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In May 2018 I took a trip to Key West for the first time. On the evening prior to my departure my Fiancé had some very bad premonitions and we almost canceled the trip. There was a lot of really bad weather around the country including what looked like the formation of a tropical depression in the Golf.

What I didn’t realize is that the rainy season as well as the hurricane season technically starts May 15. I was under the impression that it didn’t start for a few more weeks which is technically not true. Historically the end of May very rarely sees hurricanes.

In the morning I read that there was less than a 30 percent change that it would develop into a tropical storm over the next 5 days. That convinced me that it was worth the risk to go. We called the Bread and Breakfast we where staying at Alexanders Guest House and the front desk person assured my girl that it was safe. That she shouldn’t worry. So the trip was on again. We booked Alexanders based on their top 10 position on Trip Advisor and the fact that it was “straight friendly.” We thought that was cool.

Our flight took off on time and everything was looking good. The problem happened as we started to prepare for landing. The captain came on and informed us that there was a backup and we had to circle for about 15 minutes so we are going to be just slightly late. Then about 10 minutes later he came on and said it’s getting more backed up and we need to refuel so he was diverting the flight to Fort Myer. This took about an hour and we ended up missing our connecting flight to the Key West airport.

I want to add that the flight crew was particularly unfriendly. And not very helpful. When we landed we expected a wheel chair from the girl who has a bad back. We got in line for about 20 minutes to try to get a new flight. Everything at the airport was closed but the airline American had some very stale sandwiches for us. I was getting a head ache because I was dehydrated after the long flight. Good news was that they can book us on the next flight out which was in about 12 hours. But the bad news was they couldn’t provide us with any vouchers for a hotel room or a meal just the free day old sandwich.

So I got on my phone and started calling hotels. I called 6 hotels closest to the hotel that wasn’t a motel 6. No one answered. So we went to see about getting our luggage because we had a 12 hour hold over. Meds and stuff, toothbrush PJ’s the kind of stuff you need. was in there. No luck. Because there was a thunder storm it would take 8 hours for them to catch up enough to get our luggage.

I noticed a Sheraton Hotel out the window so I called their 800 number and they informed me because it was after midnight I could probably get a discounted price but they couldn’t book it at the call center I had to talk to the front desk. So they transferred me and of course they too didn’t answer. I assume late night is not a good time to call but they probably had overload of customers because everyone else was in a similar position.

Not wanting to spend 12 hours in the airport. I made an executive decision to rent a car. It was about $100 for a one way and we hit the road because the rain stopped. MY thinking was why chance it tomorrow if there is more bad weather we could get stuck again.

The drive was great. We stopped in Florida City. The attendant at the rental car place advised that. He said the area around the airport wasn’t particularly safe at night. He said the same thing about the keys. That it’s very deserted at night and probably not super safe to stop. We found a 24 hour Walmart and a Mc Donalds in Florida city and bought supplies and got some food and our adventure was started.

The entire trip was an adventure and I had an amazing time. So I decided to document everything we experienced with the hope to help others who are thinking about going.

Key West is the most impressive place I have ever been to in America. It’s unique culture and fun island vibe rocked. The art and tourist sites amazed. The food was outstanding. I recommend everyone visit at least once. It’s that impressive an experience.

The only issue we had was traveling there which wasn’t easy. Most of that was due to the airline American Airlines. I would love to hear about your experience with flying there. I have used American before. I know when we went to Pismo Beach the crew was super nice. Even better than South West. But both trips the rudeness of the staff kind of made the trip painful. Forget about the delays and lost luggage. Both going and returning in Miami, Key West and Phoenix the American staff was flat out rude.