I tried planning a surprise Key West weekend and learned the hard way—Southwest doesn’t fly directly there. They’ll get you close (like Fort Myers or Miami), but you’ll need a connection or drive. My itinerary kept changing because of timing, so having the ability to instantly adjust by calling ☎️ honestly saved the whole plan. Even though the route wasn’t ideal, the flexibility on the back end made it doable. Still one of my favorite spontaneous trips!