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8 Things to Do in Winter Park Before a Romantic Dinner at Ruth’s Chris


Whether it’s your first date or 30th anniversary, Ruth’s Chris is the perfect destination for a savory, romantic dining experience. In fact, if you’re celebrating a special occasion, feel free to notify our host so that we can offer a complimentary dessert and make your table setup extra special.

But what about the rest of your day? If you’re in the Winter Park/Orlando area and want to make your one-day getaway particularly memorable, consider any of these local destinations/activities before enjoying our food and signature cocktails. 

Additionally, we’ve added three other destinations to head to afterwards to extend your night out together.

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Charles Hosmer Morse Museum of American Art

The Morse Museum is home to the world’s most extensive collection of works by Louis Comfort Tiffany (1848-1933) - the renowned American artist and designer best known for his work in glassmaking - particularly stained glass. 

In fact, Tiffany was the very first Design Director at his family company, Tiffany & Co. - founded by his father Charles Lewis Tiffany.

While you’re there, be sure to visit the fully rescued and reconstructed Tiffany Chapel, originally exhibited at the World’s Columbian Exposition in Chicago in 1893. A beautiful, award-winning display that won him international acclaim - it was said to have touched visitors so deeply at the time that men doffed their hats in appreciation.

Click here for a breakdown of visiting hours and admission fees (it mostly closes at 4pm). In addition, a comprehensive visitor’s guide is available here to help make the most of your time. You can also view an extensive list of current and past exhibitions.

Albin Polasek Museum & Sculpture Gardens

Albin Polasek (1879-1965) was an esteemed Czech American sculptor who produced more than 400 works during his career - over 200 of which are now on display at this special location.

The museum offers guided tours of the historic Polasek residence and chapel, a 3-acre outdoor sculpture garden (with many native Florida and subtropical plant species), and a full gallery with rotating exhibits. It is listed on the National Register of Historic Places and is one of just 34 members of the National Trust’s Historic Artists’ Homes and Studios.

While Polasek did not have any offspring, he considered his sculptures to be “his children.” The Polasek is described as a “living museum,” and would make for a lovely daytime experience together.

Click here for a breakdown of visiting hours and directions. Since the Museum and Gardens close by 4pm, a dinner reservation around 5-5:30 would be perfect. If you want to get there extra early, you can even enjoy some of our happy hour specials.

The Cornell Fine Arts Museum at Rollins College

The Cornell Fine Arts Museum features rotating exhibitions, ongoing programs, and an expansive permanent collection that spans centuries - from ancient art and artifacts to contemporary art. 

It open year-round (Tuesday-Sunday), with displays that include the only European Old Master paintings in the Orlando area, an impressive American art collection, and a progressive contemporary collection viewable both at the museum itself and the nearby Alfond Inn at Rollins - a boutique hotel whose earnings help to fund student scholarships.

The museum’s self-proclaimed mission is to be “a teaching museum that stimulates transformative encounters with works of art while integrating art into daily life for campus and community.” In addition, it is described as a “diverse and growing collection experienced as intimate, innovative, and inspirational.”

After visiting this fine arts museum, you can head over to Ruth’s for some fine wine paired with a seasonal classic.

Click here for a calendar of upcoming events, and here for a list of hours (generally closes at either 4pm or 5pm). Admission is free.

Central Park 

This 11-acre park is considered the “crown jewel” out of the 11 parks citywide. It is located on Park Avenue right in the middle of the downtown district.

Central Park hosts a wide range of events and activities year-round, including the annual Winter Park Sidewalk Art Festival and the city’s Olde Fashioned 4th of July Celebration.

The park attracts thousands of visitors each year, with elegant fountains, landscape planters, and an oak tree canopy that might get you in the mood for an oak-aged chardonnay or whiskey. It’s surely an ideal spot to enjoy some free time together out in nature before settling in at our restaurant.

The Mennello Museum of American Art 

Located just a few minutes’ drive away from our restaurant, the Mennello Museum was created in 1998 to preserve, exhibit, and examine the permanent collection of paintings by Earl Cunningham (1893-1977).

Cunningham was a self-taught folk artist whose largely painted landscapes of the coasts of Maine, New York, Nova Scotia, Michigan, the Carolinas, Georgia, and Florida. After admiring the creations of the artist’s palette, you can further develop your wine palate with one of our signature pairings later on.

Nowadays, the museum features temporary exhibitions, programs, events, workshops, educational initiatives, and publications celebrating a variety of other American artists. Its collection includes artworks specifically donated by the museum’s founders - the Honorable Marilyn Logsdon Mennello and Michael A. Mennello. 

Owned and operated by the City of Orlando, it draws from the city’s Permanent Collection (Florida’s largest statewide public art collection) as part of the City of Orlando’s Public Art program.

There is plenty to do outside of the museum’s walls as well. Located right on the shore of Lake Formosa in Loch Haven Cultural Park, it is part of the 3-mile long Orlando Urban Trail. This is considered the backbone of Orlando’s bicycle and pedestrian trail network (more on that later) - with walking paths, green space, and beautiful views.

The trail also goes right through the Marilyn L. Mennello Sculpture Garden, which is most famous for the over 350-year-old sprawling live oak tree with Spanish moss named “The Mayor.” This charming lakeside garden leads visitors straight to the museum’s front door and bike rack.

Scenic Boat Tour

Soak in the sunshine and spend some time on the water during one of Winter Park’s Scenic Boat Tours. The dock is located on Lake Osceola less than 5 minutes from Park Avenue - Central Florida’s fashionable, upscale shopping district. 

The boat tour offers hour-long, guided cruises through three of the city’s seven lakes along with two slim, man-made canals along the chain. On any given tour, you might spot a large crane swooping down to grab a fish or an alligator relaxing on a nearby bank. You are also guaranteed to see lots of swaying palms, lofty cypress trees, lush ferns and a range of colorful subtropical flowers.

If some time out on the water puts you in the mood for seafood, consider having our chilled seafood tower appetizer, or sizzling surf and turf for dinner.

Admission for adults is $14 each, while operating hours are from 10am to 4pm daily (excluding Christmas).

Harry P. Leu Gardens and Museum

This is the chance to explore a 50-acre botanical retreat just minutes from downtown Orlando. Located along the shore of Lake Rowena, this beautiful space offers a wide variety of plants and flowers to admire.

Since the Central Florida climate and soil allow for a diverse array of temperate and tropical plants, new selections are consistently evaluated and added to the collection. There are currently 12 distinct gardens on the property, including a butterfly garden with flowers specifically planted to allure butterflies.

Speaking of flowers, if you call our restaurant ahead of time, you can arrange for flowers to be set on your table ahead of time for you and your date.

A number of engaging classes and workshops are regularly scheduled, along with events and gatherings, from movie showings to concerts.

Click here for a splendid visual tour of the Leu Gardens to get a better idea of the size, scope, and variety of sights and scents the gardens have to offer. 

Bike Rides

After reading a brief overview of the city’s Pedestrian and Bicycle Program, it’s no secret why the Florida Bicycle Association recognized Winter Park as the 2017 Bicycle Friendly Community of the Year.

The city’s self-proclaimed mission regarding walking and biking is: “To create and promote a viable and safe pedestrian and bicycle-friendly infrastructure and promote these modes of transportation throughout the city.” 

The aforementioned Program Overview contains links to some of the area’s top bicycle shops, where you and your partner can rent bikes and ride all around the area - from the stimulating city streets to the more secluded, scenic trails.

Later on, you can both reward yourselves with a signature cocktail, and even share a tomahawk ribeye or porterhouse for two.
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