Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Explore Orlando beyond the theme parks with a comprehensive sightseeing tour, including a scenic boat cruise through Winter Park's canals, for $85.
Discover Orlando’s local charm with this 7-hour sightseeing tour that combines city highlights, boutique shopping, and an optional scenic boat cruise through Winter Park’s picturesque lakes. Priced at $85 per person, this tour offers a practical way to see more of Orlando’s hidden corners and historic neighborhoods, especially with hotel pickup from select locations. The tour receives an overall rating of 4.0 out of 5 from 192 reviews, showcasing a solid balance of informative guiding and enjoyable stops, though some guests note room for improvement in certain areas.
What makes this experience particularly appealing is the combination of land and water exploration. The full-day option includes a scenic cruise through Winter Park’s canals, which is highly praised for its beautiful views and engaging narration. The tour is designed for those who want to avoid walking long distances, as it moves smoothly by minibus between locations. Travelers should expect a well-paced itinerary that covers downtown Orlando, Winter Park, and concludes with free time at Disney Springs.


The tour begins with a drive through Orlando’s commercial and historic areas, passing landmarks like the City Hall, Church Street, and the Courthouse. The first stop is Lake Eola Park, a central feature of downtown with a peaceful pond, swan boats, and a farmers market on Sundays. This 15-minute stop offers a chance to enjoy the scenery and take photos of the iconic fountain.
The drive around downtown provides an overview of Orlando’s urban layout, emphasizing the mix of modern development and historic buildings. The guide’s commentary helps visitors appreciate Orlando’s evolution beyond the theme parks, highlighting its civic and cultural landmarks.
Enjoy being on the water? Here are other boat experiences we've looked into in Orlando

The highlight of the full-day experience is the 1-hour scenic cruise through Winter Park’s canals and lakes. Departing from the city’s famed Chain of Lakes, the boat ride showcases luxurious homes of millionaires, lush greenery, and historic landmarks. The narration details the area’s history and architecture, making it a memorable experience for those interested in local stories.
This cruise not only offers picturesque views but also serves as a relaxing break from bus travel. Many reviews praise the fascinating stories shared by the skipper, which add depth to the leisurely ride. Since the boat tour is included in the full-day package, it’s an excellent value for those wanting to see Winter Park from the water.

After the boat cruise, the tour continues with free time on Park Avenue in Winter Park. This charming shopping district is lined with over 140 boutiques, cafes, and museums. Visitors can stroll cobbled streets, browse unique stores, or relax at sidewalk cafes. The time allocated—around an hour—is enough to soak in the quaint atmosphere and pick up souvenirs.
Guests often enjoy the mix of shopping, architecture, and local culture. The area’s historic charm makes it a peaceful contrast to downtown Orlando’s hustle, making it a favorite stop for those seeking a taste of Florida’s smaller towns.

The tour concludes with about 2 hours at Disney Springs, a lively shopping and entertainment complex. Visitors find a variety of shops, restaurants, and entertainment options. Some guests use this time to indulge in shopping, grab a meal, or simply soak in the vibrant atmosphere.
The length of this stop has received mixed reviews; while many appreciate the freedom to explore, some note it could be longer to fully enjoy the diverse offerings. Nonetheless, Disney Springs provides a convenient and fun wrap-up to the day’s sightseeing.

The tour includes hotel pickup and drop-off from selected Orlando hotels, which many find convenient. The air-conditioned minibus ensures a comfortable ride, especially during warmer days, and a restroom on board adds to the convenience.
The group size is limited to 13 travelers, fostering a more personalized experience. The licensed guide is praised for their local knowledge and engaging commentary, with some reviewers mentioning specific guides by name who made the experience more enjoyable.

Travelers wanting a rundown of Orlando and Winter Park should opt for the full-day tour with the boat cruise. This version provides more in-depth exploration, especially with the scenic boat ride included. For those short on time or preferring a more land-focused experience, a shorter land-only tour is also available, which skips the boat and focuses on downtown Orlando and Park Avenue.
The full-day tour’s price remains at $85, offering excellent value considering the boat cruise and multiple stops included.

This tour is best suited for those with moderate physical fitness, as it involves minimal walking but does include some standing and moving around during stops. The pickup starts at 9:00 am, so early risers should plan accordingly. The tour may be canceled in poor weather, with options for a different date or a full refund, so checking weather forecasts is advisable.
Guests should also be aware that food and drinks are not included, so packing snacks or spending at Disney Springs is recommended for longer visits.

This sightseeing tour from Gray Line of Orlando delivers a balanced mix of city highlights, scenic views, and leisure time. The inclusion of the scenic boat cruise is particularly popular, offering a unique perspective on Winter Park’s lakes and historic homes. The free time at Disney Springs adds a relaxed shopping and dining element at the end of the day.
While the tour offers great value, some reviews mention minor issues like occasional confusion about pickup points or the desire for longer stops at Disney Springs. The combination of knowledgeable guides, comfortable transport, and engaging stops makes this tour a solid choice for those seeking a broader look at Orlando beyond its famous theme parks.
This tour suits families, couples, or individuals eager to explore Orlando’s local neighborhoods, lakes, and shopping districts in a relaxed, guided setting. It’s ideal for visitors looking for a full-day experience that mixes sightseeing, history, and leisure with minimal hassle.
“Better itinerary than the one given to me. Visit more historical places of Orlando with places like Museums, Churchs,etc”
Is hotel pickup included in this tour?
Yes, hotel pickup and drop-off are available at selected Orlando hotels, making transportation convenient.
What is included in the full-day tour?
The full-day tour includes a scenic boat cruise through Winter Park, downtown Orlando highlights, free time at Park Avenue, and approximately 2 hours at Disney Springs.
How long does the tour last?
The entire experience takes about 7 hours, starting from 9:00 am with flexible end times depending on stops and traffic.
Can I skip the boat cruise?
Yes, shorter land-only options are available that omit the scenic boat ride, focusing instead on Orlando’s downtown and shopping districts.
What should I bring for the tour?
While food and drinks are not included, packing snacks and water is recommended. Comfortable clothing and moderate physical fitness are advised.
What is the cancellation policy?
Guests can cancel free of charge up to 24 hours in advance for a full refund. Cancellations within 24 hours are non-refundable.