Jaclyn's Guidebook
Sightseeing
Spend one hour exploring and learning about the Winter Park chain on lakes
160 locals recommend
Scenic Boat Tour
312 E Morse BlvdSpend one hour exploring and learning about the Winter Park chain on lakes
Rollins College
1000 Holt AveBeautiful college campus
Park Ave is the heart of Winter Park. Filled with fantastic restaurants & shopping, this is a great spot to spend the day wandering around.
25 locals recommend
South Park Avenue
South Park AvenuePark Ave is the heart of Winter Park. Filled with fantastic restaurants & shopping, this is a great spot to spend the day wandering around.
Harry P Leu Gardens
Harry P Leu GardensThornton Park
Food scene
Winter Park Farmers' Market
150 W New England Ave
Prato
124 N Park AveExcellent food and fantastic atmosphere
My favorite Park Ave restaurant. Farm to table food cooked in a rustic environment.
30 locals recommend
Boca Kitchen
358 N Park AveMy favorite Park Ave restaurant. Farm to table food cooked in a rustic environment.
The best dinner view in Winter Park. Step outside and find a chair to enjoy drinks pre or post dinner.
87 locals recommend
Hillstone Restaurant
215 S Orlando AveThe best dinner view in Winter Park. Step outside and find a chair to enjoy drinks pre or post dinner.
Briarpatch Restaurant
252 N Park AveKnown for its fabulous breakfast menu.
If you love trying new wines then this is your place. Through their dispense card system you can try hundreds of wines, or even buy by the glass or bottle. Great patio in front to sip your favorite wine and watch the evening go by.
99 locals recommend
The Wine Room on Park Avenue
270 S Park AveIf you love trying new wines then this is your place. Through their dispense card system you can try hundreds of wines, or even buy by the glass or bottle. Great patio in front to sip your favorite wine and watch the evening go by.
Awesome date night spot. Great cocktails and creative dishes that are all delicious!
75 locals recommend
The Ravenous Pig
565 W Fairbanks AveAwesome date night spot. Great cocktails and creative dishes that are all delicious!
If you’re craving great mexican food and some creative margaritas, then this is your place!
56 locals recommend
Agave Azul
900 South Orlando AvenueIf you’re craving great mexican food and some creative margaritas, then this is your place!
Black Bean Deli
1346 N Orange AveFantastic Cuban food!
Recently voted best BBQ in Southern Living’s “The South’s Best” 2020 edition. A local favorite!
56 locals recommend
4 Rivers Smokehouse - Winter Park BBQ
1600 W Fairbanks AveRecently voted best BBQ in Southern Living’s “The South’s Best” 2020 edition. A local favorite!
New farm to table restaurant. Menu has great options, including woodfire pizzas, grilled artichokes, fresh seafood and steaks. Plus beautiful space to sip your way through their wine list.
17 locals recommend
Sixty Vines
110 Orlando AveNew farm to table restaurant. Menu has great options, including woodfire pizzas, grilled artichokes, fresh seafood and steaks. Plus beautiful space to sip your way through their wine list.