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Date Night Hot Spots in Winter Park | Winter Park Escapes

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For Your Next Date Night, Try Out These Winter Park Hot Spots for Dining and More

Date Night Hot Spots in Winter Park

If you need to get away for some rest, relaxation, and fun with your sweetheart any time of the year, Winter Park has plenty to do. There is an array of daytime activities from skiing to hiking to pampering at a local spa. When you’re looking for a way to keep the fun and excitement of the day going into the night, the hot spots of Winter Park don’t disappoint. Delicious food, live entertainment, and more await at the town’s many popular restaurants, bars, and entertainment venues to make your date night one to remember at these Winter Park hot spots.

Strip & Tail

Amp up the romance at the popular Strip & Tail restaurant. The surf and turf restaurant offers delicious steak, lobster, and more, including many gluten-free dishes. Enjoy ‘turf’ choices that include New York strip, Buffalo ribeye, or prime rib. Your mouth will water over tastes of the sea like twin lobster tails, grilled shrimp, glazed salmon, and crab cake-stuffed trout. Reservations are required. Please wear a mask when not at your table enjoying food and drink.

The Basement

For good food and a variety of fun that changes nightly, you’ll want to check out The Basement. Don’t be fooled by the name, the venue is above ground, but is below Strip & Tail. Tasty bites include jalapeno poppers, mozzarella sticks, pizza, paninis and more. Enjoy weekly entertainment like open mic night on Wednesdays featuring local talent or try your hand at karaoke on Friday night. Please wear a mask when not at your table enjoying your meal.

Idlewild Spirits Distillery

Creating thirst-quenching combinations of original cocktails like “The Perfect Date” or “Idlewild Shrub” – which includes a secret blend of seasonal ingredients – classic cocktails including an Apple Cinnamon Toddy or Mint Julip, as well as a list of spirits longer than your arm, you’ll enjoy your time at Idlewild Spirts Distillery. A limited but delicious food menu puts the drinks in the spotlight. Enjoy pulled pork sliders or chicken pasta alfredo and delight in a fudge brownie or Rollin’ Street cheesecake for a perfect cap to the evening.

Bar Crawl at These Winter Park Hot Spots

If you can’t decide on a single place or your Winter Park respite isn’t long enough to experience all of the hot date night places in one visit, consider hitting several over the course of an evening. Many restaurants and bars are open late and offer live entertainment nightly. Designate a driver or enlist a cab or ride share and hit the town. Make sure to bring your mask, since many places require them for entry and when you’re not enjoying drinks or a meal at your table.

Feel the Love in Winter Park

You chose Winter Park for a private, fun getaway with your sweetheart. Extend the experience to your accommodations by booking a vacation rental with Winter Park Escapes. When you’re not out at one of the area’s hot spots, prepare a tasty meal in the fully equipped kitchen. Afterward, make your rental “the place to be” by settling in for a movie. For an intimate experience, we have two-bedroom units available. If you’ve planned a couples’ getaway to Winter Park, there are units as large as five bedrooms! You can even choose a premium unit for upgrades like stainless steel appliances, granite counters, hardwood floors, flat screen TVs and more!

Contact us today to start planning your hot spot-seeking Winter Park getaway!