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Winter Park Museums, Shopping and a Cruise

Enjoy cultural activities, lake cruises, upscale shopping and more on a visit to Winter Park, Fla.
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Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Length: 1 miles
Duration: Half day
Family Friendly

Overview:  Winter Park, located just north of downtown Orlando, is a city that values its history and cultural arts. It's also home to many of... more »

Tips:  This tour is best started in the morning, especially on Saturdays, when the Winter Park Farmers' Market is open along this route from ... more »

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Points of Interest

Operating since 1938, this hourlong cruise passes through three lakes and two man-made canals, where you can enjoy the natural beauty and the multimillion dollar mansions. During the tour, the guides regale guests with stories of the history of Winter Park, how the upscale snowbirds (a term for someone who lives here temporarily during the winter ... More

2. Sassafras Sweet Shoppe

Any walking tour is easier with a few sweets, and this vintage-style candy shop is a must-stop before hitting all the upscale boutiques that line nearby Park Avenue.

Featuring candy from the 1800s to today, you'll find lollipops, gummies, hard candies, chocolates, flavored popcorn, caramel apples, cotton candy and more. The store also stocks... More

3. Earth Inspired Living

This store specializes in gifts and home accessories that are eco friendly. You'll find a wide range of products here including jewelry, soy candles, organic baby gifts, and natural lotions and bath products.

Everything for sale is produced from recycled, reclaimed or sustainable materials. Recent finds included wine totes made from recycled boat... More

This museum is a must for those who love Tiffany glass works of art, as it houses the world's most comprehensive collection of works by Louis Comfort Tiffany. In fact, a whole 12,000-square-foot wing was built just to accommodate the more than 250 pieces of Tiffany the museum has on display. Among the largest items is the chapel interior he... More

Learn about the history of Winter Park via various documents, photos and revolving exhibits. It's a tiny museum, but you'll learn how the city has evolved over the last century.

Past exhibits have covered everything from the city's gardens to the history of African-Americans in the city. This is also where you can pick up pamphlets on other... More

6. Tuni's

Women looking for chic clothing that is a bit trendy, but not so much that they can wear it for only one season, will want to check out this upscale boutique, located on the corner of West New England Avenue and Park Avenue.

Tuni's stocks the latest styles seen in the fashion magazines and the staff seems to be good at pulling together outfits.... More

After a few hours of strolling the Park Avenue shops, the Wine Room is a great place to end the day.

Featured on many TV shows, including Samantha Brown's "Weekend Getaways" series, this establishment features the ability to purchase wine by the ounce using high-tech Enomatic machines. Purchase a card for a specified dollar amount,... More

Set on the beautiful Rollins College campus overlooking Lake Virginia, this art museum is considered by many to be one of the nation's most innovative, boasting more than 5,000 pieces on display. Exhibitions change seasonally and range from early Renaissance to contemporary works.

Pieces in the museum's permanent collection include works by... More

Named after Czech-born American sculptor Albin Polasek, who owned the house and grounds, the museum focuses primarily on American sculpture, with more than 200 works by Polasek.

A tour of the house includes a narrated history of Polasek's works and his life in the house, as well as the chapel on the grounds, which houses many of his sketches.... More