Florida Road Trip: Six Lessons Learned

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Florida Road Trip: A Family Affair with a Few Twists and Turns

A recent 10-day Florida road trip with my mom and stepdad proved to be a memorable experience, though not without a few lessons learned. While I wouldn’t have envisioned such a trip in my teens, in my late 30s, it turned out to be an unforgettable journey.

Our 1,200-mile adventure began in mid-November in Miami, taking us south to Key West, north to Orlando and St. Augustine, and finally back to Miami through Hollywood, with roughly two nights in each location. While this itinerary offered a taste of Florida’s diverse offerings, the fast pace proved to be a drawback.

A recurring theme in our post-trip discussions was the desire for a longer vacation. While real-life constraints like work and budget limit extended travel, a 14-day trip would have been ideal.

The frequent hotel changes and long hours on the road became tiring. A few extra days in each location would have allowed for a more relaxed experience.

Another logistical hiccup involved our flight home. Flying in and out of Miami meant a 315-mile drive south from St.

Augustine at the end of our trip. This final leg felt excessive after so much time in the car.

In retrospect, flying home from Orlando, significantly closer to St. Augustine, would have been a much better choice.

While the I-95 saved time, it lacked scenic appeal and, ironically, wasn’t as efficient as hoped due to Thanksgiving traffic. The coastal A1A highway, with its tropical scenery and ocean views, would have been a more enjoyable route, potentially offering opportunities to explore charming small towns.

Although wary of too many hotel changes, an additional stop between Key West and Orlando would have broken up the nearly 400-mile, nine-hour drive. A night in Fort Lauderdale or Boca Raton would have provided a welcome respite and a chance to explore more of the region.

Experiencing Thanksgiving in the US was fascinating, complete with festive decorations and traditional food, courtesy of our generous rental host. However, many businesses in Key West were closed on Thanksgiving Day, limiting our options. While a unique experience, I would likely avoid traveling during this holiday in the future.

Finally, while Miami Beach offered iconic sights like Ocean Drive and the opportunity to catch up with friends, two nights proved insufficient. Exploring Downtown Miami, Little Havana, or even attending a local sporting event would have enriched our experience. Miami could also have served as a base for exploring Everglades National Park.

Overall, the Florida road trip was a wonderful experience with family. However, a few adjustments, like a longer itinerary, a different return airport, more scenic routes, and strategic additional stops, would have made it even better. And perhaps skipping Thanksgiving next time!


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