Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

5-Day Orlando and Clearwater Itinerary

Friday, September 1: Arrive in Orlando

Welcome to Orlando, the theme park capital of the world! Start your trip by exploring one of the iconic theme parks in the morning. Whether you choose Walt Disney World, Universal Orlando Resort, or SeaWorld Orlando, you're in for a day of thrilling rides and magical experiences. In the afternoon, take a break from the parks and visit the Orlando Museum of Art or the Orlando Science Center. As the evening approaches, head to the vibrant International Drive for dinner and entertainment.

  • Theme Park of your choice: Prices vary, Estimated time spent: Full day
  • Orlando Museum of Art or Orlando Science Center: $15-25, Estimated time spent: 2-3 hours
  • International Drive: Prices vary, Estimated time spent: Evening
Restaurants
  • For breakfast, check out Keke's Breakfast Cafe. They offer a delicious selection of pancakes, omelettes, and breakfast sandwiches. Average cost for a meal is about $10 per person.
  • For lunch, head over to Kres Chophouse. This upscale steakhouse serves mouthwatering steaks and seafood dishes. Average cost for a meal is about $30 per person.
  • For dinner, try Santiago's Bodega. This tapas restaurant offers a variety of small plates with flavors from around the world. Average cost for a meal is about $20 per person.
Saturday, September 2: Explore Orlando

Spend the morning exploring the enchanting neighborhood of Winter Park, just outside of Orlando. Visit the Charles Hosmer Morse Museum of American Art to admire the largest collection of Tiffany glass in the world. Enjoy a leisurely boat tour on the Winter Park Chain of Lakes and stroll along Park Avenue with its charming boutiques and cafes. In the afternoon, head to the ICON Park, where you can ride the ICON Orlando, a 400-foot observation wheel, and indulge in some shopping and dining. Wrap up the day with a visit to the lively Church Street Station for some evening entertainment.

  • Winter Park: Prices vary, Estimated time spent: Morning
  • Charles Hosmer Morse Museum of American Art: $6-15, Estimated time spent: 2-3 hours
  • Boat tour on Winter Park Chain of Lakes: $14-25, Estimated time spent: 1-2 hours
  • ICON Park: Prices vary, Estimated time spent: Afternoon
  • Church Street Station: Prices vary, Estimated time spent: Evening
Sunday, September 3: Clearwater Beach Day

Escape the city and head west to Clearwater Beach. Spend the morning relaxing on the white sandy beaches, soaking up the sun, and taking a refreshing swim in the crystal-clear waters of the Gulf of Mexico. Grab a beachside lunch at one of the local seafood restaurants. In the afternoon, embark on a dolphin-watching cruise or try your hand at water sports like paddleboarding or kayaking. As the sun sets, don't miss the opportunity to witness the breathtaking sunset from Pier 60, where you can also enjoy live entertainment and local arts and crafts.

  • Clearwater Beach: Free, Estimated time spent: Morning
  • Seafood restaurant: $15-30, Estimated time spent: Lunch
  • Dolphin-watching cruise or water sports: $20-50, Estimated time spent: Afternoon
  • Pier 60: Free, Estimated time spent: Evening
Monday, September 4: Clearwater Attractions

Continue exploring Clearwater with a visit to the Clearwater Marine Aquarium in the morning. Get up close and personal with dolphins, turtles, and other marine life while learning about their conservation efforts. Enjoy a picnic lunch at the nearby Sand Key Park, known for its beautiful beach and nature trails. In the afternoon, take a leisurely bike ride along the Pinellas Trail or explore the shops and galleries in the charming town of Dunedin. Wrap up the day with a delicious seafood dinner at one of the waterfront restaurants.

  • Clearwater Marine Aquarium: $24.95-29.95, Estimated time spent: Morning
  • Sand Key Park: Free, Estimated time spent: Lunch
  • Pinellas Trail or Dunedin: Prices vary, Estimated time spent: Afternoon
  • Waterfront restaurant: $20-40, Estimated time spent: Dinner
Tuesday, September 5: Farewell Orlando

On your last day, start the morning with a visit to the Orlando Eye, a towering observation wheel offering panoramic views of the city. Afterward, explore the fascinating Kennedy Space Center Visitor Complex, where you can learn about space exploration and even meet an astronaut. Enjoy a late lunch at one of the restaurants in the nearby Port Canaveral before heading back to Orlando to catch your flight home.

  • Orlando Eye: Prices vary, Estimated time spent: Morning
  • Kennedy Space Center Visitor Complex: $57-67, Estimated time spent: 4-6 hours
  • Port Canaveral: Prices vary, Estimated time spent: Lunch

Hidden Gems and Local Favorites

While in Orlando, don't miss the chance to explore the charming neighborhood of Thornton Park. This trendy district is known for its unique boutiques, art galleries, and excellent dining options. Take a walk around Lake Eola Park, a beautiful oasis in the heart of downtown, and consider renting a swan-shaped paddleboat for a fun experience. For a taste of local flavors, head to Winter Garden, a historic town just outside Orlando, where you can find a vibrant farmers market and delightful farm-to-table restaurants.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version