Sights & Eats Walking Tours
Daycation Experiences
Group Tours
VIP Tours
Personal Tours by Locals
with Original Orlando Tours
At Original Orlando Tours, we believe that the magic of Orlando extends far beyond its famous theme parks. Beyond the theme parks, we offer immersive, locally guided tours to hidden gems and unique experiences in Central Florida. Our expert guides bring a wealth of knowledge and enthusiasm to every tour, transforming each experience into a captivating journey through Orlando’s most iconic and lesser-known sights.
From food tours that introduce you to the Central Florida area’s diverse culinary scene to historical walks that reveal our roots, we curate adventures for all ages and interests. Whether you’re a first-time visitor or a longtime resident, Original Orlando Tours offers something special for everyone. Join us, and discover the authentic Orlando that even the locals might not know exists!
Explore Central Florida
Arts / Culture / Winter Park
Embark on a Captivating Journey with the Winter Park Arts & Culture Walking Tour!
Price From:
$30.00
Price From:
$41.00
Explore food and fun with a guided tasting at several venues at ICON Park.
Price From:
$30.00
Take a bite out of the best of Winter Park and stroll down Park Avenue on our unique Flavors of Winter Park Foodie Walking Tour!
Price From:
$40.00
Welcome to our Winter Park neighborhood on this beautiful day!
Price From:
$24.00
Come along for a spooky tour through the old bricked streets of Winter Park.
Price From:
$10.00
Welcome to one of Florida’s best-kept secrets, the lovely city of Winter Park.
Price From:
$20.00
Private / Theme Park / VIP
Tour like a rock star(fish) and see all the best of SeaWorld Orlando in one day with your personal Original Orlando Tours VIP Private Guide!
Price From:
$475.00
Join us as we walk through the same streets as Fred and Joanne, see their sites and Florida home, and hear the heart-touching stories of a love affair for the ages which began and continued in beautiful Winter Park
Price From:
$20.00
Guest reviews
Rated 5 out of 5 stars. See what guests are saying.
Our Women’s Club traveled to Winter Park for our annual bus trip. Rich and his family owns Orlando Tours and provided a walking tour and a tour of the beautiful Tiffany museum- Morse Museum. Rich was easy to work with and was able to provide alternate plans when needed. It’s easy to book his tours and the communication was excellent. They have a great understanding of what visitors like and were quite helpful! We highly recommend Orlando Tours.
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Donna H.
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Donna H.
Our Women’s Club traveled to Winter Park for our annual bus trip. Rich and his family owns Orlando Tours and provided a walking tour and a tour of the beautiful Tiffany museum- Morse Museum. Rich was easy to work with and was able to provide alternate plans when needed. It’s easy to book his tours and the communication was excellent. They have a great understanding of what visitors like and were quite helpful! We highly recommend Orlando Tours.
I had a FANTASTIC time 4/25/26 on the Winter Park walking tour. Delicious food and the tour guides had great insight on the area. I will 100% do another tour in the future.
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Faith R.
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Faith R.
I had a FANTASTIC time 4/25/26 on the Winter Park walking tour. Delicious food and the tour guides had great insight on the area. I will 100% do another tour in the future.
The tour guides were knowledgeable. The walk was interesting and very doable. They were very organized and the next place was always ready for us. You did not get alot of food. We were still hungry at the end. ( We came hungry)read moreread less
Lyn W.
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Lyn W.
The tour guides were knowledgeable. The walk was interesting and very doable. They were very organized and the next place was always ready for us. You did not get alot of food. We were still hungry at the end. ( We came hungry)
Not having been a huge fan of Mr. Rogers, I was very pleasantly surprised by this tour. Our tour guide was extremely knowledgeable and brought a new understanding of the life of a man who was genius of his time! I would highly recommend taking this tour as it was very informative and gave me a new perspective on the life that Mr. Rogers led as well as the history of Winter Park.
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Ann D.
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Ann D.
Not having been a huge fan of Mr. Rogers, I was very pleasantly surprised by this tour. Our tour guide was extremely knowledgeable and brought a new understanding of the life of a man who was genius of his time! I would highly recommend taking this tour as it was very informative and gave me a new perspective on the life that Mr. Rogers led as well as the history of Winter Park.
We found this tour to be exceptional! It was a pleasant walk and the information that our guide had was incredible! The time went quickly because we were fascinated. We love Mr. Rogers and to see Winter Park in his context was great. The boat tour at the end through the canals was wonderful. I would recommend this to everybody visiting in the area.read moreread less
usnamom2001
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usnamom2001
We found this tour to be exceptional! It was a pleasant walk and the information that our guide had was incredible! The time went quickly because we were fascinated. We love Mr. Rogers and to see Winter Park in his context was great. The boat tour at the end through the canals was wonderful. I would recommend this to everybody visiting in the area.
Excellent tour - interesting stories and information set primarily on the beautiful Rollins campus. How could you not feel good after learning more about Fred Rogers?!
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Randi C.
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Randi C.
Excellent tour - interesting stories and information set primarily on the beautiful Rollins campus. How could you not feel good after learning more about Fred Rogers?!
We absolutely loved this tour. The food and drink stops were varied and all delicious. Each place did a quick talk about something about the food while we ate that was very interesting. Also the guide gave us brief overviews on Winter Park in between stops that was also interesting. Right amount of food, time and information. We’ll be back!!!read moreread less
EricNOrlando
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EricNOrlando
We absolutely loved this tour. The food and drink stops were varied and all delicious. Each place did a quick talk about something about the food while we ate that was very interesting. Also the guide gave us brief overviews on Winter Park in between stops that was also interesting. Right amount of food, time and information. We’ll be back!!!
Rich took us on the most amazing tour! He is a wealth of knowledge and provided personal anecdotes about Mr. Rogers and his family. We enjoyed every minute of this wonderful tour!read moreread less
Anne K.
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Anne K.
Rich took us on the most amazing tour! He is a wealth of knowledge and provided personal anecdotes about Mr. Rogers and his family. We enjoyed every minute of this wonderful tour!
We had a great tour of Winter Park, learned many things about the town and its history. The eating venues that we visited on the tour were well prepared and greeted the group very friendly. Throughout the tour the group exercised social distancing and wore masked where needed. The professionalism of the tour guides was exemplary. Will definitely join other tours that are offered.
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Nicholas G.
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Nicholas G.
We had a great tour of Winter Park, learned many things about the town and its history. The eating venues that we visited on the tour were well prepared and greeted the group very friendly. Throughout the tour the group exercised social distancing and wore masked where needed. The professionalism of the tour guides was exemplary. Will definitely join other tours that are offered.
Great experience, sampled several restaurants, food was good and customer service was excellent. Very professional!read moreread less
Paula A.
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Paula A.
Great experience, sampled several restaurants, food was good and customer service was excellent. Very professional!
I can't say enough about how cool this tour was for me and my friends. I wanted to book in advance but my plans weren't finalized. I was worried the tour would sell out but luckily we secured our spots. Booking was easy and fast. The tour guide is a local and they were so knowledgeable about the area. We learned a lot of interesting facts and stories about Winter Park, but the real highlight was trying all the delicious food!! OMG. Seriously great food. Like mouth watering food. And a great variety. My friend is gluten-free and the other has a nut allergy and both were accommodated by the venues, just tell the tour guide in advance. After the tour we decided to revisit one of the restaurants because our wristbands gave us a discount. This tour was a real gem and 10/10 would recommend.read moreread less
Janet M.
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Janet M.
I can't say enough about how cool this tour was for me and my friends. I wanted to book in advance but my plans weren't finalized. I was worried the tour would sell out but luckily we secured our spots. Booking was easy and fast. The tour guide is a local and they were so knowledgeable about the area. We learned a lot of interesting facts and stories about Winter Park, but the real highlight was trying all the delicious food!! OMG. Seriously great food. Like mouth watering food. And a great variety. My friend is gluten-free and the other has a nut allergy and both were accommodated by the venues, just tell the tour guide in advance. After the tour we decided to revisit one of the restaurants because our wristbands gave us a discount. This tour was a real gem and 10/10 would recommend.
Fabulous! Highly recommended. We will definitely be back to take advantage of another tour offering! Great value. Superlative hospitality. Fun & Entertaining.
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Sam H.
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Sam H.
Fabulous! Highly recommended. We will definitely be back to take advantage of another tour offering! Great value. Superlative hospitality. Fun & Entertaining.
The tour company, including Sarah, who was our guide, went out of their way to schedule a time that worked for my wife and I. She was super knowledgeable and shared lots of interesting and funny stories about Mr. Rogers, his life and the time he and his wife spent at Rollins College and elsewhere. It was just the right amount of walking. I would definitely encourage anyone who thinks they might be interested to visit both Rollins College and Winter Park. Both are beautiful.read moreread less
Brad K.
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Brad K.
The tour company, including Sarah, who was our guide, went out of their way to schedule a time that worked for my wife and I. She was super knowledgeable and shared lots of interesting and funny stories about Mr. Rogers, his life and the time he and his wife spent at Rollins College and elsewhere. It was just the right amount of walking. I would definitely encourage anyone who thinks they might be interested to visit both Rollins College and Winter Park. Both are beautiful.
We just went on the Flavors of Icon Park tour with our Fantastic tour guide, Jordan. We went to 4 different restaurants and Jordan gave us history and fun facts about each place. Each restaurant made everything from scratch and you could tell. Our last stop was a ride on the Icon Wheel!read moreread less
Mary D.
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Mary D.
We just went on the Flavors of Icon Park tour with our Fantastic tour guide, Jordan. We went to 4 different restaurants and Jordan gave us history and fun facts about each place. Each restaurant made everything from scratch and you could tell. Our last stop was a ride on the Icon Wheel!
We really enjoyed the tour. Rich’s wealth of knowledge and the easy way he tells the history ofWinter Park and his many insights into little known family dynamics of the Rodgers’ family was engaging. Some especially fond memories were hallways of Rollins College and the statue of Mr Rogers and the kids. We loved every minute. Time well spent. Reminds us that there is always something new to discover. The boat tour and lunch on our own rounded out a memorable day.read moreread less
Joe &.
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Joe &.
We really enjoyed the tour. Rich’s wealth of knowledge and the easy way he tells the history ofWinter Park and his many insights into little known family dynamics of the Rodgers’ family was engaging. Some especially fond memories were hallways of Rollins College and the statue of Mr Rogers and the kids. We loved every minute. Time well spent. Reminds us that there is always something new to discover. The boat tour and lunch on our own rounded out a memorable day.
This tour was great! I absolutely love food and this tour provided a great variety of authentic options. It also included a good amount of history of Winter Park that kept me engaged as we were walking from place to place. I’m from the central Florida area but learned quite a bit about this city. My tour guide was very knowledgeable and entertaining. I would gladly take the tour again.read moreread less
costakatiet
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costakatiet
This tour was great! I absolutely love food and this tour provided a great variety of authentic options. It also included a good amount of history of Winter Park that kept me engaged as we were walking from place to place. I’m from the central Florida area but learned quite a bit about this city. My tour guide was very knowledgeable and entertaining. I would gladly take the tour again.
This tour is great for someone who loves to experience new places and try new things. As an Orlando area native who frequents Winter Park for the cuisine, I'd only been to one of the stops on the tour prior. Each place provided something unique. The historical information was just an added bonus that brought additional value to the tour. I would absolutely recommend this to anyone who is looking for a unique way to spend a day in Winter Park.
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Tiffany P.
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Tiffany P.
This tour is great for someone who loves to experience new places and try new things. As an Orlando area native who frequents Winter Park for the cuisine, I'd only been to one of the stops on the tour prior. Each place provided something unique. The historical information was just an added bonus that brought additional value to the tour. I would absolutely recommend this to anyone who is looking for a unique way to spend a day in Winter Park.
I am a local who has lived in the Orlando area for more than 20 years. I've never been to some of these venues prior to the tour but they are hidden gems! Loved the tour guide, the info, and all the yummy food!! A+++++read moreread less
oviedogators
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oviedogators
I am a local who has lived in the Orlando area for more than 20 years. I've never been to some of these venues prior to the tour but they are hidden gems! Loved the tour guide, the info, and all the yummy food!! A+++++
Sunny’s Spotlight
popular destination guides
Winter Park
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