If you’re craving sunshine, thrills, and a sprinkle of charm, a weekend in Orlando and Winter Park is the perfect getaway. Here’s your Thursday night to Sunday afternoon guide to make the most of your visit.
Thursday Night: Arrival & Relaxation
- Fly into Orlando International Airport and check in at a comfortable yet convenient hotel, like the Hyatt Regency Grand Cypress or Hilton Orlando.
- For a low-key evening, head to ICON Park on International Drive for a casual dinner at Yard House or Tin Roof. Enjoy the lively atmosphere, a spin on The Wheel, and some light shopping.
Friday: Thrills & Adventure at Universal Studios
- Start your day early with a hearty breakfast at Keke’s Breakfast Cafe.
- Spend the day at Universal Studios Florida or Islands of Adventure for roller coasters, immersive rides, and movie magic.
- Don’t miss The Wizarding World of Harry Potter, the pulse-pounding VelociCoaster, and interactive shows throughout the park.
- Wrap up with dinner at CityWalk — VIVO Italian Kitchen or The Cowfish Sushi Burger Bar are great options.
Saturday: Shopping & Dining in Winter Park
- Fuel up with coffee at Foxtail Coffee Co. before heading to the Orlando International Premium Outlets or The Mall at Millenia for unbeatable deals and upscale finds.
- In the afternoon, make your way to Winter Park’s Park Avenue. Stroll through boutique shops like The Grove and Peterbrooke Chocolatier.
- Enjoy an elegant dinner at The Ravenous Pig or Prato, both known for fresh, locally inspired cuisine.
- End your evening with a nightcap at The Imperial Wine Bar & Beer Garden.
Sunday: Brunch & Scenic Views
- Before heading home, savor brunch at Briarpatch Restaurant, known for its decadent pancakes and charming patio seating.
- Take a scenic boat tour through Winter Park’s chain of lakes, soaking in the lush greenery and waterfront mansions.
Pro Tip: Pack comfortable shoes, sunscreen, and a refillable water bottle to stay refreshed throughout your adventure. With this itinerary, you’ll experience a thrilling yet relaxing weekend exploring the best Orlando and Winter Park have to offer!
Orlando Activities (Beyond Theme Parks)
- Walt Disney World Resort – Experience the magic at Magic Kingdom, EPCOT, Disney’s Hollywood Studios, or Animal Kingdom. Perfect for Disney fans or those seeking iconic rides and entertainment.
- Lake Eola Park – Rent a swan boat or stroll around the scenic downtown Orlando lake.
- ICON Park – Home to The Wheel, Madame Tussauds, SEA LIFE Aquarium, and great dining spots.
- Orlando Science Center – Interactive exhibits perfect for families or curious minds.
- The Florida Mall – A massive shopping destination with popular brands and unique local shops.
- Dr. Phillips Center for the Performing Arts – Check out a Broadway show, concert, or comedy act.
- Gatorland – A fun and unique Florida experience featuring alligators, zip lines, and wildlife encounters.
Winter Park Activities
- Charles Hosmer Morse Museum of American Art – Home to the world’s most comprehensive collection of Louis Comfort Tiffany’s glasswork.
- Mead Botanical Garden – A peaceful escape with walking trails, a butterfly garden, and lush greenery.
- Scenic Boat Tour – Cruise through Winter Park’s chain of lakes, learning about local history and waterfront mansions.
- Hannibal Square – A historic district with boutique shopping, art galleries, and cozy cafés.
- Albin Polasek Museum & Sculpture Gardens – A charming museum featuring sculptures and beautiful lakefront gardens.
