Come Sail Away: Winter Park Scenic Boat Tour

All photos by Kelsey Walters

Orlando and the surrounding areas have no shortage of things for tourists and locals to explore. In fact, it can be pretty overwhelming when deciding what park to visit, where to dine and what to do in between to maximize your vacation, or staycation. Given its close proximity, Orlando loves to flock to our beaches, and in turn, Volusians spend just as much time in the central Florida area at major attractions.

One of the most stressful parts about being on vacation is, well… being on vacation. Planning and the hustle of getting from place to place usually falls on one person’s shoulders (I’m looking at you, fellow moms) and the stress of it all can be very taxing. The exhaustion of visiting theme parks and more can make you second-guess your entire visit. There are, however, plenty of things you can do to actually relax and take a break during your time away!

Winter Park Scenic Boat Tour is just 10 minutes outside of downtown Orlando, but it feels like a world away. This one-hour lake and canal cruise is the ideal way to relax, where the only thing you have to do is sit back and enjoy the scenery. Whether you’re looking for a break from your trip, or a quick afternoon getaway before dinner downtown, this tour is lauded by Floridians as a “must do” in central Florida. Plus, it’s a great, cost-conscious, activity to have on-hand when you have visitors in town.

After the annual chaos of the holidays, this experience was a welcome pause for our family. It was so relaxing, in fact, that Avery fell asleep about halfway through and caught up on her rest after the non-stop holiday cheer.

Scott and I were able to take in the sights through three of the area’s chain of six lakes, including Lake Osceola, Lake Virginia and, the largest, Lake Maitland.

The lakes are connected through a series of Venetian-style canals that have been around since the 1800s, earning the area the title of “Venice of America.” These narrow canals bursting with foliage are popular spots for boaters and paddleboarders, and offer beautiful scenery as you lazily glide through on your tour. Traversing the canals feels a bit like Jurassic Park mixed with Old Florida, giving you the feeling of floating back to a different time. First sailing in 1938, this is Florida’s longest running attraction and is open 364 days a year, only docking for Christmas day.

Our tour started just across the lake from historic Rollins College, Florida’s oldest post-secondary institution established in 1885. From the water we had the chance to see various areas of the college from a unique perspective, as well as several other historic homes and unique architecture. Quite a few homes in the affluent lakeside communities are designed by famed Winter Park architect, James Gamble Rogers II.

The company’s fleet of six pontoon boats can hold up to 18 passengers each, but they tend to fill up quickly on weekends so I recommend arriving about 30 minutes early for your sail time to ensure a ticket. Tours leave every hour on the hour so don’t stress if you miss a time. They sail each hour from 10 a.m. to 4 p.m., and tickets must be purchased on-site – no presales or online tickets are available (do call ahead to schedule though if you have a large group).

The knowledgeable tour guides know this area like the back of their hands. Some of the skippers are living out their retirement years cruising the pontoon boats and couldn’t be happier. One tour guide, named Charlie, became well-known for taking his family out on the lake each year to decorate one of the lone cypress trees that stood on its own in the middle of the water. They would hang baubles and ornaments from the branches each year around Christmas, then return the next year to spruce it up and add more, leaving it decorated year-round.

Sadly, Charlie passed away a few years ago, but the beloved tradition lives on with the tour guides boating out each year to redecorate the tree (pictured above) for him each year. Lovingly dubbed “Charlie Brown’s Christmas Tree,” this was one of our favorite sights on the tour.

Whether you need a break from a hectic vacation or just from life in general, this relaxing tour really should be on your list of “top things to do in Florida.”