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Day Trips from Orlando

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

Step away from the theme parks and uncover Orlando’s hidden gems on a road trip that’s all about Old Florida charm. Think picturesque beaches, scenic boardwalks, and local markets brimming with unique finds. Along the way, explore quirky homes with stories to tell, offbeat eateries, and intriguing ruins that make for the perfect surprise day trip.

Browse all trips

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • BEST SELLING GIFT
    Offbeat Oddities

    Offbeat Oddities

    $39 CAD
    The quirkiest road trip in central Florida! Historic homes with peculiar stories, off-the- beaten-path eateries, and funky trails & ruins will keep you on your toes throughout the day.
    • Kid-Friendly
    Can depart from: Tampa Area, Orlando Area, Lakeland Area, Gainesville Area
  • BEST SELLING GIFT
    Old Florida Trail

    Old Florida Trail

    $39 CAD
    Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.
    • Kid-Friendly
    Can depart from: Orlando Area, Gainesville Area, Jacksonville Area
  • CLOSE TO ORLANDO
    Boardwalks, Brews & Markets

    Boardwalks, Brews & Markets

    $39 CAD
    The name really says it all! Explore marvelous markets with food stalls and local artisans, enjoy a couple brews, and stroll along easy boardwalk trails.
    • Accessible
    Can depart from: Orlando Area, Tampa Area, Lakeland Area, Gainesville Area
  • Great Year-Round Trip
    Mysterious Gems

    Mysterious Gems

    $39 CAD
    Truly extraordinary destinations with strange stories and history. Cemeteries abandoned ruins, historic homes and so much more await on this mysterious road trip!
    • Dog-Friendly
    Can depart from: Orlando Area, Jacksonville Area
  • CAN BE DONE IN WINTER
    Seaside Legends

    Seaside Legends

    $39 CAD
    Little local legends are sprinkled throughout your day, telling the story of an iconic area of Florida. Expect picturesque beaches, tasty eats, a historic city, and so much more.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Orlando Area, Jacksonville Area, Gainesville Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!