fun
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  • The McCachlins

    1 Review
    "Thank you for a nice day!"
    Nice relaxing day. Victoria thank you for arranging the great weather for us too! 🙂
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