Winter Park, FL Dating Guide

Published On: April 7, 2023|Categories: Dating Tips, First Dates, Local City Dating Guides|4 min read|

In need of new dating spots to try out in Winter Park and the Orlando area? Check out our 2023 Winter Park City Dating Guide! A casual date, an active outing, a unique experience, or something to enhance the romantic experience.

Enjoy delicious flavors from local eateries offering locally sourced ingredients and heartfelt hospitality. Have a day out appreciating arts and culture along with natural Florida flora and fauna. Make some memories by taking a scenic boat tour around the area or try non-alcoholic cocktails. Make things romantic with intimate lounges offering exquisite wine tastings and soulful jazz. Whatever mood you’re trying to set, we have you covered with our 2023 Winter Park City Dating Guide!

If you are currently single and want to date, get started today!

☕️ Casual Date Spots

The Parkview

The Parkview is an intimate neighborhood bar that provides elevated bar food, craft beer, and excellent hard-to-find wines. Their menu offers a mix of sandwiches, salads, flatbreads, and charcuterie boards.


Offering a cozy vibe, great food, and heartfelt hospitality. Boca is an everyday upscale restaurant that takes a fresh and seasonal approach to its menu while offering a comfortable atmosphere for any time of day.

Bulla Gastropub

A fun casual gathering place inspired by the most popular tapas restaurants in Spain. Bulla’s energetic vibe with an emphasis on quality gastronomic creations made with fresh flavors makes for a fun and delicious date!


Prato celebrates Italian cuisine by blending simplicity with traditional inspirations, seamlessly blending Italian classics with modern techniques and seasonal ingredients. Paired with their warm, contemporary atmosphere, and year-round patio seating, Prato makes for a perfect casual date.

Hamilton’s Kitchen

Located in The Alfond Inn, Hamilton’s Kitchen offers a distinct Central Florida culinary experience. Fusing locally sourced ingredients with an open-table charm, Hamilton’s Kitchen will help you discover traditional Southern fare with a modern twist.

🏃🏾‍♂️ Active Date Spots

Albin Polasek Museum & Sculpture Gardens

Explore the inspired world of internationally acclaimed Czech sculptor Albin Polasek and take a tour through his home, galleries, and sculpture gardens on Lake Osceola. The three-acre garden in particular houses numerous sculptures ranging from historical to religious and mythological subjects.

Mead Botanical Garden

Offering 47 acres to explore, the Mead Botanical Garden is a place to find tranquility with nature amidst the urban setting of Winter Park. Plus, the garden also offers hiking trails, a boardwalk, a butterfly garden, and more to have a fun day out with your date.

Rollins Museum of Art

The Rollins Museum of Art features rotating exhibitions, ongoing programs, and an extensive permanent collection that spans centuries from ancient to contemporary art. Some of the collections include European Old Master paintings, a sizable American art collection, and a forward-thinking contemporary collection.

Central Park

Located on Park Avenue in the heart of the downtown shopping district, Central Park hosts numerous events and activities year-round across its 11 acres. The park’s beautiful fountains, landscaped planters, and oak tree canopy make for a beautiful picnic date.

Farmers’ Market

Taking place every Saturday morning from 8am to 1pm in Central Park West Meadow, Winter Park Farmers’ Market is a popular community gathering place that provides fine produce, plants, baked goods and so much more.

🎭 Unique Date Spots


Located in Orlando, the BANDBOX is a fun, educational, and engaging tasting experience that boasts an entirely non-alcoholic drink menu. BANDBOX strives to offer alternative cocktails and CBD-infused beverages for those not interested in virgin takes on popular drinks.

Morse Museum

The Morse Museum houses the world’s most comprehensive collection of works by Louis Comfort Tiffany, a late 19th-century artist who specialized in glassmaking. Learn more about this artist’s discoveries about new methods of glass manufacturing while taking in all the featured works of jewelry, pottery, paintings, and much more!

Scenic Boat Tours

Offering a boat tour throughout Winter Park’s narrow man-made canals and 3 of the 7 lakes in the area. Every tour offers breathtaking views of natural Florida foliage and opulent private homes and estates along with the occasional natural wildlife.

🌹 Romantic Date Spots

Quantum Leap Winery

Offering a classy experience of tasting wines, ciders, and more in an equally classy tasting room. Quantum Leap Winery works with organic growers around the world to produce high-quality wines with a reduced carbon footprint at a great value.

Bosendorfer Lounge

The Bosendorfer Lounge is a destination oozing with intimate and alluring ambiance. This lounge, with its modern Viennese Secession-inspired design, offers many different drinks with a sizable menu of small bites to accompany your romantic evening.

Jazz Tastings

Jazz Tastings is a family-owned bar and restaurant that serves delicious, homemade food and hand-crafted drinks while getting you into the groove with their live jazz acts. Their menu changes seasonally, so you’ll be sure to find something new every time.

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