Woman holding four Guess Where Trips envelopes while on road trip

Fort Myers Area

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

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  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    Regular price $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • Can be done in winter
    The Southwest Quest

    The Southwest Quest

    $65 USD
    Plenty of sun, strolls and citrus make this the ultimate Southwest Florida road trip. From unique eateries and boardwalk trails to an eerie ghost town and a sunset beach stop, there is truly something for everyone!
    • Kid-Friendly
    • Accessible
  • Can be done in winter
    Sun-Kissed Surprises

    Sun-Kissed Surprises

    $65 USD
    Get ready to feel the ocean breeze in your hair! We've recommended multiple beaches and the cutest colorful towns full of local shops, walks and eateries.
    • Accessible
    • Kid-Friendly
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!