Key West, Florida – A Weekend Adventure

Key-West-Florida-SunsetWhat appeals to travelers most about Key West? Specifically, what exactly are you looking for in the experience? Posh eateries? Upscale boutiques? Maybe a good spa? (These are details I love on my travels but not items for which Key West is known.) Think New Orleans meets the Bahamas.

I spent time there on various trips as a child but my memories are fuzzy. The 8 year old in me remembered warm sand, unusually giddy grown-ups and loads of ice cream. As it turns out, these were things that charmed me as an adult on this trip too. Happiness is infectious and Key West is brimming with it.

Greg and I decided to fly direct into Fort Lauderdale and drive down instead of flying straight to Key West. We had a little extra time on this trip and skipping the connection flight to Key West saved us about $600. Although a bit long (about 3 hours), the drive is stunning. We headed down the Overseas Highway, the southernmost portion of U.S. Highway 1, across all 42 bridges to Key West.

Typical Key West

Typical Key West

This was Greg’s first trip to the Keys but it felt fresh for me too. The sun was pervasive and the drive flew by singing at the top of our lungs to bad country music and counting about a million crab shacks along the way. As we crossed the final bridge from Stock Island the atmosphere around us changed instantly. People were dancing down the sidewalks toting fruity cocktails, laughing and funneling into the numerous restaurants erupting with raucous live music. I looked over and Greg had the biggest grin on his face, “I’m going to like this place.”

We rolled up to the Ocean Key Resort, at the far end of the island just off Mallory Square. The staff were very friendly and the lobby was tidy, elegantly appointed and very quiet, presumably because it was a Thursday around 3pm. The grounds of the property raised questions between us of whether we had made the correct resort selection but these were quickly quelled when we arrived at the room. The room prices at the Ocean Key Resort were a bit steep, so we tracked them for a few months and scored a good deal on a beautiful ocean view suite!

We were visiting the Key for a wedding, so we quickly cleaned up and headed down to the reception on the Sunset Pier. On a side note, I have to say our friends were on to an exceptional idea; get married at the Key West court house and then throw a “family reunion” on the pier. Efficient, cost effective, STUNNING and delicious. Brilliant! Also, it gave family and friends a full three days to enjoy Key West with the bride and groom. Flawless.

Party Time

After the reception the boisterous crowd headed for Sloppy Joe’s on Duval Street; not typically our speed but pleasantly a fun band and great crowd for tearing up the dance floor. A couple of dance moves, a beverage or two and one bride on stage later, Greg and I had to head for bed or risk being “those people” at the bar drinking water and plotting to find the nearest greasy food.

If you’re planning on hitting the bars each night try not to repeat too much. There are a ton of great watering holes with live music, and while we were there the Thursday night band was also the Saturday night band. It would have been a bummer if we planned a repeat on Saturday only to find the same group.

Water Sports

The next morning we hopped out of bed grabbed Starbucks (which was right next to our hotel!) and wandered over to the local dive shop to shore up our dive plans for Saturday before Friday got away from us. We did a little wandering around downtown Key West, spent too much money at Divers Direct, and then checked in with our friends to see what their plans were for the day. They said jet skis!

Out side of most of the hotels that are on the water there are tons of options to get out on the water. You can rent small boats, go on a short cruise, or go for a jet ski tour. At first I was a bit skeptical because it was a “tour” and not just a rental. It also was about $125 per ski. But because we were with a group I had no hesitation. Boy was I wrong. Not only was the tour a good solid 2 hours, but the “tour guides” were a blast. We saw the entire island, caught some waves, and contemplated going again the next day.

Following our epic jet ski adventure we relaxed by the pool a bit and then cleaned up for a good old-fashioned booze cruise. Like I mentioned earlier, there are a ton of options for getting out on the water. Our group was headed out on one of the many catamarans that had an open bar. It was about $90 per person and I’m positive we drank at least that much on the two hour sail. The sunset was gorgeous and the crew was fun. If you’re into live music, there are a few boats that have bands aboard as well.

Scuba Diving

OK. Ok. I know what you’re thinking. Scuba Diving in Key West? Well, it’s better than you’d think. They have some decent wreak diving, and if you’re an avid diver, you should definitely consider a morning of exploring a sunken ship.

There are quite a few dive shops on the Key, and many got mixed reviews. We settled on using Southpoint Divers for our dives. They seemed to cater to experienced divers a bit more than the other shops, and had very reasonable prices. We went out with them for a two-tank morning dive on the Vandenberg.

On the morning of our dives we showed up at the shop, which was near the Hyatt a few blocks from our hotel, to grab our computers. We made the short walk to the boat and found all of our rental gear waiting for us onboard, ready to go. We were pleased to find that there were only 3 other divers with us, and they dove on their own. Our group was just the two of us and a guide–no knee draggers to be found!

The Vandenberg was a great dive and shouldn’t be missed. The dive floor is about 100 feet, so the dives were quick, but there was plenty to see. We we’re diving the aft half of the ship and swam through quite a few of it’s decks. The marine life surrounding the ship is a bit different than normal reef dives. We saw quite a few barracuda, but the highlight was a goliath grouper that was the size of a small car!


The-Hemingway-HouseAfter spending the morning diving we decided to check out some of the historical sights on the Key. We headed over to the Hemingway House for a tour. This is an absolute must if you’ve never been there before. The grounds are beautiful, but the story of the property is nothing short of entertaining.

Ernest Hemingway lived a very interesting life, the evidence of such are numerous throughout his home. Make sure you take one of the free tours they offer throughout the day. It is the only way you will be able to really experience the property. We opted not to take one at first, and explore on our own. This was a mistake. We tagged onto a tour group half way through and are glad we did.

After touring the Hemingway House we wandered down to the marker for the southernmost point of the USA. We found the landmark to be over run by tourists and there was a line to take your picture with the it. We kept walking and popped into the near by Waldorf Astoria hotel for a drink instead. Besides, we saw the thing on our epic jet ski tour the day before. I guess the southernmost point is worth seeing, but it seemed fairly underwhelming to us.

Final Thoughts

Key West is an interesting beast. It mixes together the party atmosphere of New Orleans, with the island culture of the Caribbean. Although the Key does have open container laws, they are very selectively enforced. Perhaps it’s not the best place to bring kids, although there are many family friendly options, it’s defiantly the perfect place for a weekend getaway. That being said, a long weekend is more than enough to take in everything Key West has to offer.

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