Trip Report: Key West for New Year’s Eve


New Year’s Eve is my favorite holiday. Always has been. It might be because my parents always through a party at our house for their friends, and while I was quarantined in my bedroom for all of them, I could still tell it was a rockin’ good time downstairs.

So Laura and I make a point of traveling somewhere for New Year’s Eve every year. We’ve now spent NYE in all four Lower 48 time zones, and did the countdown in Vegas, Seattle, Phoenix, Chicago, Pensacola and many, many other places. I’ve even done the Times Square madness. Once. And only once.

This year, we chose Key West. It’s our kind of town, so it has to be our kind of NYE town, right? Yes, yes it was.



As the crow flies, Key West isn’t all that far from our house in Safety Harbor, Florida. But the crow doesn’t fly there, and the airlines that do charge a heart-stopping amount to get you there during NYE. Driving is out of the question, because it’s a seven-hour drive. SEVEN. So we finally took a trip on the Key West Express, and pretty much loved it.

The Express is a high-speed ferry from Fort Myers Beach to Key West, sailing back and forth daily. It’s a quite large vessel, and well appointed. It’s all open seating, you have your choice of airline-like seats or, if you board early enough, couches with tables perfect for groups. On the way down, they showed a movie, and on the way back, they showed Monday Night Football, so there’s some free entertainment on board. There’s also a bar with a small snack bar, so the couple-hour trip can go by quickly.

The only problem for us is that it leaves very early in the morning from Fort Myers Beach, so we decided to book a hotel there the night before to avoid the early-morning drive. On the way back, we could have done the same thing, but opted to drive home after it arrived back in Fort Myers Beach late in the evening.



Somewhat surprising, considering that we didn’t decide on Key West until October, we were able to find a pretty cool hotel that didn’t break the bank. The Ibis Bay Beach Resort is an old motel that has been redecorated into a funky place to stay. We had a first-place room overlooking the bay, with a hammock and some chairs to watch the resident birds and tortoises from. It has a great pool area that includes a movie screen, with a nice restaurant and bar.

It’s a bit out of the entertainment district, but it uses old school buses to take guests to multiple stops in town and then back to Ibis.



Drag Queen

The highlight is, of course, the multiple NYE celebrations and traditions, pretty much a different one for whatever type of person you are. We chose the Drag Queen Shoe Drop at Bourbon Street Pub, because it seemed the most fun. And it was. The streets were crowded, but hey, it’s NYE. If you’re not excited about crowds, choose a different favorite holiday. But quite surprising to us, we were able to find a lot of not-as-crowded bars in town all night, so it doesn’t have to be all shoulder-to-shoulder contact if you don’t want it to be.


There are lots of great museums in the city, so I could tell you about Harry Truman’s Little White HouseErnest Hemingway’s house or the Key West Butterfly and Nature Conservatory, but if you’re going to Key West for NYE, you’re going there to drink. And drink we did! In fact, we held an impromptu contest for our Facebook friends to guess how many different bars we’d visit over the weekend. Did you guess 32? If so, you would have won a T-shirt! And don’t forget to visit Dante’s. It’s a great bar/restaurant right by the dock to the Key West Express. It has a full pool with waterfall, so it’s a great place to cool off while enjoying some drinks.


Categories: Drinking, Entertainment, Hotels, Museums, Pop Culture, Tourist Locations, Trip Reports | Tags: , , , , , | Leave a comment

The three worst hotels I’ve ever stayed in

Yes, I’m cheap. And sometimes, the old adage “I just need a bed and a shower” applies when looking for a hotel. But, um, I do actually need a bed and a shower, even when I am being cheap. Here are the three worst hotels I’ve stayed in. You’ll notice all three have “INN” in their name. A trend, perhaps? And yes, one of them didn’t have a (working) shower.

3. MASTERS INN, Atlanta, Georgia

Blood stain on a broken recliner

It’s funny how a stay can be so completely awful that you forget (almost) all of the details, but have no trouble remembering just how incredibly cruddy the place was. Well more than a decade ago, Laura and I drove from our then-home in Pensacola to Atlanta to visit the Six Flags amusement park. We just needed “a bed and shower” the night before we hit the roller coasters, and the Masters Inn room we found seemed to fit the bill. Cheap, close to the park. Yes, I’ve forgotten most of the other horrid details (though I imagine Laura has not), but I’ll never forget one thing – the recliner in the room was broken. And had a blood stain. We walked down the front desk, and in the all-time best response I’ve gotten from a manager about a complaint, here’s what the Masters Inn manager told us:  “Well, sometimes we don’t get what we want.”

We wrote to the corporate office and received a nice reply back that obviously the room was not up to the company’s standards (good to hear that at least someone in the company believes that bodily fluids shouldn’t be on furniture), but no refund or coupons for a future visit. Yes, that was the last Masters Inn we’ve stayed in.

2. DAYS INN, New Orleans, Louisiana

Laura forced to do her best Joey Tribiani impression

It was supposed to the most special vacation of our lives. The next day, we were flying to Las Vegas to meet friends and family for our wedding. But since we had an early flight out, and the airport was more than three hours from our house, we decided it was best to drive over the night before and stay somewhere close to the airport. Bad idea.

I remember saying, “How bad can it be? It’s a Days Inn.” Yeah. Last time I’ve said that. We walked into the room and immediately saw bugs flying. From the bed. The bedspread (which Laura always immediately strips from the bed and shoves in a closet) had holes in it. The place was so bad that we would have checked out and gone somewhere else, but here is the really awful part – we paid $90 for the room … and it was the cheapest room in town. There really was no place else to go.

So Laura unpacked almost all her clothes and put them all on. “I don’t want a single piece of my body to touch anything on this bed,” she said. When she was finished, she reminded me of the Friends episode where Joey and Chandler were fighting, and Joey stormed into Monica’s apartment wearing all of Chandler’s clothes. The only time since then I think we’ve stayed at a Days Inn was when the dude installing tile in our bathrooms left our house with no working toilets and we had to find a place close to our house to stay at midnight. But that’s a story for another day.

1. GOLDEN GLADES INN, Miami, Florida

Reserved parking for police officers. No, seriously.

My brother was flying to Tampa and we were driving to Miami to see the Packers play the Dolphins. I had debated back and forth whether to drive down the morning of the game, or whether it would be better to drive down the night before. In the end, I decided we’d stay the night. I did a quick Web search looking for a hotel near the stadium. First mistake.

Found one for $60 with an instant web coupon. Again, it was the cheapest in town (yes, I’ve learned my lesson now). Even with a GPS, we couldn’t figure out how to get to the actual hotel, which was in the middle of about 543* highways that criss-crossed the city. And, of  course, many of them were toll roads, so we racked up $1,456* in tolls during our madcap adventure (*some figures in this post have been inflated for literary effect). When we finally made it, the first thing we noticed was the first three parking spots had signs that said “RESERVED FOR POLICE.” The next thing we saw we’re actual police cars, with lights flashing, by the lobby door, and cops pushing a shirtless, handcuffed dude into the cruiser. Most excellent. The hotel I picked for us was a live taping of a future episode of Cops.  But wait. It gets better.

We sidestep the police and walk into the lobby to check in. The clerk didn’t have our reservation and didn’t know anything about the “web special” that I booked. Fine, whatever. Just give us a room before someone pops a cap in our ass. We make it to our room, and the carpet near the bathroom was bunched up. Water streamed from the bathtub, even though there was no water in the actual bathtub.

Somehow we managed to get some sleep. In the morning, I went to take a shower. The water just drizzled from the shower head, down the wall, over the side of the tub and … you guessed it, onto the carpet.

Categories: Hotels | Tags: , , | Leave a comment

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