Top 10 Tours in Winter Park, Florida (FL)

Enjoy a beautiful sunset and moon rise on the outstanding Winter Park Chain of Lakes. Experience the natural beauty of Florida from a unique perspective. Listen to ghost stories and toast to the stars above. It’s always a fantastic time on the lake! All kayaking or canoeing equipment and a light snack are provided.

Inclusions: Local guide, Bottled water, Light Lunch

Exclusions: Gratuities, Hotel pickup and drop-off

Get to know Orlando through a fun whirlwind tour, of all the interesting and important sites around the wonderful Florida city also known as The City Beautiful!

Inclusions: Fully guided city tour of Orlando, Boat cruise through the Chain of Lakes, Free time at Disney Springs, Park Avenue, and the ICON 360 Plaza, Ride on The Orlando Wheel, Air-conditioned vehicle

Exclusions: Food and drinks, Gratuities

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Inclusions: All taxes, fees and handling charges, Digital Copies of your scavenger hunt photos, Local taxes

Exclusions: Food and drinks, Transportation to/from attractions

Welcome to our Winter Park neighborhood on this beautiful day! While many well-known celebrities have passed through this storied village over its rich history, probably no one impacted, and was impacted by, Winter Park more than Fred McFeely Rogers, lovingly known the world over to millions of people as the unforgettable host of Mister Rogers’ Neighborhood for over 50 years now. Come along on our Mister Rogers Walking Tour as we visit the heart of town where Fred and his lifetime sweetheart, Sara Joanne Byrd Rogers, fell in love while in college and spent many years later in life. You’ll learn fascinating tidbits about how Fred was motivated by a mural in Winter Park to begin a lifetime ministry of serving others. Walk in the same places that Fred and Joanne did through different seasons of their life, as you come to better understand what inspired this legendary man to leave his unique mark on the world and impact millions of children with his special gifts.

Inclusions: 90 Minute – 2 Hour Guided Walking Tour in the Winter Park Footsteps of Fred Rogers., Legendary tales of Mister Rogers’ time in Winter Park as a student and humble TV celebrity., Stories about Winter Park and Rollins College, important places to the Rogers., 10% discount for your next Original Orlando Tours adventure (valid for 30 days)., Earn SUNNY PERKS REWARDS., A stop for a free homemade gelato treat is included!

Exclusions: Gratuities

Be ready for a paddling excursion that will showcase Winter Park’s natural beauty from the water and lead guests up to a breathtaking sunset. We’ll guide the way through narrow Venetian style canals laced with history and lined with some of Florida’s finest flora and fauna. Plenty of birds, fish, and other wildlife will no doubt make an appearance, along with the extravagant houses that are nestled among the lakes.

Inclusions: Kayak, Life Jackets, Whistle

Exclusions: Gratuities

Be ready for a glow in the dark paddling excursion that will showcase Winter Park’s natural beauty from the water and lead guests through the night. Enjoy the glow from our LED equipped kayaks as we’ll guide the way through narrow Venetian style canals laced with history and lined with some of Florida’s finest flora and fauna. Plenty of birds, fish, and other wildlife will no doubt make an appearance, along with the extravagant houses that are nestled among the lakes.

Inclusions: Use of all kayak equipment , Life Jacket, Whistle

Exclusions: Gratuities

This walking tour has been custom built with the foodie in mind. On each tour, you can expect conversation, laughs, a few interesting facts and historical references, and of course…food! Park Avenue is uniquely qualified to represent Central Florida with foodies who enjoy wine. During your guided visit, we'll take you on a journey through the heart of Winter Park in search of great wine spots with a few surprises along the way! If this is your first time in Winter Park, you will fall in love with the European feel of brick streets and canopy trees. If you are a local, we will work to share new delights and interesting stories to help you fall in love all over again!

Inclusions: Lunch, Snacks, Alcoholic Beverages, Local history and interesting stories.

Exclusions: Gratuities

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! Park Avenue is home to many internationally themed and locally owned boutique restaurants who are thrilled to share samples of their cuisine with you! During your guided visit, you will learn about the rich history of the area as well as enjoy a delicious selection of food and drinks along the way. The best way to experience Winter Park is on foot as you are able to take in the sights, sounds and tastes that locals love. The brick streets and canopy trees create an atmosphere unlike any other in Florida, and the offerings along the way will have you coming back for more afterwards! Whether this is your first time in Winter Park or you are a local who has been visiting for years, you will fall back in time while hearing fascinating tales about how this beautiful town evolved, and where to find its gastronomical gems!

Inclusions: Sample selection of delicious food and beverage items at each tour stop., VIP Guide who will share a brief history of Park Avenue and interesting facts along the way., 10% discount all day on purchases and meals after the tour given by each tour stop location., 10% discount for your next Original Orlando Tours adventure (valid for 30 days)., Earn Sunny Perks Reward Points for gift cards or other discounts., Demonstrations and presentations during each visit.

Exclusions: Gratuities

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!

Inclusions: 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.

Exclusions: Gratuities

Welcome to our Winter Park neighborhood on this beautiful day! While many well-known celebrities have passed through this storied village over its rich history, probably no one impacted, and was impacted by, Winter Park more than Fred McFeely Rogers, lovingly known the world over to millions of people as the unforgettable host of Mister Rogers’ Neighborhood for over 50 years now. Come along on our Mister Rogers Walking Tour as we visit the heart of town where Fred and his lifetime sweetheart, Sara Joanne Byrd Rogers, fell in love while in college and spent many years later in life. You’ll learn the fascinating story of how this humble man from Latrobe, PA connected with Winter Park and began a lifetime ministry of service. Walk in the same places that Fred and Joanne did through different seasons of their life, and then wrap your visit up with a one-hour boat tour of Winter Park, passing by some of the places that you visited by land and others further away from the walking tour!

Inclusions: 90 Minute – 2 Hour Guided Walking Tour in the Winter Park Footsteps of Fred Rogers., 1 Hour Cruise Along the Canals and Lakes of Winter Park., Stories about Winter Park and Rollins College, important places to the Rogers., Legendary tales of Mister Rogers’ time in Winter Park as a student and humble TV celebrity., 10% discount for your next Original Orlando Tours adventure (valid for 30 days)., Earn SUNNY PERKS REWARDS.

Exclusions: Gratuities