The Alfond Inn at Rollins

Cocina 214 in Winter Park is your go-to for Tex-Mex flair, featuring a lively atmosphere, killer margaritas, and tasty bites perfect for any occasion.

Light on the Sugar Cafe offers a cozy, inviting spot in a strip mall, serving up delightfully light pastries and warm, friendly service.

Soseki is a sleek Orlando gem offering an inventive omakase experience, where each beautifully crafted dish delights and surprises in a cozy setting.

Upscale chain eatery serving burgers, steaks & other American fare in stylish, spacious surrounds.

Upmarket 1922 property with traditional quarters, elegant dining & in-room continental breakfast. Built in 1922, this grand hotel is a minute's walk from Park Avenue shopping, 0.5 miles from the Cornell Fine Art Museum on the Rollins College campus and 6.7 miles from Orlando. Cozy, traditional rooms feature exposed-brick walls, wooden shutters and flat-screen TVs, plus free Wi-Fi and continental breakfast. Suites add furnished private balconies and/or separate living rooms. Room service is available. Amenities include a business center and a refined restaurant/bar. Valet parking is offered for a fee. Children age 3 and over are welcome.

Experience the serene beauty and rich history of Winter Park on a guided boat tour that promises a delightful hour of scenic views and insightful narration.

The Ravenous Pig is a sprawling gastropub where inventive New American dishes meet craft brews, all set in a lively atmosphere with a cozy beer garden.

This snug spot serves up delicious Thai-infused sandwiches, salads, and standout tea drinks in a cozy, friendly atmosphere perfect for a light lunch.

Sushi, sashimi & other Japanese specialties offered in a shopping-mall spot with outdoor seating.

Step into The Courtesy, a cozy speakeasy in Winter Park where festive decor meets curated cocktails and delightful bites, creating a must-visit vibe.