Fort Myers

Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 USD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! The recipient can then choose a surprise trip that suits them!
  • BEST SELLING GIFT
    The Southwest Quest

    The Southwest Quest

    $39 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 depart from: Fort Myers Area, Naples Area, Tampa Area