Browse all trips
-
The Southwest Quest
$65 USDPlenty 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
-
Sun-Kissed Surprises
$65 USDGet 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
-
Adventure in the Glades
$65 USDScenic views, unique boardwalks and funky roadside attractions can all be found when you escape to the Everglades. Just make sure you keep your eyes peeled for those pesky gators!- Accessible
- Dog-Friendly
![](http://guesswheretrips.com/cdn/shop/files/hero-funky-florals-women-walking-in-tulip-field-1440x1304.jpg?v=1669769692&width=1500)
![](http://guesswheretrips.com/cdn/shop/files/our-trips-archive-min.jpg?v=1667586827&width=1500)
CAN'T DECIDE?
Take Our Quiz to Find Out
Select your region and interests to find the best trip for you.
![](http://guesswheretrips.com/cdn/shop/files/contact-us-woman-on-roadtrip-leaning-out-window.jpg?v=1667845489&width=1500)
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!