Discover the enchanting charm of Winter Park, where serene waterways meet rich cultural heritage. Immerse yourself in unforgettable adventures, from peaceful kayaking tours through lush nature trails to captivating sightseeing cruises and historical walking tours. Whether you are seeking a romantic escape, a family adventure, or an eco-friendly exploration of local landmarks, Winter Park offers a diverse range of top-rated experiences. Book your journey today to explore hidden gems, enjoy guided excursions, and create lasting memories in this breathtaking destination.
$95–$109 typical
Wide range from $54 to $777
4.85★ average
Based on 155 pooled reviews
1.5–6.5 hours
Median duration is 5.2 hours
Sightseeing & Culture
83% are sightseeing tours, 67% are cultural
Guided & Group
100% are guided tours, 67% are group formats
Eco-friendly options
33% of tours are tagged eco-friendly
10 Products
Discover Orlando highlights and hidden gems with a city tour that includes Lake Eola and Downtown, a cruise through the Chain of Lakes in Winter Park, and free time at Disney Springs.
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 peop...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Explore Winter Park's haunted history on a 90-minute guided walking tour. Hear spine-tingling tales of spirits and eerie sites.
Join a day tour of Orlando’s unique neighborhoods. Start in Winter Park with a narrated boat cruise to see city homes and the local college from the water. Visit Downtown Orlando to see Lake Eola and its famous swans. The tour vehicle will travel through various areas, with a guide providing det...
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...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Winter Park, Park Avenue and ICON Orlando 360... Explore Orlando's most emblematic landmarks and monuments on this guided tour of the city with a boat trip.
Free cancellation up to 24 hours before the activity starts. Any cancellations after this or no-shows on the day will not be refunded.
Discover Orlando highlights and hidden gems with a city tour that includes Lake Eola and Downtown, a cruise through the Chain of Lakes in Winter Park, and free time at Disney Springs.
Explore Winter Park's haunted history on a 90-minute guided walking tour. Hear spine-tingling tales of spirits and eerie sites.
Looking for the real Orlando beyond the theme parks? Join me on a private, guided journey where you’ll discover the city’s best-kept secrets, sip and savor local flavors. ✨ Highlights of Your Day: Private Hotel Pickup – Relax as your adventure begins with hassle-free transportation. Historic Downt...
Discover Orlando on a private tour through the Magic City! Visit Lake Eola, Winter Park, and Disney Springs on a comprehensive tour with an exclusive guide.
Free cancellation up to 24 hours before the activity starts. Any cancellations after this or no-shows on the day will not be refunded.
Landmarks travelers visit on the same route as Winter Park.